Bioactive Triterpenoids from the Leaves and Twigs of Lithocarpus litseifolius and L. corneus.

Abstract

Phytochemical investigation of the leaves and twigs of Lithocarpus litseifolius and Lithocarpus corneus resulted in the isolation of four new triterpenoids (1: -4: ), three triterpenoids (5: -7: ) isolated from a natural source for the first time, and six known compounds (8: -13: ). In addition, four known triterpenoids (14: -17: ) were isolated from L. corneus. Compound 1: is a 3,4-seco-lupane-type triterpenoid, and compounds 2: -4: are lupane-type triterpenoids in different oxidation states. The structures of all isolated compounds were identified by spectroscopic methods, especially NMR and mass spectrometry data. The absolute configuration of 2: and 3: was confirmed by X-ray single crystallographic analysis. The anti-inflammatory activities of 1: -17: and anti-HIV activities of 2: -17: were evaluated. Among them, 3-epi-betulinic acid (8: ) showed a strong anti-HIV activity comparable to abacavir, a drug used for treating HIV/AIDS. 3,4-seco-4(23),20(29)-lupadiene-3,28-dioic acid (5: ) exhibited potent inhibition of superoxide-anion generation with 86.9 ± 2.8% inhibition at 1 µM.

• Authors: Yuan-Bin Cheng, Fan-Jin Liu, Chih-Hsin Wang, Tsong-Long Hwang, Yung-Fong Tsai, Chia-Hung Yen, Hui-Chun Wang, Yen-Hsueh Tseng, Ching-Te Chien, Yi-Ming Arthur Chen, Fang-Rong Chang, Yang-Chang Wu
• Journal: Planta medica (Planta Med) Vol. 84 Issue 1 Pg. 49-58 (Jan 2018) ISSN: 1439-0221 [Electronic] Germany
• PMID: 28701018 (Publication Type: Journal Article)
• Copyright: Georg Thieme Verlag KG Stuttgart · New York.

Chemical References

• Anti-HIV Agents
• Anti-Inflammatory Agents
• Plant Extracts
• Terpenes

Topics

• Anti-HIV Agents (pharmacology)
• Anti-Inflammatory Agents (pharmacology)
• Cell Line
• Cell Survival (drug effects)
• Fagaceae (chemistry)
• HIV (drug effects)
• Humans
• Magnetic Resonance Spectroscopy
• Mass Spectrometry
• Neutrophils (drug effects)
• Plant Extracts (isolation & purification, pharmacology)
• Plant Leaves (chemistry)
• Plant Stems (chemistry)
• Terpenes (isolation & purification, pharmacology)