Ring A Modified Novel Triterpenoids from Dysoxylum hainanense

Six ring A modified novel triterpenoids, dysoxyhainic acids A–E (1–3, 5, and 6) and dysoxyhainol (4), were isolated from the twigs and leaves of Dysoxylum hainanense. Compounds 1–4 are a group of triterpenoids featuring a contracted five‐membered ring A. Dysoxyhainic acid A (1) possessed an unpreced...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2009-10, Vol.2009 (28), p.4818-4824
Main Authors: He, Xiu-Feng, Wang, Xiao-Ning, Yin, Sheng, Dong, Lei, Yue, Jian-Min
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological activity
Biological and medical sciences
Biosynthesis
Chemistry
Exact sciences and technology
General aspects
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Medical sciences
Organic chemistry
Pharmacology. Drug treatments
Preparations and properties
Structural elucidation
Terpenoids
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Summary:Six ring A modified novel triterpenoids, dysoxyhainic acids A–E (1–3, 5, and 6) and dysoxyhainol (4), were isolated from the twigs and leaves of Dysoxylum hainanense. Compounds 1–4 are a group of triterpenoids featuring a contracted five‐membered ring A. Dysoxyhainic acid A (1) possessed an unprecedented 2‐nor‐1,3‐cyclotirucallane skeleton, whereas 5 and 6 possessed a rare six‐membered δ‐lactone formed between C‐2 and C‐11. The structures of 1–6 were established by extensive spectroscopic analysis, and that of 1 was confirmed by single‐crystal X‐ray diffraction. A hypothetical biosynthetic pathway for compound 1 was also proposed. All the compounds were tested on antimicrobial assays, and compounds 2 and 3 exhibited moderate antibacterial activity against Gram‐positive bacteria. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) The twigs and leaves of Dysoxylum hainanense metabolized six ring A modified novel triterpenoids, dysoxyhainic acids A–E and dysoxyhainol. The structures of these triterpenoids were elucidated. Dysoxyhainic acid A featured an unprecedented 2‐nor‐1,3‐ cyclotirucallane skeleton. Two of them exhibited moderate antibacterial activity against Gram‐positive bacteria.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200900609