Isolation and synthesis of a bioactive benzenoid derivative from the fruiting bodies of Antrodia camphorata

Pi Yu Chen; Jen Der Wu; Kai Yih Tang; Chieh Chou Yu; Yueh Hsiung Kuo; Wen-Bin Zhong; Ching Kuo Lee

doi:10.3390/molecules18077600

Isolation and synthesis of a bioactive benzenoid derivative from the fruiting bodies of Antrodia camphorata

Pi Yu Chen, Jen Der Wu, Kai Yih Tang, Chieh Chou Yu, Yueh Hsiung Kuo, Wen-Bin Zhong, Ching Kuo Lee

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

7 Citations (Scopus)

Abstract

A new enynyl-benzenoid, antrocamphin O (1,4,7-dimethoxy-5-methyl-6-(3'- methylbut-3-en-1-ynyl)benzo[d][1,3]dioxide), and the known benzenoids antrocamphin A and 7-dimethoxy-5-methyl-1,3-benzodioxole, were isolated from the fruiting bodies of Antrodia camphorata (Taiwanofungus camphoratus). The structure of antrocamphin O was unambiguously assigned by the analysis of spectral data (including 1D and 2D NMR, high-resolution MS, IR, and UV) and total synthesis. Compound 1 was prepared through the Sonogashira reaction of 5-iodo-4,7-dimethoxy-6-methylbenzene and 2-methylbut-1-en-3-yne as the key step. The benzenoids were tested for cytotoxicity against the HT29, HTC15, DLD-1, and COLO 205 colon cancer cell lines, and activities are reported herein.

Original language	English
Pages (from-to)	7600-7608
Number of pages	9
Journal	Molecules
Volume	18
Issue number	7
DOIs	https://doi.org/10.3390/molecules18077600
Publication status	Published - Jul 2013

Keywords

Antrocamphin O
Antrodia camphorate
Cytotoxic activity
Enynyl-benzenoid
Synthesis

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

UN SDGs

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

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10.3390/molecules18077600

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title = "Isolation and synthesis of a bioactive benzenoid derivative from the fruiting bodies of Antrodia camphorata",

abstract = "A new enynyl-benzenoid, antrocamphin O (1,4,7-dimethoxy-5-methyl-6-(3'- methylbut-3-en-1-ynyl)benzo[d][1,3]dioxide), and the known benzenoids antrocamphin A and 7-dimethoxy-5-methyl-1,3-benzodioxole, were isolated from the fruiting bodies of Antrodia camphorata (Taiwanofungus camphoratus). The structure of antrocamphin O was unambiguously assigned by the analysis of spectral data (including 1D and 2D NMR, high-resolution MS, IR, and UV) and total synthesis. Compound 1 was prepared through the Sonogashira reaction of 5-iodo-4,7-dimethoxy-6-methylbenzene and 2-methylbut-1-en-3-yne as the key step. The benzenoids were tested for cytotoxicity against the HT29, HTC15, DLD-1, and COLO 205 colon cancer cell lines, and activities are reported herein.",

keywords = "Antrocamphin O, Antrodia camphorate, Cytotoxic activity, Enynyl-benzenoid, Synthesis",

author = "Chen, {Pi Yu} and Wu, {Jen Der} and Tang, {Kai Yih} and Yu, {Chieh Chou} and Kuo, {Yueh Hsiung} and Wen-Bin Zhong and Lee, {Ching Kuo}",

year = "2013",

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pages = "7600--7608",

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AU - Chen, Pi Yu

AU - Wu, Jen Der

AU - Tang, Kai Yih

AU - Yu, Chieh Chou

AU - Kuo, Yueh Hsiung

AU - Zhong, Wen-Bin

AU - Lee, Ching Kuo

PY - 2013/7

Y1 - 2013/7

N2 - A new enynyl-benzenoid, antrocamphin O (1,4,7-dimethoxy-5-methyl-6-(3'- methylbut-3-en-1-ynyl)benzo[d][1,3]dioxide), and the known benzenoids antrocamphin A and 7-dimethoxy-5-methyl-1,3-benzodioxole, were isolated from the fruiting bodies of Antrodia camphorata (Taiwanofungus camphoratus). The structure of antrocamphin O was unambiguously assigned by the analysis of spectral data (including 1D and 2D NMR, high-resolution MS, IR, and UV) and total synthesis. Compound 1 was prepared through the Sonogashira reaction of 5-iodo-4,7-dimethoxy-6-methylbenzene and 2-methylbut-1-en-3-yne as the key step. The benzenoids were tested for cytotoxicity against the HT29, HTC15, DLD-1, and COLO 205 colon cancer cell lines, and activities are reported herein.

AB - A new enynyl-benzenoid, antrocamphin O (1,4,7-dimethoxy-5-methyl-6-(3'- methylbut-3-en-1-ynyl)benzo[d][1,3]dioxide), and the known benzenoids antrocamphin A and 7-dimethoxy-5-methyl-1,3-benzodioxole, were isolated from the fruiting bodies of Antrodia camphorata (Taiwanofungus camphoratus). The structure of antrocamphin O was unambiguously assigned by the analysis of spectral data (including 1D and 2D NMR, high-resolution MS, IR, and UV) and total synthesis. Compound 1 was prepared through the Sonogashira reaction of 5-iodo-4,7-dimethoxy-6-methylbenzene and 2-methylbut-1-en-3-yne as the key step. The benzenoids were tested for cytotoxicity against the HT29, HTC15, DLD-1, and COLO 205 colon cancer cell lines, and activities are reported herein.

KW - Antrocamphin O

KW - Antrodia camphorate

KW - Cytotoxic activity

KW - Enynyl-benzenoid

KW - Synthesis

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Isolation and synthesis of a bioactive benzenoid derivative from the fruiting bodies of Antrodia camphorata

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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