Pentacyclic chemical compound in plant leaves and fruit
Chemical compound
Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.[2]
Oleanolic acid biosynthesis starts with mevalonate to create squalene. Squalene monooxygenase in the next step oxidases the squalene and forms an epoxide resulting in 2,3-oxidosqualene.[5] Beta-amyrin synthase creates beta-amyrin by a ring formation cascade.[5][6] After the formation of beta amyrin, CYP716AATR2, also known as a cytochrome p450 enzyme, oxidizes carbon 28 turning it into alcohol.[6] CYP716AATR2 converts the alcohol to aldehyde and finally to a carboxylic acid forming oleanolic acid.[6]
Biosynthesis of Oleanolic Acid in Saccharomyces Cerevisiae
Pharmacological research
Oleanolic acid is relatively non-toxic, hepatoprotective, and exhibits antitumor and antiviral properties.[7] Oleanolic acid was found to exhibit weak anti-HIV[8] and weak anti-HCV activities in vitro, but more potent synthetic analogs are being investigated as potential drugs.[9]
A 2002 study in Wistar rats found that oleanolic acid reduced sperm quality and motility, causing infertility. After withdrawing exposure, male rats regained fertility and successfully impregnated female rats.[11] Oleanolic acid is also used as standard for comparison of hyaluronidase, elastase and matrix-metalloproteinase-1 inhibition of other substances in primary research (similar to diclofenac sodium for comparison of analgesic activity).[12][13]
^"Oleanolic acid (HMDB0002364)". HMDB. Canadian Institutes of Health Research. Retrieved November 29, 2018.
^Siddiqui S, Siddiqui BS, Adil Q, Begum S (1990). "Constituents of Mirabilis jalapa". Fitoterapia. 61 (5): 471. Archived from the original on 2014-01-04.)
^ a bFukushima EO, Seki H, Ohyama K, Ono E, Umemoto N, Mizutani M, et al. (December 2011). "CYP716A subfamily members are multifunctional oxidases in triterpenoid biosynthesis". Plant & Cell Physiology. 52 (12): 2050–2061. doi:10.1093/pcp/pcr146. PMID 22039103.
^ a b cDale MP, Moses T, Johnston EJ, Rosser SJ (2020-05-01). "A systematic comparison of triterpenoid biosynthetic enzymes for the production of oleanolic acid in Saccharomyces cerevisiae". PLOS ONE. 15 (5): e0231980. Bibcode:2020PLoSO..1531980D. doi:10.1371/journal.pone.0231980. PMC 7194398. PMID 32357188.
^Liu J (December 1995). "Pharmacology of oleanolic acid and ursolic acid". Journal of Ethnopharmacology. 49 (2): 57–68. doi:10.1016/0378-8741(95)90032-2. PMID 8847885.
^Mengoni F, Lichtner M, Battinelli L, Marzi M, Mastroianni CM, Vullo V, Mazzanti G (February 2002). "In vitro anti-HIV activity of oleanolic acid on infected human mononuclear cells". Planta Medica. 68 (2): 111–114. doi:10.1055/s-2002-20256. PMID 11859458.
^Yu F, Wang Q, Zhang Z, Peng Y, Qiu Y, Shi Y, et al. (June 2013). "Development of oleanane-type triterpenes as a new class of HCV entry inhibitors". Journal of Medicinal Chemistry. 56 (11): 4300–4319. doi:10.1021/jm301910a. PMID 23662817.
^Dinkova-Kostova AT, Liby KT, Stephenson KK, Holtzclaw WD, Gao X, Suh N, et al. (March 2005). "Extremely potent triterpenoid inducers of the phase 2 response: correlations of protection against oxidant and inflammatory stress". Proceedings of the National Academy of Sciences of the United States of America. 102 (12): 4584–4589. Bibcode:2005PNAS..102.4584D. doi:10.1073/pnas.0500815102. PMC 555528. PMID 15767573.
^Mdhluli MC, van der Horst G (October 2002). "The effect of oleanolic acid on sperm motion characteristics and fertility of male Wistar rats". Laboratory Animals. 36 (4): 432–437. doi:10.1258/002367702320389107. PMID 12396287. S2CID 34990111.
^Maity N, Nema NK, Sarkar BK, Mukherjee PK (2012). "Standardized Clitoria ternatea leaf extract as hyaluronidase, elastase and matrix-metalloproteinase-1 inhibitor". Indian Journal of Pharmacology. 44 (5): 584–587. doi:10.4103/0253-7613.100381. PMC 3480789. PMID 23112418.
^Nema NK, Maity N, Sarkar BK, Mukherjee PK (September 2013). "Matrix metalloproteinase, hyaluronidase and elastase inhibitory potential of standardized extract of Centella asiatica". Pharmaceutical Biology. 51 (9): 1182–1187. doi:10.3109/13880209.2013.782505. PMID 23763301. S2CID 24453413.
^ a bTsoukalas D, Fragkiadaki P, Calina D (2019). "Discovery of potent telomerase activators: Unfolding new therapeutic and anti-aging perspectives". Molecular Medicine Reports. 20 (4): 3701–3708. doi:10.3892/mmr.2019.10614. PMC 6755196. PMID 31485647.