Xyloketal F:: A strong L-calcium channel blocker from the mangrove fungus Xylaria sp (#2508) from the South China Sea coast

被引:70
作者
Wu, XY [1 ]
Liu, XH
Lin, YC
Luo, JH
She, ZG
Li, HJ
Chan, WL
Antus, S
Kurtan, T
Elsässer, B
Krohn, K
机构
[1] Zhongshan Univ, Dept Appl Chem, Guangzhou, Peoples R China
[2] Zhongshan Univ, Dept Pharm, Guangzhou, Peoples R China
[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
[4] Univ Debrecen, Dept Organ Chem, H-4032 Debrecen, Hungary
[5] Univ Gesamthsch Paderborn, Dept Chem, D-33098 Paderborn, Germany
关键词
fungal metabolites; Xylaria sp; Xyloketal F; semi synthesis; absolute configuration; quantum-mechanical CD calculation; L-calcium channel blocker;
D O I
10.1002/ejoc.200500326
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Xyloketal F (1), an unusual metabolite with strong L-calcium channel blocking activity, was isolated from the mangrove endophytic fungus Xylaria sp. (#2508) collected at the South China Sea coast. Its structure was elucidated by spectral and single-crystal X-ray diffraction analysis. The absolute configuration of 1 was determined by the method of quantum-mechanical calculation of CD spectra. Compound 1 was also synthesized by condensation of xyloketal B with formaldehyde. The L-calcium channel blocking activities of xyloketals B, A, and F were determined, and at the same concentration (0.03 mu mol/L), the inhibiting rates were 12.05%, 21.47% and 50.33 % respectively. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
引用
收藏
页码:4061 / 4064
页数:4
相关论文
共 10 条
[1]  
Bringmann G., 1998, Natural Products Analysis Eds, P195
[2]   Marine-derived fungi: a chemically and biologically diverse group of microorganisms [J].
Bugni, TS ;
Ireland, CM .
NATURAL PRODUCT REPORTS, 2004, 21 (01) :143-163
[3]   Two new metabolites of a marine endophytic fungus (No. 1893) from an estuarine mangrove on the South China Sea coast [J].
Chen, GY ;
Lin, YC ;
Wen, L ;
Vrijmoed, LLP ;
Jones, EBG .
TETRAHEDRON, 2003, 59 (26) :4907-4909
[4]  
Finar I. L., 1973, ORGANIC CHEM, V1, P706
[5]   Total synthesis of (+)-xyloketal D, a secondary metabolite from the mangrove fungus Xylaria sp. [J].
Krohn, K ;
Riaz, M .
TETRAHEDRON LETTERS, 2004, 45 (02) :293-294
[6]   Five unique compounds:: Xyloketals from mangrove fungus Xylaria sp from the South China Sea coast [J].
Lin, YC ;
Wu, XY ;
Feng, SA ;
Jiang, GC ;
Luo, JH ;
Zhou, SN ;
Vrijmoed, LLP ;
Jones, EBG ;
Krohn, K ;
Steingröver, K ;
Zsila, F .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6252-6256
[7]   A novel N-cinnamoylcyclopeptide containing an allenic ether from the fungus Xylaria sp (strain # 2508) from the South China Sea [J].
Lin, YC ;
Wu, XY ;
Feng, S ;
Jiang, GG ;
Zhou, SN ;
Vrijmoed, LLP ;
Jones, EBG .
TETRAHEDRON LETTERS, 2001, 42 (03) :449-451
[8]  
Romero M., 2003, Current Medicinal Chemistry - Cardiovascular & Hematological Agents, V1, P113, DOI 10.2174/1568016033477487
[9]   OBSERVATIONS ON VERTICAL-DISTRIBUTION OF FUNGI ASSOCIATED WITH STANDING SENESCENT ACANTHUS-ILICIFOLIUS STEMS AT MAI-PO MANGROVE, HONG-KONG [J].
SADABA, RB ;
VRIJMOED, LLP ;
JONES, EBG ;
HODGKISS, IJ .
HYDROBIOLOGIA, 1995, 295 (1-3) :119-126
[10]  
TZREL L, 1998, KOZMAT, V47, P153