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Home » Products » Phytochemicals » Ursolic Acid

Ursolic Acid



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Product Code : 16

Product Specification
Ursolic Acid
IUPAC name : 3ß-hydroxy-urs-12-en-28-oic acid
Mol. Formula: C30H48O3
Mol. Wt: 456.68

Description: Occurs as large white lustrous prisms
Solubility at 15°C: One part dissolves in 88 parts methanol, 178 parts alcohol (35 boiling alcohol), 140 parts ether, 388 parts chloroform. Soluble in hot glacial acetic acid and 2 % alcoholic NaOH. Insoluble in petroleum ether, and water.
Physical constants : M.P. 285-288 oC
Assay : Purity min. 95.00%
Category : Anti – inflammatory, hepatoprotective

Quantitative determination:
HPLC : Mobile phase : Methanol: Water (90: 10)
Wavelength : λmax  220nm  
Column : C18 column (3.9 x 300 mm), We can offer 50 % and 90 % pure ursolic acid.
 
Chemical nature of ursolic acid:
Ursolic acid is a pentacyclic triterpenoid belonging to the  - amyrin group. It rarely occurs without oleanolic acid, which is a ß - amyrin group triterpenoid. They may occur in the acid form or in glycoside form, which comprises of a triterpenoid aglycone linked to one or more sugar moieties. Ursolic acid and its derivatives are constituents of numerous plants which have diversified phytogenetic origin and taxonomic position. It has been isolated from the protective wax like coating of apples, pears, cranberries, prunes, and other fruits. Seaweeds are rich in ursolic acid derivatives. Some of the common plants containing ursolic acid are Tulsi, Rosemary, Periwinkle, Peppermint, Indian oleander and Eucalyptus.

Pharmacological actions of ursolic acid:
Ursolic acid is a powerful natural anti – inflammatory agent. The mechanism of this action involves inhibition of histamine release from mast cells. It causes inhibition of LOX and COX, which in turn reduces synthesis, and release of PGE3 and leucotrienes1,2,3,4.

Ursolic acid is found to be a hepatoprotective agent. The mechanism of hepatoprotection involves protection against chemically induced liver necrosis, suppression of cytochrome P – 450, inhibition of lipid peroxidation, prevention of fibrosis and stimulation of liver cell regeneration5,6. Ursolic acid causes inhibition of tumor promotion, which is due to inhibition of mutagenicity7,8,9.

Ursolic acid and 3 o acetyl ursolic acid decreases blood cholesterol, ß - lipoproteins and phospholipids in rabbits with experimental atherosclerosis. Acetylation of ursolic acid at C – 3 enhances anti – hyperlipidemic and anti – atherosclerotic effectiveness10Ursolic acid has been found to be a trypanocidal agent. It killed all the epimastigotes of T. cruzi11.

References:
  • Mahato, S. B., et al., Phytochemistry, 1988, 27, 3037-3067
  • Therese Ringborn; Premila Perera; Laura Segura; Ylva Noreen; Lars Bohlin; J.  Nat. Prod.; 1998, 61, 1212-1215.
  • Huguet A.-Z.; del Carmen Reico, M.; Manez S.; Giner R.-M.; Rios J.-L.; Eur. J. Phrmacol. Chem. Abstr.134: 231677c (2001).
  • Subbaramaiah Kotha; Michaluart Pedro; Sporn Michael B.; Dannenberg Andrew J.; Cancer Research, 2000, 60 (9), 2399-2404, Chem. Abstr.133: 68558h, (2000).
  • Liu, Y.P; et al., J. Pharm. Exp. Ther., 1993, 266, 1067-1613.
  • Saraswat Binduja; Visen P. K .S.; Dayal R.; Agarwal D. P.; Patnaik G.K.; Ind. J. Pharmacol., 1996, 28 (4), 232-239, Chem. Abstr., 126:126875c
  • Choi Yung Hyun; Bek Jin Hen; Yoo Mi-ae; Chung Hae-young; Kim Nam Deuk; Kim Kyu-won; Int. J. Oncol., 2000, 17 (3), 565-571, Chem. Abstr., 134: 95186n, (2001).
  • Hsu Hsuw-Yin; Yang Jenq-Jer; Lin Chun-ching; Cancer Lett., (Shannon, Irel.), 1997, 111 (1, 2), 7-13; Chem. Abstr.126: 152451f, (1997).
  • Komiya Takashi; Achiwa Yumiko; Katsuzaki Hirotaka; Imai Kunio; Sakurai Shinobu; Urakawa Kayako; Ohnishi Kazuko; Adachi Takuo; Yamada Tetsuya; Hibasami Hiroshige; Food Sci. Technol. Int., Tokyo, 1998, 4 (4), 282-284; Chem. Abstr.,130: 306224f, (1991).
  • Venkateswara, Rao K. N.; Gopalkrishnan V.; Kishore B. V. S. H.; Rajendra Prasad K.; Shrikanth P.; Ind. Drugs, 2001, 38(5), 216-224.
  • Fumiko Abe, Tatsuo Yamauchi, Tsuneatsu Nagao, Junei Kinjo, Hikaru Okabe, Hiroo Higo, and Hiroshige Akahane; Biol. Pharm. Bull., 25(11), 1485-1487 (2002).
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