Triterpenoid acids

A number of important resins are composed of triterpenoids, including the dammar resins which derive from a sub-family of the family Dipterocarpaceae. Dammar resins are fluid, balsamic oleoresins highly suited for caulking and waterproofing. Frankincense (olibanum) is known as a gum-resin collected from various Boswellia spp. and contains amyrin epimers and triterpenoid acids. The gum component is polysaccharide in origin and is water soluble. The Anacardiaceae family contains the genus Pistacia (Mills and White, 1977 21 Mills and White, 1989). 

N.A. Crataegus laevigata C. monongyna Jacq. C. oxyacantha L. Flavonoid glycosides, procyanidins, catechins, triterpenoid acid, pectins, amygdalin, proanthocyanidins, emulsin, tartaric acid, tannins, crataegus acid, rutin, coumarins, quercitin, amines 99,100,231,278,279 Therapeutic treatment of heart insufficiency, hypotensive, coronary blood supply, arrhythmia. 

Acid groups such as triterpenoid acids, dicarboxylic acids, and hydroxy acids also are present in brown coal. Although this paper is restricted to the monofatty acid levels and distributions in brown coal lithotypes, these other acid types also have been observed to vary in level and distribution with lithotype and may, in fact, prove to be useful as indicators of the depositional environments. 

A successful technique applied for the analysis of humin and humic acids was the pyrolysis with on line methylation followed by GC/MS analysis [6,9]. In one such study [9] humin deashed by treatment with HCI and FIF was pyrolysed and compared to humic acid obtained from the same soil, showing that humin contains larger amounts of carbohydrates and aliphatic compounds. This type of study also revealed the presence in the humin and humic acid pyrolysates of monocarboxylic acids with up to 32 carbon atoms, dicarboxylic acids, methoxymonocarboxylic acids with up to 26 carbon atoms, triterpenoid acids, etc. These compounds were not reported in other studies (e g. [2]) where the chromatographic separation did not allow the detection of compounds difficult to elute due to their high boiling point and polarity. 

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. ... 

Chemical studies of numy other species of Randia have shown the presence of triterpenoid acids such as oleanolic add and randialic add. Previous work on the roots of R. siamensis yielded mesembryanthemoidigenic acid, 3-P-acetyloleanolic add, ursolic acid and 3-0-(a-L-arabinosyl)-oleanolic add (Lapikanom et al., 1983 Woo et al., 1984). However, there have been no previous reports of compounds isolated from the fhiit of this plant. 

The ethanol extract from the fruit of Randia siamensis after separation by column chromatography yielded four components ursolic acid (1), pseudoginsenoside-RPi (2), pseudoginsenoside-RTi (3) and siamenoside (4). 1 is a conunonly occurring triterpenoid acid while 2 and 3 are saponins which were first isolated from Panax (Araliaceae) species and were identified by Tanaka et al. (198S). The major component isolated in our study, oleanolic acid glycoside 3, has since been reported to be present in additional species (Morita et al., 1986 Shukla and Thakur, 1988 Shukla, 1989 Ida et al., 1994 Sakai et al., 1994). In the structural elucidation of the four components from R. siamensis, NMR spectroscopy was foimd to be... 

Pholiota destruens, a white rot fungus, produces an antifungal and cytostatic illudalane sesquiterpene, pholiotic acid (82) 45), while Piptoporus hetulinus was found to produce triterpenoid acids (22). 

Beaton, J.M., and F.S. Spring Triterpenoids. 51. The Isolation and Characterization of Glabric Acid, a New Triterpenoid Acid from Liquorice Root. J. Chem. Soc. (London), 1956, 2417. 

Lu H, Xi C, Chen J, Li W (2009) Determination of triterpenoid acids in leaves of Eriobotrya japonica collected at in different seasons. Zhongguo Zhong Yao Za Zhi 34 2353-2355... 

Che S, Li Q, Huo YS, Chen XH, Bi KS (2010) RP-HPLC simultaneous determination of five triterpenoid acids in different parts of Poria cocos by UV wavelengths switch. Yao Xue Xue Bao 45 494 97... 

Zhao J, Chen X, Bi K (2009) Simultaneous HPLC determination of four triterpenoid acids in Ganoderma lucidum. Zhongguo Zhong Yao Za Zhi 34 2220-2222... 

Isolotion and Identification - There continues to be a great deal of effort expended to isolate and characterize natural products from various plant sources. The structure of cyclopamine (from Verotrum colif icum) was shown to be 11 deoxojervine. Three new alkaloids of ParavaMoris microphyllg were identified as 4iydroxy/ 7g-hydroxy, and 11a-hydroxyparavallarine Tne latter compound was converted to aldosterone. Bryonolic acid, a pentacycMc triterpenoid acid from roots of Bryonio dioica was shown to be 3g-hydroxymultiflor en 29-oic acid. ... 

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