Triterpenoids, fruit

GOODWIN T w and goad l j (1971) Carotenoid and triterpenoids , in Hulme A C, The Biochemistry of Fruits and their Products, London, Academic Press, 305-28. 

Moved] Cranberry fruit of Early Black cultivar was fractionated chromatographically and fractions were analyzed for flavonoid content. The effects of the flavonoid fractions and ursolic acid, an abundant triterpenoid in cranberry peel, were assessed in two models of colon cancer and one model of breast cancer. Clonogenic soft agar assays were used to determine the effect of these compounds on tumor colony formation in HCT-116, HT-29 and MCF-7 cells. MTT and trypan blue assays were performed to assess their ability to inhibit tumor cell proliferation. TUNEL assays were performed to assess apop-totic response to the cranberry compounds. The proanthocyanidins inhibited tumor colony formation in HCT-116 and HT-29 cells in a dose-dependent manner, with greater effect on the HCT-116 cell line. Ursolic acid strongly inhibited tumor colony formation in both colon cell lines. These compounds also decreased proliferation in all three tumor cell lines with the HCT-116 cell line most strongly affected. (150 words)... 

Paquot, C., and H. Kaller. Evolutions of the sterols and the triterpenoid alcohols during the ripening of the fruits of the olive tree. C R Acad Sci SerC 1976 282 1041. 

As previously discussed by Maier and co-workers (Chapter 4), in Navel, Shamouti and certain other orange cultivars, the presence of limonin, a bitter triterpenoid, causes many economic and organoleptic problems and greatly affects the taste quality of processed fruit. Limonin is also prevalent in the grapefruit but the intrinsic quality of this fruit is further complicated by the presence of naringin, a bitter flavanone neohesperidoside (Chapter 5). 

Bitterness, caused by naringin, is also removed by an enzyme, naringinase. Another possibility would be to eliminate one or more of the enzymes in the limonin biosynthetic pathway by using recombinant DNA techniques. Limonin, a triterpenoid, is probably synthesized via the mevalonate pathway, as are the monoterpenoid flavor compounds. It appears that nomilin, a precursor of limonin, is synthesized in the stems and roots of citrus and then the precursor transported to the fruit where it is converted by several enzymes to limonin and other bitter limonoids (46). 

Epi-isomasticadienolalic acid (50) is a further new compound from Schinus molle. The galls of Pistacia palestrina contain several known compounds including 3j8-hydroxytirucalla-7,24-diene (see Vol. 8, p. 162). Structure (51) has been proposed for a triterpenoid from the fruits of Melia azedarach. The lack of an oxygen substituent at C-3 is unusual. Four new apotirucallol derivatives (52)—(55) have been isolated from the wood of Chisocheton paniculatus. ... 

From the fruit of Crataegus pirmatifida var. psilosa (Rosaceae) several triterpenoids were isolated, among them corosolic acid (35). This compound displayed potent cytotoxic activity similar to that of ursolic acid against several human cancer cell lines. The ED50 of corosolic acid was 0.4-5.0 pg/ml depending on the cell line. The cytotoxic effect of corosolic acid was probably due in part to the inhibition of PKC activity because it... 

Triterpenoid Carotenoids. Two novel triterpenoid xanthophylls from Streptococcus faecium have been identified " as 4,4 -diapo-7, 8 -dihydro-i/, / -caroten-4-al (16) and 4,4 -diapo-i/, A-caroten-4-al (17). Two other C30 carotenoids, jS-citraurinene 8 -apo-/S-caroten-3-ol (18)] and /8-citrauroP [8 -apo-/3-carotene-3,8 -diol (19)], both isolated from citrus fruits, are likely to be derived from C40 carotenoids. Spectroscopic data were presented for both compounds. 

Xanthoceraside is a triterpenoid saponin extracted from the fruit husks of Xanthoceras sorbifolia Bunge with biological properties to reverse the cognitive deficits observed in several AD animal models. Xanthoceraside treatment rescued memory deficits, as well as IR and IGF-1R protein expression levels in STZ animals, and reversed the decreased phosphorylation of CREB induced by STZ [252],... 

GOODWIN TW and goad lj. 1970. Carotenoids and triterpenoids. In The Biochemistry of Fruits and their Products, Vol. 1. Ed. Hulme, AC. Academic Press. London, New York and San Francisco, 305-368. 

Reverse-phase (RP)-HPLC is probably the best system for purifying triterpenoids, principally when mixtures of isomers are present [35]. Gunther and Wagner in 1996 [36] carried out the separation and quantification of active triterpenes from Centella asiatica employing an RP system with acetonitrile-water as mobile phase. Recently, Gaspar et al. [37] described the complete separation of a mixture of triterpenoid isomers from the fruit of Arbutus unedo by HPLC coupled to a mass spectrophotometer by means of a particle beam interface (HPLC-PBMS). The separation of different quassinoids from crude bark of Quassia amara was developed by Vitanyi et al. [38] using a reverse-phase HPLC-MS... 

Mogroside V (2) is a cucurbitane-type triterpenoid glycoside isolated from the fruits of Siraitia grosvenorii (Swingle) C. Jeffrey... 

There has been fruitful activity towards the total synthesis of unsymmetrical pentacyclic triterpenoids. 

Konoshima, T. Yasuda, I. Kashiwada, Y. Corentino, C.M. Lee, K.H. Anti-AIDS Agents, 21. Triterpenoid Saponins as Anti-HIV Principles from Fruits of Gleditsia japonica and Gymnocladus chinensis and A Structure Activity Correlation. J. Nat. Prod. 1995, 58, 1372-1375. 

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... 

Russula pigments. The yellow, red, and violet colors of russula mushrooms (Russula, Basidiomycetes) are caused by polar compounds, some of which exhibit intense fluorescence under UV light and are associated with the riboflavin- and pteridine metabolisms ( russupteridines). Russula flavida is an exception, its fruit bodies have an orange-yellow layer consisting of lipophilic triterpenoids of the russulaflavidin type. Ut. Z. Pilzkd. 39, 45 (1973) (review) Zechmeister 51, 210-215. 

S. A C30H4SO7, Mr 518.69, needles, mp. 145-146°C, [a]o +78.1° (CHCI3). Cytotoxic triterpenoids from the fruit bodies of the toadstool Tricholoma saponaceum (Basidiomycetes). The fungus also contains the 10-de-oxy derivative S. B C30H44O6, Mr 502.69, cryst., mp. 134-136°C, [aJu +17.9° (CHjClj)), as well as the (75)-7- and 3/5-hydroxy derivative S. C and D., respectively. The unusual S. system is probably formed bio-genetically by attack of a famesyl cation on a molecule of famesyl diphosphate. 

Many active molluscicides are saponins (Farnsworth et al., 1987 Henderson et al., 1987 Marston and Hostettmann, 1991). These compounds are important because of the potential for controlling the snail vectors for schistosomiasis (bil-harzia), which affects about 300 million people worldwide. Four triterpenoid saponins with strong moUuscicidal activity are found in the fruits of ivy Hedera helix Araliacene), and others in the fruits of Lonicera japonica (Caprifoliaceae) (Hostettmann, 1986). 

The genus Daphniphyllum (Daphniphyllaceae) is the source of complex triterpenoid alkaloids. Daphniphyllum macropo-dum, a tall tree from Japan, has been particularly studied (Yamamura, 1986 Yamamura and Hirata, 1975). At least 19 alkaloids have been isolated from the bark, leaves, and fruit of this plant. Daphniphylline (106) and codaphniphyl-line (107) are the two major alkaloids of the bark (Fig. 36.24). 

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