3-O-Acetyloleanolic acid

Biotechnol Lett. 2013 Nov;35(11):1807-15.

3-O-Acetyloleanolic acid exhibits anti-angiogenic effects and induces apoptosis in human umbilical vein endothelial cells.[Pubmed: 23801119]

3-O-Acetyloleanolic acid, a pentacyclic triterpenoid isolated from cowpea seeds, inhibited proliferation, migration and tube formation of human umbilical vein endothelial cells (HUVECs) in a dose-dependent manner. HUVECs.
METHODS AND RESULTS:
The induced apoptosis was characterized by detection of cell surface annexin V and sub-G1 populations. The number of cells immunostained with annexin V-fluorescein isothiocyanate increased after treatment with 3-O-Acetyloleanolic acid. The sub-G1 cell populations were also increased in treated HUVECs. 3-O-Acetyloleanolic acid induced activation of caspase 3, a critical mediator of apoptosis signaling. It also significantly inhibited angiogenesis in an in vivo Matrigel plug assay.
CONCLUSIONS:
3-O-Acetyloleanolic acid thus exhibits anti-angiogenic effects and induces apoptosis in HUVECs and the results suggest that it has a potential use for suppression of the tumor growth stimulated by angiogenesis.

J Nat Prod. 2006 Dec;69(12):1687-91.

Antihyperglycemic activity and chemical constituents of Eysenhardtia platycarpa.[Pubmed: 17190443]

The methanolic extracts from branches (BEP) and leaves (LEP) of Eysenhardtia platycarpa significantly decreased the blood glucose levels in normal and streptozotocin (STZ)-induced diabetic rats.
METHODS AND RESULTS:
One new flavone, (1"R)-5,4',1"-trihydroxy-6,7-(3",3"-dimethylchroman)flavone (1), together with the known compounds 5,7-dihydroxy-6-methyl-8-prenylflavanone (3), 5,7-dihydroxy-8-methyl-6-prenylflavanone (4), 5,7-dihydroxy-6-prenylflavanone (5), 5,7-dihydroxy-8-prenylflavanone (6), 3-O-Acetyloleanolic acid (7), oleanolic acid, 3beta-acetoxy-11alpha,12alpha-epoxy-oleanan-28,13beta-olide, lupeol, betulinic acid, beta-sitosterol, beta-sitosteryl beta-D-glucopyranoside, beta-sitosteryl palmitate, and 3-O-methyl-myo-inositol were isolated from BEP. Additionally, one new flavanone, (2S)-4'-O-methyl-6-methyl-8-prenylnaringenin (2), as well as the known compounds 3, 4, 6, 4'-O-methyl-8-prenylnaringenin (8), and 5-hydroxy-7-methoxy-8-prenylflavanone (9) were isolated from LEP. 3-O-Acetyloleanolic acid (7), identified as the major constituent of BEP, showed a significant decrease (31 mg/kg of body weight, P < 0.05) in the glucose level of STZ-induced diabetic rats.
CONCLUSIONS:
The obtained results correlate with the traditional use of this species.

Phytother Res. 2012 Oct;26(10):1541-6.

3-O-acetyloleanolic acid induces apoptosis in human colon carcinoma HCT-116 cells.[Pubmed: 22359244 ]

The cytotoxic effect of 3-O-Acetyloleanolic acid, an oleanolic acid derivative isolated from the seeds of Vigna sinensis K., was investigated in human colon carcinoma HCT-116 cells.
METHODS AND RESULTS:
3-O-Acetyloleanolic acid dose-dependently inhibited the viability of HCT-116 cells. Apoptosis was characterized by detection of cell surface annexin V and sub-G1 apoptotic cell populations. The number of immunostained cells with annexin V-FITC was increased after treatment with 3-O-Acetyloleanolic acid. The sub-G1 cell population was also increased. Expression of TRAIL-mediated apoptosis signaling-related death receptor DR5 was increased in 3-O-Acetyloleanolic acid-treated HCT-116 cells. Activation of caspase-8 and caspase-3, critical mediators of extrinsic apoptosis signaling, was also increased by 3-O-Acetyloleanolic acid.
CONCLUSIONS:
The results indicate that 3-O-Acetyloleanolic acid induces apoptosis in HCT-116 cells mediated by an extrinsic apoptosis signaling cascade via up-regulation of DR5.