Helvetica Chimica Acta p. 2531 - 2537 (1980)
Update date:2022-08-02
Topics:
Buchecker, Richard
Eugster, Conrad Hans
The carotenoid mixture isolated from the yellow flowers of Lamium montanum PERS. (Labiatae) consists of more than 75percent of carotenoids with allenic end groups.Besides 32percent of neoxanthin/neochrome we isolated 44percent of mimulaxanthin (1a), a very rare carotenoid so far only found in Mimulus sp. (Scrophulariaceae).Its absolute configuration was determined by oxidative degradation to the known ketone 3 ("grasshopper ketone") and by spectroscopic and chiroptical comparisons with neoxanthin (6).Mimulaxanthin (1a) therefore is (3S,5R,6R,3'S,5'R,6'R)-6,7,6',7'-tetradehydro-5,6,5',6'-tetrahydro-β,β-carotene-3,5,3',5'-tetraol.Deepoxyneoxanthin, which was reisolated from Mimulus sp. is (3S,5R,6R,3'R)-6,7-didehydro-6,7-dihydro-β,β-carotene-3,5,3'-triol (2), as shown by spectroscopic and chemical correlation with neoxanthin (6; de-epoxydation by BuLi/FeCl3).
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