Planta Med 2018; 84(01): 49-58
DOI: 10.1055/s-0043-113826
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

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

Yuan-Bin Cheng*
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
Research Center for Natural Products & Drug Development, Kaohsiung Medical University, Kaohsiung, Taiwan
Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung, Taiwan
Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung, Taiwan
,
Fan-Jin Liu*
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Chih-Hsin Wang
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Tsong-Long Hwang
Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan, Taiwan
Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, and Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan, Taiwan
Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan, Taiwan
,
Yung-Fong Tsai
Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan, Taiwan
Research Center for Chinese Herbal Medicine, Research Center for Food and Cosmetic Safety, and Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan, Taiwan
Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan, Taiwan
,
Chia-Hung Yen
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Hui-Chun Wang
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Yen-Hsueh Tseng
Department of Forestry, National Chung Hsing University, Taichung, Taiwan
,
Ching-Te Chien
Division of Silviculture, Taiwan Forestry Research Institute, Taipei, Taiwan
,
Yi-Ming Arthur Chen
Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung, Taiwan
Department of Microbiology and Institute of Medical Research, College of Medicine, Kaohsiung Medical University, Kaohsiung, Taiwan
,
Fang-Rong Chang
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
Cancer Center, Kaohsiung Medical University Hospital, Kaohsiung, Taiwan
,
Yang-Chang Wu
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan
Research Center for Natural Products & Drug Development, Kaohsiung Medical University, Kaohsiung, Taiwan
Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung, Taiwan
› Author Affiliations
Further Information

Publication History

received 24 November 2016
revised 23 May 2017

accepted 13 June 2017

Publication Date:
12 July 2017 (eFirst)

Abstract

Phytochemical investigation of the leaves and twigs of Lithocarpus litseifolius and Lithocarpus corneus resulted in the isolation of four new triterpenoids (14), three triterpenoids (57) isolated from a natural source for the first time, and six known compounds (813). In addition, four known triterpenoids (1417) were isolated from L. corneus. Compound 1 is a 3,4-seco-lupane-type triterpenoid, and compounds 24 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 117 and anti-HIV activities of 217 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.

* These authors contributed equally to this work.


Supporting Information