Echinulin, a novel cyclic dipeptide carrying a triprenylated indole moiety from an Anacardiaceae, a Cucurbitaceae and two Orchidaceae plants : detailed high resolution 2D-NMR and mass spectral studies
| Autor: | Sudipta Kumar Mandal, Paramita Kar, Asis Bhaumik, Sunil Kumar Talapatra, Susmita Mukhopadhyay, Amarendra Patra, Bani Talapatra |
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| Jazyk: | angličtina |
| Rok vydání: | 2001 |
| Předmět: |
Indole test
Aspergillus eclrinulatus Dipeptide biology Stereochemistry Absolute configuration General Medicine Piperazinedione Carbon-13 NMR biology.organism_classification Rhus parviflora Cymbidium aloifolium chemistry.chemical_compound chemistry Organic chemistry Anacardiaceae Trichosanthes Cucurbitaceae Two-dimensional nuclear magnetic resonance spectroscopy Orchidaceae plants Dendrobium fimbriatum and Cymbidium uloifolium |
| DOI: | 10.5281/zenodo.5902107 |
| Popis: | Centre of Advanced Studies on Natural Products, Department of Chemistry, University College of Science, 92 Acharya Prafulla Chandra Road, Kolkata-700 009, India E-mail: banitalapatra@yahoo.co.in I talapatrask@yahoo.com Manuscript received 18 September 2001 A levorotatory compound, C29H39 N3O2 was isolated from the edible fruits of Rhus parviflora (Anacardiaceae) along with citric acid 2-methyl ester. A detailed 1H and 13C NMR spectral studies including 1H-1H correlation, long range 13C-1H correlation (HMBC and HMQC) and also NOESY confirmed its structure as 3S,6S,3-[[2-(1,1-dimethylallyl)-5,7-bis(3,3- dimethylallyl-1H-indo-3-yl]methyl]-6-methyl-2,5-piperazinedione (1) and allowed the unambiguous assignments of each carbon and proton signals. This biogenetically interesting novel cyclic dipeptide was designated echinulin, being reported first in 1943 from the moulds of Aspergillus eclrinulatus; later on it was reported from the moulds of the A. glaucus group. Echinulin has since been isolated in this laboratory from three other plants, viz. two Orchidaceae plants, Dendrobium fimbriatum and Cymbidium aloifolium and the peels of an edible vegetable (fruits, Bengali name Potul) ofTrichosanthes dioica (Cucurbitaceae). To our knowledge, this is the first report on the occurrence of this mould metabolite, echinulin in four higher plants belonging to three different families. The absolute configuration (S) at each of its two chiral centres and its mass fragmentation have also been discussed. |
| Databáze: | OpenAIRE |
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