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Homoisoflavonoids and cardenolides from cultivated Ornithogalum species: Ornithogalum dubium Houtt. and Ornithogalum ponticum ‘Sochi’

Langat, L., Langat, M.K. and Mulholland, D.A. (2019) Homoisoflavonoids and cardenolides from cultivated Ornithogalum species: Ornithogalum dubium Houtt. and Ornithogalum ponticum ‘Sochi’ South African Journal of Botany.

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Abstract

Three new homoisoflavonoids, (3R)-3,5-dihydroxy-7-methoxy-3-(4’-hydroxybenzyl)-4-chromanone, 4, and its 5-O-β-D-glucopyranoside and 5-O-β-D-gentiobiose derivatives, 5 and 6, along with the known homoisoflavonoids, (3S)-5-hydroxy-7-methoxy-3-(4-methoxybenzyl)-4-chromanone, 1, (3R)-5-hydroxy-7-methoxy-3-(4-methoxybenzyl)-4-chromanone (2) and (3S)-5-hydroxy-7-methoxy-3-(4-hydroxybenzyl)-4-chromanone, 3, were isolated from the bulbs of Ornithogalum dubium Houtt.. In addition, three known cardenolides, 3β-(O-α-L-rhamnoside)-5β,14β-dihydroxy-19-oxocardenolide 7, 3β-(O-α-L-rhamnoside)-5β,11α,14β-trihydroxy-19-oxocardenolide, 8 and 3β-(O-α-L-rhamnoside)-5β,11α,14β,19-tetrahydroxycard-20(22)-enolide, 9, were isolated from Ornithogalum ponticum ‘Sochi’. Yields of homoisoflavonoids were low (0.0002 % - 0.0003 %) so stereospecific synthetic methodology needs further refinement to produce antiangiogenic (3R)-3-benzylchromanones and (3S)-3-hydroxyhomoisoflavonoid analogues for further evaluation. This work confirms that, apart from producing cardenolides, the absolute configuration at C-3 of homoisoflavonoids produced by Ornithogalum is 3R (H-3β) for the 3-benzylchromanones and 3S (3-OH β) for the 3-hydroxy benzylchromanones, in agreement with our earlier reports.

Item Type: Article
Divisions : Faculty of Engineering and Physical Sciences > Chemistry
Authors :
NameEmailORCID
Langat, L.
Langat, M.K.ml0019@surrey.ac.uk
Mulholland, D.A.D.Mulholland@surrey.ac.uk
Date : 2019
Copyright Disclaimer : © 2019. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
Uncontrolled Keywords : Asparagaceae; Cardenolides; Homoisoflavonoids; Homoisoflavonoid glycosides; Ornithogalum dubium Houtt.; Ornithogalum ponticum ‘Sochi’
Related URLs :
Depositing User : Clive Harris
Date Deposited : 15 May 2019 07:22
Last Modified : 15 May 2019 07:22
URI: http://epubs.surrey.ac.uk/id/eprint/851828

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