A novel ascochlorin glycoside from the insect pathogenic fungus Verticillium hemipterigenum BCC 2370.
Vertihemipterin A, the ascochlorin glycoside, and its aglycone, 4',5'-dihydro-4'-hydroxyascochlorin, were isolated from the insect pathogenic fungus Verticillium hemipterigenum BCC 2370. A new analog, 8'-hydroxyascochlorin, and five known compounds, ascochlorin, LL-Z1272delta, 8',9'-dehydroascochlorin, ascofuranone and ascofuranol, were also isolated from the same fermentation broth. Structures of these compounds were elucidated by spectroscopic methods. Stereochemistry of the known compound, 4',5'-dihydro-4'-hydroxyascochlorin, was addressed by NMR spectral analyses and the modified Mosher's method. Antiviral (HSV-1) and cytotoxic activities of these ascochlorin analogs were evaluated.
Seephonkai
Prapairat
P
Department of Chemistry, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand.
Isaka
Masahiko
M
Kittakoop
Prasat
P
Boonudomlap
Uraiwan
U
Thebtaranonth
Yodhathai
Y
D000475:Alkenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D002522:Chlorocebus aethiops; D002850:Chromatography, Gel; D005285:Fermentation; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018139:Simplexvirus / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D014709:Vero Cells; D020172:Verticillium / Q000737:chemistry* / Q000378:metabolism
D000475:Alkenes; D000998:Antiviral Agents; D006027:Glycosides; D010636:Phenols; C415745:ascochlorin