Bioactive Steroidal Saponins from <i>Smilax medica</i>

Sautour, Marc; Miyamoto, Tomofumi; Lacaille‐Dubois, Marie‐Aleth

doi:10.1055/s-2006-931582

Cited by 17 publications

(9 citation statements)

References 12 publications

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“…Plants produce metabolites with antimicrobial properties when they have been exposed to microorganisms. The antifungal activity of essential oils [17,18], saponins [19] and some alkaloids [20] has already been reported.…”

Section: Introductionmentioning

confidence: 99%

In Vitro Antioxidant and Anti-rhizopus Activities of Lamiaceae Herbal Extracts

López

Akerreta

Casanova

et al. 2007

Plant Foods Hum Nutr

142

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Eighty-eight extracts of different polarity obtained from 18 Lamiaceae medicinal and aromatic plants were screened for their antioxidant and antifungal properties. A TLC analysis combined with two bioassays were used to detect these activities. In most cases the highest radical scavenger capacity was detected in methanolic and aqueous extracts and polyphenols may be responsible. The most interesting antioxidant activity was observed in polar extracts obtained from Lycopus europaeus, Melissa officinalis, Origanum vulgare subsp. virens and Lavandula latifolia. On the contrary, the best results for the antifungal test against Rhizopus stolonifer were produced by non-polar herbal extracts. Phlomis lychnitis, Salvia pratensis and Calamintha sylvatica caused the highest inhibition on Rhizopus growth.

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Section: Introductionmentioning

confidence: 99%

In Vitro Antioxidant and Anti-rhizopus Activities of Lamiaceae Herbal Extracts

López

Akerreta

Casanova

et al. 2007

Plant Foods Hum Nutr

142

View full text Add to dashboard Cite

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“…However, many Smilax species from other parts of the world such as Smilax china have been submitted to numerous chemical and biological studies due to their interesting properties. These species have been shown to contain steroidal saponins and phenolic compounds Sashida et al, 1992;Bernardo et al, 1996;Shu et al, 2002;Sautour et al, 2006;Xu et al, 2006) and have demonstrated interesting anti-inflammatory, anti-conceptive, cytotoxic, antioxidant, immunomodulatory, anticancer, hypoglycaemic, uricosuric and antifungal activities (Giachetti et al, 1988;Suh et al, 1996;Fukunaga et al, 1997;Lee et al, 2001;Jiang and Xu, 2003;Cox et al, 2005;Kuo et al, 2005;Sautour et al, 2005;Thabrew et al, 2005;Xu et al, 2005;Chu and Ng, 2006;Huang et al, 2006;Wang et al, 2006;Li et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

Diuretic activity of Smilax canariensis, an endemic Canary Island species

Abdala

Martín-Herrera

Benjumea

et al. 2008

Journal of Ethnopharmacology

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“…According to our previous observations, saponins having a furostan skeleton (2, 4, 5, 6) were devoid of activity against the tested fungi. 5,6,[10][11][12] Concerning the spirostanol saponins, only compound 3, having two sugars for the osidic chain showed an antifungal activity against the yeast tested with minimum inhibitory concentration (MIC) values between 25 and 50 mg/ml (Table 4). Antifungal activities were also observed previously with SS 1 which differ of 3 by the (1→6) linkage of the second glucose.…”

Section: C-nmr Shift Of 25r-spirostanes (D C 171-172)mentioning

confidence: 99%

“…5,6) As part of our ongoing search for new antifungal steroid saponins, 5,6,[10][11][12] we have investigated the roots of Smilax aspera subsp. mauritanica.…”

mentioning

confidence: 99%

Steroidal Saponins from the Roots of Smilax aspera subsp. mauritanica

et al. 2008

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The genus Smilax contains 350 species, which are distributed widely mainly in tropical regions of east Asia, and South and North America. Several Smilax species have already been studied chemically and found to contain steroidal saponins.1-6) From a biological point of view, some species were documented to exhibit antiinflammatory, 7) NO-modulating 8) and antileprosic 9) activity and recently, antifungal steroidal saponins were isolated from the rhizome of S. medica. 5,6) As part of our ongoing search for new antifungal steroid saponins, 5,6,[10][11][12] we have investigated the roots of Smilax aspera subsp. mauritanica. The present paper reports the isolation and characterization of two new steroidal saponins (1, 2) along with four known saponins (3-6) and the phenolic compound resveratrol (7). Their structures were determined by spectroscopic methods including 1D and 2D NMR experiments and FAB-MS and HR-ESI-MS. Furthermore, their antifungal activity was tested against three human pathogenic yeasts (Candida albicans, C. glabrata, and C. tropicalis).The n-BuOH-soluble fraction of the MeOH-H 2 O (7 : 3) extract of the roots of S. aspera subsp. mauritanica was purified by precipitation with diethyl ether to give a crude saponin mixture. This mixture was submitted to multiple chromatographic steps involving vacuum-liquid chromatography (VLC) on reversed-phase C 18 silica gel and mediumpressure liquid chromatography (MPLC) on normal silica gel to yield compounds 1-6. The diethyl ether fraction was submitted to multiple MPLC to give the pure phenolic compound 7.Compound 1, a white amorphous powder, exhibited in FAB-MS (negative-ion mode) a quasimolecular ion peak at m/z 885 , corresponding to the successive loss of one deoxy-hexosyl and one hexosyl moieties. Acid hydrolysis of 1 yielded glucose, rhamnose (TLC) and their absolute configuration was determined to be D and L by GC analysis of chiral derivatives of the sugars in the acid hydrolysate (see Experimental). The aglycon was identified as sarsapogenin [(25S)-5b-spirostane3b-ol] 13,14) from the 1D and 2D NMR spectral data of 1 (see Table 1). The A/B cis-ring fusion was confirmed by observation of the signals at d C 35.3 (C-5), 39.8 (C-9), and 23.6 (C-19), indicating that the aglycon is a 5b-steroidal sapogenin. 15)The 25S stereochemistry of the 27-methyl group was deduced based on the presence of the two proton signals [d Compound 2 was isolated as a white amorphous powder. Its HR-ESI-MS (positive-ion mode) exhibited a pseudo-molecular ion peak at m/z 1089.5195 [MϩNa] ϩ (Calcd for C 51 Two new steroidal saponins (1, 2) were isolated from the roots of Smilax aspera subsp. mauritanica (POIR.) ARCANG. (Liliaceae), together with the known curillin G (3), asparagoside E (4), asparoside A (5), asparoside B (6) and the phenolic compound resveratrol (7). Their structures were established mainly on the basis of 600 MHz 2D-NMR spectral data. 3 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (minimum i...

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Bioactive Steroidal Saponins from Smilax medica

Cited by 17 publications

References 12 publications

In Vitro Antioxidant and Anti-rhizopus Activities of Lamiaceae Herbal Extracts

In Vitro Antioxidant and Anti-rhizopus Activities of Lamiaceae Herbal Extracts

Diuretic activity of Smilax canariensis, an endemic Canary Island species

Steroidal Saponins from the Roots of Smilax aspera subsp. mauritanica

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