Acylated Flavonoid Glucoside from Marrubium vulgare

Author(s): Nuha I. Sweidan, Musa H. Abu Zarga

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 4 , 2016

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Graphical Abstract:


Background: Marrubium vulgare is used in traditional medicine in some countries such as Jordan in the treatment of diabetes and wounds. The plant is reported to possess vasorelaxant, antihypertensive, analgesic, anti-inflammatory and antioxidant properties. Earlier phytochemical investigations of M. vulgare led to the characterization of the diterpene marrubiin (2) which is the major constituent of the plant [8], and exhibits potent antinociceptive properties and vasorelaxant activity, marruboside and marrubic acid. The aim of this work is to isolate and identify new compounds from Jordanian M. vulgare.

Method: The crude ethanolic extract of air- dried defatted whole plants was partitioned into aqueous methanol (MA), butanol (MB) and hexane extracts. The aqueous methanol and butanol extracts were chromatographied on a silica gel columns. Each fraction was purified by a combination of CC, TLC and/ or recrystalization using suitable solvent systems to produce 10 compounds. NMR, MS, and UV spectral analyses were used for structure elucidation of the isolated compounds.

Results: The methanol extract yielded eight pure compounds, which were identified as the new compound apigenin7-O- (3",6"- E-p-dicoumaroyl)-β-glucoside 1 and the known compounds marrubiin 2, the major constituent of Marrubuim vulgare, pectolinarigenin 3, apigenin-7-methyl ether 4, labd-13(14)-en-9a, 15, 16-triol 5, apigenin 6, β-sitosteryl glucoside 7, apigenin-7-O-(6"-O- E-p-coumaroyl)-β-glucoside 8. In a similar manner, the butanol extract (MB) was treated as mentioned with the (MA) extract and the resulting fraction afforded the two known compounds: luteolin-7-O-glucoside 9 and acteoside 10 which is reported for first time from Marrubium vulgare.

Conclusion: The treatment of the air- dried defatted whole plant of Marrubium vulgare led to the isolation of ten pure compounds, two of them were isolated for the first time from this plant: apigenin7-O-(3",6"- E-p-dicoumaroyl)-β- glucoside 1and acteoside 10.

Keywords: Acteoside, acylated flavonoid glucosides, analgesic, antihypertensive, anti-inflammatory, antioxidant, lamiaceae, Marrubium vulgare, vasorelaxant.

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Article Details

Year: 2016
Page: [277 - 282]
Pages: 6
DOI: 10.2174/1570178613666160209230106
Price: $65

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