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At least 73 records · Page 4Linked to original sources

Isolation of steroidal sapogenins implicated in experimentally induced cholangiopathy of sheep grazing Brachiaria decumbens in Brazil.

As part of an experimental study, crystal-associated cholangiopathy was induced in 9 sheep by grazing pure pastures of Brachiaria decumbens in Brazil. One of these sheep showed characteristic lesions of photosensitization. The analysis of the B decumbens samples by acidic hydrolysis followed by TLC and infrared spectrum revealed diosgenin as the principal sapogenin present in the plant. In the rumen contents samples from the B decumbens-grazing group were identified by TLC, 1H and 13C NMR and EIMS as epismilagenin, episarsasapogenin, and a mixture of smilagenin and sarsasapogenin. In the bile samples from the B decumbens-grazing group, TLC analysis demonstrated 2 compounds similar to epismilagenin and episarsasapogenin. However, by this same method, those compounds were not observed in the rumen contents and bile from 2 sheep which served as control animals. The P chartarum spore counts remained very low during the experimental period.

Animals↗

Triterpenoid sapogenin from Anthyllis vulneraria L.

Triterpene pentacyclic sapogenin, 3beta,22beta,24-trihydroxy-olean-12-ene, soyasapogenol B, was isolated for the first time from the Anthyllis vulneraria L.. Identification and structure assignment was performed by 1H and 13C NMR spectroscopy.

Europe↗

The isolation and identification of steroidal sapogenins in switchgrass.

Switchgrass (Panicum virgatum L.) has been reported to be hepatotoxic, causing photosensitization in lambs and horses. In this study we show the presence of steroidal saponins in two samples of switchgrass that has been implicated in the poisonings of sheep and horses. After hydrolysis of the saponins, diosgenin was determined to be the major sapogenin in both switchgrass samples. We also confirmed the presence of diosgenin in kleingrass after hydrolysis of saponins extracted from it.

Chromatography, High Pressure Liquid↗

[New triterpenoidal sapogenins from the roots of Glycyrrhiza yunnanensis].

Two new pentacyclic triterpenoidal sapogenins of oleanane type, namely glyyunnansapogenin A (I) and glyyunnansapogenin B (II), together with a known compound beta-sitosterol were isolated and characterized from the roots of Glycyrrhiza yunnanensis Cheng f. et L. K. Tai, family Leguminosae, collected in Yunnan Province, China. I was obtained as its methyl ester (Ia), mp 276-277 degrees C, which formed a diacetate (Ic), mp 244-245 degrees C. II, mp 287-289 degrees C, gave a triacetate (IIb), mp 286-287 degrees C and a monomethyl ester (IIa), mp 272-275 degrees C, which further formed a triacetate (IIc), mp 187-189 degrees C and a diacetate (IId), mp 243-245 degrees C after treatment with acetic anhydride and pyridine over night at room temperature. The structures of I and II were established by spectral analyses of IR, 1H NMR, 13CNMR, MS, CD and ORD. Glyyunnansapogenin A (I) was proved to be 3 beta, 24-dihydroxy-16-oxo-olean-12-en-29-oic acid and glyyunnansapogenin B (II) 3 beta, 21 alpha, 24-trihydroxy-olean-12-en-30-oic acid respectively.

Chemical Phenomena↗

The isolation and identification of steroidal sapogenins in Kleingrass.

Kleingrass (Panicum coloratum L) has been reported to cause hepatogenous photosensitization in sheep and goats in West Texas since 1973. The toxin in Kleingrass has been suspected of being a steroidal saponin as Kleingrass produced characteristic birefringent crystals similar to those produced by saponin-containing plants such as Agave lecheguilla and Tribulus terrestris. In this present study, steroidal saponis were isolated from Kleingrass and their sapogenins were identified as diosgenin and yamogenin by means of thin-layer chromatography and infrared spectrophotometric analysis.

Chromatography, Thin Layer↗

[Spectrum properties of steroid hormones, sapogenins and alkaloids in the Chugaev reaction: effect of the structure].

Spectral characteristics of the products of the Chugaev reaction with steroid hormones, sapogenins and alkaloids are analyzed by spectrophotometry and fluorescent spectroscopy. They are established to be dependent on a degree of nonsaturation, position of double bonds, nature and position of substitutes in the molecule structure. The reaction is shown possible to be used for quantitative determination of a number of steroids. The fluorescent spectroscopy application essentially increases sensitivity of the method.

Alkaloids↗

Preliminary pharmacobiological study of new steroidal sapogenins.

The chemotherapeutic study of a limited series of steroidal sapogenins from several endemic species of the flora of the Canary Islands is presented here. On the whole, they possess a very weak antibacterial activity, a slight antifungal effect and one of them, vespertilin, displays interesting cytostatic activity (ID50 = 5 micrograms/ml). A pharmacodynamic screening carried out on this product mainly revealed very slight toxicity, antihistaminic activity and a light tranquilizing effect. The data obtained justify further research.

Animals↗

[Studies on sapogenins of Aesculus wilsonii Rehd].

Three sapogenins were isolated from the hydrolysate of the saponin mixture extracted from the seeds of Aesculus wilsonii. They were identified as 21-angeloyl-protoaescigenin., aescigenin and protoaescigenin by physicochemical propertise and spectroscopic analysis.

Drugs, Chinese Herbal↗

Ruizgenin, a new steroidal sapogenin diol from Agave lecheguilla.

From the leaves of Agave lecheguilla Torrey, two steroidal sapogenin diols have been isolated. Mass spectral, infra-red and nuclear magnetic resonance data of these two compounds showed them to be (25R)-spirost-5-ene-2 alpha, 3 beta-diol (yuccagenin) and (25R)-5 beta-spirostane-3 beta, 6 alpha-diol. The latter is a new compound to which the trivial name ruizgenin has been given.

Chromatography, Thin Layer↗

Ovine metabolism of lithogenic sapogenins. Synthesis of [2,2,4,4-(2)h(4)]sarsasapogenone, [2,2,4,4-(2)h(4)]sarsasapogenin, and [2,2,4,4-(2)h(4)]episarsasapogenin and evaluation of deuterium retention in a sheep-dosing trial.

The suitability of [2,2,4,4-(2)H(4)]sarsasapogenone (1b), [2,2,4,4-(2)H(4)]sarsasapogenin (2b), and [2,2,4,4-(2)H(4)]episarsasapogenin (3b) as isotopically labeled dosing substrates to determine the levels of free and conjugated sapogenins present in feces from sheep grazing saponin-containing plants implicated in the development of ovine heptagenous photosentization diseases was investigated. A 1:4 mixture of [2,2,4,4-(2)H(4)]sarsasapogenin (2b) and [2,2,4,4-(2)H(4)]episarsasapogenin (3b), obtained by reduction of [2,2,4,4-(2)H(4)]sarsasapogenone (1b), was found to retain 94% of incorporated deuterium, when dosed to one sheep. The recovery of the dosed mixture of genins 2b and 3b was calculated to be 85%. Considerable loss of deuterium and a lower recovery of genin material were observed when [2,2,4,4-(2)H(4)]sarsasapogenone (1b) was dosed.

Animals↗

Steroidal Sapogenins from Tacca leontopetaloides.

Diosgenin and its ring-F-hydroxylated derivatives isonarthogenin {spirost-5-ene-3,27-diol {3beta, 22 R, 25 S)} and isonuatigenin {spirost-5-ene-3,25-diol (3beta, 22 R, 25 S)}, together with the 22,25-epoxyfurost-5-ene isomer nuatigenin {furost-5-ene-3,26-diol-22,25-epoxy (3beta, 22 R, 25 S)}, were identified as the major steroidal sapogenins of the acid hydrolysate of an extract of leaves of TACCA LEONTOPETALOIDES by IR, (1)H-NMR, (13)C-NMR, and mass spectroscopy. A diosgenin ester was isolated which apparently arose by ring closure of a glycosylated furostene during hydrolysis.

Journal Article↗

On the polymorphism of a sapogenin monohydrate induced by different rotations of water molecules.

The structure of 1beta,3beta,11alpha-trihydroxyspirosta-5,25(27)-diene (C(27)H(40)O(5); a steroidal sapogenin) isolated from Helleborus serbicus Adam 1906 (Ranunculaceae) and crystallized from absolute ethanol as a monohydrate (melting point 519-522 K) had been characterized by two symmetry-independent binary (steroid-water) layers, cross-linked by hydrogen bonds [Kálmán et al. (1985). Acta Cryst. C41, 1645-1647]. Recently, a novel monohydrate was crystallized again from absolute ethanol (source: Helleborus multifidus subspecies serbicus) with a somewhat higher melting point of 525-526 K. X-ray analysis of these crystals [Argay et al. (1998). Acta Chim. Hung. 135, 449-456] revealed a novel polymorph (hereinafter denoted polymorph B), which is also built up by two binary layers of C(27)H(40)O(5) and H(2)O, but in which the relative position of these layers differs from that found in the first modification (polymorph A). Comparing the two polymorphs, layers of one type are found to be similar, displaying identical hydrogen bonding, whereas layers of the second type differ with respect to the orientations adopted by the water molecules; these orientations also differ from those in the layers of the first type. Consequently, by these water rotations, hydrogen bonds, at least partly, are reversed. This leads to two different close packings: in form A four consecutive layers are cross-linked by two homomolecular (hydroxyl.hydroxyl and water.water) hydrogen-bond pairs, while in B there are only heteromolecular hydroxyl.water bonds. These hydrogen-bond dissimilarities together with the differences in the weak CH.X etc. interactions explain the greater stability of the higher melting-point form B.

Journal Article↗

[Experimental study of the anabolic activity of 6-ketoderivatives of certain natural sapogenins].

It is shown that 6-ketoderivatives of natural sapogenins, viz. agigenin, diosgenin and alliogenin, display the anabolic activity and do not manifest any androgenic properties. The compoud IV/(25 R)-5alpha-spirostan-2alpha, 3beta, 5alpha-triol-6-OH/produces an accelerated gain of weight in rats, and also an increase in the weight of the liver, heart, kidneys, musculus tibiliasis anterior and augments the total amount of protein therein. All of the above-mentioned changes become more pronounced with the study substance introduced to young animals. Castration of sexually immature rats greatly mitigates the anabolic effect of the compound IV.

Anabolic Agents↗

[Studies on the triterpene sapogenins from Albizziae Cortex].

A new sapogenin named Julibrogenin A was isolated from the stem bark of Albizzia julibrissin Durazz (Albizziae Cortex). Based on chemical and spectral studies, their structure has been identified as 21-O-(2-hydroxymethyl-6-methyl-6-methoxyl-2,7-octadienoyl)-acacic acid. In addition, machaerinic acid lactone, machaerinic acid methylester, acacigenin B and julibrotriterpenoidal lactone A were also isolated from this plant and characterised.

Drugs, Chinese Herbal↗