Isolation and Characterization of the ‘Flavonoid Crystals’ of Three Species of Prosthechea: Chemotaxonomic Considerations of the Genera Prosthechea and Encyclia

Bhattacharyya, Jnanabrata; Pires, Maria De Fátima De Oliveira; Félix, Leonardo P.; Silva, Tania M. S.; Majetich, George

doi:10.1177/1934578x0700200710

Cited by 2 publications

(2 citation statements)

References 10 publications

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“…On the basis of integration of signals in the 1D 1 H NMR spectrum the relative proportions of the major and minor rotamers of 6 were determined to be 70:30. Only a very limited number of natural products containing a chinovosyl unit have hitherto been reported, including three flavone C -glycosides − .…”

Section: Resultsmentioning

confidence: 99%

Flavone C-Glycosides from Seeds of Fenugreek, Trigonella foenum-graecum L.

Rayyan

Fossen²,

Andersen³

2010

J. Agric. Food Chem.

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Fenugreek (Trigonella foenum-graecum L.) is particularly used in Asia, Africa, and Mediterranean countries for its nutritional and medicinal value. The flavone C-glycosides, apigenin 6-C-beta-chinovopyranosyl-8-C-beta-galactopyranoside (6) and apigenin 6-C-beta-xylopyranosyl-8-C-(6'''-O-(3-hydroxy-3-methylglutaroyl)-beta-glucopyranoside) (7), in addition to the known flavone C-glycosides, apigenin 6,8-C-di-beta-galactopyranoside (1), apigenin 6-C-beta-xylopyranosyl-8-C-beta-galactopyranoside (2), apigenin 6-C-beta-arabinopyranosyl-8-C-beta-galactopyranoside (3), luteolin 8-C-beta-glucopyranoside (4), luteolin 6-C-beta-glucopyranoside (5), apigenin 8-C-beta-glucopyranoside (8), apigenin 6-C-beta-glucopyranoside (9), luteolin 8-C-(2''-O-(E)-p-coumaroyl-beta-glucopyranoside) (10), and apigenin 8-C-(2''-O-(E)-p-coumaroyl-beta-glucopyranoside) (11) were isolated from fenugreek seeds. Compounds 1, 5, and 10 were reported for the first time in this species. Signal duplication in the NMR spectra, with exception of spectra of the mono-6-C-substituted compounds, revealed the presence of rotameric conformers, created by rotational hindrance at the C (sp(3))-C (sp(2)) glycosyl-flavone linkage in these flavone C-glycosides.

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Section: Resultsmentioning

confidence: 99%

Flavone C-Glycosides from Seeds of Fenugreek, Trigonella foenum-graecum L.

Rayyan

Fossen²,

Andersen³

2010

J. Agric. Food Chem.

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“…The phenanthrene 4,7-dihydroxy-2methoxy-9,10-dihydrophenanthrene (25) was identified from the species Encyclia longifolia (Bhattacharyya et al 2006). A symmetric dimeric diphenanthrene (26) was isolated from Prosthechea michuacana (synonym Encyclia michuacana), which contains an unusual prenylation, unique among New World orchids, and which has shown potent antioxidant activity (Gutierrez 2010).…”

Section: Phenanthrenesmentioning

confidence: 99%

Bioactive natural products from orchids native to the Americas - A review

POMINI,

SAHYUN,

OLIVEIRA

et al. 2023

An. Acad. Bras. Ciênc.

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The purpose of this review is to provide information on the traditional uses, phytochemical and pharmacological studies performed with species of orchids native to the Americas and the Caribbean Islands. The treatment of inflammation is the most traditional use for plants of this family, specially in Central America, while anti-inflammatory and anticancer assays are oftenly reported in pharmacological investigations. From the chemical point of view, they are sources of phenanthrenoids and stilbenes, rare secondary metabolites not commonly found in other families of plants, as well as cycloartane triterpenes, pyrrolizidine alkaloids and flavonoids. Since just few species were chemically and pharmacologically studied, in comparison to the large number of native species (less than 0.5% of the total), the orchids of the New World may be an interesting niche for the discovery of new, bioactive natural products.

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Isolation and Characterization of the ‘Flavonoid Crystals’ of Three Species of Prosthechea: Chemotaxonomic Considerations of the Genera Prosthechea and Encyclia

Cited by 2 publications

References 10 publications

Flavone C-Glycosides from Seeds of Fenugreek, Trigonella foenum-graecum L.

Flavone C-Glycosides from Seeds of Fenugreek, Trigonella foenum-graecum L.

Bioactive natural products from orchids native to the Americas - A review

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