Rubescins F–H, new vilasinin-type limonoids from the leaves of Trichilia rubescens (Meliaceae)
-
Armelle Tontsa Tsamo
,
Julio Issah Mawouma Pagna
Abstract
Three new limonoids, designated as rubescins F (1), G (2), and H (3), together with two known compounds of this type, TS1 (4) and trichirubine A (5), were isolated from methylene chloride/methanol extracts of Trichilia rubescens leaves. The structures of these compounds were elucidated based on 1D and 2D nuclear magnetic resonance (NMR) analysis and complemented by electrospray ionization high-resolution mass spectrometry results and by comparison to data of related compounds described in the literature and ab initio calculations. Rubescin F (1) is the first limonoid from Trichilia spp. with an oxetane ring between C-7 and C-14, which seems to be formed by the isomerization of TS1 (4). The γ-hydroxybutenolide rubescin G (2) is a potential precursor of trichirubine A (5), whereas rubescin H (3) is the first example of a triterpenoid with a single bond between C-7/C-14, forming a cyclopropane ring. The absolute configuration of these limonoids was derived from biosynthetic considerations and ab initio calculations of NMR and optical rotation dispersion data.
Dedicated to: Prof. Dr. Axel Zeeck on the occasion of his 80th birthday.
Acknowledgments
A.T.T. thanks the German Academic Exchange Service (DAAD) for a research grant (A/13 91525630/50015537) at the University of Göttingen. We are especially thankful to Dr. Jochen Junkers for his introduction into using COCON. We are very thankful to Drs. Sean Ohlinger and Warren Hehre (Wavefunction, Inc., Irvine, CA, USA) for many helpful suggestions for the use of SPARTAN. The authors are also indebted to Dr. H. Frauendorf and R. Machinek for the MS and NMR measurements, respectively, and V. Nana and F. Lissy for technical assistance.
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Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2018-0187).
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Articles in the same Issue
- Frontmatter
- Research Articles
- Ishige sinicola extract stimulates osteoblast proliferation and differentiation via the bone morphogenetic protein 2/runt-related gene 2 signalling pathway
- Rubescins F–H, new vilasinin-type limonoids from the leaves of Trichilia rubescens (Meliaceae)
- Impact of water-soluble zwitterionic Zn(II) phthalocyanines against pathogenic bacteria
- Influence of amide versus ester linkages on the anticancer properties of the new flavone–biotin conjugates
- Metabolomic discrimination of the edible mushrooms Kuehneromyces mutabilis and Hypholoma capnoides (Strophariaceae, Agaricales) by NMR spectroscopy
- Components of rice husk biochar in promoting the growth, sporulation and iturin A production of Bacillus sp. strain IA
