Botcinins E and F and Botcinolide from Botrytis cinerea and structural revision of botcinolides

Journal of Natural Products
H TaniH Nakajima

Abstract

Botcinins E and F were isolated together with the known botcinolide. The structures of botcinins E and F were determined to be 3-O-deacetylbotcinin A (5) and 3-O-deacetyl-2-epi-botcinin A (6), respectively, by spectroscopic methods and chemical conversion. The structure of botcinolide was revised on the basis of spectroscopic data and chemical conversion. Botcinolide was originally reported as a nine-membered lactone (7), but the revised structure is the seco acid of botcinin E (13). Thus botcinolide is renamed botcinic acid, and homobotcinolide is renamed botcineric acid. Reinvestigation of the spectroscopic data reported for all botcinolide analogues indicates that 4-O-methylbotcinolide and 3-O-acetyl-2-epibotcinolide are the same as a methyl ester of botcinic acid (13a) and botcinin A (1), respectively, and that 2-epibotcinolide may be the same as botcinin E (5). Compounds 5, 6, and 13 showed weak antifungal activity against Magnaporthe grisea, a pathogen of rice blast disease.

References

Apr 1, 1996·Bioscience, Biotechnology, and Biochemistry·H G CutlerP R Schreiner
Nov 26, 2002·Journal of Natural Products·Ana J ColmenaresIsidro G Collado

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Citations

Oct 12, 2007·Bioscience, Biotechnology, and Biochemistry·Emi SakunoHiromitsu Nakajima
Aug 25, 2015·Frontiers in Plant Science·Tünde PusztahelyiIstván Pócsi
Jan 28, 2015·Molecular Plant-microbe Interactions : MPMI·Julia SchumacherBettina Tudzynski
Jun 16, 2017·Organic & Biomolecular Chemistry·Gabriel Franco Dos SantosIsidro G Collado
Dec 4, 2012·Chembiochem : a European Journal of Chemical Biology·Michelli MassaroliRosario Hernández-Galán
Jun 14, 2014·Organic & Biomolecular Chemistry·J M Botubol-AresR Hernández-Galán
Jan 13, 2009·Chemical Communications : Chem Comm·Isamu Shiina, Hiroki Fukui
Jun 14, 2008·Organic Letters·Hiroki Fukui, Isamu Shiina
Nov 6, 2014·The Journal of Organic Chemistry·José Manuel BotubolRosario Hernández-Galán
Apr 8, 2017·The Journal of Organic Chemistry·Saurabh MaityDebendra K Mohapatra
Nov 3, 2006·Organic Letters·Isamu ShiinaHiroki Fukui

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