Structural confirmation of 15-norlubiminol and 15-norepilubiminol, isolated from Solanum aethiopicum, by chemical conversion from lubimin and epilubimin, and their antifungal activity.

Article abstract of DOI:10.1271/bbb.65.1805

15-Norlubiminol and 15-norepilubiminol were obtained from Solanum aethiopicum as an inseparable 1:1 mixture in a relatively poor yield to that of the major phytoalexins, lubimin and epilubimin. Their structures were confirmed by chemical conversion starting from lubimin and epilubimin. Baeyer-Villiger oxidation of the protected lubimins with m-chloroperoxybenzoic acid provided the desired formates. Deoxygenation with triphenylphosphine selenide and subsequent methanolysis provided 15-norlubiminols, whose 1H-NMR spectra were respectively identical with that of the corresponding isomer in the natural 15-norlubiminol mixture. The antifungal activity of 15-norlubiminols would be weaker than that of lubimins.

Full text of DOI:10.1271/bbb.65.1805

This article was downloaded by: [Northeastern University]
On: 14 November 2014, At: 14:54
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer
House, 37-41 Mortimer Street, London W1T 3JH, UK
Bioscience, Biotechnology, and Biochemistry
Publication details, including instructions for authors and subscription information:
http://www.tandfonline.com/loi/tbbb20
Structural Confirmation of 15-Norlubiminol
and 15-Norepilubiminol, Isolated from Solanum
aethiopicum, by Chemical Conversion from Lubimin
and Epilubimin, and their Antifungal Activity
Ayako WATANABEab, Hiroaki TOSHIMAa, Hiroshi NAGASEa, Toshinori NAGAOKAc & Teruhiko
YOSHIHARAab
a Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University
b CREST, Japan Science and Technology Corporation
c Faculty of Applied Biological Science, Hiroshima University
Published online: 22 May 2014.
To cite this article: Ayako WATANABE, Hiroaki TOSHIMA, Hiroshi NAGASE, Toshinori NAGAOKA & Teruhiko YOSHIHARA
(2001) Structural Confirmation of 15-Norlubiminol and 15-Norepilubiminol, Isolated from Solanum aethiopicum, by
Chemical Conversion from Lubimin and Epilubimin, and their Antifungal Activity, Bioscience, Biotechnology, and
Biochemistry, 65:8, 1805-1811, DOI: 10.1271/bbb.65.1805
To link to this article: http://dx.doi.org/10.1271/bbb.65.1805
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained
in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no
representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of
the Content. Any opinions and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied
upon and should be independently verified with primary sources of information. Taylor and Francis shall
not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other
liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or
arising out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any substantial or systematic
reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any
form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://
www.tandfonline.com/page/terms-and-conditions