Nasimaluns A and B:  neo-Clerodane Diterpenoids from Barringtonia racemosa

Abstract

An ethanolic extract of the roots of Barringtonia racemosa afforded two novel neo-clerodane-type diterpenoids, methyl-15, 16-epoxy-12-oxo-3,13(16),14-neo-clerodatrien-18, 19-olide-17-carboxylate (nasimalun A, 1) and dimethyl-15,16-epoxy-3, 13(16),14-neo-clerodatrien-17,18-dicarboxylate (17-carboxymethylhardwickiic acid methyl ester, nasimalun B, 2) by NMR and MS analyses and by comparison of their spectral data with related compunds. The relative stereochemistry of the asymmetric centers in 1 and 2 was determined by selective 1D NOESY experiments.

Inhibition of α‐glucosidase and amylase by bartogenic acid isolated from Barringtonia racemosa Roxb. seeds

“…Phytochemical analysis of B. racemosa stem bark revealed the presence of 3,3′-dimethoxy ellagic acid, dihydromyticetin, gallic acid, bartogenic acid and stigmasterol (Sun et al, 2006), olean-18-en-3-β-O-Ecoumaroyl ester and olean-18-en-3-β-O-Z-coumaroyl esters along with germanicol, germanicone, betulinic acid, lupeol and taraxerol (Yang et al, 2006). Analysis of the ethanol extract of roots showed the presence of the neo-clerodane type diterpenoids, nasimalun A and nasimalun B (Hasan et al, 2000).…”

α-Glucosidase inhibitory monoacylated polyhydroxytriterpenoids from the fruits of Barringtonia racemosa

“…Compounds (1-2) encountered in our study represents the co-occurrence of monoacylated barringtogenol C (1b) and R 1 -barrigenol (2b) is unusual in the same plant while diacylated triterpenoids of either 1b or 2b are reported from Foetidia Africana 10 and B. asiatica 11 Table 2 (1) and (2) Alkaline hydrolysis of 1 yielded barringtogenol C (1b), the structure of which was deduced on the basis of comparison of spectroscopic data with reported data. 13 The relative configuration of 1 was determined from the magnitude of coupling constants of the relevant hydrogens and from the observed 1 H-1 H NOESY (Table 2) (Figure 3).…”

“…Barringtonia is an important old world genus, and consists of 20 species that are distributed from tropical Africa to Formosa, Polynesia, and northern Australia. 4 Plants of the genus Barringtonia in the Lecythidaceae family are well known as a rich natural resource of acylated triterpenoids in the pharmacologically important cyclosqualenoid structural framework. 5 Our continuing study [6][7] on the acylated triterpenoids of B. racemosa has now led to the isolation and characterization of rare class of two novel monoacylated polyhydroxylated triterpenoids (1 and 2) along with three known compounds.…”

Ethnobotanical Profiles and Phytochemical Constituents of Barringtonia racemosa L. for Potential Scrutiny of Bioactive Compounds through Plant Biotechnology

“…In year 2000, a research had been documented 58 which reported the presence of two novel neoclerodane type diterpenoids which were methyl-15, 59 from the extract of stem bark. In 2008, NurulMaryam et al, 60 reported that great amount of β-carotene and lycopene were found in the ethanolic extract of B. racemosa leaf.…”