Self gelating isoracemosol A, new racemosaceramide A, and racemosol E from Barringtonia racemosa

Abstract

Phytochemical investigation into the CHCl extract of the fruits of Barringtonia racemosa resulted in the isolation of two new metabolites along with isoracemosol A and betulinic acid as known metabolites. The new compounds were characterised as phytosphingosine-type ceramide [(2S,3S,4R)-2-[(2R)-2-hydroxyhexadecanoyl amino]-hexacos-8(E)-ene-1,3,4-triol, 1] and racemosol E [21β-acetoxy-22α-(2-methylbutyroxy)-olean-12-ene-3β,16α,28-triol, 2] on the basis of extensive spectroscopic data analysis and chemical modifications. In addition, the self-gelating property of isoracemosol A (3) was investigated for the first time, which leads to the unexpected agglomerated porous-like morphology.

Indigenous Uses, Phytochemical Analysis, and Anti-Inflammatory Properties of Australian Tropical Medicinal Plants

“…Bangladesh, China, India, Taiwan, and Vietnam Stem bark; seeds; roots; leaves Olean-18-en-3β-O-E-coumaroyl ester, Olean-18-en-3β-O-Z-coumaroyl ester, Germanicol, Germanicone, Betulinic acid, Lupeol, Taraxerol [56]; 3,3'-Dimethoxy ellagic acid, Dihydromyticetin, Gallic acid, Bartogenic acid, Stigmasterol [57,58]; Rutin [59,60]; Nasimalun A and B [61]; Barringtin D1-D3, and M1, Casuarictin, Tellimagrandin I, Valoneic acid dilactone, Schimawalin A [62]; Isoracemosol A, Racemosaceramide A, Racemosol A and E [58,63]; Barringtogenol C [58]; 3β-p-E-Coumaroymaslinic acid, cis-Careaborin, Careaborin, Maslinic acid, 2α,3β,19α-Trihydroxyolean-12-ene-24,28-dioic acid, 3β-p-Z-coumaroylcorosolic acid, Corosolic acid, 1α,2α,3β,19α-Tetrahydroxyurs-12-en-28-oic acid, 19α-Hydroxyl ursolic acid, 3α,19α-Dihydroxyurs-12-en-24,28-dioic acid, Tormentic acid, 3-Hydroxy-7,22-dien-ergosterol [64]; Barringosides G-I [65].…”

Biotransformation of Artemisinin to 14-Hydroxydeoxyartemisinin: C-14 Hydroxylation by Aspergillus flavus

“…As part of our ongoing program on the isolation − and biotransformation , of bioactive compounds, we carried out biotransformation of artemisinin ( 1 ), which afforded four metabolites. They were identified as a new 14-hydroxydeoxyartemisinin ( 2 ) and three known metabolites ( 3 – 5 , Figure ).…”