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Die Darstellungen von 20oz-Homo-β-amyrin (Id) und seines 20s-Isomeren (Ib) erfolgen ausgehend von der Glycyrrhetinsaure (Ia).

Die Inkubation des Titelepoxids (I) in einem Cyclase-System aus Pisum sativum fuhrt zu einer nach Acetylierung isolierten cyclischen Verbindung, die aufgrund von massenspektroskopischen und chromatographischen Vergleichen sowie unter Verwendung markierter Substanzen als Acetat (IIb) identifiziert wird.

Chemical Laboratories, University of Rajasthan, Jaipur-302 004 Manuscript received 20 February 1981, revised 5 June 1981, accepted 15 July 1981 GLC studies of Portulaca quadrifida. seed oil along with isolation of hexacosanyl acetate, eicosanic acid, cerotin, palmitic acid, \(\beta\)-sitosterol and \(\beta\)-amyrin from petroleum ether extract with quantitative and qualitative determinations of sugars from aqueous extract of seed have been reported. Besides these, an acyclic long chain aliphatic ester (VI), hitherto unknown in plant kingdom, has also been isolated from the petroleum ether extract.

Department of Chemistry, University of Rajasthan,Jaipu. (Rajasthan)-302 004 Manuscript received 21 November 1979, accepted 29 October 1980 Chemical Constituents of the Roots of Millingtonia hortensis Linn and Acacia nilotica (Linn.) Del.

A phytochemical examination of Couroupita amazonica (Lecythidaceae) led to the isolation of β-amyrin and ellagic acid.

We previously described the visceral antinociceptive property of alpha, beta-amyrin in a mouse model of cystitis induced by cyclophosphamide (CPM). This study examined the contribution of vanilloid-1 (TRPV1), peripheral NK1 receptors to CPM-evoked nociceptive behaviors and bladder edema, and its possible modulation by alpha, beta-amyrin.The effect of alpha, beta-amyrin (10, 30, and 100 mg/kg, p. o.) and N-acetylcysteine (NAC) on CPM (400 mg/kg, i. p.)-induced cystitis was studied in mice. Sensory deafferentation was done by a high dose capsaicin. The parameters analysed were: CPM-evoked noxious behaviors, bladder edema, vascular permeability, and NK(1) immunoreactivity. To assess the role of K(+) (ATP) channels in alpha, beta-amyrin effect, animals were pretreated with glibenclamide.alpha, beta-amyrin (30 and 100 mg/kg) and NAC significantly (p0.01) suppressed the visceral pain-related behaviors and NK(1) immunoreactivity, but bladder edema was reduced weakly. Glibenclamide reversed the effects of alpha, beta-amyrin. Sensory deafferentation by capsaicin significantly reduced the nociceptive responses and the NK(1) immunoreactivity to noxious stimulation by CPM.alpha, beta-amyrin attenuates CPM-induced visceral pain and bladder edema by mechanisms that involve, at least in part, a block either of Substance P release or its receptor function, and partly by opening K(+) (ATP) channels.

In order to verify the topical antiinflammatory effect of epicuticular wax from leaves of Eugenia beaurepaireana, it was tested in mice croton oil-induced inflammation. Our findings show that topical application of Eugenia beaurepaireana epicuticular wax was significantly active in inhibiting both oedema (Inhibitory dose 50 % (ID50) = 0.31 (0.26 - 0.39) mg.ear -1, inhibition = 79 ± 6 %) and tissue myeloperoxidase activity (indicative of polymorphonuclear leukocytes influx) (ID50 =0.34 (0.20 - 0.41) mg.ear -1, inhibition = 77 ± 4 %) in mice ear treated with croton oil. Two main compounds were detected on epicuticular wax of E. beaurepaireana. These compounds were identified as α- and β-amyrin by flame ionization detection (GC-FID) and spectroscopic methods (IR, NMR ¹H and 13C). In conclusion, the results indicate a topical antiinflammatory activity for the Eugenia specie studied and, that, at least in part, α- and β-amyrin are responsible for this activity.A atividade antiinflamatória tópica da cera epicuticular das folhas de Eugenia beaurepaireana foi avaliada pelo modelo do edema de orelha induzido pelo óleo de cróton em camundongos. Os resultados do estudo mostram que a aplicação tópica da cera epicuticular de Eugenia beaurepaireana inibiu significativamente a formação do edema (Dose inibitória 50 % (DI50) = 0,31 (0,26 - 0,39) mg.orelha-1, inibição = 79 ± 6 %) e a atividade da mieloperoxidase tissular (indicativo do influxo de leucócitos polimorfonucleares) (DI50 =0,34 (0,20 - 0,41) mg.orelha-1, inibição = 77 ± 4 %) em camundongos tratados com o óleo de cróton. Dois compostos majoritários foram detectados e isolados da cera epicuticular de E. beaurepaireana. Estes compostos foram identificados como os triterpenos α-amirina e β-amirina, através de técnicas cromatográficas (CG-FID) e espectroscópicas (IV, RMN ¹H e 13C). Em conclusão, os resultados indicam que a espécie E. beaurepaireana apresenta um efeito antiinflamatório tópico relevante, sendo os compostos α-amirina e β-amirina responsáveis, pelo menos em parte, por esta atividade.

Rhaponticum carthamoides plants ("maral root") are widely used in Siberian folk medicine. The present study reports for the first time the presence of pentacyclic terpenoid, α-amyrin, in methanol extract from leaves of this plant. α-Amyrin induced proliferation of human keratinocytes (HaCaT) by about 18% while other extract components were ineffective. A panel of biochemical and cell-based assays testing the antioxidative and cytoprotective activites of α-amyrin indicated no antioxidative activity of this compound. α-Amyrin did not protect HaCaT cells against the damage caused by UVB radiation.

Air-​dried whole plants of S. acmella were extd. and chromatographed to yield α- and β-​amyrin esters (with acetic, lauric, myristic, palmitic, linoleic, and linolenic acids)​, myricyl alc., α- and β-​amyrins, stigmasterol, and sitosterol-​O-​β-​D-​glucoside. The absence of any sesquiterpene was considered significant.

It was shown that the aglycone of the main saponin of Primula elatior (L.) Hill is not primulagenin A but protoprimulagenin A with an oxide ring between C-13 β and C-28 in the β amyrin ring system.

Treatment of 19β-hydroxyolean-11,13(18)-dien-3β-yl acetate with boron trifluoride etherate yields 11-oxo-α-amyrin acetate, together with olean-9(11),12,18-trien-3β-yl acetate and an unidentified trienyl acetate.

A specifically tritiated specimen of the bicyclic epoxide (11) undergoes enzymic cyclization in a homogenate from Pisum sativum to give β-amyrin (5) without randomization of label.

DUE mainly to the extensive and brilliant researches of Ruzicka and his school, a large majority of the well-characterized triterpenoid compounds have been classified as being related to one or other of the three isomeric alcohols, α-amyrin, β-amyrin or lupeol, and their relationships with these three parent compounds have been rigorously established1. Such a grouping is also indicated by the results of studies of molecular rotation differences2.

It was first proved that the 20α-methyl group, as well as the 4β-, 8-, 10-, 14-, and 17-methyls of β-amyrin biosynthesized from [6-D3-mevalonic acid in Pisum sativum are stereospecifically derived from the 3-methyl group of the acid. The result has substantiated the stereospecificity in the enzymatic cyclization of squalene to β-amyrin.

The distribution of deuterium in squalene and β-amyrin biosynthesized from [6-D3]-mevalonic acid in Pisum sativum has been analyzed by NMR spectroscopy. It was thus proved that the cis-terminal methyls of squalene and the 4β-methyl group of β-amyrin are stereospecifically derived from the 3-methyl group of mevalonic acid.

WE have elsewhere described the isolation of a diethenoid alcohol, C30H50O, accompanying -amyrin and lupeol in the non-saponifiable fraction of shea nut oil1. We have now found that this alcohol, for which we propose the name basseol, is very readily cyclized by a variety of reagents to -amyrin. This reaction is, we believe, the first example of the conversion of a naturally occurring tetracyclic triterpene to a likewise naturally occurring pentacyclic triterpene. It is of considerable biological importance in that it supplies an experimental realization of one stage in the natural evolution of a pentacyclic triterpene from presumably an acyclic structure of the squalene type by means of step wise cyclizations.

The bark of Zanthoxylum dominianum Merr. & Perry gave suberosin and canthin-6-one in about the same high yields that were previously reported from Z. suberosum C. T. White. The result confirms the previous work and supports the recently expressed view that the names are synonymous. Minor constituents isolated were palmitic acid, ?sitosterol?, β- amyrin, isopimpinellin, 7-methoxycoumarin-6-aldehyde, and two new coumarins, ?suberenol? and ?cyclobisuberodiene?. The structure of suberenol has been established as (X), and evidence in favour of (XXI) as the structure of cyclobisuberodiene obtained.