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

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

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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.

Original language	English
Pages (from-to)	49-58
Number of pages	10
Journal	Planta Medica
Volume	84
Issue number	1
DOIs	https://doi.org/10.1055/s-0043-113826
Publication status	Published - Jan 1 2018
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1055/s-0043-113826

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@article{fca6b8b8dfd34ea3ab656c5a6cef7aba,

title = "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.",

keywords = "anti-HIV, anti-inflammatory, Fagaceae, Lithocarpus corneus, Lithocarpus litseifolius, triterpenoids",

author = "Cheng, {Yuan Bin} and Liu, {Fan Jin} and Wang, {Chih Hsin} and Hwang, {Tsong Long} and Tsai, {Yung Fong} and Yen, {Chia Hung} and Wang, {Hui Chun} and Tseng, {Yen Hsueh} and Chien, {Ching Te} and Chen, {Yi Ming Arthur} and Chang, {Fang Rong} and Wu, {Yang Chang}",

note = "Funding Information: This work was supported by grants from the Ministry of Science and Technology of Taiwan (MOST103-2628-B‑037-001-MY3 awarded to Y.-B C.), the National Health Research Institute (NHRI-EX103-10241BI), and in part from a grant from Chinese Medicine Research Center, China Medical University (the Ministry of Education, the Aim for the Top University Plan). This study was supported partially by Kaohsiung Medical University (Aim for the Top Universities Plan, grant No. KMU-TP105E32), the Ministry of Health and Welfare of Taiwan (MOHW106-TDU-B-212-144007), and the Health and Welfare surcharge of tobacco products. Publisher Copyright: {\textcopyright} 2017 Georg Thieme Verlag KG Stuttgart · New York.",

year = "2018",

month = jan,

day = "1",

doi = "10.1055/s-0043-113826",

language = "English",

volume = "84",

pages = "49--58",

journal = "Planta Medica",

issn = "0032-0943",

publisher = "Georg Thieme Verlag",

number = "1",

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TY - JOUR

T1 - Bioactive Triterpenoids from the Leaves and Twigs of Lithocarpus litseifolius and L corneus

AU - Cheng, Yuan Bin

AU - Liu, Fan Jin

AU - Wang, Chih Hsin

AU - Hwang, Tsong Long

AU - Tsai, Yung Fong

AU - Yen, Chia Hung

AU - Wang, Hui Chun

AU - Tseng, Yen Hsueh

AU - Chien, Ching Te

AU - Chen, Yi Ming Arthur

AU - Chang, Fang Rong

AU - Wu, Yang Chang

N1 - Funding Information: This work was supported by grants from the Ministry of Science and Technology of Taiwan (MOST103-2628-B‑037-001-MY3 awarded to Y.-B C.), the National Health Research Institute (NHRI-EX103-10241BI), and in part from a grant from Chinese Medicine Research Center, China Medical University (the Ministry of Education, the Aim for the Top University Plan). This study was supported partially by Kaohsiung Medical University (Aim for the Top Universities Plan, grant No. KMU-TP105E32), the Ministry of Health and Welfare of Taiwan (MOHW106-TDU-B-212-144007), and the Health and Welfare surcharge of tobacco products. Publisher Copyright: © 2017 Georg Thieme Verlag KG Stuttgart · New York.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - 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.

AB - 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.

KW - anti-HIV

KW - anti-inflammatory

KW - Fagaceae

KW - Lithocarpus corneus

KW - Lithocarpus litseifolius

KW - triterpenoids

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SN - 0032-0943

VL - 84

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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