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DOI: 10.1055/s-0031-1280347
© Georg Thieme Verlag KG Stuttgart · New York
Metabolites of the Mangrove Fungus Xylaria sp. BL321 from the South China Sea
Publikationsverlauf
received August 24, 2010
revised September 20, 2011
accepted October 14, 2011
Publikationsdatum:
14. November 2011 (online)

Abstract
Two new lactones, 1 and 2, together with five known compounds, 3–7, were isolated from the marine mangrove fungus Xylaria sp. BL321. Their structures were determined by comprehensive analysis of their MS and NMR spectroscopic data. The absolute configurations of 1 and 2 were established on the basis of electronic circular dichroism calculations. It was found that the exocyclic double bond of 1 rearranged into a cyclic double bond to form a new crystal compound (1a) in diluted NaOH solution. Compound 3 was isolated for the first time as a natural product; its absolute configuration was determined by single-crystal X-ray crystallography. Compounds 4–7 displayed cytotoxicity against human breast cancer cell lines MCF-7 and MDA-MB-435, while compounds 1–3 were inactive (IC50 > 50 µM).
Key words
Xylaria sp. - Acanthus ilicifolius L. - Acanthaceae - mangrove fungus - lactone - electronic circular dichroism
References
- 1
McDonald L A, Barbieri L R, Bernan V S, Janso J, Lassota P, Garter G T.
07H239-A, a new cytotoxic eremophilane sesquiterpene from the marine-derived Xylariaceous
fungus LL-07H239.
J Nat Prod.
2004;
67
1565-1567
Reference Ris Wihthout Link
- 2
Pittayakhajonwut P, Usuwan A, Intaraudom C, Veeranondha S, Srikitikulchai P.
Sesquiterpene lactone 12, 8-eudesmanolides from the fungus Xylaria ianthinovelutina.
Planta Med.
2009;
75
1431-1435
Reference Ris Wihthout Link
- 3
Boonphong S, Kittakoop P, Isaka M, Pittayakhajonwut D, Tanticharoen M, Thebtaranonth Y.
Multiplolides A and B, new antifungal 10-membered lactones from Xylaria multiplex.
J Nat Prod.
2001;
64
965-967
Reference Ris Wihthout Link
- 4
Healy P C, Hocking A, Tran-Dinh N, Pitt J I, Shivas R G, Mitchell J K, Kotiw M, Davis R A.
Xanthones from a microfungus of the genus Xylaria.
Phytochemistry.
2004;
65
2373-2378
Reference Ris Wihthout Link
- 5
Aldridge D C, Turner W B.
Structures of cytochalasins C and D.
J Chem Soc (C).
1969;
923-928
Reference Ris Wihthout Link
- 6
Abate D, Abraham W R, Meyer H.
Cytochalasins and phytotoxins from the fungus Xylarila obobata.
Phytochemistry.
1997;
44
1443-1448
Reference Ris Wihthout Link
- 7
Lin Y C, Wu X Y, Feng S, Jiang G C, Luo J H, Zhou S N, Vrijmoed L L P, Jones E B G, Krohn K, Steingrçver K, Zsila F.
Five unique compounds: xyloketals from mangrove fungus Xylaria sp. from the south China Sea Coast.
J Org Chem.
2001;
66
6252-6256
Reference Ris Wihthout Link
- 8
Wu X Y, Liu X H, Lin Y C, Luo J H, She Z G, Li H J, Chan L W, Antus S, Kurtan T, Elsasser B, Krohn K.
Xyloketal F: A strong L-calcium channel blocker from the mangrove fungus Xylaria sp. (#2508) from the South China Sea coast.
Eur J Org Chem.
2005;
4061-4064
Reference Ris Wihthout Link
- 9
Wu X Y, Liu X H, Jiang G C, Lin Y C, Chan W, Vrijmoed L L P.
Xyloketal G, a novel metabolite from the mangrove fungus Xylaria sp. 2508.
Chem Nat Compd.
2005;
41
27-29
Reference Ris Wihthout Link
- 10
Liu X, Xu F, Zhang Y, Liu L, Huang H, Cai X, Lin Y, Chan W.
Xyloketal H from the mangrove endophytic fungus Xylaria sp. 2508.
Russ Chem B.
2006;
6
1091-1092
Reference Ris Wihthout Link
- 11
Lin Y, Wu X, Feng S, Jiang G, Zhou S, Vrijmoed L L P, Jones E B G.
A novel N-cinnamoylcyclopeptide containing an allenic ether from the fungus Xylaria sp. (strain c2508) from the South China Sea.
Tetrahedron Lett.
2001;
42
449-451
Reference Ris Wihthout Link
- 12
Huang H R, She Z G, Lin Y C, Vrijmoed L L P, Lin W H.
Cyclic peptides from an endophytic fungus obtained from a mangrove leaf (Kandelia candel).
J Nat Prod.
2007;
70
1696-1699
Reference Ris Wihthout Link
- 13
Wang S Y, Xu Z H, Mao W W, She Z G, Tan N, Li C R, Lin Y C.
Four new aromatic allenic ethers from the fungus Xylaria sp. No. 2508.
Nat Prod Res.
2008;
22
612-617
Reference Ris Wihthout Link
- 14
Xu F, Zhang Y, Wang J J, Pang J Y, Huang C H, Wu X Y, She Z G, Vrijmoed L L P, Jones E B G, Lin Y C.
Benzofuran derivatives from the mangrove endophytic fungus Xylaria sp. (#2508).
J Nat Prod.
2008;
71
1251-1253
Reference Ris Wihthout Link
- 15
Singh S B, Felock P, Hazuda D J.
Chemical and enzymatic modifications of integric acid and HIV-1 integrase inhibitory
activity.
Bioorg Med Chem Lett.
2000;
10
235-238
Reference Ris Wihthout Link
- 16
Ahmad H, Snatzke G, Atta-ur-Rahman.
The CD in situ complexation method as a tool for determination of absolute configurations of cottonogenic
derivatives.
J Am Chem Soc.
1993;
115
12533-12544
Reference Ris Wihthout Link
- 17 Gaussian03. Gaussian, Inc. Available at http://www.gaussian.com Accessed 2011
Reference Ris Wihthout Link
Prof. Dr. Lan Liu
Prof. Dr. Yong-Cheng Lin
School of Chemistry and Chemical Engineering
Sun Yat-sen University
135 Xingang West Road
Guangzhou 510275
P. R. China
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