ent-labdane diterpenoid lactone stereoisomers from Andrographis paniculata
Chen, Lixia1; Zhu, Huajie2; Wang, Rui3; Zhou, Kailan1; Jing, Yongkui4; Qiu, Feng1
AbstractTwo 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 (13)C 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 GI(50)'s of 9.33 and 6.30 mu M, respectively.
KeywordRay Crystallographic Analysis Minor Diterpenoids Nees
Subject AreaPlant Sciences ; Chemistry ; Medicinal ; Pharmacology & Pharmacy
Indexed BySCI ; IC
WOS Research AreaPlant Sciences ; Pharmacology & Pharmacy
WOS SubjectPlant Sciences ; Chemistry, Medicinal ; Pharmacology & Pharmacy
WOS IDWOS:000256180600022
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Cited Times:35[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Affiliation1.Shenyang Pharmaceut Univ, Sch Tradit Chinese Mat Med, Shenyang 110016, Peoples R China
2.Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China
3.Shenyang Pharmaceut Univ, Sch Pharm, Shenyang 110016, Peoples R China
4.Mt Sinai Sch Med, Dept Med, New York, NY 10029 USA
Recommended Citation
GB/T 7714
Chen, Lixia,Zhu, Huajie,Wang, Rui,et al. ent-labdane diterpenoid lactone stereoisomers from Andrographis paniculata[J]. JOURNAL OF NATURAL PRODUCTS,2008,71(5):852-855.
APA Chen, Lixia,Zhu, Huajie,Wang, Rui,Zhou, Kailan,Jing, Yongkui,&Qiu, Feng.(2008).ent-labdane diterpenoid lactone stereoisomers from Andrographis paniculata.JOURNAL OF NATURAL PRODUCTS,71(5),852-855.
MLA Chen, Lixia,et al."ent-labdane diterpenoid lactone stereoisomers from Andrographis paniculata".JOURNAL OF NATURAL PRODUCTS 71.5(2008):852-855.
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