NMR fingerprinting of liverworts. Part 9 - Plagiochilines T and U, 2,3-secoaromadendranes from the liverwort Plagiochila carringtonii from Scotland

Rycroft, D.S., Cole, W.J. and Lamont, Y.M. (1999) NMR fingerprinting of liverworts. Part 9 - Plagiochilines T and U, 2,3-secoaromadendranes from the liverwort Plagiochila carringtonii from Scotland. Phytochemistry, 51(5), pp. 663-667. (doi: 10.1016/S0031-9422(99)00093-X)

Abstract

NMR fingerprinting of five samples of Plagiochila carringtonii has shown that the species in Scotland is characterized by the presence of plagiochilines T and U, two new 2,3- secoaromadendranes, in the ratio 2:1, respectively. Plagiochilines T and U were isolated, characterized by GC-MS and H-1 NMR and the structures elucidated as 2 alpha,15- diacetoxy-2,3-epoxy-2, 3-seco(1 alpha,5 alpha,6 beta,7 beta)- aromadendra-3, 10(14)-dien-13-al and methyl 2 alpha: 15- diacetoxy-2,3-epoxy-2,3-seco-( 1 alpha, 5 alpha,6 beta, 7 beta)-aromadendra-3,10(14)-dien-13-oate, respectively. They differ from plagiochiline C by oxidation of the cyclopropyl beta-methyl substituent to an aldehyde and a methyl ester respectively and are the first recorded examples with oxidation beyond the alcohol level at this position. P. carringtonii may be assigned to the most common Plagiachila chemotype, the 2,3- secoaromadendrane group.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Rycroft, Dr David
• Authors: Rycroft, D.S., Cole, W.J., and Lamont, Y.M.
• Subjects: Q Science > QK Botany
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Phytochemistry
• ISSN: 0031-9422