Novel Steroidal Glycosides from two Indian Caralluma species, C. stalagmifera and C. indica

Kunert, Olaf; Rao, Belvotagi Venkatrao Adavi; Babu, Gummadi Sridhar; Padmavathi, M.; Kumar, Bobbala Ravi; Alex, Robert Michael; Schühly, Wolfgang; Simić, Nebojša; Kühnelt, Doris; Rao, A. S.

doi:10.1002/hlca.200690022

Cited by 16 publications

(8 citation statements)

References 12 publications

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“…It exhibited a UV absorption at 229 nm, and its specific rotation [a] 13 C-NMR data of the aglycone were in agreement with those of stalagmoside II isolated from C. stalagmifera [8]. Therefore, the structure of the aglycone of 1 was determined as (5a) -5,6-dihydrosarcostin 12-acetate 20-benzoate (= (3b,5a,12b,14b,17a,20S)-12-acetoxy-3,8,14,17-tetrahydroxypregnan-20-yl benzoate H-COSY spectra suggested that 1 comprised two 2,6-dideoxy sugars.…”

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confidence: 56%

“…The replacement of an AcO group at C(12) by a BzO group was inferred from the 1 H-NMR spectrum (Table 3) The NMR spectroscopic data of the aglycone of 3 were basically identical to those of stalagmoside IV [8], including the deshielding effect observed between the BzO groups. Thus, the structure of 3 was elucidated as (3b,5a,12b,14b,17a,20S)-12,20-bis-(benzoyloxy) -8,14,17-trihydroxypregnan-3-…”

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confidence: 99%

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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: 56%

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confidence: 99%

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].…”

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confidence: 96%

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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“…Two known compounds, carumbelloside III and dihydrorusselioside B [13,24] were also isolated from C. pauciflora and β-sitosterol, lupeol, and a known pregnane glycoside were isolated from C. adscendens var. gracilis.…”

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confidence: 99%