Pregnane glycosides from Caralluma retrospiciens

Halim, Ahmed F.; Khalil, Ashraf Taha

doi:10.1016/0031-9422(96)00029-5

Cited by 38 publications

(25 citation statements)

References 11 publications

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“…4)-b-cymaropyranosyl. The same side chain has been found in a pregnane glycoside isolated from C. retrospiciens [9], and its 13 C-NMR spectroscopic data assured the structure of the oligosaccharide moiety. From the above data, the structure of caradalzieloside A (1) was unequivocally determined as (3b,5a,12b,14b,17a,20S)-12-acetoxy-20-(benzoyloxy)-8,14,17-trihydroxypregnan-3-yl b-oleandropyranosyl-(1 !…”

mentioning

confidence: 51%

Five New Steroidal Glycosides from Caralluma dalzielii

Oyama

Iliya

Tanaka

et al. 2007

Helvetica Chimica Acta

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Five 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.Introduction. -As a part of our studies on Nigerian folkloric medicinal plants [1] [2], we have investigated the chemical constituents of Caralluma dalzielii N. E. BROWN, which has been used as a tonic, aphrodisiac, analgesic, and antiemetic [3]. The plant is a perennial succulent with quadrangular branches belonging to the family of Asclepiadaceae, which is still treated as an independent family. However, modern molecular and genetic studies suggest that it should be incorporated into the Apocynaceae family [4] [5]. On the basis of the new taxonomy, the genus Caralluma is classified into the subfamily Asclepiadoideae, tribe Ceropegieae [4].In previous studies on C. dalzielii, tomentogenin (= 3,12,14,17,20-pentahydroxypregnane) esters [6] and their glycosides [7] were identified. Herein, we report the isolation and structure elucidation of five new steroidal glycosides named caradalzielosides A -E (1 -5), resp. from this plant. They consist of 5,6-dihydrosarcostins (= 3,8,12,14,17,20-hexahydroxypregnanes) with acetyl (Ac) and/or benzoyl (Bz) groups as aglycones and oligosaccharide chains originating from two to four sugar units.

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confidence: 51%

Five New Steroidal Glycosides from Caralluma dalzielii

Oyama

Iliya

Tanaka

et al. 2007

Helvetica Chimica Acta

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“…Complete assignment of NMR resonances and comparison with literature data [7] indicated that 1 was (5a,17S)-12-O-benzoyl-3b,8b,12b,14b-tetrahydroxypregnan-20-one ( Table 1). The same skeleton has been found as aglycone in some of the steroidal glycosides isolated from Caralluma species [8]. The same substance was also produced by acid hydrolysis of glycosides obtained from C. retrospiciens [9].…”

Section: For [M à H]mentioning

confidence: 79%

Pregnane Glycosides from Caralluma adscendens var. fimbriata

Kunert¹,

Rao²,

Babu³

et al. 2008

Chemistry & Biodiversity

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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.

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“…Staphyloxanthin (197) has been isolated as the major pigment from Staphylococcus aureus [166]. The carotenoid composition of the myxobacterium Chondromyces apiculatus was also reported [167].…”

Section: Formation Of Fatty Acid Glucuronides 16 ± 18 In Human Livermentioning

confidence: 98%

“…Pregnane glycoside ester 270 was isolated from the aerial parts of Caralluma retrospiciens [197]. Certain pregnane glycosides were recently proved to induce differentiation of mouse myeloid leukaemia cells into phagocytic cells [198].…”

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confidence: 99%