Chemical constituents from the bark of Anisopus mannii

Abstract

A minor novel 1,7-naphthyridine alkaloid with an unprecedented skeleton, named anisopusine (1), was isolated from the CH2Cl2 soluble materials of an acetone extract of the bark of Anisopus mannii (Asclepiadaceae) together with four known compounds 5α-hydroxy-lup-20(29)-en-3β-yl eicosanoate (2), [6]-gingerdione (3), [6]-dehydrogingerdione (4), and ferulic acid (5). Their structures were determined on the basis of spectroscopic data, including 1D and 2D NMR, HR-EI-MS. Compounds (2–5) were characterized for the first time from this genus.

Fruits of wild and semi‐domesticated Diospyros tree species have contrasting phenological, metabolic, and antioxidant activity profiles

“…[10]‐Gingerdione was, possibly, another discriminant D. rekoi fruit metabolite. It has been mostly reported as a pungency factor in rhizomes of the monocot ginger plant, although the chemically related [6]‐gingerdione, was identified in the bark of a perennial herbaceous shrub phylogenetically close to the Ericales . Other discriminant metabolites were kaurane diterpenoids such as annoglabasin A (methyl‐16 β ‐acetoxy‐19‐al‐ ent ‐kauran‐17‐oate)/annoglabasin B (16 α ‐hydro‐19‐acetoxy‐ ent ‐kauran‐17‐oic acid).…”

“…It has been mostly reported as a pungency factor in rhizomes of the monocot ginger plant, although the chemically related [6]-gingerdione, was identified in the bark of a perennial herbaceous shrub phylogenetically close to the Ericales. 60 Other discriminant metabolites were kaurane diterpenoids such as annoglabasin A (methyl-16 -acetoxy-19-alent-kauran-17-oate)/annoglabasin B (16 -hydro-19-acetoxy-entkauran-17-oic acid). These have been principally reported in fruits of Annona glabra, although they may be present in plant species belonging to several families, including mannic acid, a novel dimeric ent-kaurane diterpene identified in various Diospyros mannii tissues.…”

Domino Reaction of Arylglyoxals with Pyrazol-5-amines: Selective Access to Pyrazolo-Fused 1,7-Naphthyridines, 1,3-Diazocanes, and Pyrroles

“…Representative Synthesis of 4: (3,4,5,6,7,4′,3′-g] [1,3]diazocine-5,10-diyl)bis(phenylmethanone) (4a). Typically, 2,2-dihydroxy-1phenylethanone (1a; 2.2 mmol, 0.334 g, 1.1 equiv) and 1-methyl-3phenyl-1H-pyrazol-5-amine (2c; 2.0 mmol, 0.346 g, 1.0 equiv) were introduced into a 10 mL Initiator reaction vial, and p-TsOH (1.0 equiv) and DMF (1.5 mL) were then added successively.…”

“…The structural range and biological importance of functional 1,7-naphthyridines have made them attractive targets of research for many years. 1 Their derivatives are found in various natural alkaloids such as eburnamonine, 2 anisopusine, 3 and tacamonine 4 (Figure 1 ), which have appreciable chemical and biological importance. In addition, a variety of synthetic 1,7-naphthyridine derivatives have possessed widespread biological activities, including hypotensive activity, 5 neurokinin NK1-receptor antagonists, 6 antimalarial agents, 7 selective Tpl2 kinase inhibitors, 8 anti-inflammatory activity, 9 and antagonistic agents.…”

Chemical composition and antimicrobial activity of hexane leaf extract of Anisopus mannii (Asclepiadaceae)

“…Previously, the proximate composition, mineral elements and anti-nutritional factors of A. mannii were reported [ 7 ]. The phytochemical and antimicrobial screening of the stem aqueous extract [ 8 ], the analgesic and anti-inflammatory studies of methanol leaf extract [ 9 ] as well as the isolation of chemical constituents such as 1, 7-naphthyridine alkaloid- named anisopusin, 5-hydroxy-lup-20(29)-en-3-yl eicosanoate, 6-gingerdione, 6-dehydrogingerdione and ferulic acid from acetone extract of the stem bark have been reported [ 10 ]. However, no previous phytochemical or biological studies on the non-polar constituents of A. mannii have been reported.…”