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COX-2 inhibitory activity of homoisoflavanones and xanthones from the bulbs of the Southern African Ledebouria socialis and Ledebouria ovatifolia (Hyacinthaceae: Hyacinthoideae).

Waller, CP, Thumser, AE, Langat, MK, Crouch, NR and Mulholland, DA (2013) COX-2 inhibitory activity of homoisoflavanones and xanthones from the bulbs of the Southern African Ledebouria socialis and Ledebouria ovatifolia (Hyacinthaceae: Hyacinthoideae). Phytochemistry, 95. pp. 284-290.

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Abstract

The bulbs of Ledebouria socialis (Hyacinthaceae) yielded the benzocyclobutene homoisoflavonoid, (R)-2',5-dihydroxy-3',4',7-trimethoxyspiro{2H-1-benzopyran-3-(4H)-9-bicyclo[4.2.0]octa[1,3,5]triene}-4-one, socialinone (1). Ledebouria ovatifolia yielded (2ε,3R)-2,5-dihydroxy-7-methoxyspiro[2H-1-benzopyran-3(4H), 5'(6'H)-cyclobuta[f][1,3]benzodioxol]-4-one (2) and the homoisoflavanone, (E)-3-(3',4'-dihydroxybenzylidene)-5,7-dihydroxychroman-4-one, ovatifolionone (5), the dihydrochalcone, 4,4'-dihydroxy-2',6'-dimethoxydihydrochalcone (3), and xanthone, 1,6-dihydroxy-2,3,5-trimethoxy-8-methyl-9H-xanthen-9-one (4) along with 21 known compounds. Structures were determined using spectroscopic techniques. The anti-inflammatory activities of the homoisoflavonoids and xanthones isolated were evaluated against cyclooxygenase-1 and -2 isoenzymes. (R)-3-(3',4'-Dihydroxybenzyl)-7-hydroxy-5-methoxychroman-4-one (7), (E)-3-(3',4'-dihydroxybenzylidene)-7-hydroxy-5-methoxychroman-4-one (10), 1,3,6-trihydroxy-2-methoxy-8-methylxanthen-9-one (6) and ovatifolionone acetate (5Ac) exhibited significant activity against cyclooxygenase-2 at <10μM.

Item Type: Article
Divisions : Faculty of Engineering and Physical Sciences > Chemistry
Authors :
AuthorsEmailORCID
Waller, CPUNSPECIFIEDUNSPECIFIED
Thumser, AEUNSPECIFIEDUNSPECIFIED
Langat, MKUNSPECIFIEDUNSPECIFIED
Crouch, NRUNSPECIFIEDUNSPECIFIED
Mulholland, DAUNSPECIFIEDUNSPECIFIED
Date : 13 July 2013
Identification Number : 10.1016/j.phytochem.2013.06.024
Uncontrolled Keywords : Anti-inflammatory, Cyclooxygenase activity, Homoisoflavanone, Hyacinthaceae, Ledebouria ovatifolia, Ledebouria socialis, Ovatifolionone, Socialinone, Xanthone
Related URLs :
Additional Information : NOTICE: this is the author’s version of a work that was accepted for publication in Phytochemistry. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Phytochemistry, July 2013, DOI 10.1016/j.phytochem.2013.06.024.
Depositing User : Symplectic Elements
Date Deposited : 28 Aug 2013 13:28
Last Modified : 07 Oct 2014 13:33
URI: http://epubs.surrey.ac.uk/id/eprint/794981

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