Flavone aglycones in glandular hairs of Origanum x intercedens

Bosabalidis, Artemios M.; Gabrieli, Chrysi; Niopas, Ioannis

doi:10.1016/s0031-9422(98)00186-1

Cited by 64 publications

(29 citation statements)

References 19 publications

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“…Because it appears that flavonoid 7-O-methylation is a prerequisite for 6-hydroxylation in these two mint species, the first question is whether this route is common in the Lamiaceae and whether it is shared by non-mints producing identical or very similar flavones, such as Alnus (48), Rubus (49), and Eupatorium (50), all of which are reported to accumulate SALV. In the Lamiaceae, phytochemical data for some groups, such as Thymus (51,52), Origanum (53), and Orthosiphon (54), indicate that they only accumulate 6-substituted flavonoids possessing 7-O-methylated hydroxyl moieties and therefore could well follow the same pattern. Likewise, the discovery of the flavonoid 7-O-demethylation prompts an investigation into the frequency of demethylation in flavonoid metabolism.…”

Section: Discussionmentioning

confidence: 99%

The Roles of a Flavone-6-Hydroxylase and 7-O-Demethylation in the Flavone Biosynthetic Network of Sweet Basil

Berim

Gang

2013

Journal of Biological Chemistry

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Background: Late steps of lipophilic flavone biosynthesis in mints are unknown. Results: CYP82D monooxygenases catalyze 6-hydroxylation of 7-O-methylated precursor, whose 7-methyl group is subsequently removed by demethylation in basil but not in peppermint. Conclusion: Flavone biosynthesis in basil involves an unusual loop. Significance: Novel mechanisms elucidated in basil suggest a new hypothesis for similar metabolic networks in other plants.

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Section: Discussionmentioning

confidence: 99%

The Roles of a Flavone-6-Hydroxylase and 7-O-Demethylation in the Flavone Biosynthetic Network of Sweet Basil

Berim

Gang

2013

Journal of Biological Chemistry

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“…The structures of the isolated flavones were identified as 5-hydroxy-3,7-dimethoxyflavone (1), tectochrysin (2), 5-hydroxy-3,7,4¢-trimethoxyflavone (3), 5-hydroxy-3,7,3¢,4¢-tetramethoxyflavone (4), 3,5,7-trimethoxyflavone (5), 5,7,4¢-trimethoxyflavone (6), 5,7-dimethoxyflavone (7), 3,5,7,4¢-tetramethoxyflavone (8), 3,5,7,3¢,4¢-pentamethoxyflavone (9), 5-hydroxy-7,4¢-dimethoxyflavone (10), 5,3¢-dihydroxy-3,7,4¢-trimethoxyflavone (11),5-hydroxy-7,3¢,4¢-trimethoxyflavone (12) and genkwanin (13) by comparison of their physical and spectroscopic data with literature values (Bosabalidis et al, 1998;Dong et al, 1999;Yenjai et al, 2004;Sutthanut et al, 2007).…”

Section: Methodsmentioning

confidence: 99%

Anticholinesterase activity of 7‐methoxyflavones isolated from Kaempferia parviflora

Sawasdee

Sabphon

Sitthiwongwanit

et al. 2009

Phytotherapy Research

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The rhizome of Kaempferia parviflora or kra-chai-dum (in Thai) is used traditionally as a folk medicine. The preliminary cholinesterase inhibitory screening of this plant extract exhibited significant acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. Thirteen known methoxyflavones (1-13) were isolated and their structures were completely elucidated based on NMR analysis and compared with literature reports. Minor compounds 12-13 were reported for the first time from this species. The cholinesterase inhibitory test results showed that the highest potential inhibitors toward AChE and BChE were 5,7,4'-trimethoxyflavone (6) and 5,7-dimethoxyflavone (7), respectively, with the percentage inhibitory activity varying over 43-85%. The structure-activity relationship study led to the conclusion that compounds bearing 5,7-dimethoxy groups and a free substituent at C-3 had a significant inhibitory effect at a concentration of 0.1 mg/mL, but those bearing a 5-hydroxyl group reduced the inhibitory potency. On the other hand, flavones bearing a 3'- or 5'-methoxy group did not influence the inhibitory effect. Interestingly, 5,7-dimethoxyflavone (7) exhibited strong selectivity for BChE over AChE which may be of great interest to modify as a treatment agent for Alzheimer's disease.

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“…There is no evidence indicating the presence of flavonoids in glandular trichomes, however, it is know that in Betulaceae family and in the genera Populus and Aesculus flavonoids are secreted by glandular trichomes or by a secretory epithelium (Wollenweber 1980). Acylated kaempferol glycosides have also been detected in leaf glandular trichomes from Quercus ilex (Skaltsa et al 1994), and flavone aglycones from Origanum x intercedens (Bosabalidis et al 1998) and from Mentha x piperita (Voirin et al 1993).…”

Section: Flavonoid Biosynthesismentioning

confidence: 99%

Secondary metabolism in cannabis

2008

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Cannabis sativa L. is an annual dioecious plant from Central Asia. Cannabinoids, flavonoids, stilbenoids, terpenoids, alkaloids and lignans are some of the secondary metabolites present in C. sativa. Earlier reviews were focused on isolation and identification of more than 480 chemical compounds; this review deals with the biosynthesis of the secondary metabolites present in this plant. Cannabinoid biosynthesis and some closely related pathways that involve the same precursors are disscused.

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Flavone aglycones in glandular hairs of Origanum x intercedens

Cited by 64 publications

References 19 publications

The Roles of a Flavone-6-Hydroxylase and 7-O-Demethylation in the Flavone Biosynthetic Network of Sweet Basil

The Roles of a Flavone-6-Hydroxylase and 7-O-Demethylation in the Flavone Biosynthetic Network of Sweet Basil

Anticholinesterase activity of 7‐methoxyflavones isolated from Kaempferia parviflora

Secondary metabolism in cannabis

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