19 alpha-Hydroxyasiatic acid

Ursolic acid analogues: non-phenolic functional food components in Jamaican raspberry fruits[Reference: WebLink]

Food Chemistry, 2009, 116(3):633-637.

The Rubus genus produces numerous species that are known for their medicinal properties. Rubus rosifolius, called the red raspberry, grows wild in elevated regions in Jamaica.
METHODS AND RESULTS:
Phytochemical examination of the ethyl acetate extract of the fruit yielded eight compounds of the 19-α-hydroxyursane type: euscaphic acid (1), 1-β-hydroxyeuscaphic acid (2), hyptatic acid B (3), 19 alpha-Hydroxyasiatic acid(4), trachelosperogenin (5), 4-epi-nigaichigoside F1 (6), nigaichigoside F1 (7), and trachelosperoside B-1 (8), as confirmed by NMR spectroscopy. Inhibition of cell proliferation by these compounds were determined by using MCF-7 (breast), SF-268 (CNS), NCI H460 (lung), HCT-116 (colon) and AGS (gastric) human tumour cells. Among the human tumour cell lines assayed, only compounds 3 and 6 displayed significant growth inhibition and was specific to colon tumour cells by 56% and 40%, respectively. These ursolic acid analogues were also tested for anti-inflammatory activity using in vitro cycloxegenase-1 (COX-1) and cycloxegenase-2 (COX-2) enzyme inhibitory assays.
CONCLUSIONS:
Compounds 1, 2 and 3 showed selective COX-1 enzyme inhibitory activity (13%, 25% and 35%) at 25 μg/ml. In the lipid peroxidation (LPO) inhibitory assays, compounds 2, 4, 7 and 6 inhibited LPO by 62%, 60%, 53% and 68%, respectively, at 25 μg/ml.

Production of triterpene acids by cell suspension cultures of Olea europaea.[Pubmed: 17473469 ]

Chem Pharm Bull (Tokyo). 2007 May;55(5):784-8.

Olive (Olea europaea) contains large quantity of triterpene acids including oleanolic acid (6) as a major one. Varieties of biological activities exhibited by triterpene acids attracted our attentions, especially from pharmaceutical viewpoints. Cell culture of olive plant was induced and its triterpene constituents were studied.
METHODS AND RESULTS:
From the cell suspension cultures, six ursane type triterpene acids; ursolic acid (9), pomolic acid (10), rotundic acid (11), tormentic acid (12), 2alpha-hydroxyursolic acid (13) and 19 alpha-Hydroxyasiatic acid (14), and two oleanane type acids; oleanolic acid and maslinic acid (7), have been isolated. Quantity of ursane type triterpene acids produced by cell cultures was larger than that of oleanane type. Further, a multifunctional oxidosqualene cyclase (OSC) named OEA was cloned by homology based PCRs from the same cultured cells.
CONCLUSIONS:
Major product of OEA is alpha-amyrin (ursane skeleton), showing good accordance to higher content of ursane-type triterpene acids in the cultured cells, and strongly suggesting OEA to be a major contributor OSC for their production.

The anticoagulant effects ofGeum japonicum extract and its constituents.[Reference: WebLink]

Phytotherapy Research, 1998, 12(2):146-148.

METHODS AND RESULTS:
Anticoagulation activity-guided fractionation led to the isolation of seven triterpenoid compounds from the methanol extract of the whole plant of Geum japonicum and their identification was based on spectroscopic methods.
CONCLUSIONS:
Of these compounds, 19 alpha-Hydroxyasiatic acid (2α, 3β, 19α, 23-tetrahydroxy-12-ursen-28-oic-acid) showed significant anticoagulant effect on the extrinsic pathway.