Spiroleptosphol isolated from Leptosphaeria doliolum.

作者: Masaru Hashimoto , Taro Tsushima , Takanori Murakami , Masahiro Nomiya , Noboru Takada

DOI: 10.1016/J.BMCL.2008.05.087

关键词: NMR spectra databaseCircular dichroismChemistryStereochemistryNuclear magnetic resonance spectroscopyAbsolute configurationMoietyBicyclic moleculeLeptosphaeriaProton NMR

摘要: A novel gamma-methylidene-spirobutanolide spirolephtoshol (1) was isolated from ascomycetous fungus Leptosphaeria doliolum as a cytotoxic compound. The relative structure established by the NMR analysis involving NOE experiments. Absolute of bicyclic moiety determined chemical derivation followed CD analysis. and absolute stereochemistry side chain comparison (1)H spectra chiral GC chromatograms degradation product with synthetic samples.

参考文章(12)
Jun Doi, Akira HIROTA, Masahira NAKAGAWA, Heiichi SAKAI, Akira ISOGAI, Structure of a new antibiotic oxaspirol A Agricultural and biological chemistry. ,vol. 49, pp. 2247- 2248 ,(1985) , 10.1271/BBB1961.49.2247
Alberto Albinati, Sergio Brückner, Lorenzo Camarda, Nasini Gianluca, Rosigenin, an unusual metabolite from mycosphaerella rosigena Tetrahedron. ,vol. 36, pp. 117- 121 ,(1980) , 10.1016/0040-4020(80)85033-2
William A. Ayer, Peter A. Craw, John Neary, Metabolites of the fungus Arthropsistruncata Canadian Journal of Chemistry. ,vol. 70, pp. 1338- 1347 ,(1992) , 10.1139/V92-172
Hyuncheol Oh, Dale C. Swenson, James B. Gloer, Carol A. Shearer, New bioactive rosigenin analogues and aromatic polyketide metabolites from the freshwater aquatic fungus Massarina tunicata Journal of Natural Products. ,vol. 66, pp. 73- 79 ,(2003) , 10.1021/NP020342D
Nobuyuki Harada, Koji Nakanishi, Determining the chiralities of optically active glycols Journal of the American Chemical Society. ,vol. 91, pp. 3989- 3991 ,(1969) , 10.1021/JA01042A073
AKIKO FUKAMI, YOSUKE TANIGUCHI, TOMONORI NAKAMURA, MUN-CHUAL RHO, KANAKO KAWAGUCHI, MASAHIKO HAYASHI, KANKI KOMIYAMA, SATOSHI OMURA, New members of the macrosphelides from Microsphaeropsis sp. FO-5050 IV. The Journal of Antibiotics. ,vol. 52, pp. 501- 504 ,(1999) , 10.7164/ANTIBIOTICS.52.501
William A. Ayer, Peter A. Craw, Biosynthesis and biogenetic interrelationships of metabolites of the fungus Arthropsistruncata Canadian Journal of Chemistry. ,vol. 70, pp. 1348- 1355 ,(1992) , 10.1139/V92-173
Mourad Kaouadji, Norma Buarque de Gusmão, Regine Steiman, Françoise Seigle-Murandi, Mycosporulone, a metabolite from Coniothyrium sporulosum Journal of Natural Products. ,vol. 56, pp. 2189- 2192 ,(1993) , 10.1021/NP50102A026
JAN RETHER, GERHARD ERKEL, TIMM ANKE, OLOV STERNER, Oxaspirodion, a new inhibitor of inducible TNF-alpha expression from the ascomycete Chaetomium subspirale The Journal of Antibiotics. ,vol. 57, pp. 493- 495 ,(2004) , 10.7164/ANTIBIOTICS.57.493