Aflavinine, a novel indole-mevalonate metabolite from tremorgen-producing aspergillus flavus species
✍ Scribed by Rex T. Gallagher; Terrence McCabe; Ken Hirotsu; Jon Clardy; Judith Nicholson; Benjamin J. Wilson
- Book ID
- 104212769
- Publisher
- Elsevier Science
- Year
- 1980
- Tongue
- French
- Weight
- 211 KB
- Volume
- 21
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The structure of sflavanine, a new diterpene indole from A flavus, is presented. Strams of Aspergillus flavus which produce the tremorgenic toxic indole &atrem, I, 2 co-produce snother major mdole metabolite of very unusual structure. We now report the novel structure 1 for this indole, which we name aflavmine. Y OH 1 Aflavinme, obtained as colorless needles, m.p. 102-4 "C from EtOAc, after column chromatography on silica gel with CHC13 used to produce aflatrem, I,3 cyclohexane (1:s) of a crude CHC13 extract of A. flavus cultures was found by high-resolution MS to have a molecular ion of elemental composition C28H3sN0, MW 405. Crystals of composition, C28H3sN0. CH3 i!!O CH2CH3, were grown from an ethyl acetate solution. These crystals are trmlinic and belong determined from a least-squares fit of fifteen 2 = 10.477(3)1, a = 98.29(2), g = 102 Sl(2). to the chiral space group Pl Accurate cell constants high angle reflections were: 2 = 8 288(2), k = 8.853(3), and y = 79.49(2) All unique diffraction maxima with