Myriceric acid B

Eur. J.Org. Chem. 2011, 2011(20-21): 3809-14.

Protoberberine Alkaloids and Cancer Chemopreventive Properties of Compounds from Alangium salviifolium[Reference: WebLink]

METHODS AND RESULTS:
New protoberberine alkaloids, namely alangiumkaloids A (1) and B (2), 27-O-trans-caffeoylcylicodiscic acid (3), and β-d-glucopyranos-1-yl N-methylpyrrole-2-carboxylate (5) together with Myriceric acid B (4), isoalangiside (6), alangiside (7), 3-O-demethyl-2-O-methylalangiside (8), and demethylalangiside (9) have been isolated from Alangium salviifolium. The cancer chemopreventive properties and cytotoxic activities of the isolated compounds were evaluated.
CONCLUSIONS:
Compounds Myriceric acid B, 4, and 9 scavenged DPPH free radicals with IC50 values of 21.4, 21.8, and 24.0 μm, respectively. Alangisides 7 and 9 inhibited superoxide anion radical formation in the xanthine/xanthine oxidase (XXO) assay with IC50 values of 19.4 and 5.3 μm, respectively. Compounds 6–9 showed excellent antioxidant activity in the oxygen radical absorbance capacity (ORAC) assay with 12.8–24.9 ORAC units. Compounds 3 and Myriceric acid B inhibited aromatase activity with IC50 values of 4.7 and 6.8 μm, respectively. Although the isolated compounds showed only weak cytotoxicity or were inactive, compounds 3 and Myriceric acid B exhibited cytotoxic activity towards the MOLT-3 cell line with IC50 values of 5.6 and 3.9 μm, respectively.

Chinese Pharmacological Bulletin, 2010, 26(4):447-451+452.

The anti-HIV-1 entrance activity and mechanism of action of myriceric acid B from Rhoiptelea chiliantha Diels et Hand-Mazz.[Reference: WebLink]

To investigate the HIV-1 entry inhibitory activities of Myriceric acid B and C isolated from Rhoiptelea chiliantha Diels et Hand-Mazz and their mechanism of action.
METHODS AND RESULTS:
The plasmids encoding envelope proteins of HIV-1 (pHXB2) and VSV (pVSV-G) were cotransfected 293T cells with pNL4-3. Luc. R-E- to produce HIV-1 Env pseudovirus and VSV-G pseudovirus, respectively, which were used for testing the antiviral activities of these compounds. ELISA and molecular docking were used to study the mechanism of action of the active compounds. Myriceric acid B could significantly inhibit the infection of HIV-1 Env pseudovirus with an IC50 of (8.3 ± 0.2) mg·L-1. The carbonoxyl group at C-28 position and the hydroxyl group at the C-3 position of Myriceric acid B are important for its anti-HIV-1 activity. Like other HIV-1 entry inhibitors targeting gp41 (eg, ADS-J1 and NB-64), Myriceric acid B could also block the gp41 six-helix bundle formation. Molecular docking analysis suggests that Myriceric acid B may bind to the hydrophobic cavity of the gp41 N-trimeric coiled coil.
CONCLUSIONS:
Myriceric acid B is a potent HIV-1 entry inhibitor targeting gp41 and can serve as a lead compound for developing novel anti-HIV-1 drug.