Steroid Glucosides Research Articles

Elaeagnoside, chymotrypsin inhibiting steroidal glucoside from Elaeagnus orientalis

Elaeagnoside (1), a new steroidal glucoside, has been isolated from the chloroform fraction of Elaeagnus orientalis along with β-sitosterol and 12-hydroxy-8,10-octadecadienoic acid. The structure of 1 has been elucidated with the help of chemical and spectral studies. It showed significant inhibitory activity against the enzyme chymotrypsin.

New principles from seeds of Nigella sativa

A new triterpene saponin and known steroidal glucoside were isolated from the alcohol extract, and a new cycloartenol from n-hexane extract of seeds of Nigella sativa L. and were identified as 3-O-[β-D-xylopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl]-11-methoxy-16,23-dihydroxy-28-methylolean-12-enoate (1), stigma-5,22-dien-3-β-D-glucopyranoside (2) and cycloart-23-methyl-7,20, 22-triene-3β,25-diol (3), respectively. They were characterised on the basis of spectral analysis and comparison with literature data. The hexane and alcohol extract of the seeds showed antimicrobial activity. The antioxidant activity of hexane extract is also described.

Two new steroidal glucosides from Ophiopogon japonicus (L.f.) Ker-Gawl

Two new steroidal glucosides, 26- O-β- d-glucopyranosyl (25 S)-furost-5-ene-1β,3β,22α,26-tetraol 1-O-β- d-xylopyranosyl-(1 → 3)-[α- l-rhamnopyranosyl-(1 → 2)]-β- d-fucopyranoside and (25R) spirost-5-ene-3β,14α -diol-3-β- O-β- l–rhamnopyranosyl(1 → 2)-[β- d-xylopyranosyl(1 → 4)]-β- d-glucopyranoside, were isolated from the Ophiopogon japonicus (L.f.) Ker-Gaw . Their structures were elucidated by spectroscopic methods.

Structural determination of kochiosides A–C, new steroidal glucosides from Kochia prostrata, by 1D and 2D NMR spectroscopy

Kochiosides A-C, three new steroidal glucosides, have been isolated from the ethyl acetate fraction of Kochia prostrata and their structures assigned from its (1)H and (13)C NMR spectra, DEPT and by 2D COSY, NOESY, HMQC and HMBC experiments.

Kopetdaghins A−E, Sesquiterpene Derivatives from the Aerial Parts and the Roots of Dorema kopetdaghense

Three new sesquiterpene derivatives, kopetdaghins A-C (1-3), one known prenylated coumarin (7), and two known steroid glucosides, sitosterol 3-O-glucoside and stigmasterol 3-O-glucoside, were isolated from the aerial parts of Dorema kopetdaghense. In addition, two new sesquiterpene derivatives, kopetdaghin D (4) and kopetdaghin E (5), together with kopetdaghins A-C and one known sesquiterpene coumarin (6), were isolated from the roots of the plant. The structures of these compounds were elucidated by various 1D and 2D NMR techniques as well as high-resolution positive-ion ESIMS.

Prenylated Flavonoids and Flavonostilbenes from Sophora pachycarpa. Roots

Seven known compounds including three prenylated flavonoids (sophoraisoflavanone A, sophoraflavanone G, and 3′-isoprenylgenistein), two flavonostilbenes (alopecurone A and alopecurone B), in addition to two steroid glucosides (sitosterol 3-O.-glucoside and stigmasterol 3-O.-glucoside), were isolated using silica gel column chromatography and preparative thin layer chromatography from the roots of Sophora pachycarpa. C. A. Mey. (Papilionaceae) for the first time. The structures were characterized by 1D and 2D NMR experiments.

Recurvosides A and B, Antifungal Novel Steroidal Glucosides from Haloxylon recurvum.

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Recurvosides A and B, Antifungal Novel Steroidal Glucosides from Haloxylon recurvum

Abstract Recurvosides A (1) and B (2), new steroidal glucosides, have been isolated from the ethyl acetate soluble fraction of Haloxylon recurvum and their structures elucidated by spectroscopic techniques including two-dimensional NMR. Both the compounds exhibited potent antifungal activity.

The bioactivity‐guided isolation and structural identification of toxic cucurbitacin steroidal glucosides from stemodia kingii

A histologically validated murine model for the ovine intoxication by Stemodia kingii was used as a bioassay to guide the isolation of several groups of toxins from Stemodia kingiL Two of the toxins from one group were purified sufficiently to allow structural analysis and a determination of their median lethal doses (LD50) for oral administration to mice. A combination of acid hydrolysis, elemental analysis, HPLC-MS, 1D-NMR (1H, 13C) and 2D-NMR (1H-1H COSY, 13C-1H HSQC and HMBC, and gNOESY) was used to define stemodiosides B3 and B4 as cucurbitacin steroidal glucosides. Thus stemodioside B3 is (24Z)-3 alpha-(beta-glucopyranosyloxy)-2 beta,20,27-trihydroxy- 19-(10 -9 beta)-abeo-10alpha-lanost-5,24-diene- 11-one and stemodioside B4 is (23E)-3 alpha-(beta-glucopyranosyloxy)-20,20,22,27-tetrahydroxy- 19-( 10-9 beta)-abeo- 10 alpha-lanost-5,23-diene- 11-one. The approximate oral LD50s for stemodiosides B3 and B4 in mice were estimated to be 99 and 42 mg/kg body weight, respectively.

A New Clerodane Diterpene and Other Constituents from Ajuga chamaepitys ssp. laevigata

Abstract From Ajuga chamepitys ssp. laevigata, a new clerodane diterpene, ajugalaevigatic acid, has been isolated besides five known compounds, a diterpene, (13S)-15-hydroxylabd-8(17)-en-19-oic acid, a steroidal glucoside, 3-O-β -D-glucopyranosyl-stigmasta-5,25-diene, and triterpenes,α- and β -amyrin and ursolic acid. Their structural elucidation is based on NMR and MS spectroscopic analyses. For the new compound 2D NMR experiments were carried out. Ajugalaevigatic acid was tested against a panel of cytotoxic cell lines, and only found to be active against the A2780 human ovarian cancer cell line.

TEMPO‐Mediated Regiospecific Oxidation of Glucosides to Glucuronides.

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Feeding stimulative activity of steroidal and secoiridoid glucosides and their hydrolysed derivatives toward the olive weevil (Dyscerus perforatus).

Beta-sitosteryl-D-glucoside and oleuropein isolated from the olive tree (Olea europaea) and their hydrolysed derivatives were tested by a feeding stimulative activity bioassay using the olive weevil (Dyscerus perforatus). Although the steroidal glucoside showed potent feeding stimulative activity, the activity of the aglycone (beta-sitosterol) was significantly lower than that of the glucoside. On the other hand, the difference in the activity between oleuropein, a secoiridoid glucoside, and the hydrolysed derivatives was not significant.

TEMPO-Mediated Regiospecific Oxidation of Glucosides to Glucuronides

A TEMPO/hypochlorite/bromide oxidant has been used for the conversion of aryl and steroidal glucosides to the corresponding glucuronide conjugates in good (48-74%) yield. An isoflavone glucoside failed to undergo this transformation.

A novel sterol from Chinese truffles Tuber indicum.

From the fruiting bodies of Ascomycetes Tuber indicum, a new steroidal glucoside with polyhydroxy ergosterol nucleus, tuberoside (2), has been isolated along with additional four known ergosterol derivatives, (22E, 24R)-ergosta-7, 22-dien-3beta, 5alpha, 6beta-triol (1), 5alpha, 8alpha-epidioxy-(22E, 24R)-ergosta-6, 22-dien-3beta-ol (3), (22E, 24R)-ergosta-5, 22-dien-3beta-ol (4), and (22E, 24R)-ergosta-4, 6, 8(14), 22-tetraen-3-one (5). The structure of new compound was established as 3-O-beta-D-glucopyranosyl-(22E, 24R)-ergosta-7, 22-dien-5alpha, 6beta-diol (2) on the basis of chemical and spectroscopic means ((1)H NMR, (13)C NMR, HMQC, HMBC, MS, and IR). This is the first example of isolation of a polyhydroxylated ergosterol glucoside from higher fungi in nature.

A new acylated steroid glucoside from Perovskia atriplicifolia

Atroside (1), an acylated steroid glucoside, has been isolated from Perovskia atriplicifolia along with other known compounds.

Aggregation agents in German cockroach Blattella germanica : Examination of efficacy

Aggregation behavior and reduced locomotory activity in the German cockroach is known to be caused by chemical compounds in the feces. The attractive and/or arrestant efficacy of three relevant substances was tested in first instars by a two-choice aggregation test and in adults with a locomotion compensator apparatus that allows quantification of taste-directed orientation and walking speed as a function of antennal stimulation. The three substances tested were a feces crude extract; a mixture of six carboxylic acids (mix G) out of a total of 29 that were identified in the feces extract and tested as single compounds and in various combinations; and a steroid glucoside denoted as blattellastanoside A, which has been suggested as an aggregation arrestant pheromone in Blattella germanica. With both of our test methods, feces extract and mix G proved to be very attractive, whereas the effects of blattellastanoside A were, if anything, very poor. Possible reasons for discrepancies are discussed.

Tropical plant‐associated nephropathy

SUMMARY: In the tropical area, nephrotoxicity can be caused by certain plants or plant materials. These include djenkol bean, mushroom, Callilepis laureola, Semicarpus anacardium, Securidaca longipe dunculata and Vicis favus. Djenkol beans consumed by people in South‐east Asia can cause toxicity or djenkolism. Renal manifestrations of djenkolism include dysuria, hematuria, proteinuria, urolithiasis, and acute renal failure. Djenkolic acid in the bean can cause renal dysfunction by mechanical irritation of djenkolic acid crystals and by direct toxicity. Renal involvement in mushroom poisoning is generally caused by certain species of Amanita and Galerina. Amanita toxins produced by such mushrooms could exhibit their toxic effects on several metabolic pathways of all eukaryotic cells including hepatocytes and renal cells. Renal failure is severe with a high mortality rate. Phenolic compounds in the sap of Semecarpus anacrdium, the marking‐nut tree of India, can cause renal failure following prolonged exposure to the sap. Atractyloside, an alkaloid found in the tuber of Callilepis laureola, can cause hypoglycemia and nephrotoxicity. Gaultherin, an amorphous steroid glucoside found in Securidaca longipe dunculata, can cause extensive damage to the kidney. Divicine and isouramil found in Vicis favus, broad bean, can trigger hemolysis in certain subjects with G‐6 PD deficiency, resulting in reversible acute renal failure. Gossypol, the principal ingredient of cotton seed oil, could cause distal renal tubular acidosis.

(20R)-15a-Hydroxy-8ß, 9a, 14a, 17a-Pregn-4-En-3-One 20-O-ß-D-Glucopyranoside: A Minor Constituent of the Seeds of Centaurea moschata

Photo-diode-array detector-assisted RP- and NP-HPLC analysis of a methanol extract of the seeds of Centaurea moschata L. (Compositae) led to the isolation of a novel steroidal glucoside which, on the basis of spectroscopic evidence, was identified as (20 R) -15a-hydroxy-8ß, 9a, 14a, 17a-pregn-4-en-3-one 20- O -ß-D-Glucopyranoside [1].

Steroidal glucosides from leaves of Cordyline stricta

A phytochemical study on the leaves of Cordyline stricta yielded four new spirostanol saponins, three new furostanol saponins and a new pregnane glucoside. The structures were determined by detailed analysis of their 1H and 13C NMR spectra, acid-catalysed hydrolysis and by comparison with spectral data of known compounds. Each of the isolated steroidal compounds contained a 3α-hydroxyl group bearing a glucose as the common structural feature. © 1997 Elsevier Science Ltd. All rights reserved

Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach

Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5β-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5β-cholestane skeleton, 1b with the 5β-androstane skeleton, 1c with a fluorine substituent instead of the chlorine and 1d with a β- d-galactopyranose instead of the β- d-glucopyranose of the original pheromone. Their bioassay shows that 1a and 1c are active, while 1b and 1d are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active.