New apocarotenoids and β-carotene cleavage in Blakeslea trispora

Mixed cultures of strains of opposite sex ("mated" cultures) of Blakeslea trispora contain trisporic acids and other apocarotenoids, some of which mediate the sexual responses of this fungus and other Mucorales. In mated cultures of the wild-type strains F986 and F921 we identified eleven...

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Published in:Organic & biomolecular chemistry 2011-10, Vol.9 (20), p.7190-7195
Main Authors: Barrero, Alejandro F, Herrador, M Mar, Arteaga, Pilar, Gil, Jesús, González, Jose-Antonio, Alcalde, Eugenio, Cerdá-Olmedo, Enrique
Format: Article
Language:English
Subjects:
beta Carotene - chemistry
beta Carotene - isolation & purification
Carotenoids - chemistry
Carotenoids - isolation & purification
Fungi - chemistry
Molecular Structure
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Summary:Mixed cultures of strains of opposite sex ("mated" cultures) of Blakeslea trispora contain trisporic acids and other apocarotenoids, some of which mediate the sexual responses of this fungus and other Mucorales. In mated cultures of the wild-type strains F986 and F921 we identified eleven apocarotenoids: two C(18) trisporoids, three C(15) compounds with a monocyclofarnesane skeleton, a C(13) compound, and five C(7) compounds with a 2-methylhexane skeleton. Six of them are new natural products and two others are new for Blakeslea. Their structures were established by NMR and mass spectra and those of the C(7) and C(13) compounds were confirmed by chemical synthesis. The finding of these compounds and the presence of approximately equimolecular amounts of the C(18), C(15), and C(7) families led to the conclusion that β-carotene is initially split in three fragments by cleavage of its 13,14 and 11',12' double bonds.
ISSN:1477-0520
1477-0539
DOI:10.1039/c1ob05712j