Homaloside D

J Ethnopharmacol. 2010 Jul 20;130(2):272-4.

Antimalarial compounds from the aerial parts of Flacourtia indica (Flacourtiaceae).[Pubmed: 20457242]

In the Comoros Islands, the aerial parts of Flacourtia indica are used in traditional medicine to treat malaria. Because of the important use of this plant, the phytochemistry of the aerial parts was investigated.
METHODS AND RESULTS:
Three compounds were isolated from the decoction of this plant material, pyrocatechol, Homaloside D and poliothrysoside. The in vitro antiplasmodial activity on the chloroquine-resistant strain (W2) of Plasmodium falciparum and the cytotoxicity on two complementary human cell lines (THP1, HepG2), of AcOEt extract obtained after liquid/liquid extraction of the decoction and pure compounds, were evaluated. The poliothrysoside isolated from the AcOEt extract presented a strong antiplasmodial activity (IC(50)=7.4 microM) and a good selectivity index (>28) similar to chloroquine.
CONCLUSIONS:
This study reports for the first time antiplasmodial activity for Flacourtia indica, for its AcOEt extract and the three major constituents and confirms its traditional use.

J Nat Prod. 1993 May;56(5):699-707.

A phytochemical investigation of Homalium ceylanicum.[Pubmed: 8326319]

METHODS AND RESULTS:
Vacciniin [4] (6-O-benzoyl-D-glucopyranoside) and two new benzenoid glucosides, homaloside A [1] (1''-O-benzyl-3''-O-benzoyl-alpha-L-arabinopyranosyl(1'''-->4'')- beta-D-glucopyranoside) and Homaloside D [2] [1-(1'-hydroxy-6'-oxocyclohex-2'-ene-carboxymethyl)- 5-hydroxyphenyl-6''-O-benzoyl-beta-D-glucopyranoside], were isolated from the n-BuOH fraction of Homalium ceylanicum (Flacourtiaceae). A novel cyclohexenone carboxylic acid ester, 1-hydroxy-6-oxocyclohex-2-enoic acid methyl ester [3], was also isolated from this fraction.
CONCLUSIONS:
The structures were elucidated by chemical and nmr (COLOC, FLOCK, and selective INEPT) techniques.