A New Depside from Usnea aciculifera Growing in Vietnam

Abstract

From Usnea aciculifera, a new depside aciculiferin A (1) was isolated, together with eleven known compounds, (+)-(12R)-usnic acid (2), methyl haematommate (3), methyl β-orsellinate (4), methyl orsellinate (5), atranol (6), 7-hydroxy-5-methoxy-6-methylphthalide (7), norstictic acid (8), stictic acid (9), atranorin (10), barbatinic acid (11) and diffractaic acid (12). Their chemical structures were elucidated by 1D and 2D NMR spectroscopic as well as HR-ESI-MS analysis. Usnic acid (2) and depside diffractaic acid (12) presented in high yield of around 1.5% of the dried material. Some lichen substances inhibited the growth of some cancer cell lines. Three depsides, 1, 11 and 12, were evaluated for their cytotoxic activity against HeLa (human epithelial carcinoma), NCI-H460 (human lung cancer) and MCF-7 (human breast cancer) cell lines at the concentration of 100 μg/mL. Depside 1 showed good and depside 12 strong cytotoxic activity against three surveyed cancer cell lines.

Keywords

Usnea aciculifera Depside Depsidone Cytotoxic activity against HeLa NCI-H460 and MCF-7

References

Podterob

A.P.

(2008) Chemical composition of lichens and their medical applications. Pharmaceutical Chemistry Journal, 42, 582–588.

(a) Gabriele

M.K.

, Anthony

D.W.

(1999) 1H and ¹³C-NMR and biological activity investigations of four lichen-derived compounds. Phytochemical Analysis, 10, 279–284; (b) Marante TFJ, Castellano GA, Rosas EF, Aguiar QJ, Barrera BJ. (2003) Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: phytotoxicity and antioxidative activity. Journal of Chemical Ecology, 29, 2049–2071.

(a) Hylands

P.J.

, Kristin

(1985) The isolation of methyl β-orsellinate from Stereocaulon apinan and comments on the isolation of 4,6-dihydroxy-2-methoxy-3-methoxylacetophenone from Stereocaulon species. Phytochemistry, 24, 127–129; (b) Lopes TIB, Coelho RG, Yoshida NC, Honda NK. (2008) Radical-scavenging activity of orsellinates. Chemical and Pharmaceutical Bulletin, 56, 1551–1554; (c) Elix JA, Jayanthi VK. (1987) Synthetic confirmation of the structure of the lichen benzyl esters electorialic and barbatolic acid. Australian Journal of Chemistry, 40, 1841–1850.

Mendiondo

M.E.

, Coussio

J.D.

(1972) Usnic, norstictic and salazinic acids from Usnea densirostra and Usnea angulata. Phytochemistry, 11, 424.

(a) Pejin

, Iodice

, Bogdanovic

, Kojic

, Tesevic

(2013) Stictic acid inhibits cell growth of human colon adenocarcinoma HT-29 cells, Arabian Journal of Chemistry, 8, 1–3; (b) Nishitoba Y, Nishimura H, Nishiyama T, Mizutani J. (1987) Lichen acids, plant growth inhibitors from Usnea longissima. Phytochemistry, 26, 3181–3185; (c) Brandão LFG, Alcantara GB, Matos MFC, Bogo D, Freitas DS, Oyama NM, Honda NK. (2013) Cytotoxic evaluation of phenolic compounds from lichens against melanoma cells. Chemical and Pharmaceutical Bulletin, 61, 176–183.

(a) Skehan

, Storeng

, Scudiero

, Monks

, McMahon

, Vistica

, Warren

J.T.

, Bokesch

, Kenney

, Boyd

M.R.

(1990) New colorimetric cytotoxicity assay for anticancer-drug screening. Journal of the National Cancer Institute, 82, 1107–1112; (b) Keepers YP, Pizao PE, Peters GJ, Otte JA, Winograd B, Pinedo HM. (1991) Comparison of sulforhodamine B protein and tetrazolium (MTT) assay for in vitro chemosensitivity testing. European Journal of Cancer, 27, 897–900.

Supplementary Material

Please find the following supplemental material available below.

For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.

For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.

0.00 MB

1.09 MB