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ent-Labdane Diterpenoid Lactone Stereoisomers from Andrographis paniculata

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School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, 110016, Peopleʼs Republic of China, State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Kunming, 650204, Yunnan, Peopleʼs Republic of China, School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, 110016, Peopleʼs Republic of China, and Department of Medicine, Mount Sinai School of Medicine, New York, New York 10029-6547
* To whom correspondence should be addressed. Tel: +86-24-23986463. Fax: +86-24-23993994. E-mail: [email protected].
†School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University.
‡Kunming Institute of Botany.
§School of Pharmacy, Shenyang Pharmaceutical University.
⊥Mount Sinai School of Medicine.
Cite this: J. Nat. Prod. 2008, 71, 5, 852–855
Publication Date (Web):March 22, 2008
https://doi.org/10.1021/np0704452
Copyright © 2008 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    Two pairs of ent-labdane diterpenoid lactone stereoisomers (1−4) including three new compounds (1−3) were isolated from the 85% EtOH extract of the aerial parts of Andrographis paniculata. The structures of these compounds were identified as 7R-hydroxy-14-deoxyandrographolide (1), 7S-hydroxy-14-deoxyandrographolide (2), 12S,13S-hydroxyandrographolide (3), and 12R,13R-hydroxyandrographolide (4) by spectroscopic data analyses and calculated 13C NMR data at the B3LYP/6-311++G(2d,p)//B3LYP/6-31G* level using the GIAO method. The 12S-configuration of 4 was revised to 12R based on the spectroscopic data. The antiproliferative activities of the two pairs of stereoisomers and 14 other ent-labdane diterpenoid derivatives were determined in human leukemia HL-60 cells. Andrographolide (7) and isoandrographolide (12) exhibited higher antiproliferative activities than other ent-labdane diterpenoids with GI50ʼs of 9.33 and 6.30 µM, respectively.

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