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A comparative investigation has been made of the action of 14 steroid glycosides of the spirostan and furostan series on highly purified Na,K-ATPase from the medullary layer of porcine kidneys (∼90% purity in terms of protein). It has been shown that alliospirosides A, B, and D, isolated from the collective fruit ofAllium sepaL., are capable of inhibiting the activity of the Na,K-ATPase The inhibition of the activity of the transport enzyme by alliospirosides A and B is of the uncompetitive type and by alliospiroside D of the competitive type. It is desirable to test alliospirosides on the intact organism.

In this review steroids of the spirostan and furostan series produced by the genusAllium are considered. A description is given of 26 genins (25 of the spirostan and one of the 22,25-epoxyfurostan series) and of 40 glycosides (29 of the spirostan series, 10 of the furostan series and one of the 22,25-epoxyfurostan series).

A new genin of the spirostan series — anzurogenin B having the structure of 2a,5a-epoxy-(25R)-spirostan-3ß,6ß-diol — has been isolated form the collective fruit of the cocultivatedAllium suvorovii Rgl. andAllium stipitatum Rgl. (family Liliaceae).

Two new steroid glycosides of the spirostan series have been isolated from the fruit ofAllium cepaL. (family Liliaceae): alliospirosides C and D. On the basis of chemical transformations and spectral characteristics it has been established that the aglycon of both glycosides is a new steroid sapogenin — cepagenin — having the structure of (24S,25R)-spirost-5-ene-1β,3β,24-triol. Alliospirosides C and D are cepagenin 1-O-[O-α-L-rhamnopyranosyl-(1→2)α-L-arabinopyranoside] and 1-O-[O-α-L-rhamnopyranosyl-(1→2)-O-β-D-galactopyranoside], respectively.

The EI and LSIMS mass spectra of alliosterol and its dehydration product and of allosides A and B have been studied. The spectra of alliosterol show features characteristic for sterols of the cholestane series. A comparison of the B/E spectra of some fragments of the ions from alliosterol and its dehydro product has shown the unimportance of the conversion of the former into the latter under mass-spectrometric conditions.

Two new glycosides of the cholestane series (allosides A and B) have been isolated from the fruit of the cocultivatedAllium suvorovii Rgi. andAllium stipitatum Rgl. (family Liliaceae, local name “anzur”). The acid hydrolysis of both compounds gave a sterol not previously described, which has been called alliosterol and has the structure of (22S)-cholest-5-ene-1ß, 3ß, 16ß, 22-tetraol, and the product of its dehvdration, which is (16S, 22S)-furost-5-ene-1ß, 3ß-diol. Alloside A is the 16-O-ß-D-galactopyranoside, and alloside B the 16-O-ß-D-galactopyranoside 1-O-ß-D-glucopyranoside of alliosterol.

A new steroid glycoside of the spirostan series, anzuroside, has been isolated from the collective fruits of the cocultivatedAllium suvoroviiRgl. andA. stipitatumRgl. (family Liliaceae, local name “anzur”). Enzymatic cleavage of the glycoside has given the previously undescribed steroid sapogenin anzurogenic C, which has the structure of (24S, 25S)-2α,3β,5,24-tetrahydroxy-5β-spirostan-6-one. Anzuroside is the 24-O-β-D-glucopyranoside of anzurogenin C.

Two new steroid glycosides have been isolated from the generative organs (pericarps and peduncles) ofAllium cepa L.: alliospiroside A and alliofuroside A. According to chemical transformations and spectral characteristics, alliospiroside A has the structure of (25S)-spirost-5-ene-1ß,3ß-diol 1-O-[O-a-L-rhamnopyranosyl-(1 ? 2)-a-L-arabinopyranoside]. The structure of (25S)-furost-5-ene-1ß,3ß,22a,26-tetraol 20-O-ß-D-glucopyranoside 1-O-[O-a-L-rhamnopyranosyl-(1 ? 2)-a-L-arabinopyranoside] has been established for alliofuroside A.