Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2013 Jun 28;18(7):7600-8.
doi: 10.3390/molecules18077600.

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

Affiliations

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

Pi-Yu Chen et al. Molecules. .

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.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Structures of 1–3 from the fruiting bodies of A. camphorate.
Scheme 1
Scheme 1
The synthetic route to compound 1.
Figure 2
Figure 2
Effects of AC1-derived compounds on cell survival inhibition. Colon cancer cells were either treated with compound 1–3, or 5-FU for 48 h. MTT test was used to exam the relative cell number. 1–3, and 5-FU concentration-dependently inhibited the cell viability in 4 clones of colon cancer cells. Values represent the means ± S.E.M. (n = 3). Significance was accepted at p < 0.05.

References

    1. Geethangili M., Tzeng Y.M. Review of Pharmacological Effects of Antrodia camphorata and Its Bioactive Compounds. Evid. Based Complement. Alternat. Med. 2011:212641. - PMC - PubMed
    1. Huang H.C., Liaw C.C., Yang H.L., Hseu Y.C., Kuo H.T., Tsai Y.C., Chien S.C., Amagaya S., Chen Y.C., Kuo Y.H. Lanostane triterpenoids and sterols from Antrodia camphorata. Phytochemistry. 2012;84:177–183. doi: 10.1016/j.phytochem.2012.08.011. - DOI - PubMed
    1. Shi L.S., Chao C.H., Shen D.Y., Chan H.H., Chen C.H., Liao Y.R., Wu S.J., Leu Y.L., Shen Y.C., Kuo Y.H., et al. Biologically active constituents from the fruiting body of Taiwanofungus camphorates. Bioorg. Med. Chem. 2011;19:677–683. doi: 10.1016/j.bmc.2010.10.032. - DOI - PMC - PubMed
    1. Tsai Z.T., Liaw S.L. The Use and the Effect of Ganoderma. Sang-Yun Press; Taichung, Taiwan: 1982. p. 116.
    1. Lee Y.P., Tsai W.C., Ko C.J., Rao Y.K., Yang C.R., Chen D.R., Yang M.H., Yang C.C., Tzeng Y.M. Anticancer effects of eleven triterpenoids derived fromantrodia camphorate. Anticancer Res. 2012;32:2727–2734. - PubMed

Publication types

MeSH terms