Epi-Neotigogenin and Epi-Tigogenin, Two New Steroidal Sapogenins From Cordyline cannifolia Leaves

Blunden, Gerald; Jaffer, Jaffer A.; Jewers, K.; Griffin, William J.

doi:10.1021/np50005a007

Cited by 11 publications

(13 citation statements)

References 7 publications

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“…This suggests that distinct groups of compounds exist in the two plant parts. Chemical analysis of the CE obtained from the rhizomes of C. drucaenoides revealed the presence of phytosteroids and steroidal saponins, confirming previous studies which demonstrated the presence of glucorticoid-like substances in this and in related species (Jewers et al, 1974a, b;Griffin et al, 1976;Itoh et al, 1977a, b;Blunden et al, 1979;1981). Due to limitations in the supply of botanical material, phytochemical analysis with the extracts of roots or stems was not carried out.…”

Section: Discussionsupporting

confidence: 73%

“…Chemical studies conducted on this plant have demonstrated the existence of steroid saponins including 1,3-hydroxysaponins, (Jewers et al, 1974a,b;Griffin et al, 1976;Itoh et al, 1977a,b;Blunden et al, 1979). However, a pharmacological analysis of C. dracaenoides extract has not been reported to date.…”

Section: Introductionmentioning

confidence: 99%

“…Cordyline dracaenoides (Kunth), a plant belonging to the family Agavaceae, is used in traditional medicine in the south of Brazil as an antiinflammatory preparation for the treatment of rheumatoid and related diseases. Chemical studies conducted on this plant have demonstrated the existence of steroid saponins including 1,3-hydroxysaponins, (Jewers et al, 1974a,b;Griffin et al, 1976;Itoh et al, 1977a,b;Blunden et al, 1979). However, a pharmacological analysis of C. dracaenoides extract has not been reported to date.…”

Section: Introductionmentioning

confidence: 99%

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Chemical and pharmacological analysis of the crude aqueous/alcoholic extract from Cordyline dracaenoides

Calixto¹,

Lima²,

Morato³

et al. 1990

Phytotherapy Research

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Chemical analysis of Cordyline dracaenoides (Kunth) demonstrated the presence of steroidal saponins and anthocyanidins in the stem, rhizome and root. Small amounts of tannins were also detected in its stem and rhizome. Pharmacological analysis revealed different effects according to the part of the plant used. Crude aqueous/alcoholic extract (CE) from the rhizome inhibited carrageenan-induced rat paw oedema, while the CE obtained from the root significantly decreased the locomotor activity and potentiated barbiturate-induced hypnosis in mice. The CE from the roots inhibited noradrenaline-induced contraction in the rat vas deferens in a concentration-dependent and a noncompetitive manner, while the CE from the rhizome caused a parallel displacement to the left of noradrenaline concentration response curves. In the isolated rat stomach, the CE from the roots promoted a concentration-dependent displacement to the right of the serotonin concentration response curve allied to a marked inhibition of its maximal response, while the CE from the rhizome produced only an inhibition of about 40% of serotonin-contractile responses. These results suggest that the CE from C. dracaenoides exhibits a potent and long lasting antioedematogenic effect, has central depressant effects and potentiates noradrenaline-induced contractile responses of the isolated rat vas deferens. AU these effects may be, at least in part, related to the presence of steroidal saponins in this plant.

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Section: Discussionsupporting

confidence: 73%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Chemical and pharmacological analysis of the crude aqueous/alcoholic extract from Cordyline dracaenoides

Calixto¹,

Lima²,

Morato³

et al. 1990

Phytotherapy Research

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“…All solvents used were of spectrophotometric grade (Aldrich). Gas-liquid chromatography (glc) (6) and thin-layer chromatography (tic) (7) were performed according to published procedures.…”

Section: Methodsmentioning

confidence: 99%

High Performance Liquid Chromatographic Separation of Steroidal Sapogenins

Tal¹,

Goldberg²

1981

J. Nat. Prod.

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“…Reduction of 4 (25.9 mg) using NaBH* (Blunden et al, 1979) followed by purification using flash chromatography (eluent D) gave episarsasapogenin (5) (22.5 mg) as a colorless solid, mp (ethanol-water) 209-211 °C; NMR (CeDgN) 0.84 (s, CH3), O. 92 (s, CHS), 1.09 (d, J = 7.0 Hz, CHC#3), 1.16 (d, J = 6.9 Hz, CHCH3) 3.37 (d, J = 10.9 Hz, H-26a), 3.86 (m, H-3/3), 4.07 (dd, J = 2.6,10.9 Hz, H-260), 4.58 (br q, J = 6.6 Hz, H-16); l3C NMR (C5D5N) 14.9 (q), 16.3 (q), 16.7 (q), 20.9 (t), 23.7 (q), 26.2 (t), 26.4 (t), 27.0 (t), 27.6 (t), 27.6 (d), 31.4 (t), 32.2 (t), 35.0 (s), 35.7 (d), 36.0 (t), 37.3 (t), 40.3 (t), 40.9 (s), 40.9 (d), 42.5 (d), 42.5 (d), 56.5 (d), 63.0 (d), 65.1 (t), 70.1 (d), 81.3 (d), 109.6 (s); 13C NMR (CD3C02D) , see Table I.…”

Section: Generalmentioning

confidence: 99%

Identification of insoluble salts of the .beta.-D-glucuronides of episarsasapogenin and epismilagenin in the bile of lambs with alveld and examination of Narthecium ossifragum, Tribulus terrestris, and Panicum miliaceum for sapogenins

Miles¹,

Wilkins²,

Munday³

et al. 1993

J. Agric. Food Chem.

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Crystalloid material soluble in acetic acid was isolated from the bile of lambs with alveld (a hepatogenous photosensitization disease which develops after grazing Narthecium ossifragum). The main components of these bile extracts were shown by hydrolysis, GC-MS, TLC, LSIMS, and 13C NMR, and X-ray analysis to be salts of a 4:1 mixture of episarsasapogenin /3-D-glucuronide (1) and epismilagenin /3-Dglucuronide (2). The 13C NMR spectrum of 1 was fully assigned by comparison with the NMR spectra of model compounds. A metabolic route for conversion of the sarsasapogenin saponins oiN. ossifragum into 1 is proposed. Saponins were extracted from the foliage of N. ossifragum, Tribulus terrestris, and Panicum miliaceum. The saponins were hydrolyzed to sapogenins, which were examined by NMR spectroscopy and GC-MS. P. miliaceum afforded a 4:1 mixture of diosgenin and yamogenin, T. terrestris gave a 5:1 mixture of diosgenin and tigogenin, and N. ossifragum yielded a mixture (82:9:5:4) of sarsasapogenin, smilagenin, yamogenin, and another spirostanol, tentatively identified as neotigogenin.

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Epi-Neotigogenin and Epi-Tigogenin, Two New Steroidal Sapogenins From Cordyline cannifolia Leaves

Cited by 11 publications

References 7 publications

Chemical and pharmacological analysis of the crude aqueous/alcoholic extract from Cordyline dracaenoides

Chemical and pharmacological analysis of the crude aqueous/alcoholic extract from Cordyline dracaenoides

High Performance Liquid Chromatographic Separation of Steroidal Sapogenins

Identification of insoluble salts of the .beta.-D-glucuronides of episarsasapogenin and epismilagenin in the bile of lambs with alveld and examination of Narthecium ossifragum, Tribulus terrestris, and Panicum miliaceum for sapogenins

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