Triterpenoid Saponins from Symplocos lancifolia

Abstract

Three new bidesmosidic saponins (1-3) and a new ursane triterpenoid, 2α,3β,11α,23-tetrahydroxyurs-12-en-28-oic acid (4), along with seven known compounds, were isolated from a methanolic extract of the leaves of Symplocos lancifolia. The bidesmosidic saponins were found to possess the same sugar unit part, composed of two β-d-glucose moieties and one α-l-rhamnose moiety, linked to maslinic acid, arjunolic acid, and asiatic acid, respectively. Their structures were elucidated by interpretation of their 1D and 2D NMR spectra and completed by analysis of the HRESIMS data. The antibacterial activity of the isolated triterpenoids was evaluated against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa, and several showed activity against Gram-positive bacteria.

Antimicrobial Constituents from Leaves of Dolichandrone spathacea and Their Relevance to Traditional Use

“…The presence of 36 carbons was observed in the 13 C-NMR spectrum including 6 carbons for a β-D-glucopyranose and 30 carbons for a Δ 12 ursene skeleton with δ C 130.0 (CH-12) and 138.9 (C-13; ▶ table 2). The glucose unit was linked to the triterpene moiety at position C-28 since an HMBC correlation was observed between the anomeric proton H-1' and the carbonyl C-28 at δ C 178.5 [36]. The aglycone was determined to be triterpene uncaric acid (or 3β,6β,19α-trihydroxyurs-12-en-28-oic acid) [37].…”

Metabolites from Combretum dolichopetalum and its associated endophytic fungus Nigrospora oryzae — Evidence for a metabolic partnership

“…Our chemical examination of the roots of C. dolichopetalum led to the isolation of six known compounds including ellagic acid (1) [15], 3,3′,4-tri-O-methylellagic acid (2) [16], arjunolic acid (3) [17], 4′-dihydrophaseic acid (4) [18], echinulin (5) [19] and arestrictin B (6) [20]. Investigation of the EtOAc extract of the endophytic fungus N. oryzae yielded the new altersolanol derivative, 4-dehydroxyaltersolanol A (9), in addition to two known sesquiterpenoids, (S)-7′-hydroxyabscisic acid (7) [21] and (S)-abscisic acid (8) [22] (Fig.…”

A Fatty Acid Glycoside from a Marine-Derived Fungus Isolated from Mangrove Plant Scyphiphora hydrophyllacea

“…The stereochemistry of the asymmetric center of 1 at C-3 was proposed to be R by acid hydrolysis, similar to R -3-hydroxydecanoic acid methylester [9], based on the negative sign of its specific rotation ([α] 21 D −20.5, ( c 1.0, CHCl 3 )). Meanwhile, the sugar moiety of 1 was determined as L -rhamnose based on the positive sign of its specific rotation [11]. Thus, the structure of 1 was established as R -3-hydroxyundecanoic acid methylester-3- O -α-l-rhamnopyranoside.…”