2',6'-Dihydroxy-4'-methoxyacetophenone

Phytochemistry, 1994, 35(2):331-3.

2',6'-Dihydroxy-4'-methoxyacetophenone, a phytoalexin from the roots of Sanguisorba minor[Reference: WebLink]

METHODS AND RESULTS:
The root tissue of Sanguisorba minor produced 2',6'-Dihydroxy-4'-methoxyacetophenone as a phytoalexin after fungal inoculation with Botrytis cinerea or UV light irradiation.
CONCLUSIONS:
The ED50 of this compound on spore germination inhibition was 45 and 410 μM for Botrytis cinerea and Phomopsis perniciosa, respectively.

Journal of the Japan Wood Research Society, 1997, 43:108-111.

Antifungal activity of 2′,6′-dihydroxy-4′-methoxyacetophenone and related compounds[Reference: WebLink]

METHODS AND RESULTS:
We investigated the relationship between the antifungal activity of 2',6'-Dihydroxy-4'-methoxyacetophenone, a component found in the leaves of Rhododendron dauricum L. and of related compounds and their chemical structures, using several common plant pathogenic fungi. Acetophenones having hydroxyl and/or methoxyl substituents on their aromatic rings showed strong activity against all fungal species tested at a concentration of 500 μml-1. Mono-, 2′,4′-di-, 2′,5′-di-, 2′,6′-di- and 2′,4′,6′-tri-substituted acetophenones were generally more active than 3′4′-di-, 3′,5′-di-and 3′,4′,5′-tri-substituted ones. Although the hyphal growths of some fungi almost were inhibited completely by mono- and 2′,5′-di-substituted acetophenones, none of the fungi, with a few exceptions, were killed.
CONCLUSIONS:
2′,6′-Dihydroxyacetophenone and 2',6'-Dihydroxy-4'-methoxyacetophenone exhibited significant antifungal activities against all test fungi, whereas 2′-hydroxy-6′-methoxyacetophenone had limited activity. The ortho-hydroxyls to the acetyl in the molecules play an important role in antifungal activities, because methylation of the hydroxyls resulted in reduced activities. In contrast, the antifungal activities of 2′,4′-dihydroxyacetophenone and 2′,4′,6′-trihydroxyacetophenone were enhanced by the methylation of para-hydroxyl. The limited activity of 2′,4′,6′-trihydroxycetophenone suggested that one of the hydroxyls in the molecule was unfavorable for antifungal activity.

Chin J Nat Med. 2012 Jan;10(1):36-9.

Chemical constituents of Allophylus longipes.[Pubmed: 23302528 ]

To investigate the chemical constituents of Allophylus longipes.
METHODS AND RESULTS:
Compounds were isolated and purified by various chromatographic techniques and their structures were elucidated by physicochemical characteristics and spectral data. Twenty-five compounds were isolated and identified as cycloart-24-en-3β, 26-diol (1), 3-oxotrirucalla-7, 24-dien-21-oic acid (2), zizyberenalic acid (3), colubrinic acid (4), ent-4(15)-eudesmene-1β, 6α-diol (5), 4(15)-eudesmene-1β, 8α-diol (6), 4(15)-eudesmene-1β, 5α-diol (7), methyl asterrate (8), betulin (9), betulinic aldehyde (10), betulinic acid (11), 3β-hydroxy-5α, 8α-epidioxyergosta-6, 22-dien (12), 3-oxo-19α-hydroxyurs-12-en-28-oic acid (13), ursolic acid (14), scopoletin (15), fraxidin (16), cleomiscosin A (17), 4-hydroxy-3-methoxybenzaldehyde (18), 4-hydroxy-3-methoxycinnamaldehyde (19), 2',6'-Dihydroxy-4'-methoxyacetophenone (20), p-(aminoalkyl)-benzoic acid (21), 4-hydroxy-3-methoxybenzoic acid (22), 1-O-p-coumaroylglucose (23), β-sitosterol (24), and poriferast-5-ene-3β, 4β-diol (25).
CONCLUSIONS:
All the compounds were isolated from Allophylus longipes for the first time.