Pregnane Glycosides Research Articles

Two New C21 Steroidal Glycosides from the Stems of Marsdenia tenacissima

AbstractTwo new pregnane glycosides, (3β,5α,12β,14β,17α)‐3‐(β‐cymaropyranosyloxy)‐8,14,17,20‐tetrahydroxypregnan‐12‐yl benzoate (1) and (3β,5α,12β,14β,17α)‐3‐(β‐cymaropyranosyloxy)‐8,14,17,20‐tetrahydroxypregnan‐12‐yl cinnamate (2) were isolated from the stems of Marsdenia tenacissima. The structures and relative configurations of the new compounds were elucidated by spectroscopic methods, including mass spectrometry and NMR spectroscopy.

Pregnane glycosides and steroid saponins from Smilax bockii Warb. and their NGF-potentiating activity

The chemical constituents of the roots of Smilax bockii Warb. were investigated and two pregnane glycosides and three steroid saponins were isolated. Their structures were established as 3β-hydroxypregna-5,16-dien-20-one-3-O-α-L-rhamnopyranosyl(1 → 4)-α-L-rhamnopyranosyl(1 → 4)-[α-L-rhamnopyranosyl(1 → 2)]-β-D-glucopyranoside (1), 3β-hydroxypregna-5,16-dien-20-one-3-O-α-L-rhamnopyranosyl(1 → 2)-[α-L-rhamnopyranosyl(1 → 4)]-β-D-glucopyranoside (2), dioscin (3), methyl protodioscin (4), 26-O-β-D-glucopyranosyl-22α-methoxyl-(25R)-furost-5-en-3β, 26-diol 3-O-α-L-rhamnopyranosyl(1 → 4)-α-L-rhamnopyranosyl(1 → 4)-[α-L-rhamnopyranosyl(1 → 2)]-β-D-glucopyranoside (5) on the basis of spectral analysis and chemical methods. Compound 1 is a new natural product and compounds 2, 5 were first isolated from the genus Smilax. Compound 5 showed enhancing activity of nerve growth factor (NGF)-induced neurite outgrowth in PC 12D cells.

Acylated pregnane glycosides from Caralluma tuberculata and their antiparasitic activity

Five pregnane glycosides were isolated from Caralluma tuberculata (1–5), in addition to a known one (russelioside E, 6). The structures of the isolated compounds were elucidated by the analysis of NMR data and FAB–MS experiments. All the isolated compounds were tested for their antimalarial and antitrypanosomal activities as well as their cytotoxicity against human diploid embryonic cell line (MRC5).

Periplocoside A, a pregnane glycoside from Periploca sepium Bge, prevents concanavalin A-induced mice hepatitis through inhibiting NKT-derived inflammatory cytokine productions

Periploca sepium Bge, a traditional Chinese herb medicine, is widely used for treating rheumatoid arthritis in china. Periplocoside A (PSA), a pregnane glycoside, is a new nature product compound isolated from P. sepium Bge. We examined the protective effects of PSA, on concanavaline A (ConA)-induced hepatitis. Pretreatment with PSA dramatically ameliorated ConA-induced liver injury, which was characterized by reducing serum alanine transaminase (ALT), pathogenic cytokines of interleukin (IL)-4 and interferon (IFN)-γ levels, impeding the liver necrosis, and thus elevating the survival rate. In vitro, PSA inhibited IL-4 and IFN-γ productions of α-galactosylceramide (α-GalCer) or anti-CD3-activated Natural killer T (NKT) cells. Enzyme Linked Immunosorbent Assay (ELISA) and Reverse Transcription Polymerase Chain Reaction (RT-PCR) assays revealed PSA suppressed IL-4 transcription and IFN-γ translation. In conclusion, PSA had significantly preventative effect on ConA-induced hepatitis, which was closely associated with inhibition of NKT-derived inflammatory cytokine productions. These findings suggested that PSA has the therapeutic potential for treatment of human autoimmune-related hepatitis.

Steroidal Saponins from the Seeds of Hyoscyamus Niger L.

Ten steroidal saponins have been isolated form the seeds of Hyoscyamus niger L. for the first time and their structures have been elucidated. Seven saponins belong to spirostane series, two are furostane-type and one is pregnane glycoside. Hyoscyamosides B, C and C2 are new steroidal saponins, which have never been reported before in literature. Complete assignments of the 1H and 13C NMR chemical shifts for all these glycosides were achieved by means of one- and two-dimensional NMR techniques, including 1H–1H COSY, HSQC, HMBC and ROESY spectra.

Two New Cytotoxic Pregnane Glycosides from Cynanchum auriculatum

Two new pregnane glycosides, kidjoranin 3- O- alpha-diginopyranosyl-(1-->4)- beta-cymaropyranoside (1) and kidjoranin 3-O-beta-digitoxopyranoside (2), together with one known compound caudatin 3 -O-beta-cymaropyranoside (3), were isolated from the roots of Cynanchum auriculatum. Their structures were established on the basis of NMR analyses. Compounds 1 - 3 were tested for their in vitro inhibitory activity against the growth of human tumor cell lines SMMC-7721, HeLa and MCF7; all of them displayed marked cytotoxic activities against cells SMMC-7721 and HeLa with IC (50) values ranging from 8.6 microM to 58.5 microM, yet no activity against the cell line MCF7 was detected.

Rapid structural determination of modified pregnane glycosides from Cynanchum forrestii by liquid chromatography–diode-array detection/electrospray ionization multi-stage tandem mass spectrometry

The fragmentation behaviors of the two types of modified pregnane glycosides from Cynanchum forrestii were investigated by positive ion electrospray ionization multi-stage tandem mass spectrometry equipped with an ion trap analyzer. The spectral data further illuminated the predominance of ESI-MS n technique on the identification of pregnane glycosides, especially of two sorts of modified pregnane glycosides with aglycone skeletons of 13,14:14,15-disecopregnane-type and 14,15-secopregnane-type, which differed in the presence of the characteristic [M−46+Na] + ion. For sugar residues, the fragment ions were analyzed and some possible fragmentation pathways were proposed, especially for 3-demethyl-2-deoxythevetose, the glycosidic cleavage reaction was easier to occur than those of other sugar units in its moiety. The natures and differences of the pregnane cores, and the types and linked sequences of sugar residues were illustrated. According to these conclusions, eight new pregnane glycosides in the fraction of Cynanchum forrestii were structurally elucidated by HPLC/HRMS and HPLC–DAD/ESI-MS n techniques. Results of the present studies can benefit the rapid identification and structural determination of analogous constituents in crude plant extracts.

Pregnane Glycosides from Caralluma adscendens var. fimbriata

Eleven novel pregnane glycosides, 2-7 and 9-13, of which four, i.e., 10-13, comprised a new pregnane-type genin exhibiting a hydroxymethylene instead of a Me group at C(19), and the known pregnane glycoside stalagmoside V (8) were isolated from whole plants of Caralluma adscendens var. fimbriata, a native Indian succulent plant. Their structures were elucidated by extensive 2D-NMR spectroscopic studies.

LC-ESI-MSD-TOF and Ion-Trap Tandem Mass Spectrometry for Identification and Structural Characterization of Eight Pregnane Glycosides including P57 (Appetite Suppressant) in Hoodia gordonii

LC-ESI-MSD-TOF and Ion-Trap Tandem Mass Spectrometry for Identification and Structural Characterization of Eight Pregnane Glycosides including P57 (Appetite Suppressant) in Hoodia gordonii

A Pregnane Glycoside from Overripe Tomato

A new pregnane glycoside, 3-O-beta-lycotetraosyl 5alpha-pregna-3beta,26beta-diol-20-one was isolated from overripe tomato, the fruit of Lycopersicon esculentum MILL.

Pregnane glycosides from Cynanchum atratum

Five new pregnane glycosides, cynanosides K–O ( 1– 5) with a 14,15-seco-pregnane-type skeleton as the aglycon, together with five known compounds, cynascyroside C, sublanceoside E 1, sublanceoside I 1, atratoside A and atratoside B, were isolated from the roots of Cynanchum atratum. Their structures were determined on the basis of spectroscopic analysis and chemical evidence.

Pregnane glycosides from Solanum nigrum

Two new pregnane saponins, solanigroside A (1) and solanigroside B (2), along with two known compounds (3 and 4), were isolated from 60% ethanolic extract of the dried herb of Solanum nigrum L. The structures of 1 and 2 were elucidated as 5α-pregn-16-en-3β-ol-20-one 3-O-β-d-xylopyranosyl-(1 → 3)-O-[α-l-arabinopyranosyl-(1 → 2)]-O-β-d-glucopyranosyl-(1 → 4)-O-[α-l-rhamnopyranosyl-(1 → 2)]-O-β-d-galactopyranoside (1) and 5α-pregn-16-en-3β-ol-20-one 3-O-β-d-glucopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 3)]-O-β-d-glucopyranosyl-(1 → 4)-O-β-d-galactopyranoside (2), respectively, on the basis of extensive spectroscopic analysis as well as comparison with reported spectroscopic data of related compounds. This paper deals with the isolation and structural characterisation of pregnane glycosides from S. nigrum L.

New calogenin glycosides from Hoodia gordonii

Ten new pregnane glycosides ( 1, 3– 11) were isolated from organic extracts of aerial parts of Hoodia gordonii, which is sold as an appetite suppressant herbal supplement. The aglycone was identified as calogenin, based on the spectroscopic data of products obtained upon chemical and enzymatic degradation of parent glycoside. The structures of the glycosides were established by chemical degradation studies and extensive spectroscopic techniques that included one-dimensional and two-dimensional NMR.

New pregnane glycosides from the roots of Cynanchum otophyllum

Six new pregnane glycosides with an acyl at C-12 and a straight sugar chain at C-3, namely otophyllosides H–M ( 1–6), were isolated from the roots of Cynanchum otophyllum (Asclepiadaceae) collected from Eryuan County in Yunnan province of China. Their structures were characterized to be qingyangshengenin 3- O-β- d-glucopyranosyl-(1 → 4)-β- d-glucopyranosyl-(1 → 4)-β- d-cymaropyranosyl-(1 → 4)-β- d-oleandropyranosyl-(1 → 4)-β- d-digitoxopyranoside ( 1), qingyangshengenin 3- O-β- d-glucopyranosyl-(1 → 4)-β- d-oleandropyranosyl-(1 → 4)-β- d-cymaropyranosyl-(1 → 4)-β- d-digitoxopyranoside ( 2), qingyangshengenin 3- O-β- d-glucopyranosyl-(1 → 4)-β- d-cymaropyranosyl-(1 → 4)-β- d-oleandropyranosyl-(1 → 4)-β- d-cymaropyranosyl-(1 → 4)-β- d-digitoxopyranoside ( 3), qingyangshengenin 3- O-β- d-glucopyranosyl-(1 → 4)-β- d-thevetopyranosyl-(1 → 4)-β- d-cymaropyranosyl-(1 → 4)-β- d-digitoxopyranoside ( 4), caudatin 3- O-β- d-glucopyranosyl-(1 → 4)-β- d-glucopyranosyl-(1 → 4)-β- d-cymaropyranosyl-(1 → 4)-β- d-oleandropyranosyl-(1 → 4)-β- d-cymaropyranoside ( 5), caudatin 3- O-β- d-glucopyranosyl-(1 → 4)-β- d-cymaropyranosyl-(1 → 4)-β- d-oleandropyranosyl-(1 → 4)-β- d-cymaropyranosyl-(1 → 4)-β- d-cymaropyranoside ( 6), respectively, on the basis of detailed spectroscopic analysis and chemical method.

An appetite suppressant from Hoodia species

Studies conducted at the Council for Scientific and Industrial Research (CSIR, South Africa) identified extracts from Hoodia species, in particular Hoodia pilifera and Hoodia gordonii, as possessing appetite suppressing properties. Two pregnane glycosides were isolated by fractionation of the dried stems of H. gordonii. Their structures were determined as 3β-[β- d-thevetopyranosyl-(1→4)-β- d- cymaropyranosyl-(1→4)-β- d-cymaropyranosyloxy]-12β-tigloyloxy-14β-hydroxypregn-5-en-20-one ( 1) and 3β-[β- d-cymaropyranosyl-(1→4)-β- d-6-thevetopyranosyl-(1→4)-β- d-cymaropyranosyl-(1→4)-β- d-cymaropyranosyloxy]-12β-tigloyloxy-14β-hydroxypregn-5-en-20-one ( 2) on the basis of spectroscopic studies and conversion to known compounds. Compounds 1 and 2 were also isolated from H. pilifera. Compound 1 was tested for its appetite suppressant properties in rats by oral gavage at 6.25–50 mg/kg and the results showed that all doses resulted in a decrease of food consumption over an eight day period and a body mass decrease when compared to the control sample receiving only the vehicle. In a comparative study against a fenfluramine control sample, compound 1 resulted in a reduction in food intake over the study period, with a concomitant overall decrease in body weight while fenfluramine resulted in a small decrease in food intake, but an increase in body weight (though less than control group) over the same period of time.

Acylated pregnane glycosides from Caralluma russeliana

The chloroform extract of the aerial parts of Caralluma russeliana yielded four acylated pregnane glycosides, namely russeliosides E– H, three were found now. The structures of the compounds were elucidated using MS, 1H NMR, 13C NMR, 1H– 1H COSY, HMQC, NOESY and HMBC experiments.

Expeditious and convenient synthesis of pregnanes and its glycosides as potential anti-dyslipidemic and anti-oxidant agents

A series of new pregnane derivatives and its glycosides were synthesized in order to find new ‘leads’ against some important targets. The 3β-hydroxy-16α-(2-hydroxy ethoxy) pregn-5-en-20-one ( 5) was synthesized from 3β-hydroxy-5,16-pregnadiene-20-one ( 2) by adopting general modified procedure using BF 3:Et 2O as a catalyst. Reduction of 5, with sodium borohydride yielded 3β,20β-dihydroxy-16α-(2-hydroxy ethoxy) pregn-5-en ( 7) as the major isolable product. O-alkylation of the C-20-oxime-pregnadiene ( 9) with 1,5-dibromopentane yielded 20-( O-5-bromopentyl)-oximino-3β-hydroxy-pregn-5,16-diene ( 11). Synthesis of C-16 substituted pregnane glycosides ( 20) and ( 21) were accomplished with the imidate method using BF 3:Et 2O. The synthesis of 4-chlorobenzoate ( 3) and 2-chlorobenzoate ( 4), derivatives of 2 were also accomplished. These compounds were evaluated for their anti-dyslipidemic and anti-oxidant activity and amongst them compounds 3 and 7 showed more lipid lowering and anti-oxidant activity.

Phytoconstituents from the root of Streptocaulon tomentosum and their chemotaxonomical relevance for separation from S. juventas

A new cardenolide, 17β-H-periplogenin-3- O-β- d-digitoxoside ( 1), and a new pregnane glycoside, Δ 5-pregnene-3β,16α-diol-d- O-[2,4- O-diacetyl-β-digitalopyranosyl-(1 → 4)-β- d-cymaropyranoside]-16- O-[β- d-glucopyranoside] ( 2) were isolated from the roots of Streptocaulon tomentosum (Asclepiadaceae) together with a series of known compounds. Their chemotaxonomic significance for the separation of S. tomentosum from Streptocaulon juventas is discussed, suggesting a rather clear distinction of these species.

Four New Pregnane Glycosides from the Stems of Marsdenia tenacissima.

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Five New Steroidal Glycosides from Caralluma dalzielii

AbstractFive new pregnane glycosides, caradalzielosides A–E (1–5), were isolated from the aerial parts of Caralluma dalzielii. Their structures were elucidated by extensive 1D‐ and 2D‐NMR spectroscopic analysis as well as by HR‐FAB‐MS experiments.