Triterpenic alcohols

Despite aU of betulinic add pharmacological potential, it is obtained by extrachon of barks or core of some plant species or by synthetic processes, e.g. using the betulin (alcohol triterpene) as a S)Tithetic intermediate isolated from the bark of Betula alba and Betula pendula [Galgon., et al. 1999]. Therefore, research is necessary to identify new natural sources, which produce large... 

Three other GC analyses now used in authentication, largely for olive and other oils which should not be refined or solvent extracted, are the determination of waxes, aliphatic alcohols, triterpene alcohols (uvaol and erythrodiol), and stigmastadiene and other sterol-dehydration products (EEC, 1991). These analyses are used at present not to detect adulteration with other oils, but with solvent-extracted or refined oils. However, it is possible that, with solvent-extracted oils, wax, aliphatic alcohol and terpene alcohol compositions, could prove useful in differentiating or detecting different oils. 

The method applied consists in a prior, basic hydrolysis (saponification) of the oil sample, followed by thin layer chromatography (TLC) fractionation of the classes of compounds, namely hydrocarbons, tocopherols, long-chain aliphatic alcohols, triterpenic alcohols, methyl sterols, sterols and triterpenic dialcohols. This procedure loses all information about the combination of polycyclic triter-penes with fatty acids. 

The triglyceride composition is summarized in Tables 3.142 and 3.143. Unsaponifiable components occur at levels of 0.2-1% of the oil and include hydrocarbons, aliphatic alcohols, triterpene alcohols (Table 3.147), sterols (Tables 3.145, 3.146 and 3.50) and tocopherols (Table 3.51). jS-Carotene and lutein are the major pigments, their level decreasing in the oil as the seed matures. Changes in the major lipid classes during maturation have been studied (Pattee et aL,1969 Sanders, 1980). Oleic acid increases as maturation progresses. 

Triphenodioxazines 411 Triphosphate (cyclic) 172 Tripolyphoqjhate 172 Trisacchaiic 331 Triterpene 70,206,210,211,430 -, alcohols 404 -, derivatives 43 -, glycosides 62 Triton X-100 108 Trough chambers 125 Tryptamine 76, 98,254, 364 Tryptophan 76,246, 364 Tungsten cations 398 Tungsten incandescent lamp 21,22 Twin-trough chamber 87,126 T)framine 355... 

Classical examples of anti-inflammatory Asteraceae are Arnica montana and Calendula officinalis, both used in European medicine to treat bruises and contusions. There is an expanding body of evidences to suggest that Asteraceae could be a useful source of anti-inflammatories, such as sesquiterpene lactones and/or triterpene alcohols, the latter being known to inhibit 12-O-tetra-decanoylphorbol-13-acetate (TPA)-induced inflammation in mice as efficiently as commercial indomethacine by possible inhibition of phospholipase A2 (10). 

Akihisa T, Ken Y, Hirotoshi O, Yoshimasa K. Triterpene alcohols from the flowers of Compositae and their anti-inflammatory effects. Phytochemistry 1996 43 1255-1260. 

Storax resin is extracted from Liquidambar orientalis (Hammamelidiaceae) and Altingia and its major components are cinnamyl cinnamate and 3-phenylpropanyl cinnamate, with significant amounts of benzoic and cinnamic acids, and 3-phenylpropanol and cinnamyl alcohols [130,131]. The volatile content is very low and triterpenes (oleanonic and 3-epioleanolic acids and liquid ambronovic acid) have also been observed [130,132]. 

SEGURA, M.J.R., MEYER, M.M., MATSUDA, S.P.T., Arabidopsis thaliana LUP1 converts oxidosqualene to multiple triterpene alcohols and a triterpene diol, Org. Letts., 2000, 2, 2257-2259. 

It is of interest that carotenoid pigments (xanthophylls), sterols (spinasterol and chondrillasterol) and a triterpene alcohol have been identified in cucurbit seed oil (31, 3 , 37L However, cucurbit oils such as that from Buffalo gourcT are amenable to refining, bleaching and deodorizing (38). 

Itoh, T., T. Tamura and T. Matsu-moto. Tirucalla-7,24-dienol a new triterpene alcohol from tea seed oil. Lipids 1975 11 434. 

CS095 Itoh, O., T. Uetsuki, T. Tamura and A. Matsumoto. Characterization of triterpene alcohols of seed oils from some species of Theaaceae, Phytolac-caceae and Sapotaceae. Lipids 1980 ... 

Nishibe, S., H. Tsukamoto, I. Agata, S. Hisada, K. Shima, and T. Takemoto. Isolation of phenolic compounds from stems of Olea europaea. Shokugaku Zasshil981 35 251-254. Tsukamoto, H., S. Hisada, and S. Nishibe. Studies on the lignans from Oleaceae plants. Proc 26th Symposium on the Chemistry of Natural Products, Kyoto, Japan 1983 26 181—188. Paganuzzi, V. Use of silver nitrate TLC in the analysis of olive oil triterpene alcohols. I. Oils obtained from various anatomical parts of the olives. Riv Ital Sostanze Grasse 1981 58(8) 285-393. 

Fresh ambergris is almost black, but it turns light gray and develops a pleasant odor when exposed to light and seawater over a period of time. The major components of ambergris are epicoprosterol and the odorless triterpene alcohol, ambrein [473-03-0]. 

The all-tra 5 -squalene (C30H50), discovered in shark liver oil in the 1920s, is a triterpene, but one in which the isoprene rule at violated in one point. Rather than a head-to-tail arrangement of six units of isoprene, there appear to be farnesyl units that have been connected tail to tail. Almost aU steroids are biosynthesized from cholesterol. Cholesterol is biosynthesized from squalene, which is first converted to lanosterol. The conversion of squalene to the steroid skeleton is an oxirane, squalene-2,3-oxide, which is transformed by enzymes into lanosterol, a steroid alcohol naturally found in wool fat. The whole process is highly stereoselective. 

Cholesterol was isolated in the eighteenth century, but its structure is so complex that its correct constitution was not determined until 1932 and its stereochemistry not verified until 1955. Steroids are characterized by the tetracyclic ring system shown in Figure 26.9a. As shown in Figure 26.9b, cholesterol contains this tetracyclic skeleton modified to include an alcohol function at C-3, a double bond at C-5, methyl groups at C-10 and C-13, and a CBH17 side chain at C-17. Isoprene units may be discerned in various portions of the cholesterol molecule, but the overall correspondence with the isoprene rule is far from perfect. Indeed, cholesterol has only 27 carbon atoms, three too few for it to be classed as a triterpene. 

Esterification with a fatty acid or with ferulic acid at C-3 of triterpene alcohols exerted almost no influence on the activity as has been observed with lupane- (264/265) and cycloartane- (66/67, 72/73) type compounds and a C-3 monohydroxy triterpenoid (264/266). However, esterification at C-3 with a fatty acid reduced the inhibitory activity of some dihydroxy triterpenoids (138/139,140 202/203, 204 230/231 232/233, 234). 

The basic compound is a triterpene glycoside. It is extracted from the licorice root, of which the principal sources are China, Russia, Spain, Italy, France, Iran, Iraq, and Turkey. The roots, containing 10% moisture, are dned and shredded, after which they are extracted with aqueous ammonia, concentrated in vacuum evaporators, precipitated with sulfuric acid, and crystallized with 95% ethyl alcohol. 

Soulier et al. (35) isolate eight triterpenic alcohols from sal and illipe butters besides other compounds. They separate these compounds after saponification of the fatty matter and fractionation of the unsaponifiable on an aluminium oxide column (hydrated at 5%). Two successive HPLC separations and a TLC-AgN03 permit the isolation of highly purified fractions. Through the use, among others, of the H-NMR and MS techniques, they identify nine... 

Recently Amelio et al. (7) described a method which may find routine applications and which makes use of SPE for the separation and clean-up of the unsaponifiable from olive oil, from which the aliphatic alcohols are separated by means of HPLC (besides sterols and the two triterpenic dialcohols erythrodiol and uvaol). The alkanols are then derivatized and analyzed by means of HRGC. The use of an autosampler and a fraction collector for use with HPLC permits a considerable automatization of the analysis. (Reprinted from Ref. 1, p. 581, by courtesy of Marcel Dekker Inc.)... 

T Akihisa, Y Kimura, K Roy, P Ghosh, S Thakur, T Tamura. Triterpene alcohols and 3-oxo steroids of nine leguminosae seeds. Phytochemistry 35(5) 1309-1313, 1994. 

Double Sharpless epoxidation was also applied to the synthesis of a key intermediate 10 to the meso-compound 11 that is related to teurilene, abioactive polycyclic triterpene isolated from red alga Laurencia obtusa,4 The reaction of ( , )-Bisallylic alcohol 9 gave the bisglycidic alcohol 10 with 80% de and 89% ee for each epoxidation (Scheme 6AA.4). 

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