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Cladospirones B to I from Sphaeropsidales sp. F‐24′707 by Variation of Culture Conditions
Author(s) -
Bode Helge Björn,
Walker Martina,
Zeeck Axel
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:18<3185::aid-ejoc3185>3.0.co;2-3
Subject(s) - chemistry , stereochemistry , carbon skeleton , hydroxylation , secondary metabolite , algae , organic chemistry , botany , biochemistry , gene , enzyme , biology
Variation of the culture conditions − static surface cultures in particular − of the fungus Sphaeropsidales sp. (strain F‐24′707), which produces cladospirone bisepoxide ( 1 ), led to the isolation of eight new spirobisnaphthalenes − the cladospirones B to I ( 8 − 15 ) − together with seven known representatives of this class of secondary metabolites. Cladospirones C ( 9 ) and D ( 11 ) show antibiotic activity against bacteria and algae. The structures of cladospirone B ( 8 ) and E ( 12 ) were confirmed by X‐ray structure analysis. Cladospirones C ( 9 ) and G to I ( 10 , 14 − 15 ) represent new members of the spirobisnaphthalene family, thanks to their hydroxylation patterns. Moreover, they underline the extraordinary status of this interesting class of compounds as the most diverse secondary metabolites, allowing for their small number of carbon atoms, described to date. Almost all possible permutations of stereochemistry and oxygen substitution pattern on the C 10 skeleton are produced by different fungi.