Triterpene lactones

Arburinol Aescin, aescinidin etc. Gypsogenin (hi / 25) Gypsogenin lactone (hi / 85) Triterpenes from- Lycopodium Triterpene lactones... 

Waters RP Nova-Pak C18, (15 cm X 4.6 mm) Acetonitrile-water (65/35), postcolumn addition of 0.1% of 1 m ammonium acetate UV-Vis detector, 254 nm, MS Eco-triterpene lactone type quassinoids [94]... 

Immortelle (H. angustifalhm) contains a small amount (0.075-0.2%) of volatile oil, two phthalides (5-methoxy-7-hydroxyphthalide and 5,7-dimethoxyphthaUde), helipyrone, triterpenes (a-amyrin, uvaol, and ursolic acid) and a triterpene lactone (ursolic acid lactone), wax consisting mostly of C31 and C29 -alkanes (ca. 2 1 ratio), flavonoids, P-sitosterol, caffeic acid, and others (list and horhammer). ... 

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). 

FIGURE 11.5 Terpenoids, (a) The basic five-carbon units isopentane and isoprene. (b) The monoterpenes borneol and a-pinene. (c) A monoterpene lactone, nepetalactone. (d) A sesquiterpene, germacrone. (e) A triterpene, papyriferic acid, from paper birch. 

By using betulin as substrate, some mechanistic studies were performed and it was demonstrated that these reactions are catalyzed by Brpnsted acid species generated in situ from the hydrolysis of Bi(0Tf)3-.vH20. This process was also applied to other terpenic compounds. The sesquiterpene ( )-caryophyllene oxide originated clov-2-en-9a-ol by a cariophyllene-clovane rearrangement (Scheme 41) whereas 3-oxo- l 8a-olean-28- l 3(3-olide was obtained from oleanonic acid (Scheme 42). With this triterpene derivative, only 28,13(3-lactonization occurred, with inversion of the configuration of the stereocenter at C18 [133],... 

The biological activity and toxicity of terpenoids to herbivores has been discussed (56,84) and representatives of each major type of terpene are known to be active. Well known examples are sesquiterpene lactones, pyrethrins, and several classes of diter-penes and triterpenes. 

N.A. Achilleine, tannins, cineole, chamazulene, sesquiterpene, lactones, menthol, camphor, sterols, triterpenes.98,99,100,101,102 103 Reduce fever, anti-inflammatory, treat common cold, diarrhea, dysentery, hypertension, and gastrointestinal complaints. 

Main actives Sesquiterpene lactones, which are bitter flavoured, triterpenes, steroids, flavonoids, mucilages and an inulin content that varies from 2 to 40% in the autumn. Benefits The bitter components were used to promote the flow of digestive juices in the upper intestinal tract. 

Sunflower is a rich source of sesquiterpenes,21 especially sesquiterpene lactones.23,28 31 44 Due to its economic importance, sunflower has been extensively studied, thus leading to the isolation and chemical characterization of phenolic compounds (benzoic acid derivatives,9 39,51 coumarins,51 and flavonoids6,10,19), diterpenes, and triterpenes. Most of these studies were performed using... 

GR133487 (5,5-rra/is-fused cyclic lactone euphane triterpene) Lantana camara (Verbenaceae) a-Chymotrypsin (10 nM), Factor Xla (1 pM), Plasmin (6 pM), a-Thrombin (4 nM), Trypsin (120 nM) [112]... 

Lactonizalion of y,6-unsaturated acids. Treatment of acid la or lb, or of a mixture, with 98% H2SO4 for 2 hours at 25° results only in the cw-y-lactone 3 in nearly quantitative yield. The lactone 2 is formed under kinetip control, but rearranges to 3, the most stable of the four possible y-lactones. Indeed use of other acid catalysts (HCOOH, SnCU) results in a mixture of 3 and 2 in the ratio 3 2. Neither of the two possible franx-lactones is observed in any case. The stereochemistry of 3 is a feature of many triterpenes. 

In 2001 and 2002, additional squalene-derived triterpenes from L. viridis were isolated and characterized. Fig. (6) [13,14]. The compounds show some divergence from the common backbone structures previously observed. For example, clavidol (22) lacks the C-ring, dioxepandehydrothyrsiferol (24) contains a framework with two rra 5 -fused 7-membered ether rings, and lactodehydrothyrsiferol (25) contains a lactone in place of the A-ring bromoether. 

The biological activities depend on the structures of holothurian triterpene glycosides [42-44]. The structures of both an aglycon part and a carbohydrate chain are very important for the antifungal activity. The 18(20)-lactone presence is necessary for the activity, because the derivative 49 without the lactone does not show antifungal properties. 

The importance of a linear tetrasaccharide fragment and an 18(20)-lactone for biological activity, the absence of a significant contribution of 4-0-sulfate at first xylose to activities of tetraosides and, in contrast, its important role for activity of biosides were shown for hemolytic action of triterpene glycosides from sea cucumbers [33]. It confirmed a common mechanism of their activity against membranes of both erythrocytes and fungal cells. 

One step in the production of (5), a key intermediate in a synthesis of the tetracyclic triterpene a-onocerin, involved allylic oxidation of the a,)3-unsaturated ester (1). This was accomplished with Se02 in boiling acetic acid.18b The unsaturated hydroxy lactone produced (2) was next to be converted into the saturated keto acid (5), presumably by a stepwise process. However, the Israeli investigators were pleas-... 

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