A new sesquiterpenoid belonging to the subgroup seco-eudesmanolides and named inuloxin E was isolated from Dittrichia viscosa, together with the already known sesquiterpenoids inuloxins A–D and -costic acid. Inuloxin E was characterized by spectroscopic data (essentially NMR and ESIMS) as 3-methylene-6-(1-methyl-4-oxo-pentyl)-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one. Its relative configuration was determined by comparison with the closely related inuloxin D and chemical conversion of inuloxin E into inuloxin D and by the observed significant correlation in the NOESY spectrum. Both inuloxins D and E induced germination of the parasitic weed Orobanche cumana, but were inactive on the seeds of Orobanche minor and Phelipanche ramosa. The germination activity of some hemisynthetic esters of inuloxin D was also investigated.
Inuloxin E, a New Seco-Eudesmanolide Isolated from Dittrichia viscosa, Stimulating Orobanche cumana Seed Germination / Masi, M.; Fernandez-Aparicio, M.; Zatout, Roukia; Boari, A.; Cimmino, A.; Evidente, A.. - In: MOLECULES. - ISSN 1420-3049. - 24:19(2019), p. 3479. [10.3390/molecules24193479]
Inuloxin E, a New Seco-Eudesmanolide Isolated from Dittrichia viscosa, Stimulating Orobanche cumana Seed Germination
Masi M.Writing – Original Draft Preparation
;ZATOUT, ROUKIAFormal Analysis
;Cimmino A.
Writing – Review & Editing
;Evidente A.Supervision
2019
Abstract
A new sesquiterpenoid belonging to the subgroup seco-eudesmanolides and named inuloxin E was isolated from Dittrichia viscosa, together with the already known sesquiterpenoids inuloxins A–D and -costic acid. Inuloxin E was characterized by spectroscopic data (essentially NMR and ESIMS) as 3-methylene-6-(1-methyl-4-oxo-pentyl)-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one. Its relative configuration was determined by comparison with the closely related inuloxin D and chemical conversion of inuloxin E into inuloxin D and by the observed significant correlation in the NOESY spectrum. Both inuloxins D and E induced germination of the parasitic weed Orobanche cumana, but were inactive on the seeds of Orobanche minor and Phelipanche ramosa. The germination activity of some hemisynthetic esters of inuloxin D was also investigated.File | Dimensione | Formato | |
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