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Ring A Modified Novel Triterpenoids from Dysoxylum hainanense
Author(s) -
He XiuFeng,
Wang XiaoNing,
Yin Sheng,
Dong Lei,
Yue JianMin
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900609
Subject(s) - chemistry , triterpenoid , stereochemistry , ring (chemistry) , antimicrobial , antibacterial activity , terpene , lactone , organic chemistry , bacteria , biology , genetics
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)