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Pentacyclic chemical compound in plant leaves and fruit
Oleanolic acid[1]
Names
IUPAC name
3β-Hydroxyolean-12-en-28-oic acid
Systematic IUPAC name
(4aS S R R S R R S 2 H
Other names
Oleanic acid
Identifiers
CAS Number
3D model (JSmol )
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.347
EC Number
IUPHAR/BPS
PubChem CID
UNII
CompTox Dashboard (EPA )
InChI=1S/C30H48O3/c1-25(2 )14-16-30(24(32 )33)17-15-28(6 )19(20(30 )18-25)8-9-22-27(5 )12-11-23(31 )26(3,4)21(27 )10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1 Y
Key: MIJYXULNPSFWEK-GTOFXWBISA-N Y
InChI=1S/C30H48O3/c1-25(2 )14-16-30(24(32 )33)17-15-28(6 )19(20(30 )18-25)8-9-22-27(5 )12-11-23(31 )26(3,4)21(27 )10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1
Key: MIJYXULNPSFWEK-GTOFXWBIBS
Key: MIJYXULNPSFWEK-GTOFXWBISA-N
O=C(O )[C@@]54[C@H](/C3=C/C[C@H]1[C@](CC[C@@H]2[C@]1(C )CC[C@H](O )C2(C )C)(C )[C@]3(C )CC4)CC(C )(C )CC5
Properties
Chemical formula
C 30 H 48 O 3
Molar mass
−1
Appearance
White
Melting point
> 300 °C (572 °F; 573 K )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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]
Natural occurrence [ edit ]
Oleanolic acid can be found in olive oil , Phytolacca americana Syzygium Olea europaea [3] Rosa woodsii Prosopis glandulosa Phoradendron juniperinum Syzygium claviflorum Hyptis capitata Mirabilis jalapa [4] Ternstroemia gymnanthera Syzygium species including java apple (Syzygium samarangense Ocimum tenuiflorum
Biosynthesis of oleanolic acids [ edit ]
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] [5] [6] [6] [6]
Biosynthesis of Oleanolic Acid in Saccharomyces Cerevisiae
Pharmacological research [ edit ]
Oleanolic acid is relatively non-toxic, hepatoprotective , and exhibits antitumor and antiviral properties.[7] HIV [8] HCV activities in vitro analogs are being investigated as potential drugs.[9]
An extremely potent synthetic triterpenoid analog of oleanolic acid was found in 2005, that is a powerful inhibitor of cellular inflammatory processes. They work by the induction by IFN-γ of inducible nitric oxide synthase (iNOS) and of cyclooxygenase 2 in mouse macrophages . They are extremely potent inducers of the phase 2 response (e.g., elevation of NADH-quinone oxidoreductase and heme oxygenase 1 ), which is a major protector of cells against oxidative and electrophile stress.[10]
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] 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 activates telomerase in peripheral blood mononuclear cells (PBMCs) 5.9-fold, more than any other compounded tested, with the exception of Centella asiatica [14] Astragalus TA-65 2.2-fold, and maslinic acid 2-fold.[14]
See also [ edit ]
References [ edit ]
^ "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 b Fukushima 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 c Dale 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 b Tsoukalas 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 .
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Oleanolic_acid&oldid=1215701684 " C a t e g o r i e s : ● T r i t e r p e n e s ● S e c o n d a r y a l c o h o l s ● H y d r o x y a c i d s H i d d e n c a t e g o r i e s : ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a ● C h e m i c a l a r t i c l e s w i t h m u l t i p l e c o m p o u n d I D s ● M u l t i p l e c h e m i c a l s i n a n i n f o b o x t h a t n e e d i n d e x i n g ● A r t i c l e s w i t h o u t K E G G s o u r c e ● A r t i c l e s w i t h c h a n g e d E B I i d e n t i f i e r ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● A r t i c l e s w i t h G N D i d e n t i f i e r s
● T h i s p a g e w a s l a s t e d i t e d o n 2 6 M a r c h 2 0 2 4 , a t 1 7 : 0 8 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
