Preparative separation of glycoalkaloids α-solanine and α-chaconine by centrifugal partition chromatography

Attoumbré, Jacques; Lesur, David; Giordanengo, Philippe; Baltora-Rosset, Sylvie

doi:10.1016/j.jchromb.2012.09.025

Cited by 8 publications

(6 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We have recently shown that CPC is an attractive method to isolate bioactive compounds from Solanum species . Hence, it was decided to implement this technique to the fractionation of S. somalense leaves that are a rich source of caffeic acid derivatives with potential interest.…”

Section: Resultsmentioning

confidence: 99%

5‐O‐Caffeoylshikimic acid from Solanum somalense leaves: Advantage of centrifugal partition chromatography over conventional column chromatography

Chideh

Pilard²,

Attoumbré³

et al. 2014

J of Separation Science

Self Cite

View full text Add to dashboard Cite

Solanum somalense leaves, used in Djibouti for their medicinal properties, were extracted by MeOH. Because of the high polyphenol and flavonoid contents of the extract, respectively, determined at 80.80 ± 2.13 mg gallic acid equivalent/g dry weight and 24.4 ± 1.01 mg quercetin equivalent/g dry weight, the isolation and purification of the main polyphenols were carried out by silica gel column chromatography and centrifugal partition chromatography. Column chromatography led to 11 enriched fractions requiring further purification, while centrifugal partition chromatography allowed the easy recovery of the main compound of the extract. In a solvent system composed of CHCl3/MeOH/H2O (9.5:10:5), 21.8 mg of this compound at 97% purity was obtained leading to a yield of 2.63%. Its structure was established as 5-O-caffeoylshikimic acid by mass spectrometry and NMR spectroscopy. This work shows that S. somalense leaves contain very high level of 5-O-caffeoylshikimic acid (0.74% dry weight), making it a potential source of production of this secondary metabolite that is not commonly found in nature but could be partly responsible of the medicinal properties of S. somalense leaves.

show abstract

Section: Resultsmentioning

confidence: 99%

5‐O‐Caffeoylshikimic acid from Solanum somalense leaves: Advantage of centrifugal partition chromatography over conventional column chromatography

Chideh

Pilard²,

Attoumbré³

et al. 2014

J of Separation Science

Self Cite

View full text Add to dashboard Cite

show abstract

“…In Solanaceae family, steroidal glycoalkaloids comprise an essential group of pharmaceutically important bioactive compounds. [ 8 ] Solasodine and α-solanine are among those present in large amount in Solanum plants. These two alkaloids are blessed with many important pharmacological properties.…”

Section: Introductionmentioning

confidence: 99%

Elicitation based enhancement of secondary metabolites in Rauwolfia serpentina and Solanum khasianum hairy root cultures

2016

View full text Add to dashboard Cite

Background:Rauwolfia serpentina and Solanum khasianum are well-known medicinally important plants contained important alkaloids in their different parts. Elicitation of these alkaloids is important because of associated pharmaceutical properties. Targeted metabolites were ajmaline and ajmalicine in R. serpentina; solasodine and α-solanine in S. khasianum.Objective:Enhancement of secondary metabolites through biotic and abiotic elicitors in hairy root cultures of R. serpentina and S. khasianum.Materials and Methods:In this report, hairy root cultures of these two plants were established through Agrobacterium rhizogenes mediated transformation by optimizing various parameters as age of explants, duration of preculture, and co-cultivation period. NaCl was used as abiotic elicitors in these two plants. Cellulase from Aspergillus niger was used as biotic elicitor in S. khasianum and mannan from Saccharomyces cerevisiae was used in R. serpentina.Results:First time we have reported the effect of biotic and abiotic elicitors on the production of important metabolites in hairy root cultures of these two plants. Ajmalicine production was stimulated up to 14.8-fold at 100 mM concentration of NaCl after 1 week of treatment. Ajmaline concentration was also increased 2.9-fold at 100 mg/l dose of mannan after 1 week. Solasodine content was enhanced up to 4.0-fold and 3.6-fold at 100 mM and 200 mM NaCl, respectively, after 6 days of treatments.Conclusion:This study explored the potential of the elicitation strategy in A. rhizogenes transformed cell cultures and this potential further used for commercial production of these pharmaceutically important secondary metabolites.SUMMARY Hairy roots of Rauwolfia serpentina were subjected to salt (abiotic stress) and mannan (biotic stress) treatment for 1 week. Ajmaline and ajmalicine secondary metabolites were quantified before and after stress treatmentAjmalicine yield was enhanced up to 14.8-fold at 100 mM concentration of NaCl. Ajmaline content was also stimulated 2.9-fold at 100 mg/l dose of mannan after 1 weekHairy roots of Solanum khasianum were treated with cellulase (biotic elicitor) and salt (abiotic stress)Solasodine content was improved up to 4.0-fold and 3.6-fold at 100 mM and 200 mM NaCl, respectively, after 6.days of treatmentsThe α-solanine content increased to 1.6-fold after 24 h of treatment at 100 μg/mL cellulase concentration. Abbreviations used: MS medium: Murashige and Skoog medium, B5 medium: Gamborg B5 medium, OD: Optical Density, NaCl: Sodium Chloride.

show abstract

“…The amount of solanidine obtained in these conditions was then quantified by analytical HPLC and was 29.04 mg/50 g fresh weight (FW) for skin and 41.13 mg/50 g FW for sprouts (Table ). In a previous study , we showed that the average content of GAs present in sprouts from S. tuberosum cv Pompadour was about 108 mg/50 g FW which corresponds to 45 mg/50 g FW of solanidine considering the molecular weight difference. Based on these data showing that these conditions allow the hydrolysis of all the GAs, we decided to work with sprouts and to use the hydrolysis conditions mentioned above, i.e.…”

Section: Resultsmentioning

confidence: 92%

“…a loading value of 6 mg/mL, which is high compared to the average loading of 2.2 mg/mL observed in the literature and could contribute to produce peak broadening and overlapping . However, the unusual shape of the chromatogram is not linked to the quality of the separation since this rather unusual form of peaks together with a successful separation of GAs was already observed . Each fraction collected during the separation process was analyzed by HPLC [Fig.…”

Section: Resultsmentioning

confidence: 99%

Solanidine isolation from Solanum tuberosum by centrifugal partition chromatography

Attoumbré¹,

Giordanengo

Baltora-Rosset

2013

J. Sep. Science

Self Cite

View full text Add to dashboard Cite

The aim of this investigation was the preparative isolation of solanidine (aglycone of the two main potato glycoalkaloids: α-chaconine and α-solanine) from fresh Solanum tuberosum (cv. Pompadour) material by implementing a new preparation scheme using centrifugal partition chromatography (CPC). A setup for obtaining solanidine by hydrolysis of the glycoalkaloids found in the skin and sprouts of S. tuberosum was first developed. Then its isolation was carried out by the development of CPC conditions: the solvent system used for separation was ethyl acetate/butanol/water in the ratio 42.5:7.5:50 v/v/v, 0.6 g of crude extract were separated with a 8 mL/min flow rate of mobile phase while rotating at 2500 rpm. A run yielded 98 mg of solanidine (86.7% recovery from the crude extract) in a one-step separation. The purity of the isolated solanidine was over 98%. Thus, CPC has proven to be the method of choice to get solanidine of very high purity from S. tuberosum biomass in large quantities.

show abstract

Preparative separation of glycoalkaloids α-solanine and α-chaconine by centrifugal partition chromatography

Cited by 8 publications

References 18 publications

5‐O‐Caffeoylshikimic acid from Solanum somalense leaves: Advantage of centrifugal partition chromatography over conventional column chromatography

5‐O‐Caffeoylshikimic acid from Solanum somalense leaves: Advantage of centrifugal partition chromatography over conventional column chromatography

Elicitation based enhancement of secondary metabolites in Rauwolfia serpentina and Solanum khasianum hairy root cultures

Solanidine isolation from Solanum tuberosum by centrifugal partition chromatography

Contact Info

Product

Resources

About