Unusual C,O-Fused Glycosylapigenins from Serjania marginata Leaves

Abstract

A phytochemical study of a Serjania marginata leaf extract with antiulcer activity afforded 15 compounds, including the new 3-O-α-l-arabinopyranosyl(1→3)-α-l-rhamnopyranosyl(1→2)[β-d-glucopyranosyl(1→4)]-α-l-arabinopyranosyloleanolic acid (1) and 7,5″-anhydroapigenin 8-C-α-(2,6-dideoxy-5-hydroxy-ribo-hexopyranosyl)-4'-O-β-d-glucopyranoside (4). The structures of the new compounds were determined by spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry, and chemical methods. Compound 4 is a C-hexopyranosylapigenin with an unusual cyclic ether linkage between C-5″ and C-7 of apigenin. The isolated proanthocyanidins have high antioxidant activities, and these compounds are probably responsible for the gastroprotective effect of the extract.

Ethnopharmacology, Chemistry and Biological Properties of Four Malian Medicinal Plants

“…After our report on this, cassiaoccidentalin A was found in Serjania marginata (Sapindaceae) leaves [27]. To our knowledge, no other sources for this compound are known.…”

Total Synthesis of Viniferifuran, Resveratrol‐Piceatannol Hybrid, Anigopreissin A and Analogues – Investigation of Demethylation Strategies

“…Our interest in this intriguing family of natural products stems from the finding that the resveratrol tetramer (−)‐hopeaphenol blocks type III secretion, an indispensable virulence system, in the Gram‐negative pathogens Yersinia pseudotuberculosis and Pseudomonas aeruginosa 8. While (−)‐hopeaphenol can be obtained in gram quantities from natural sources9 we focused on the de novo synthesis of partial structures and recently published total syntheses of (±)‐ampelopsin B ( 6 )10 and (±)‐ ϵ ‐viniferin ( 1 ),10 the key intermediate to form almost, if not all, higher order of stilbene structures (Figure 1). 1 To further advance our understanding of structural features that affect inhibition of type III secretion, we have continued to prepare resveratrol dimers.…”

Botanical Extracts of the Brazilian Savannah Affect Feeding and Oviposition of Plutella xylostella (Linnaeus, 1758) (Lepidoptera: Plutellidae)

“…Nevertheless, the scientific literature describes Serjania species to possess different biological properties, such as gastroprotective, antifungal, analgesic, anti-inflammatory, antioxidant, anticancer, and antiprotozoal activities. Phytochemical studies on plants of the genus Serjania reveal the presence of a range of compounds, including saponins, flavonoids, terpenes, steroids, tannins, alkaloids, and fatty acids (Heredia-Vieira et al, 2015).…”