Methyl ursolate

Acetylhydroxy-L-proline, 1014 Acetyl hypobromite, 12-13 N-Acetylimidazole, 13 S-Acetylmercaptosuccinic anhydride, 13 Acetyl methyl ursolate, 823... 

Micheli applied this epoxide procedure to acetyl methyl ursolate, which contains II highly hindered double bond, and isolated the ketone formulated in high yield. 

In order to obtain more information on the chemical reactions involved in the LOX inhibitory effect of triterpenes, ursolic acid and its analogues (uvaol, oleanolic acid and methyl ursolate) were studied on LOX activity. The best inhibitors of soybean 15-LOX were ursolic and oleanolic acids, with IC50 values of 0.175 and 0.265 mM, respectively. These results showed that the carboxylic group in the position 28 in ursolic acid is implicated in the inhibition of LOX activity because methylation of this functional group abolished it. Other structural features of ursolic acid are also relevant for its inhibitory effect, for oleanolic acid is less active than ursolic acid, and yet they only differ in the position of one methyl group (at C-20 instead of C-19) [101]. 

Ursolic acid and methyl ursolate Malus domestica HSCCC n-hexane AcOEt MeOH water ESI- MS [133]... 

Microbial transformation of methyl ursolate by Mucor plumbeus ATCC 4740 [85],... 

Methyl ursolate, 3p,28-dihydroxy-urs-12-ene (100), and the 3p,28-bis (dimethylcarbamoxy) derivative of 100 were incubated with Mucor plumbeus ATCC 4740 by Collins et al. [85]. Only methyl ursolate xmderwent hydroxylation to give the novel compoxmd 3p,7p,2ip-trihydrox30irsa-9(ll),12-dien-28-oic acid methyl ester as the sole product (Figure 28.34). 

Mipando. Cardiotonic and antidys-rhythmic effects of oleanolic and ursolic acids, methyl maslinate and uvanol. Phytomedicine 2004 11(2-3) 121-129. 

Punica granatum L. Shi Liu Pi (Pomegranate) (pericarp, root bark) Pelletierine, isopelletierine, methylisopelletierine, methyl-pelletierine, pseudopelletierine, gallotannic acid, sitosterol, ursolic acid, maslinic acid, elegic and gallic acid.33-450 This herb is toxic. Purges intestinal parasites. 

Methylation at C-4 of sterol nucleus was one of the other factors affecting activity enhancement. Thus, in general, 4-methylsterols (14,15) and 4,4-dimethylsterols (8,13) exhibited higher activity than 4-desmethylsterols. A similar structure-activity relationship was observed also in the HHPA-induced inflammation on mouse ear [35]. Whereas cholesterol (7) did not show inhibitory activity, several 4,4-dimethylcholestane derivatives, 0-12, exhibited activity. 4,4-Dimethylcholestane-3a,5a-diol (12) was the most potent inhibitor its activity was comparable to that of ursolic acid (210) [35]. Compound 12 reduced also the inflammation induced by teleocidin B (3), one of the indole alkaloid-type of tumor promoters [53]. 

Ursolic acid methyl ester (ursene triterpene) Semi-synthetic from Ursolic acid HIV-1 protease (14 pM) [53]... 

Other common plant-derived triterpenoid acids, such as oleanolic and ursolic acid, exhibit weak antiinflammatory and antitumor activities, and studies have been directed at the synthesis of new analogues having increased potencies. These studies have led to the synthesis of 2-cyano-3,12-dioxoolean-l,9-dien-28-oic acid (CDDO) (54) and its methyl ester (55), which exhibit potent in vitro and in vivo antitumor activity against a wide range of tumors, including breast and pancreatic carcinomas and leukemias. ... 

In the Croteau and Fogerson study, the triperpenic alcohols and sterols were derivatized into their trimethylsilyl ether derivatives using bis-trimethylsilylacetamide. The isopropanol-chloroform extract contained higher amounts of sterols and triteipenic alcohols such as p-sitosterol and amyrin compared to the SF extract. This could be due to the high polarity of the extracting liquid solvent as opposed to the supercritical fluid, and the increased volatility of the silylated sterols and triteipenic compounds relative to our fatty acid methyl esters, in addition to these compounds, the isopropanol-chloroform extract reported earlier also contained ursolic acid, a polar triteipenic acid, which was not extracted with pure CO2. 

Lonicera angustifolia Wallich ex DC is a deciduous, erect shrub 1.8-3.6 m high, with sweet edible berries, found in the Himalaya from Kashmir to Kumoan, Nepal, Arunachal Pradesh at an altitude of 1,800 -3,600 m. [67,153]. Oleanolic acid, ursolic acid and methyl 4-hydroxy benzoate with iridoids and secoiridoids sweroside, loganin and 6 -0-p-apiofuranosyl sweroside (121) have been isolated from leaves [182]. Its fruits are used in folk medicine to relieve gastric troubles in cattle, flowers are useful source of be-forage. 

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