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

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

doi:10.1055/s-0043-113826

Planta Medica, Table of Contents

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^*

¹Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

²Research Center for Natural Products & Drug Development, Kaohsiung Medical University, Kaohsiung, Taiwan

³Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung, Taiwan

⁴Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung, Taiwan

,

Fan-Jin Liu^*

¹Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

,

Chih-Hsin Wang

¹Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

,

Tsong-Long Hwang

⁵Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan, Taiwan

⁶Research 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

⁷Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan, Taiwan

,

Yung-Fong Tsai

⁵Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan, Taiwan

⁶Research 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

⁷Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan, Taiwan

,

Chia-Hung Yen

¹Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

³Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung, Taiwan

,

Hui-Chun Wang

¹Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

,

Yen-Hsueh Tseng

⁸Department of Forestry, National Chung Hsing University, Taichung, Taiwan

,

Ching-Te Chien

⁹Division of Silviculture, Taiwan Forestry Research Institute, Taipei, Taiwan

,

Yi-Ming Arthur Chen

³Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung, Taiwan

¹⁰Department of Microbiology and Institute of Medical Research, College of Medicine, Kaohsiung Medical University, Kaohsiung, Taiwan

,

Fang-Rong Chang

¹Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

¹¹Cancer Center, Kaohsiung Medical University Hospital, Kaohsiung, Taiwan

,

Yang-Chang Wu

¹Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

²Research Center for Natural Products & Drug Development, Kaohsiung Medical University, Kaohsiung, Taiwan

⁴Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung, Taiwan

› Author Affiliations

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.

Key words

Lithocarpus litseifolius - Lithocarpus corneus - Fagaceae - triterpenoids - anti-inflammatory - anti-HIV

Full Text

References

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