New flavonoids from the Saudi Arabian plant Retama raetam which stimulates secretion of insulin and inhibits α-glucosidase

Retama raetam is a bush which is a member of the family Fabaceae. It is used traditionally in North Africa and Saudi Arabia for the treatment of diabetes. Several flavonoids and alkaloids are already known from this plant. Chromatographic fractionation and purification led to the isolation of three...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-01, Vol.17 (5), p.1266-1276
Main Authors: Nur-E-Alam, Mohammad, Yousaf, Muhammad, Parveen, Ifat, Hafizur, Rahman M, Ghani, Usman, Ahmed, Sarfaraz, Hameed, Abdul, Threadgill, Michael D, Al-Rehaily, Adnan J
Format: Article
Language:English
Subjects:
Alkaloids
Animals
Chromatography, High Pressure Liquid
Derivatives
Diabetes
Diabetes mellitus
Drug development
Fabaceae - chemistry
Flavones
Flavonoids
Flavonoids - chemistry
Flavonoids - isolation & purification
Flavonoids - pharmacology
Fractionation
Glucosidase
Glycoside Hydrolase Inhibitors - pharmacology
Insulin
Insulin - metabolism
Isoflavones
Male
Mice
Mice, Inbred BALB C
Natural products
NMR
Nuclear magnetic resonance
Pancreas
Plant Extracts - pharmacology
Purification
Retama raetam
Saudi Arabia
Secretion
Spectrum Analysis - methods
α-Glucosidase
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Summary:Retama raetam is a bush which is a member of the family Fabaceae. It is used traditionally in North Africa and Saudi Arabia for the treatment of diabetes. Several flavonoids and alkaloids are already known from this plant. Chromatographic fractionation and purification led to the isolation of three new derivatives of prenylated flavones, retamasin C-E, and four new derivatives of prenylated isoflavones, retamasin F-I, in addition to two isoflavones which have not been previously reported in this plant. Particularly interesting structures included isoflavones containing 3,5-dihydro-2H-2,5-methanobenzo[e][1,4]dioxepine and 3a,8b-dihydro-7-hydroxyfuro[3,2-b]benzo[2,1-d]furan units, both of which are new amongst natural product flavonoids. Five new examples (two flavones and three isoflavones) strongly enhanced the glucose-triggered release of insulin by murine pancreatic islets and one isoflavone was a potent inhibitor of α-glucosidase. This study may rationalise the traditional medicinal use of R. raetam and provide new leads for drug design in the treatment of diabetes.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02755b