Biologically active quinoline and quinazoline alkaloids part I
Xiao-Fei Shang
School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
Key Laboratory of Veterinary Pharmaceutical Development of Ministry of Agriculture, Lanzhou Institute of Husbandry and Pharmaceutical Sciences, Chinese Academy of Agricultural Sciences, Lanzhou, P.R. China
Search for more papers by this authorSusan L. Morris-Natschke
Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina
Search for more papers by this authorCorresponding Author
Ying-Qian Liu
School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
Additional correspondence author: Kuo-Hsiung Lee Email: [email protected]
Correspondence
Ying-Qian Liu, School of Pharmacy, Lanzhou University, Lanzhou 730000, P.R. China.
Email: [email protected]
Search for more papers by this authorXiao Guo
Key Laboratory of Veterinary Pharmaceutical Development of Ministry of Agriculture, Lanzhou Institute of Husbandry and Pharmaceutical Sciences, Chinese Academy of Agricultural Sciences, Lanzhou, P.R. China
Search for more papers by this authorXiao-Shan Xu
School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
Search for more papers by this authorMasuo Goto
Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina
Search for more papers by this authorJun-Cai Li
School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
Search for more papers by this authorGuan-Zhou Yang
School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
Search for more papers by this authorKuo-Hsiung Lee
Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina
Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung, Taiwan
Additional correspondence author: Kuo-Hsiung Lee Email: [email protected]
Search for more papers by this authorXiao-Fei Shang
School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
Key Laboratory of Veterinary Pharmaceutical Development of Ministry of Agriculture, Lanzhou Institute of Husbandry and Pharmaceutical Sciences, Chinese Academy of Agricultural Sciences, Lanzhou, P.R. China
Search for more papers by this authorSusan L. Morris-Natschke
Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina
Search for more papers by this authorCorresponding Author
Ying-Qian Liu
School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
Additional correspondence author: Kuo-Hsiung Lee Email: [email protected]
Correspondence
Ying-Qian Liu, School of Pharmacy, Lanzhou University, Lanzhou 730000, P.R. China.
Email: [email protected]
Search for more papers by this authorXiao Guo
Key Laboratory of Veterinary Pharmaceutical Development of Ministry of Agriculture, Lanzhou Institute of Husbandry and Pharmaceutical Sciences, Chinese Academy of Agricultural Sciences, Lanzhou, P.R. China
Search for more papers by this authorXiao-Shan Xu
School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
Search for more papers by this authorMasuo Goto
Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina
Search for more papers by this authorJun-Cai Li
School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
Search for more papers by this authorGuan-Zhou Yang
School of Pharmacy, Lanzhou University, Lanzhou, P.R. China
Search for more papers by this authorKuo-Hsiung Lee
Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina
Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung, Taiwan
Additional correspondence author: Kuo-Hsiung Lee Email: [email protected]
Search for more papers by this authorAbstract
Quinoline and quinazoline alkaloids, two important classes of N-based heterocyclic compounds, have attracted tremendous attention from researchers worldwide since the 19th century. Over the past 200 years, many compounds from these two classes were isolated from natural sources, and most of them and their modified analogs possess significant bioactivities. Quinine and camptothecin are two of the most famous and important quinoline alkaloids, and their discoveries opened new areas in antimalarial and anticancer drug development, respectively. In this review, we survey the literature on bioactive alkaloids from these two classes and highlight research achievements prior to the year 2008 (Part I). Over 200 molecules with a broad range of bioactivities, including antitumor, antimalarial, antibacterial and antifungal, antiparasitic and insecticidal, antiviral, antiplatelet, anti-inflammatory, herbicidal, antioxidant and other activities, were reviewed. This survey should provide new clues or possibilities for the discovery of new and better drugs from the original naturally occurring quinoline and quinazoline alkaloids.
REFERENCES
- 1Prajapati SM, Patel KD, Vekariya RH, Panchal SN, Patel HD. Recent advances in the synthesis of quinolines: a review. RSC Adv. 2014; 4: 24463–24476.
- 2Wiesner J, Ortmann R, Jomaa H, Schlitzer M. New antimalarial drugs. Angew Chem Int Ed. 2003; 42: 5274–5293.
- 3Manske RH. The chemistry of quinolines. Chem Rev. 1942; 30: 113–144.
- 4Tumer RR, Woodward RR. The chemistry of the Cinchona alkaloids. In: RHF Manske, ed. The Alkaloids. New York: Academic Press; 1953: 16.
- 5Wall ME, Wani MC, Cook CE, Palmer KH, McPhail AT, Sim GA. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminate. J Am Chem Soc. 1966; 88: 3888–3890.
- 6Liu YQ, Li WQ, Morris-Natschke SL, et al. Perspectives on biologically active camptothecin derivatives. Med Res Rev. 2015; 35: 753–789.
- 7Anjali PD, Singh D. Quinoline: a diverse therapeutic agent. Int J Pharm Sci Res. 2016; 7: 1–13.
- 8Kshirsagar UA. Recent developments in the chemistry of quinazolinone alkaloids. Org Biomol Chem. 2015; 13: 9336–9352.
- 9Armarego WLF. Naturally occurring and biologically active quinazolines. Chemistry of Heterocyclic Compounds: Fused Pyrimidines, Part I, Quinazolines. 2008: 490. Chapter XI.
- 10Khan I, Ibrar A, Abbas N, Saeed A. Recent advances in the structural library of functionalized quinazoline and quinazolinone scaffolds: synthetic approaches and multifarious applications. Eur J Med Chem. 2014; 76: 193–214.
- 11Johne SP. The quinazoline alkaloids. Prog Chem Org Nat Prod. 1984; 46: 159–229.
- 12Shang XF, Guo X, Li B, et al. Microwave-assisted extraction of three bioactive alkaloids from Peganum harmala L. and their acaricidal activity against Psoroptes cuniculi in vitro. J Ethnopharmacol. 2016; 192: 350–361.
- 13Mhaske SB, Argade NP. The chemistry of recently isolated naturally occurring quinazolinone alkaloids. Tetrahedron. 2006; 62: 9787–9826.
- 14Witt A, Bergman J. Recent developments in the field of quinazoline chemistry. Curr Org Chem. 2003; 7: 659–677.
- 15Armarego WLF. Quinazolines. Adv Heterocycl Chem. 1979; 24: 1.
- 16Johne S. In: MF Ansell, ed. Rodd's Chemistry of Carbon Compounds. Amsterdam: Elsevier; 1995: 223–240. Supplements to the 2nd ed.
- 17Brown DJ. Quinazolines. The Chemistry of Heterocyclic Compounds. New York: Wiley; 1996: 55. Supplement I.
- 18Ďyakonov AL, Telezhenetskaya MV. Quinazoline alkaloids in nature. Chem Nat Comp. 1997; 33: 221–267.
- 19Johne S. In: M Sainsbury, ed. Rodd's Chemistry of Carbon Compounds. Amsterdam: Elsevier; 2000: 203. Second Supplements to the 2nd ed.
- 20Padala SR, Padi PR, Thipireddy V. A review on 2-heteryl- and heteroalkyl-4(3H)-quinazolinones. Heterocycles. 2003; 60: 183–226.
10.3987/REV-01-540 Google Scholar
- 21Ma Z, Hano Y, Nomura T. Luotonin A: a lead toward anti-cancer agent development. Heterocycles. 2005; 65: 2203–2219.
- 22Khan I, Ibrar A, Ahmed W, Saeed A. Synthetic approaches, functionalization and therapeutic potential of quinazoline and quinazolinone skeletons: the advances continue. Eur J Med Chem. 2015; 90: 124–169.
- 23Madapa S, Tusi Z, Batra S. Advances in the syntheses of quinoline and quinoline-annulated ring systems. Curr Org Chem. 2008; 12: 1116–1183.
- 24Kouznetsov VV, Méndez LYV, Gómez CMM. Recent progress in the synthesis of quinolines. Curr Org Chem. 2005; 9: 141–161.
- 25Afzal O, Kumar S, Haider MR, et al. A review on anticancer potential of bioactive heterocycle quinoline. Eur J Med Chem. 2015; 97: 871–910.
- 26Kumar S, Bawa S, Gupta H. Biological activities of quinoline derivatives. Mini-Rev Med Chem. 2009; 9: 1468–1454.
- 27Chung PY, Bian ZX, Pun HY, et al. Recent advances in research of natural and synthetic bioactive quinolines. Future Med Chem. 2015; 7: 947–967.
- 28Witt A, Bergman J. Recent developments in the field of quinazoline chemistry. Cur Org Chem. 2003; 7: 659–677.
- 29Connolly DJ, Cusack D, O'Sullivan TP, Guiry PJ. Synthesis of quinazolinones and quinazolines. Tetrahedron. 2005; 61: 10153–10202.
- 30Khan I, Zaib S, Batool S, et al. Quinazolines and quinazolinones as ubiquitous structural fragments in medicinal chemistry: an update on the development of synthetic methods and pharmacological diversification. Bioorg Med Chem. 2016; 24: 2361–2381.
- 31Asif M. Quinolene derivatives as anti-cancer agents: a review. J der Pharm Forschung. 2014; 2: 81–96.
- 32Grundon MF. In: MF Grundon, ed. The Alkaloids. London: The Royal Society of Chemistry; 1979: 79. Specialist Periodical Reports.
- 33Grundon MF. In: MF Grundon, ed. The Alkaloids. London: The Royal Society of Chemistry; 1981: 72. Specialist Periodical Reports.
- 34Grundon MF. In: MF Grundon, ed. The Alkaloids. London: The Royal Society of Chemistry; 1983: 100–116. Specialist Periodical Reports.
- 35Grundon MF. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1984; 1: 195–200.
- 36Grundon MF. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1985; 2: 393–400.
- 37Grundon MF. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1987; 4: 225–36.
- 38Grundon MF. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1988; 5: 293–307.
- 39Grundon MF. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1990; 7: 131–138.
- 40Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1991; 8: 53–68.
- 41Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1992; 9: 25–35.
- 42Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1993; 10: 99–108.
- 43Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1994; 11: 163–172.
- 44Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1995; 12: 77–89.
- 45Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1995; 12: 465–475.
- 46Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1997; 14: 11–20.
- 47Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1997; 14: 605–618.
- 48Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1998; 15: 595–606.
- 49Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 1999; 16: 697–709.
- 50Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 2000; 17: 603–620.
- 51Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 2001; 18: 543–559.
- 52Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 2002; 19: 742–760.
- 53Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 2003; 20: 476–493.
- 54Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 2004; 21: 650–668.
- 55Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 2005; 22: 627–646.
- 56Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 2007; 24: 223–246.
- 57Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep. 2008; 25: 166–187.
- 58Anand P, Kunnumakkara AB, Sundaram C, et al. Cancer is a preventable disease that requires major lifestyle changes. Pharm Res. 2008; 25: 2097–2116.
- 59Gallo RC, Whang-Peng J, Adamson RH. Studies on the antitumor activity, mechanism of action, and cell cycle effects of camptothecin. Natl J Cancer Inst. 1971; 46: 789–795.
- 60Herben VM, ten Bokkel Huinink WW, Beijnen JH. Clinical pharmacokinetics of topotecan. Clin Pharmacokinet. 1996; 31: 85–102.
- 61Jones CB, Clements MK, Wasi S, Daoud SS. Enhancement of camptothecin-induced cytotoxicity with UCN-01 in breast cancer cells: abrogation of S/G2 arrest. Cancer Chemother Pharmacol. 2000; 45: 252–258.
- 62Takahashi P, Polson A, Reisman D. Elevated transcription of the p53 gene in early S-phase leads to a rapid DNA-damage response during S-phase of the cell cycle. Apoptosis. 2011; 16: 950–958.
- 63Zhou Y, Gwadry FG, Reinhold WC, et al. Transcriptional regulation of mitotic genes by camptothecin-induced DNA damage. Cancer Res. 2002; 62: 1688–1695.
- 64Koshkina NV, Kleinerman ES, Waidrep C, Jia SF, Worth LL, Gilbert BE. 9-Nitrocamptothecin liposome aerosol treatment of melanoma and osteosarcoma lung metastases in mice. Clin Cancer Res. 2000; 6: 2876–2880.
- 65Verschraegen CF, Gilbert BE, Huaringa AJ, Newman R, Harris N, Leyva FJ. Feasibility, phase I, and pharmacological study of aerosolized liposomal 9-nitro-20(S)-camptothecin in patients with advanced malignancies in the lungs. Ann NY Acad Sci. 2000; 922: 352–354.
- 66Takimoto CH, Thomas R. The clinical development of 9-aminocamptothecin. Ann NY Acad Sci. 2000; 922: 224–236.
- 67Pratesi G, Beretta GL, Zunino F. Gimatecan, a novel camptothecin with a promising preclinical profile. Anticancer Drugs. 2004; 15: 545–552.
- 68Haridas K, Hausheer FH. Preparation of highly lipophilic camptothecin derivatives. US patent 6057303. 2000.
- 69Bom D, Curran DP, Zhang J, Zimmer SG, Bevins R, Kruszewski S. The highly lipophilic DNA topoisomerase I inhibitor DB-67 displays elevated lactone levels in human blood and potent anticancer activity. J Control Rel. 2001; 74: 325–333.
- 70Wani MC, Nicholas AW, Wall ME. Plant antitumor agents. 23. Synthesis and antileukemic activity of camptothecin analogs. J Med Chem. 1986; 29: 2358–2363.
- 71van Hattum AH, Pinedo HM, Schluper HMM, Erkelens CAM, Tohgo A, Boven E. The activity profile of the hexacyclic camptothecin derivative DX-8951f in experimental human colon cancer and ovarian cancer. Biochem Pharm. 2002; 64: 1267–1277.
- 72Royce ME, Rowinsky EK, Hoff PM, Coyle J, DeJager R, Pazdur R. A phase II study of intravenous exatecan mesylate (DX-8951f) administered daily for five days every three weeks to patients with metastatic adenocarcinoma of the colon or rectum. Invest New Drugs. 2004; 22: 53–61.
- 73Stevenson JP, DeMaria D, Sludden J, Kaye SB, Paz-Ares L, Grochow LB. Phase I/ pharmacokinetic study of the topoisomerase I inhibitor GG211 administered as a 21-day continuous infusion. Ann Oncol. 1999; 10: 339–344.
- 74Giles FJ, Tallman MS, Guillermo GM, Cortes JE, Thomas DA, Wierda WG. Phase I and pharmacokinetic study of a low clearance, unilamellar liposomal formulation of lurtotecan, a topoisomerase I inhibitor, in patients with advanced leukemia. Cancer. 2004; 100: 1449–1458.
- 75Dong P, Zuo C, Chen ZL, Gao Y, inventors: Jiangsu Chiatai Tianqing Pharmaceutical Co. Ltd, assignee. Pharmaceutical composition of camptothecin derivative and preparation method thereof. China Patent CN102764260.A. 2012. 11.7.
- 76Yu Y, Zhan Y, Chen Z, Zhang Y, Zhong D. Development and validation of a sensitive LC-MS/MS method for simultaneous quantification of sinotecan and its active metabolite in human blood. J Chromatogr B. 2014; 951–952: 62–68.
- 77Demarquay D, Huchet M, Coulomb H. The homocamptothecin BN 80915 is a highly potent orally active topoisomerase I poison. Anticancer Drugs. 2001; 12: 9–19.
- 78Lavergne O, Lesueur-Ginot L, Pla Rods M, et al. Homocamptothecins: synthesis and antitumor activity of novel E-ring-modified camptothecin analogs. J Med Chem. 1998; 41: 5410–5419.
- 79Bayés M, Rabasseda X, Prous JF. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003; 25: 747–771.
- 80Bayés M, Rabasseda X, Prous JF. Gateways to clinical trials. March 2003. Methods Find Exp Clin Pharmacol. 2003; 25: 145–168.
- 81Onishi H, Machida Y. Macromolecular and nanotechnological modification of camptothecin and its analogs to improve the efficacy. Curr Drug Discover Technol. 2005; 2: 169–183.
- 82Lerchen HG, Baumgarten J, von dem Bruch K, et al. Design and optimization of 20-O-linked camptothecin glycoconjugates as anticancer agents. J Med Chem. 2001; 44: 4186–4195.
- 83Singer JW, Bhatt R, Tulinsky J, et al. Water-soluble poly-(l-glutamic acid)-Gly-camptothecin conjugates enhance camptothecin stability and efficacy in vivo. J Control Release. 2001; 74: 243–247.
- 84Greenwald RB, Pendri A, Conover C, Gilbert C, Yang R, Xia J. Drug delivery systems. 2. Camptothecin 20-O-polyethylene glycol ester transport forms. J Med Chem. 1996; 39: 1938–1940.
- 85Houghton PJ, Cheshire PJ, Myers L, Stewart CF, Synold TW, Houghton JA. Evaluation of 9-dimethylaminomethyl-10-hydroxycamptothecin against xenografts derived from adult and childhood solid tumors. Cancer Chemother Pharmacol. 1992; 31: 229–239.
- 86Kunimoto T, Nitta K, Tanaka T, et al. Antitumor activity of 7-ethyl-10-[4-(1-piperidino)-1-piperidino] carbonyloxycamptothecin, a novel water soluble derivative of camptothecin, against murine tumors. Cancer Res. 1987; 47: 5944–5947.
- 87Ahn SK, Choi NS, Jeong BS, Kim KK, Journ DJ, Kim JK. Practical synthesis of (S)-7-(2-isopropylamino)ethylcamptothecin hydrochloride, potent topoisomerase I inhibitor. J Heterocycl Chem. 2000; 37: 1141–1144.
- 88Liu YQ, Tian X, Yang L, Zhan ZC. First synthesis of novel spin-labeled derivatives of camptothecin as potential antineoplastic agents. Eur J Med Chem. 2008; 43: 2610–2614.
- 89Liu YQ, Dai W, Wang CY, et al. Design and one-pot synthesis of new 7-acyl camptothecin derivatives as potent cytotoxic agents. Bioorg Med Chem Lett. 2012; 22: 7659–7661.
- 90Wang MJ, Liu YQ, Chang LC, et al. Design, synthesis, mechanisms of action, and toxicity of novel 20(S)-sulfonylamidine derivatives of camptothecin as potent antitumor agents. J Med Chem. 2014; 57: 6008–6018.
- 91Stallard S, Kaye SB. Reversal of resistance in the breast cancer cell line MCF-7/AdrR was most effective with the modulating agent quinidine. Bri J Cancer. 1989; 60: 500–505.
- 92Jones RD, Kerr DJ, Harnett AN, Rankin EM, Ray S, Kaye SB. A pilot study of quinidine and epirubicin in the treatment of advanced breast cancer. Brit J Cancer. 1990; 62: 133–135.
- 93Chauffert B, Pelletier H, Corda C, et al. Potential usefulness of quinine to circumvent the anthracycline resistance in clinical practice. Bri J Cancer. 1990; 62: 395–397.
- 94Chen IS, Wu SJ, Tsai IL, et al. Chemical and bioactive constituents from Zanthoxylum simulans. J Nat Prod. 1994; 57: 1206–1211.
- 95Chen IS, Tsai IW, Teng CM, et al. Pyranoquinoline alkaloids from Zanthoxylum simulans. Phytochemistry. 1997; 46: 525–529.
- 96Ulubelen A. Alkaloids from Haplophyllum suaveolens. Phytochemistry. 1984; 23: 2123–2124.
- 97Jansen O, Akhmedjanova V, Angenot L, et al. Screening of 14 alkaloids isolated from Haplophyllum A. Juss. for their cytotoxic properties. J Ethnopharmacol. 2006; 105: 241–245.
- 98Cui B, Chai H, Dong Y, et al. Quinoline alkaloids from Acronychia laurifolia. Phytochemistry. 1999; 52: 95–98.
- 99Wu TS, Shi LS, Wang JJ, et al. Cytotoxic and antiplatelet aggregation principles of Ruta graveolens. J Chin Chem Soc. 2003; 50: 171–178.
- 100Chen JJ, Huang HY, Duh CY, Chen IS. Cytotoxic constituents from the stem bark of Zanthoxylum pistaciiflorum. J Chin Chem Soc. 2004; 51: 659–663.
- 101Chaturvedula VSP, Schilling JK, Miller S, Andriantsiferana R, Rasamison VE, Kingston DGI. New cytotoxic alkaloids from the wood of Vepris punctate from the Madagascar rainforest. J Nat Prod. 2003; 66: 532–534.
- 102Komala I, Rahmani M, Sukari MA, Ismail HBM, Lian GEC, Rahmat A. Furoquinoline alkaloids from Melicope bonwickii (F. Muell.) T. Hartley. Nat Prod Res. 2006; 20: 355–360.
- 103Chou HC, Chen JJ, Duh CY, Huang TF, Chen IS. Cytotoxic and anti-platelet aggregation constituents from the root wood of Melicope semecarpifolia. Planta Med. 2005; 71: 1078–1081.
- 104Grougnet R, Magiatis P, Fokialakis N, et al. Koniamborine, the first pyrano[3,2-b]indole alkaloid and other secondary metabolites from Boronella koniambiensis. J Nat Prod. 2005; 68: 1083–1086.
- 105Moon SS, Cho N, Shin J, Seo Y, Lee CO, Choi SU. Jineol, a cytotoxic alkaloid from the centipede Scolopendra subspinipes. J Nat Prod. 1996; 59: 777–779.
- 106Morita H, Hirasawa Y, Yoshida N, Kobayashi J. Senepodine A, a novel C22N2 alkaloid from Lycopodium chinense. Tetrahedron Lett. 2001; 42: 4199–4201.
- 107Chen SB, Gao GY, Li YS, Yu SC, Xiao PG. Cytotoxic constituents from Aquilegia ecalcarata. Planta Med. 2002; 68: 554–556.
- 108Ruiz-Mesía L, Ruiz-Mesía W, Reina M, et al. Bioactive Cinchona alkaloids from Remijia peruviana. J Agric Food Chem. 2005; 53: 1921–1926.
- 109Nunes FM, Barros-Filho BA, de Oliveira MCF, et al. 3,3-Diisopentenyl-N-methyl-2,4-quinoldione from Esenbeckia almawillia: the antitumor activity of this alkaloid and its derivatives. Nat Prod Commun. 2006; 1: 313–318.
- 110Jacquemond-Collet I, Benoit-Vical F, Valentin A, Stanislas E, Mallié M, Fourasté I. Antiplasmodial and cytotoxic activity of galipinine and other tetrahydroquinolines from Galipea officinalis. Planta Med. 2002; 68: 68–69.
- 111Ratnayake S, Fang XP, Anderson JE, McLaughlin JL, Evert DR. Bioactive constituents from the twigs of Asimina parviflora. J Nat Prod. 1992; 55: 1462–1467.
- 112Kubanek J, Williams DE, de Silva ED, Allen T, Anderse RJ. Cytotoxic alkaloids from the flatworm Prostheceraeus villatus and its tunicate prey Clavelina lepadiformis. Tetrahedron Lett. 1995; 36: 6189–6192.
- 113Wright AD, Goclik E, König GM, Kaminsky R. Lepadins D-F: antiplasmodial and antitrypanosomal decahydroquinoline derivatives from the tropical marine tunicate Didemnum sp. J Med Chem. 2002; 45: 3067–3072.
- 114Kim WG, Kim JP, Kim CJ, Lee KH, Yoo ID. Benzastatins A, B, C, and D: new free radical scavengers from Streptomyces nitrosporeus 30643 I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities. J Antibiot. 1996; 49: 20.
- 115Kim WG, Kim JP, Yoo ID. Benzastatins A, B, C, and D: new free radical scavengers from Streptomyces nitrosporeus 30643 II. Structure determination. J Antibiot. 1996; 49: 26–30.
- 116Kurosawa K, Takahashi K, Tsuda E. SW-163C and E, novel antitumor depsipeptides produced by Streptomyces sp. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot. 2001; 54: 615–621.
- 117Takahashi K, Koshino H, Esumi Y, Tsuda E, Kurosawa K. SW-163C and E, novel antitumor depsipeptides produced by Streptomyces sp. II. Structure elucidation. J Antibiot. 2001; 54: 622–627.
- 118He J, Lion U, Sattler I, et al. Diastereomeric quinolinone alkaloids from the marine-derived fungus Penicillium janczewskii. J Nat Prod. 2005; 68: 1397–1399.
- 119Shen L, Ye YH, Wang XT, et al. Structure and total synthesis of aspernigerin: a novel cytotoxic endophyte metabolite. Chem Eur J. 2006; 12: 4393–4396.
- 120Kozlovsky AG, Zhelifonova VP, Antipova TV, et al. Quinocitrinines A and B, new quinoline alkaloids from Penicillium citrinum Thom 1910, a permafrost fungus. J Antibiot. 2003; 56: 488–491.
- 121Ito C, Itoigawa M, Sato A, et al. Chemical constituents of Glycosmis arborea: three new carbazole alkaloids and their biological activity. J Nat Prod. 2004; 67: 1488–1491.
- 122Konishi M, Ohkuma H, Sakai F, et al. BBM-928, a new antitumor antibiotic complex III. Structure determination of BBM-928 A, B and C. J Antibiot. 1981; 34: 148–159.
- 123Huang CH, Mong S, Crooke ST. Interactions of a new antitumor antibiotic BBM-928A with deoxyribonucleic acid. Bifunctional intercalative binding studied by fluorometry and viscometry. Biochemistry. 1980; 19: 5537–5542.
- 124Huang CH, Prestayko AW, Crooke ST. Bifunctional intercalation of antitumor antibiotics BBM-928A and echinomycin with DNA. Effects of intercalation on DNA degradative activity of bleomycin and phleomycin. Biochemistry. 1982; 21: 3704–3710.
- 125Huang CH, Mirabelli CK, Mong S, Crooke ST. Intermolecular cross-linking of DNA through bifunctional intercalation of an antitumor antibiotic, luzopeptin A (BBM-928A). Cancer Res. 1983; 43: 2718–2724.
- 126Huang CH, Crooke ST. Effects of structural modifications of antitumor antibiotics (luzopeptins) on the interactions with deoxyribonucleic acid. Cancer Res. 1985; 45: 3768–3773.
- 127Wang H, Yeo SL, Xu J, et al. Isolation of streptonigrin and its novel derivative from Micromonospora as inducing agents of p53-dependent cell apoptosis. J Nat Prod. 2002; 65: 721–724.
- 128Okada H, Suzuki H, Yoshinari T, Arakawa H, Okura A, Suda H. A new topoisomerase II inhibitor, BE-22179, produced by a Streptomycete. I. Producing strain, fermentation, isolation and biological activity. J Antibiot. 1994; 47: 129–135.
- 129Yoshinar T, Okada H, Yamada A, et al. Inhibition of topoisomerase II by a novel antitumor cyclic depsipeptide, BE-22179. Jpn J Cancer Res. 1994; 85: 550–555.
- 130Romero F, Espliego F, Baz JP, et al. Thiocoraline, a new depsipeptide with antitumor activity produced by a marine Micromonospora. I. Taxonomy, fermentation, isolation, and biological activities. J Antibiot. 1997; 50: 734–737.
- 131Perez Baz J, Cañedo LM, Fernández-Puentes JL, Silva Elipe MV. Thiocoraline, a novel depsipeptide with antitumor activity produced by a marine Micromonospora. II. Physico-chemical properties and structure determination. J Antibiot. 1997; 50: 738–741.
- 132Boger DL, Ichikawa S. Total syntheses of thiocoraline and BE-22179: establishment of relative and absolute stereochemistry. J Am Chem Soc. 2000; 122: 2956–2957.
- 133Boger DL, Ichikawa S, Tse WC, Hedrick MP, Jin Q. Total syntheses of thiocoraline and BE-22179 and assessment of their DNA binding and biological properties. J Am Chem Soc. 2001; 123: 561–568.
- 134Chen JJ, Duh CY, Huang HY, Chen IS. Furoquinoline alkaloids and cytotoxic constituents from the leaves of Melicope semecarpifolia. Planta Med. 2003; 69: 542–546.
- 135Fokialakis N, Magiatis P, Aligiannis N, Mitaku S, Tillequin F, Sévenet T. Furomegistines I and II, two furanopyridine alkaloids from the bark of Sarcomelicope megistophylla. Phytochemistry. 2001; 57: 593–596.
- 136Fokialakis N, Mitakua S, Mikros E, Skaltsounis AL, Tillequin F. Megistosarcimine and megistosarconine, two alkaloids from Sarcomelicope megistophylla. Phytochemistry. 1999; 52: 1745–1748.
- 137Fokialakis N, Magiatis P, Terzis A, Tillequin F, Skaltsounis AL. Cyclomegistine, the first alkaloid with the new cyclobuta[b]quinoline ring system from Sarcomelicope megistophylla. Tetrahedron Lett. 2001; 42: 5323–5325.
- 138Chung HS. A quinolone alkaloid, from the aleurone layer of Oryza sativa cv. Mihyangbyo, inhibits growth of cultured human leukemia cell. Nutraceuticals Food. 2002; 7: 119–122.
- 139Larsen TO, Gareis M, Frisvad JC. Cell cytotoxicity and mycotoxin and secondary metabolite production by common penicillia on cheese agar. J Agric Food Chem. 2002; 50: 6148–6152.
- 140Chen MY, Yang RY, Shao CL, et al. Isolation, structure elucidation, crystal structure, and biological activity of a marine natural alkaloid, viridicatol. Chem Nat Comp. 2011; 47: 322–325.
- 141Numata A, Takahashi C, Matsushita T, et al. Fumiquinazolines, novel metabolites of a fungus isolated from a saltfish. Tetrahedron Lett. 1992; 33: 1621–1624.
- 142Takahashi C, Matsushita T, Doi M, et al. Fumiquinazolines A-G, novel metabolites of a fungus separated from a Pseudolabrus marine fish. J Chem Soc Perkin Trans 1. 1995: 2345–2353.
- 143Barrow CJ, Sun HH. Spiroquinazoline, a novel substance P inhibitor with a new carbon skeleton, isolated from Aspergillus flavipes. J Nat Prod. 1994; 57: 471–476.
- 144Ma ZZ, Hano Y, Nomura T, Chen YJ. Two new pyrroloquinazolinoquinoline alkaloids from Peganum nigellastrum. Heterocycles. 1997; 46: 541–546.
- 145Ma ZZ, Hano Y, Nomura T, Chen YJ. Two new quinazoline-quinoline alkaloids from Pegnaum nigellastrum. Heterocycles. 1999; 51: 1883–1889.
- 146Ma Z, Hano Y, Nomura T, Chen Y. Novel quinazoline-quinoline alkaloids with cytotoxic and DNA topoisomerase II inhibitory activities. Bioorg Med Chem Lett. 2004; 14: 1193–1196.
- 147Cagir A, Jones SH, Gao R, Eisenhauer BM, Hecht SM. Luotonin A. a naturally occurring human DNA topoisomerase I poison. J Am Chem Soc. 2003; 125: 13628–13629.
- 148Liang JL, Cha HC, Jahng Y. Recent advances in the studies on luotonins. Molecules. 2011; 16: 4861–4863.
- 149Dallavalle S, Merlini L, Beretta GL, Tinelli S, Zunino F. Synthesis and cytotoxic activity of substituted luotonin A derivatives. Bioorg Med Chem Lett. 2004; 14: 5757–5761.
- 150Cagir A, Jones SH, Eisenhauer BM, Gao R, Hecht SM. Synthesis and biochemical properties of E-ring modified luotonin A derivatives. Bioorg Med Chem Lett. 2004; 14: 2051–2054.
- 151Cagir A, Eisenhauer BM, Gao R, Thomas SJ, Hecht SM. Synthesis and topoisomerase I inhibitory properties of luotonin A analogues. Bioorg Med Chem Lett. 2004; 12: 6287–6299.
- 152Zou J, Huang L. Isolation, structure elucidation, and synthesis of tryptanthrin and qingdainone from Baphicacanthus cusia (Nees) Bremek. Yaoxue Xuebao. 1985; 20: 45–48.
- 153Kimoto T, Hino K, Koya-Miyata S, et al. Cell differentiation and apoptosis of monocytic and promyelocytic leukemia cells (U-937 and HL-60) by tryptanthrin, an active ingredient of Polygonum tinctorium Lour. Pathol Int. 2001; 51: 315–325.
- 154Koya-Miyata S, Kimoto T, Micallef MJ, et al. Prevention of azoxymethane-induced intestinal tumors by a crude ethyl acetate-extract and tryptanthrin extracted from Polygonum tinctorium Lour. Anticancer Res. 2001; 21: 3295–3300.
- 155Motoki T, Takami Y, Yagi Y, Tai A, Yamamoto I, Gohda E. Inhibition of hepatocyte growth factor induction in human dermal fibroblasts by tryptanthrin. Biol Pharm Bull. 2005; 28: 260–266.
- 156Wu X, Liu Y, Sheng W, Sun J, Qin G. Chemical constituents of Isatis indigotica. Planta Med. 1997; 63: 55–57.
- 157Chen JJ, Fang HY, Duh CY, Chen IS. New indolopyridoquinazoline, benzo[c] phenanthridines and cytotoxic constituents from Zanthoxylum. Planta Med. 2005; 71: 470–475.
- 158Morita H, Sato Y, Chan KL, et al. Samoquasine A, a benzoquinazoline alkaloid from the seeds of Annona squamosa. J Nat Prod. 2000; 63: 1707–1708.
- 159Morita H, Sato Y, Chan KL, et al. Samoquasine A, a benzoquinazoline alkaloid from the seeds of Annona squamosa. J Nat Prod. 2002; 65: 1748.
- 160Monsieurs K, Tapolcsányi P, Loones KTJ, et al. Is samoquiasine A indeed benzo(f)phthalazin-4(3H)-one. Unambiguous, straightforward synthesis of benzo(f)phthalazin-4(3H)-one and its regioisomer benzo(f)phthalazin-1(2H)-one. Tetrahedron. 2007; 63: 3870–3881.
- 161Timmons C, Wipf P. Densioty functional theory calculation of 13C NMR shifts of diazaphenanthrene alkaloids: reinvestigations of the structure of samoquasine A. J Org Chem. 2008; 73: 9168–9170.
- 162Tzantrizos YS, Xu XJ, Sauriol F, Hynes RC. Novel quinazolinones and enniatins from Fusarium lateritium Nees. Can J Chem. 1994; 72: 1415.
- 163Tzantrizos YS, Xu XJ, Sauriol F, Hynes RC. Novel quinazolinones and enniatins from Fusarium lateritium Nees. Can J Chem. 1993; 71: 1362–1367.
- 164 World Malaria Report, 2015 http://www.who.int/malaria/publications/world-malaria-report-2015/report/en/.
- 165Mishra M, Mishra VK, Kashaw V, Iyer AK, Kashaw SK. Comprehensive review on various strategies for antimalarial drug discovery. Eur J Med Chem. 2017; 125: 1300–1320.
- 166Quinine. Scientific American. 1848; 3: 326. doi:10.1038/scientificamerican07011848-326d.
- 167White NJ, Looareesuwan S, Warrel DA, et al. Quinine loading dose in cerebral malaria. Am J Trop Med Hyg. 1983; 32: 1–5.
- 168Kelsey FE, Oldham FK, Cantrell W, Geiling EMK. Antimalarial activity and toxicity of a metabolic derivative of quinine. Nature. 1946; 157: 440.
- 169Ball P. History of science: quinine steps back in time. Nature. 2008; 28: 451.
- 170Bateman DN, Dyson EH. Quinine toxicity. Adverse Drug React Poisoning Rev. 1986; 4: 215–233.
- 171 World Health Organization (WHO). Guidelines for the treatment of malaria, 1st ed. Geneva, Switzerland.
- 172Gantier JC, Fournet A, Munos MH, Hocquemiller R. The effect of some 2-substituted quinolines isolated from Galipea longiflora on Plasmodium vinckei petteri infected mice. Planta Med. 1996; 62: 285–286.
- 173Basco LK, Mitaku S, Skaltsounis AL, et al. In vitro activities of furoquinoline and acridone alkaloids against Plasmodium falciparum. Antimicrob Agents Chemother. 1994; 38: 1169–1171.
- 174Christopher E, Bedir E, Dunbar C, et al. Indoloquinazoline alkaloids from Araliopsis tabouensis. Helv Chim Acta. 2003; 86: 2914–2918.
- 175Bultel-Poncé V, Berge JP, Debitus C, Nicolas JL, Guyot M. Metabolites from the sponge-associated bacterium Pseudomonas species. Mar Biotechnol. 1999; 1: 384–390.
- 176Koepfli M, Mead JF, Brockmen Jr JA. An alkaloid with high antimalarial activity from Dichor febrifuga. J Am Chem Soc. 1947; 69: 1837.
- 177Koepfli M, Brockmen Jr JA. Alkaloids of Dichroa febrifuga. I. isolation and degradative studies. J Am Chem Soc. 1949; 71: 1048.
- 178Koepfli M, Brockmen Jr JA, Moffat J. The structure of febrifugine and isofebrifugine. J Am Chem Soc. 1950; 72: 3323.
- 179Takeuchi Y, Azuma K, Takakura K, et al. Asymmetric synthesis of (+)-febrifugine and (+)-isofebrifugine using yeast reduction. Tetrahedron. 2001; 57: 1213–1218.
- 180Takaya Y, Tasaka H, Chiba T, et al. New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite. J Med Chem. 1999; 42: 3163–3166.
- 181Murata K, Takano F, Fushiya S, Oshima Y. Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga. J Nat Prod. 1998; 61: 729–733.
- 182Ishih A, Suzuki T, Watanabe M, Miyase T, Terada M. Combination effects of chloroquine with the febrifugine and isofebrifugine mixture against a blood-induced infection with chloroquine-resistant Plasmodium berghei NK65 in ICR mice. Phytother Res. 2003; 17: 1234–1236.
- 183Hirai S, Kikuchi H, Kim HS, et al. Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite. J Med Chem. 2003; 46: 4351–4359.
- 184Jaidane M, Ali-El-Dein B, Ounaies A, Hafez AT, Mohsen T, Bazeed M. The use of halofuginone in limiting urethral stricture formation and recurrence: an experimental study in rabbits. J Urol. 2003; 170: 2049–2052.
- 185Özçlik MF, Pekmezci S, Saribeyoğlu K, Ünal E, Gümüstas K, Doğusoy G. The effect of halofuginone, a specific inhibitor of collagen type 1 synthesis, in the prevention of esophageal strictures related to caustic injury. Am J Surg. 2004; 187: 257–260.
- 186Xavier S, Piek E, Fujii M, et al. Amelioration of radiation-induced fibrosis. Inhibition of transforming growth factor-β signaling by halofuginone. J Biol Chem. 2004; 279: 15167–15176.
- 187Pitzer KK, Kyle DE, Gerena L. Indolo[2,1-b]quinazole-6,12-dione antimalarial compounds and methods of treating malaria therewith. Patent 6. 2001; 284: 772.
- 188Bhattacharjee AK, Hartell MG, Nichols DA, et al. Structure-activity relationship study of antimalarial indolo[2,1-b]quinazoline-6,12-diones (tryptanthrins). Three dimensional pharmacophore modeling and identification of new antimalarial candidates. Eur J Med Chem. 2004; 39: 59–67.
- 189Sprogøe K, Manniche S, Larsen TO, Christophersen C. Janoxepin and brevicompanine B: antiplasmodial metabolites from the fungus Aspergillus janus. Tetrahedron. 2005; 61: 8718–8721.
- 190 World Health Organization (WHO). 2017. Leishmaniasis (http://www.who.int/mediacentre/factsheets/fs375/en/). Accessed 04/2017.
- 191Rocha LG, Almeida JRGS, Macêdo RO, Barbosa-Filho JM. A review of natural products with antileishmanial activity. Phytomedicine. 2005; 12: 514–535.
- 192Fournet A, Angelo Barrios A, Muiios V, et al. Antiprotozoal activity of quinoline alkaloids isolated from Galipea longiflora, a Bolivian plant used as a treatment for cutaneous leishmaniasis. Phytother Res. 1994; 8: 174–178.
- 193Fournet A, Angelo Barrios A, Muiioz V, Hocquemiller R, Cave A, Bruneton J. 2-Substituted quinoline alkaloids as potential antileishmanial drugs. Antimicrob Agents Chemother. 1993; 37: 859–863.
- 194Fournet A, Gantier JC, Gautheret A, et al. The activity of 2-substituted quinoline alkaloids in BALB/c mice infected with Leishmania donovani. J Antimicrob Chemother. 1994; 33: 537–544.
- 195Fournet A, Ferreira ME, de Arias AR, et al. In vivo efficacy of oral and intralesional administration of 2-substituted quinolines in experimental treatment of new world cutaneous leishmaniasis caused by Leishmania amazonensis. Antimicrob Agents Chemother. 1996; 40: 2447–2451.
- 196Belliard AM, Leroy C, Banide H, Farinotti R, Lacour B. Decrease of intestinal P-glycoprotein activity by 2-n-propylquinoline, a new oral treatment for visceral leishmaniasis. Exp Parasitol. 2003; 103: 51–56.
- 197Nakayama H, Ferreira ME, de Arias AR, et al. Experimental treatment of chronic Trypanosoma cruzi infection in mice with 2-n-propylquinoline. Phytother Res. 2001; 15: 630–632.
- 198Mester I. The occurrence of the alkaloids in Rutaceae. Fitoterapia. 1973; 44: 123–152.
- 199Napolitano HB, Silva M, Ellena J, et al. Redetermination of skimmianine: a new inhibitor against the Leishmania APRT enzyme. Acta Crystallogr Sect E Struct Rep Online. 2003; 59: 1503–1505.
10.1107/S1600536803019913 Google Scholar
- 200Ambrozin ARP, Mafezoli J, Vieira PC, et al. New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity. J Braz Chem Soc. 2005; 16: 434–439.
- 201Jagadeesh SG, Krupadanam GLD, Srimannarayana G. Antifeedant activity of the constituents of Evodia lunu-ankenda. Indian J Chem Sect B: Org Chem Incl Med Chem. 2000; 39: 475–476.
- 202Liu ZL, Xu YJ, Wu J, Goh SH, Ho SH. Feeding deterrents from Dictamnus dasycarpus Turcz against two stored-product insects. J Agri Food Chem. 2002; 50: 1447–1450.
- 203Rios MY, Delgado G. Terpenoids and alkaloids from Esenbeckia belizencis. Spontaneous oxidation of furoquinoline alkaloids. J Nat Prod. 1992; 55: 1307–1309.
- 204Kim YC, Kim NY, Jeong SJ, Sohn DH, Miyamoto T, Higuchi R. Biologically active quinolone alkaloids from Evodia rutaecarpa on Artemia salina. Planta Med. 1998; 64: 490.
- 205Bringmann G, Schlauer S, Rischer H, et al. Antidesmone, a novel antitrypanosomal alkaloid. Pharm Pharmacol Lett. 2001; 11: 47–48.
- 206Biavatti MW, Vieira PC, das GF da Silva MF, et al. Biological activity of quinoline alkaloids from Raulinoa echinata and X-ray structure of flindersiamine. J Braz Chem Soc. 2002; 13: 66–70.
- 207Perrett IS, Whitfield PJ. Atanine (3-dimethylallyl-4-methoxy-2-quinolone), an alkaloid with anthelmintic activity from the Chinese medicinal plant, Evodia rutaecarpa. Planta Med. 1995; 61: 276–278.
- 208Abe M, Imai T, Ishii N, Usui M, Okuda T, Oki T. Quinolactacide, a new quinolone insecticide from Penicillium citrinum Thom F 1539. Biosci Biotechnol Biochem. 2005; 69: 1202–1205.
- 209Abe M, Imai T, Ishii N, Usui M. Synthesis of quinolactacide via an acyl migration reaction and dehydrogenation with manganese dioxide, and its insecticidal activities. Biosci Biotechnol Biochem. 2006; 70: 303–306.
- 210Kusano M, Koshino H, Uzawa J, Fujioka S, Kawano T, Kimura Y. Nematicidal alkaloids and related compounds produced by the fungus Penicillium cf. simplicissimum. Biosci Biotechnol Biochem. 2000; 64: 2559–2568.
- 211Nakatsu T, Johns T, Kubo I, et al. Isolation, structure, and synthesis of novel 4-quinolinone alkaloids from Esenbeckia leiocarpa. J Nat Prod. 1990; 53: 1508–1813.
- 212Thoms C, Wolff M, Padmakumar K, Ebel R, Proksch P. Chemical defense of Mediterranean sponges Aplysina cavernicola and Aplysina aerophoba. Z Naturforsch C. 2004; 59: 113–122.
- 213Uchida R, Imasato R, Shiomi K, Tomoda H, Omura S. Yaequinolones J1 and J2, novel insecticidal antibiotics from Penicillium sp. FKI-2140. Org Lett. 2005; 7: 5701–5704.
- 214Hayashi H, Nakatani T, Inoue Y, Nakayama M, Nozaki H. New dihydroquinolinone toxic to Artemia salina produced by Penicillium sp. NTC-47. Biosci Biotech Biochem. 1997; 61: 914–916.
- 215Saxena BP, Tikku K, Atal CK, Koul O. Insect antifertility and antifeedant allelochemics in Adhatoda vasica. Insect Sci Its Appl. 1986; 7: 489–493.
- 216Seifert K, Unger W. Insecticidal and fungicidal compounds from Isatis tinctoria. Z Naturforsch Teil C. 1994; 49: 44–48.
- 217Scovill J, Blank E, Konnick M, Nenortas E, Shapiro T. Antitrypanosomal activities of tryptanthrins. Antimicrob Agents Chemother. 2002; 46: 882–883.
- 218Wang SF, Braekman JC, Daloze D, et al. Nα-Quinaldyl-l-arginine·HCl, a new defensive alkaloid from Subcoccinella-24-punctata (Coleoptera, Coccinellidae). Experientia. 1996; 52: 628–630.
- 219Kato M, Inaba M, Itahana H, et al. Studies on anticoccidial constituents of crude drugs and related plants (I). Isolation and biological activities of cis- and trans-febrifugine from Hydrangea macrophylla. Shoyakugaku Zasshi. 1990; 44: 288–292.
- 220Leal WS, Zarbin PHG, Wojtasek H, Kuwahara S, Hasegawa M, Ueda Y. Medicinal alkaloid as a sex pheromone. Nature. 1997; 385: 213.
- 221Wojtasek H, Leal WS. Degradation of an alkaloid pheromone from the pale-brown chafer, Phyllopertha diversa (Coleoptera: Scarabaeidae), by an insect olfactory cytochrome P450. FEBS Lett. 1999; 458: 333–336.
- 222Rho TC, Bae EA, Kim DH, et al. Anti-Helicobacter pylori activity of quinolone alkaloids from Evodiae fructus. Biol Pharm Bull. 1999; 22: 1141–1143.
- 223Hamasaki N, Ishii E, Tominaga K, et al. Highly selective antibacterial activity of novel alkyl quinolone alkaloids from a Chinese herbal medicine, Gosyuyu (Wu-Chu-Yu), against Helicobacter pylori in vitro. Microbiol Immunol. 2000; 44: 9–15.
- 224Tominaga K, Higuchi K, Hamasaki N, et al. In vivo action of novel alkyl methyl quinolone alkaloids against Helicobacter pylori. J Antimicrob Chemother. 2002; 50: 547–552.
- 225Adams M, Wube AA, Bucar F, Bauer R, Kunert O, Haslinger E. Quinolone alkaloids from Evodia rutaecarpa: a potent new group of antimycobacterial compounds. Int J Antimicrob Agents. 2005; 26: 262–264.
- 226Islam SKN, Gray AI, Waterman PG, Ahasan M. Screening of eight alkaloids and ten flavonoids isolated from four species of the genus Boronia (Rutaceae) for antimicrobial activities against seventeen clinical microbial strains. Phytother Res. 2002; 16: 672–674.
- 227Aguilar-Guadarrama AB, Rios MY. Geranyl N-dimethylallylanthranilate, a new compound from Esenbeckia yaaxhokob. Planta Med. 2004; 70: 85–86.
- 228Hanawa F, Fokialakis N, Skaltsounis AL. Photo-activated DNA binding and antimicrobial activities of furoquinoline and pyranoquinolone alkaloids from rutaceae. Planta Med. 2004; 70: 531–535.
- 229El Sayed K, Al-Said MA, El-Feraly FS, Ross SA. New quinoline alkaloids from Ruta chalepensis. J Nat Prod. 2000; 63: 995–997.
- 230Fokialakis N, Magiatis P, Chinou I, Mitaku S, Tillequin F. Megistoquinones I and II, two quinoline alkaloids with antibacterial activity from the bark of Sarcomelicope megistophylla. Chem Pharm Bull. 2002; 50: 413–414.
- 231Jain SC, Pandey MK, Upadhyay RK, Kumar R, Hundal G, Hundal MS. Alkaloids from Toddalia aculeata. Phytochemistry. 2006; 67: 1005–1010.
- 232Cho JH, Lee CH, Lee HS. Antimicrobial activity of quinoline derivatives isolated from Ruta chalepensis toward human intestinal bacteria. J Microbiol Biotechnol. 2005; 15: 646–651.
- 233Kumru M, Küçük V, Akyürek P. Vibrational spectra of quinoline-4-carbaldehyde: Combined experimental and theoretical studies. Spectrochimica Acta A: Mol Biomol Spect. 2013; 113: 72–79.
- 234Homma Y, Sato Z, Hirayama F, Konno K, Shirahama H, Suzui T. Production of antibiotics by Pseudomonas cepacia as an agent for biological control of soilborne plant pathogens. Soil Biol Biochem. 1989; 21: 723–728.
- 235Roitman JN, Mahoney NE, Janisiewicz WJ, Benson M. A new chlorinated phenylpyrrole antibiotic produced by the antifungal bacterium Pseudomonas cepacia. J Agric Food Chem. 1990; 38: 538–541.
- 236Kamigiri K, Tokunaga T, Shibazaki M, et al. YM-30059, a novel quinolone antibiotic produced by Arthrobacter sp. J Antibiot. 1996; 49: 823–825.
- 237Kunze B, Hofle G, Reichenbach H. The aurachins, new quinoline antibiotics from myxobacteria: production, physico-chemical and biological properties. J Antibiot. 1987; 40: 258–265.
- 238Asolkar RN, Schröder D, Heckmann R, Lang S, Wagner-Döbler I, Laatsch H. Helquinoline, a new tetrahydroquinoline antibiotic from Janibacter limosus Hel 1+. J Antibiot. 2004; 57: 17–23.
- 239Dekker KA, Inagaki T, Gootz TD, et al. New quinolone compounds from Pseudonocardia sp. with selective and potent anti-Helicobacter pylori activity: taxonomy of producing strain, fermentation, isolation, structural elucidation and biological activities. J Antibiot. 1998; 51: 145–152.
- 240Dawson S, Malkinson JP, Paumier D, Searcy M. Bisintercalator natural products with potential therapeutic applications: isolation, structure determination, synthetic and biological studies. Nat Prod Rep. 2007; 24: 109–126.
- 241Puar MS, Chan TM, Hegde V, et al. Sch 40832: a novel thiostrepton from Micromonospora carbonacea. J Antibiot. 1998; 51: 221–224.
- 242Long RA, Qureshi A, Faulkner DJ, Azam F. 2-n-Pentyl-4-quinolinol produced by a marine Alteromonas sp. and its potential ecological and biogeochemical roles. Appl Environ Microbiol. 2003; 69: 568–576.
- 243Macfoy C, Danosus D, Sandit R, et al. Alkaloids of anuran skin: antimicrobial function. Z Naturforsch C. 2005; 60c: 932–937.
- 244Cantrell CL, Schrader KK, Mamonov LK, et al. Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii. J Agri Food Chem. 2005; 53: 7741–7748.
- 245de Souza RC, Fernandes JB, Vieira PC, et al. A new imidazole alkaloid and other constituents from Pilocarpus grandifloras and their antifungal activity. Z Naturforsch B. 2005; 60b: 787–791.
- 246Zhao W, Wolfender JL, Hostettmann K, Xu R, Qin G. Antifungal alkaloids and limonoid derivatives from Dictamnus dasycarpus. Phytochemistry. 1998; 47: 7–11.
- 247Oliva A, Meepagala KM, Wedge DE, et al. Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid. J Agri Food Chem. 2003; 51: 890–896.
- 248Pearce AN, Appleton DR, Babcock RC, Copp BR. Distomadines A and B, novel 6-hydroxyquinoline alkaloids from the New Zealand ascidian, Pseudodistoma aureum. Tetrahedron Lett. 2003; 44: 3897–3899.
- 249Böhlendorf B, Forche E, Bedorf N, et al. Antibiotics from gliding bacteria, LXXIII† indole and quinoline derivatives as metabolites of tryptophan in myxobacteria. Liebigs Ann. 1996: 49–53.
- 250Fakhouri W, Walker F, Vogler B, Armbruster W, Buchenauer H. Isolation and identification of N-mercapto-4-formylcarbostyril, an antibiotic produced by Pseudomonas fluorescens. Phytochemistry. 2001; 58: 1297–1303.
- 251Omura S, Nakagawa A, Hashimoto H, et al. Virantmycin, a potent antiviral antibiotic produced by a strain of Streptomyces. J Antibiot. 1980; 33: 1395–1396.
- 252Nakagawa A, Iwai Y, Hashimoto H, et al. Virantmycin, a new antiviral antibiotic produced by a strain of Streptomyces. J Antibiot. 1981; 34: 1408–1415.
- 253Mitscher LA, Baker WR. A search for novel chemotherapy against tuberculosis amongst natural products. Pure Appl Chem. 1998; 70: 365–371.
- 254Kataoka M, Hirata K, Kunikata T, et al. Antibacterial action of tryptanthrin and kaempferol, isolated from the indigo plant (Polygonum tinctorium Lour.), against Helicobacter pylori-infected Mongolian gerbils. J Gastroenterol. 2001; 36: 5–9.
- 255Belofsky GN, Anguera M, Jensen PR, Fenical W, Köck M. Oxepinamides A‒C and fumiquinazolines H‒I: bioactive metabolites from a marine isolate of a fungus of the genus Acremonium. Chem Eur J. 2000; 6: 1355–1360.
10.1002/(SICI)1521-3765(20000417)6:8<1355::AID-CHEM1355>3.0.CO;2-S CASPubMedWeb of Science®Google Scholar
- 256Hollman A. Quinine and quinidine. Bri Heart J. 1991; 66: 301.
- 257Wenckebach KF. Cinchona derivatives in the treatment of heart disorders. J Am Med Assoc. 1923; 81: 472.
10.1001/jama.1923.02650060042012 Google Scholar
- 258Mancini MA, Graubner W. Antagonism between quinine and adrenaline-like substances. Boll Soc Ital Biol. 1940; 15: 380.
- 259Roberts J, Baer R. A method for evaluation of depressants of subatrial rhythmic function in the heart of the intact animal. J Pharm Exper Ther. 1960; 129: 36–41.
- 260Dresel PE, Hart MC, Strümblad BCR. Cardiac arrhythmias induced by injection of isoproterenol into the coronary arteries [of dogs]. J Pharm Exper Ther. 1963; 140: 67–72.
- 261Nye E, Roberts J. Effect of reserpine on the reactivity of atrial and ventricular pacemakers to quinidine. Nature. 1966; 210: 1376–1377.
- 262Wedd AM, Blair HA, Gosselin RE. The action of quinine on the cold blood heart. J Pharm Exper Ther. 1942; 75: 251.
- 263Schmid PG, Nelson LD, Mark AL, Heistad DD, Abboud FM. Inhibition of adrenergic vasoconstriction by quinine. J Pharm Exper Ther. 1974; 188: 124–134.
- 264Lee KS, Hume JR, Giles W, Brown AM. Sodium current depression by lidocaine and quinidine in isolated ventricular cells. Nature. 1981; 291: 325–327.
- 265Johnson EA, Robertson PA. Effect of acetylcholine and quinidine on atrial cellular potentials. Nature. 1957; 180: 1483–1484.
- 266Bridges JM, Baldini M. Effect of quinidine and related compounds on uptake and release of serotonin by blood platelets. Nature. 1966; 210: 1364–1365.
- 267Chen IS, Wu SJ, Lin YC, et al. Dimeric 2-quinolone alkaloid and antiplatelet aggregation constituents of Zanthoxylum simulans. Phytochemistry. 1994; 36: 237–239.
- 268Sheen WS, Tsai IL, Teng CM, Chen IS. Nor-neolignan and phenyl propanoid from Zanthoxylum ailanthoides. Phytochemistry. 1994; 36: 213–216.
- 269Chen KS, Chang YL, Teng CM, Chen CF, Wu YC. Furoquinolines with antiplatelet aggregation activity from leaves of Melicope confusa. Planta Med. 2000; 66: 80–81.
- 270Chen IS, Chen HF, Cheng MJ, et al. Quinoline alkaloids and other constituents of Melicope semecarpifolia with antiplatelet aggregation activity. J Nat Prod. 2001; 64: 1143–1147.
- 271Chen IS, Lin YC, Tsai IL, et al. Coumarins and anti-platelet aggregation constituents from Zanthoxylum schinifolium. Phytochemistry. 1995; 39: 1091–1097.
- 272Tsai IL, Lin WY, Teng CM, et al. Coumarins and antiplatelet constituents from the root bark of Zanthoxylum schinifolium. Planta Med. 2000; 66: 618–623.
- 273Cheng JT, Chang SS, Chen IS. Cardiovascular effect of skimmianine in rats. Arch Int Pharmacodyn Ther. 1990; 306: 65–74.
- 274Chen JJ, Chang YL, Teng CM, Su CC, Chen IS. Quinoline alkaloids and anti-platelet aggregation constituents from the leaves of Melicope semecarpifolia. Planta Med. 2002; 68: 790–793.
- 275Nam KW, Je KH, Shin YJ, Kang SS, Mar W. Inhibitory effects of furoquinoline alkaloids from Melicope confusa and Dictamnus albus against human phosphodiesterase 5 (hPDE5A) in vitro. Arch Pharm Res. 2005; 28: 675–679.
- 276Lee HS, Oh WK, Choi HC, et al. Inhibition of angiotensin II receptor binding by quinolone alkaloids from Evodia rutaecarpa. Phytother Res. 1998; 12: 212–214.
- 277Sheen WS, Tsai IL, Teng CM, Ko FN, Chen IS. Indolopyridoquinazoline alkaloids with antiplatelet aggregation activity from Zanthoxylum integrifoliolum. Planta Med. 1996; 62: 175–176.
- 278Chang GJ, Wu MH, Chen WP, Kuo SC, Su MJ. Electrophysiological characteristics of antiarrhythmic potential of acrophyllidine, a furoquinoline alkaloid isolated from Acronychia halophylla. Drug Dev Res. 2000; 50: 170–185.
- 279Chiou WF, Liao JF, Chen CF. Comparative study on the vasodilatory effects of three quinazoline alkaloids isolated from Evodia rutaecarpa. J Nat Prod. 1996; 59: 374–378.
- 280Gupta OP, Sharma ML, Ghatak BJR, Atal CK. Pharmacological investigations of vasicine and vasicinone‒the alkaloids of Adhatoda vasica. Indian J Med Res. 1977; 66: 680–691.
- 281Sharma RL, Prabhakar A. Synthesis of some new ring A subsituted vasicine analogues. Orient J Chem. 1994; 10: 2–5.
- 282Loya S, Rudi A, Tal R, Kashman Y, Loya Y, Hizi A. 3,5,8-Trihydroxy-4-quinolone, a novel natural inhibitor of the reverse transcriptases of human immunodeficiency viruses type 1 and type 2. Arch Biochem Biophys. 1994; 309: 315–322.
- 283McCormick JL, McKee TC, Cardellina II JH, MR Boy. HIV inhibitory natural products. 26. Quinoline alkaloids from Euodia roxburghiana. J Nat Prod. 1996; 59: 469–471.
- 284Cheng MJ, Lee KH, Tsai IL, Chen IS. Two new sesquiterpenoids and anti-HIV principles from the root bark of Zanthoxylum ailanthoides. Bioorg Med Chem. 2005; 13: 5915–5920.
- 285Boger DL, Chen JH, Saionz KW, Jin Q. Synthesis of key sandramycin analogs: systematic examination of the intercalation chromophore. Bioorg Med Chem. 1998; 6: 85–102.
- 286Take Y, Inouye Y, Nakamura S, Allaudeen HS, Kubo A. Comparative studies of the inhibitory properties of antibiotics on human immunodeficiency virus and avian myeloblastosis virus reverse transcriptases and cellular DNA polymerases. J Antibiot. 1989; 42: 107–115.
- 287Boger DL, Ledeboer MW, Kume M. Total synthesis of luzopeptins A‒C. J Am Chem Soc. 1999; 121: 1098–1099.
- 288Morimoto Y, Shirahama H. Synthetic studies on virantmycin. 2. Total synthesis of unnatural (+)–virantmycin and determination of its absolute stereochemistry. Tetrahedron. 1996; 52: 10631–10652.
- 289Fournet A, Hocquemiller R, Roblot F, et al. Les Chimanines, nouvelles quinoleines substituees en 2, isolees d'Une plante bolivienne antiparasitaire: Galipea longiflora. J Nat Prod. 1993; 56: 1547–1552.
- 290Fournet A, Vagneur B, Richomme P, Bruneton J. Aryl-2 et alkyl-2 quinoléines nouvelles isolées d'une Rutacée bolivienne: Galipealongiflora. Can J Chem. 1989; 67: 2116–2118.
- 291Fournet A, Mahieux R, Fakhfakh MA, Franck X, Hocquemiller R, Figadère B. Substituted quinolines induce inhibition of proliferation of HTLV-1 infected cells. Bioorg Med Chem Lett. 2003; 13: 891–894.
- 292Ito C, Itoigawa M, Otsuka T, Tokuda H, Nishino H, Furukawa H. Constituents of Boronia pinnata. J Nat Prod. 2000; 63: 1344–1348.
- 293Lal B, Bhise NB, Gidwani RM, Lakdawala AD, Joshi K, Patvardhan S. Isolation, characterization, total synthesis, biological activity of alkaloid evolitrine and its analogues. ARKIVOC. 2005; 2005: 77–97.
- 294Ito C, Itoigawa M, Furukawa A, et al. Quinolone alkaloids with nitric oxide production inhibitory activity from Orixa japonica. J Nat Prod. 2004; 67: 1800–1803.
- 295Kakinuma N, Iwai H, Takahashi S, et al. Quinolactacins A, B and C: novel quinolone compounds from Penicillium sp. EPF-6. I. Taxonomy, production, isolation and biological properties. J Antibiot. 2000; 53: 1247–1251.
- 296Takahashi S, Kakinuma N, Iwai H, et al. Quinolactacins A, B and C: novel quinolone compounds from Penicillium sp. EPF-6. II. Physico-chemical properties and structure elucidation. J Antibiot. 2000; 53: 1251–1256.
- 297Jin HZ, Lee JH, Lee D, et al. Quinolone alkaloids with inhibitory activity against nuclear factor of activated T cells from the fruits of Evodia rutaecarpa. Biol Pharm Bull. 2004; 27: 926–928.
- 298Ishihara T, Kohno K, Ushio S, Iwaki K, Ikeda M, Kurimoto M. Tryptanthrin inhibits nitric oxide and prostaglandin E2 synthesis by murine macrophages. Eur J Pharmacol. 2000; 407: 197–204.
- 299Micallef MJ, Iwaki K, Ishihara T, et al. The natural plant product tryptanthrin ameliorates dextran sodium sulfate-induced colitis in mice. Int Immunopharmacol. 2002; 2: 565–578.
- 300Danz H, Stoyanova S, Thomet OAR, et al. Inhibitory activity of tryptanthrin on prostaglandin and leukotriene synthesis. Planta Med. 2002; 68: 875–880.
- 301Takei Y, Kunikata T, Aga M, et al. Tryptanthrin inhibits interferon-gamma production by Peyer's patch lymphocytes derived from mice that had been orally administered staphylococcal enterotoxin. Biol Pharm Bull. 2003; 26: 365–367.
- 302Oberthür C, Heinemann C, Elsner P, Benfeldt E, Hamburger M. A comparative study on the skin penetration of pure tryptanthrin and tryptanthrin in Isatis tinctoria extract by dermal microdialysis coupled with isotope dilution ESI-LC-MS. Planta Med. 2003; 69: 385–389.
- 303Heinemann C, Schliemann-Willers S, Oberthür C, Hamburger M, Elsner P. Prevention of experimentally induced irritant contact dermatitis by extracts of Isatis tinctoria compared to pure tryptanthrin and its impact on UVB-induced erythema. Planta Med. 2004; 70: 385–390.
- 304Molina P, Tárraga A, Gonzalez-Tejero A, et al. Inhibition of leukocyte functions by the alkaloid isaindigotone from Isatis indigotica and some new synthetic derivatives. J Nat Prod. 2001; 64: 1297–1300.
- 305Li L, Yang G, Dong T, Chen Z. Studies on the chemical constituents of dyers woad (Isatis tinctoria). Zhongcaoyao. 1996; 27: 389–391.
- 306Choi YH, Shin EM, Kim YS, Cai XF, Lee JJ, Kim HP. Anti-inflammatory principles from the fruits of Evodia rutaecarpa and their cellular action mechanisms. Arch Pharm Res. 2006; 29: 293–297.
- 307Cheng JT, Chang TK, Chen IS. Skimmianine and related furoquinolines function as antagonists of 5-hydroxytryptamine receptors in animals. J Auton Pharmacol. 1994; 14: 365–374.
- 308Seya K, Miki I, Murata K, et al. Pharmacological properties of pteleprenine, a quinoline alkaloid extracted from Orixa japonica, on guinea-pig ileum and canine left atrium. J Pharm Pharmacol. 1998; 50: 803–807.
- 309Jaén JC, Gregor VE, Lee C, Davis R, Emmerling M. Acetylcholinesterase inhibition by fused dihydroquinazoline compounds. Bioorg Med Chem Lett. 1996; 6: 737–742.
- 310Kim WG, Song NK, Yoo ID. Quinolactacins A1 and A2, new acetylcholinesterase inhibitors from Penicillium citrinum. J Antibiot. 2001; 54: 831–835.
- 311Lee MK, Hwang BY, Lee SA, et al. 1-Methyl-2-undecyl-4(1H)-quinolone as an irreversible and selective inhibitor of type B monoamine oxidase. Chem Pharm Bull. 2003; 51: 409–411.
- 312Lee IK, Yun BS, Han G, Cho DH, Kim YH, Yoo ID. Dictyoquinazols A, B, and C, new neuroprotective compounds from the mushroom Dictyophora indusiata. J Nat Prod. 2002; 65: 1769–1772.
- 313Wong SM, Musza LL, Kydd GC, Kullnig R, Gillum AM, Cooper R. Fiscalins: new substance P inhibitors produced by the fungus Neosartorya fischeri. Taxonomy, fermentation, structures, and biological properties. J Antibiot. 1993; 46: 545–553.
- 314Hale AL, Meepagala KM, Oliva A, Aliotta G, Duke SO. Phytotoxins from the leaves of Ruta graveolens. J Agri Food Chem. 2004; 52: 3345–3349.
- 315Kimura Y, Kusano M, Koshino H, Uzawa J, Fujioka S, Tani K. Penigequinolones A and B, pollen-growth inhibitors produced by Penicilium sp., No. 410. Tetrahedron Lett. 1996; 37: 4961–4964.
- 316Oettmeier W, Dostatni R, Majewski C, et al. The aurachins, naturally occurring inhibitors of photosynthetic electron flow through photosystem II and the cytochrome b6/f-complex. Z Naturforsch Teil C. 1990; 45: 322–328.
- 317Meunier B, Madgwick SA, Reil E, Oettmeier W, Rich PR. New inhibitors of the quinol oxidation sites of bacterial cytochromes bo and bd. Biochemistry. 1995; 34: 1076–1083.
- 318Don MJ, Lewis DFV, Wang SY, Tsai MW, Ueng YF. Effect of structural modification on the inhibitory selectivity of rutaecarpine derivatives on human CYP1A1, CYP1A2, and CYP1B1. Bioorg Med Chem Lett. 2003; 13: 2535–2538.
- 319Lee SK, Kim NH, Lee J, et al. Induction of cytochrome P450s by rutaecarpine and metabolism of rutaecarpine by cytochrome P450s. Planta Med. 2004; 70: 753–757.
- 320Ueng YF, Wang JJ, Lin LC, Park SS, Chen CF. Induction of cytochrome P450-dependent monooxygenase in mouse liver and kidney by rutaecarpine, an alkaloid of the herbal drug Evodia rutaecarpa. Life Sci. 2001; 70: 207–217.
- 321Ueng YF, Jan WC, Lin LC, Chen TL, Guengerich FP, Chen CF. The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes. Drug Metab Dispos. 2002; 30: 349–353.
- 322Ueng YF, Tsai TH, Don MJ, Chen RM, Chen TL. Alteration of the pharmacokinetics of theophylline by rutaecarpine, an alkaloid of the medicinal herb Evodia rutaecarpa, in rats. J Pharm Phamacol. 2005; 57: 227–232.
- 323Galetin A, Clarke SE, Houston JB. Quinidine and haloperidol as modifiers of CYP3A4 activity: multisite kinetic model approach. Drug Metab Dispos. 2002; 30: 1512–1522.
- 324López-Gresa MP, Gonz′alez MC, Primo J, Moya P, Romero V, Estornell E. Circumdatin H, a new inhibitor of mitochondrial NADH oxidase, from Aspergillus ochraceus. J Antibiot. 2005; 58: 416–419.
- 325Ohtsu Y, Sasamura H, Tsurumi Y, et al. The novel gluconeogenesis inhibitors FR225659 and related compounds that originate from Helicomyces sp. No. 19353. I. Taxonomy, fermentation, isolation and physico-chemical properties. J Antibiot. 2003; 56: 682–688.
- 326Ohtsu Y, Sasamura H, Shibata T, Nakajima H, Hino M, Fujii T. The novel gluconeogenesis inhibitors FR225659 and related compounds that originate from Helicomyces sp. No. 19353. II. Biological profiles. J Antibiot. 2003; 56: 689–693.
- 327Zenkoh T, Hatori H, Tanaka H, et al. Design and synthesis of a solid-supported FR225659 derivative for its receptor screening. Org Lett. 2004; 6: 2477–2480.
- 328Ko JS, Rho MC, Chung MY, et al. Quinolone alkaloids, diacylglycerol acyltransferase inhibitors from the fruits of Evodia rutaecarpa. Planta Med. 2002; 68: 1131–1133.
- 329Yoon MA, Jeong TS, Park DS, et al. Antioxidant effects of quinoline alkaloids and 2,4-di-tert-butylphenol isolated from Scolopendra subspinipes. Biol Pharm Bull. 2006; 29: 735–739.
- 330Chung HS, Woo WS. A quinolone alkaloid with antioxidant activity from the aleurone layer of anthocyanin-pigmented rice. J Nat Prod. 2001; 64: 1579–1580.
- 331Amin AH, Merta DR. A bronchodilator alkaloid (vasicinone) from Adhatoda vasica Nees. Nature. 1959; 184: 1317–1320.
- 332Cambridge GW, Jansen ABA, Jaeman DA. Bronchodilating action of vasicinone and related compounds. Nature. 1962; 196: 1217.
- 333Kamikawa T, Hanaoka Y, Fujie S, et al. SRS-A antagonist pyranoquinolone alkaloids from east African Fagara plants and their synthesis. Bioorg Med Chem. 1996; 4: 1317–1320.
- 334Paulini H, Eilert U, Schimmer O. Mutagenic compounds in an extract from rutae herba (Ruta graveolens L.). I. Mutagenicity is partially caused by furoquinoline alkaloids. Mutagenesis. 1987; 2: 271–273.
- 335Häfele F, Schimmer O. Mutagenicity of furoquinoline alkaloids in the Salmonella/microsome assay. Mutagenicity of dictamnine is modified by various enzyme inducers and inhibitors. Mutagenesis. 1988; 3: 349–353.
- 336Schimmer O, Leimeister U. The SCE-inducing potency of the furoquinoline alkaloid, gamma-fagarine, and a gamma-fagarine-containing tincture from Rutae Herba, in cultured human lymphocytes. Mutagenesis. 1989; 4: 467–470.
- 337Fujita H, Kakishima H. Further evidence for photoinduced genotoxicity of dictamnine as shown by prophage induction. Chem Biol Interactions. 1989; 72: 105–111.
- 338Yoshida S, Aoyagi T, Harada S, et al. Production of 2-methyl-4[3H]-quinazolinone, an inhibitor of poly(ADP-ribose) synthetase, by bacterium. J Antibiot. 1991; 44: 111–112.
- 339Funayama S, Tanaka R, Kumekawa Y, et al. Rat small intestine muscle relaxation alkaloids from Orixa japonica leaves. Biol Pharm Bull. 2001; 24: 100–102.
- 340Madappa C, Sankaranarayanan A, Sharma PL. A study on the selectivity of action of (+) INPEA and vasicine in different isolated tissue preparations. Indian J Pharmacol. 1989; 21: 144–152.
- 341Nazrullaev SS, Bessonova IA, Akhmedkhodzhaeva KS. Estrogenic activity as a function of chemical structure in haplophyllum quinoline alkaloids. Chem Nat Comp. 2001; 37: 551–555.