Conversion of 3-demethylthiocolchicine into thiocolchicoside by Centella asiatica suspension cultures

Bouhouche, Naima; Solet, Jean-Michel; Simon-Ramiasa, A.; Bonaly, J.; Cosson, L.

doi:10.1016/s0031-9422(97)00676-6

Cited by 9 publications

(5 citation statements)

References 25 publications

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“…The stationary phase was achieved after 13-14 days. Similar findings were reported by Bouhouche et al (1998) who reported a latent phase between 0 and 3 days and an exponential growth phase from 3 to 12 days and a stationary phase from 12 to 14 days under the same conditions. Nath and Buragohain (2005) found an initial lag phase up to day 10 of incubation for C. asiatica cell suspensions followed by a steep rise in growth rate until the third week.…”

Section: Resultssupporting

confidence: 90%

“…Explants from stems of Type-1 and Type-2 was cultivated and maintained in agar solidified Murashige and Skoog (MS) medium with vitamins (50 mg nicotinic acid, 50 mg thiamine HCl, 10 mg pyridoxine HCl and 10 g myo-inositol per 100 ml, Highveld Biologicals, South Africa) supplemented with 1 lM 2,4-D, 1 lM BAP, 30 g l -1 sucrose and 1 g l -1 casein hydrolysate (Bouhouche et al 1998). To obtain callus proliferation, 1 g of callus was transferred aseptically to solid MS salt solution as described above.…”

Section: Preparation Of Callus and Cell Culturesmentioning

confidence: 99%

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Characterisation of two phenotypes of Centella asiatica in Southern Africa through the composition of four triterpenoids in callus, cell suspensions and leaves

James

Meyer

Dubery

2008

Plant Cell Tiss Organ Cult

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Two morphologically distinct phenotypes of Centella asiatica (Type-1 and Type-2) in South Africa were compared in relation to the levels of triterpenoid saponins with the aim of assessing their potential for biotechnological manipulation of triterpenoid synthesis. The metabolites investigated included madecassoside and asiaticoside and their sapogenins madecassic-and asiatic acid; produced in cultured undifferentiated cells (cell suspensions and calli) and leaves. Weight determination in plant cell suspensions and the accumulation of secondary metabolites after 16 days for Type-1 and 20 days for Type-2 were investigated since these secondary metabolites accumulate during the period that follows the active growth phase. The four triterpenoids of interest were analysed and quantified by HPLC in crude ethanolic extracts. A difference in bioactive triterpenoids was exhibited that was tissue specific and varied between the two phenotypes. The triterpenoids from leaf tissue were more easily quantifiable in each phenotype than in the case of the undifferentiated cells (callus and cell suspensions), which had lower, but still quantifiable, levels of these targeted secondary metabolites. Leaves contained the highest triterpenoid levels (ranging from 1.8 to 5% dry weight for the triterpenoid acids and their glycosides, respectively), with the free acids occurring in a ratio of approximately 1:2.5 in relation to the glycoside content.

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Section: Resultssupporting

confidence: 90%

Section: Preparation Of Callus and Cell Culturesmentioning

confidence: 99%

Characterisation of two phenotypes of Centella asiatica in Southern Africa through the composition of four triterpenoids in callus, cell suspensions and leaves

James

Meyer

Dubery

2008

Plant Cell Tiss Organ Cult

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“…One approach used to regulate metabolic pathways favouring the production of specific secondary metabolites has been to add precursors to the culture medium [ 89 ], though it is not known if this option has been investigated for enhanced production of triterpenoids in C. asiatica cells. The instability of cell cultures for the continued production of secondary products poses another problem; some cell lines lose the ability to synthesize the desired compound after prolonged culture.…”

Section: Manipulation Of Centelloside Production In Cell and Tissue Cmentioning

confidence: 99%

Pentacyclic Triterpenoids from the Medicinal Herb, Centella asiatica (L.) Urban

2009

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Centella asiatica accumulates large quantities of pentacyclic triterpenoid saponins, collectively known as centelloids. These terpenoids include asiaticoside, centelloside, madecassoside, brahmoside, brahminoside, thankuniside, sceffoleoside, centellose, asiatic-, brahmic-, centellic- and madecassic acids. The triterpene saponins are common secondary plant metabolites and are synthesized via the isoprenoid pathway to produce a hydrophobic triterpenoid structure (aglycone) containing a hydrophilic sugar chain (glycone). The biological activity of saponins has been attributed to these characteristics. In planta, the Centella triterpenoids can be regarded as phytoanticipins due to their antimicrobial activities and protective role against attempted pathogen infections. Preparations of C. asiatica are used in traditional and alternative medicine due to the wide spectrum of pharmacological activities associated with these secondary metabolites. Here, the biosynthesis of the centelloid triterpenoids is reviewed; the range of metabolites found in C. asiatica, together with their known biological activities and the chemotype variation in the production of these metabolites due to growth conditions are summarized. These plant-derived pharmacologically active compounds have complex structures, making chemical synthesis an economically uncompetitive option. Production of secondary metabolites by cultured cells provides a particularly important benefit to manipulate and improve the production of desired compounds; thus biotechnological approaches to increase the concentrations of the metabolites are discussed.

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“…6 Proposed metabolic relationships between 2′OHF, vestitone and conjugates produced in transgenic IFRexpressing tobacco cell cultures. The structure of V2 was conclusively demonstrated to be vestitone 2′-O-glucoside by NMR and other techniques; the structures of V1, HF1, and HF2 are tentative, based on available data mulation of glucosides in other studies, such as the glucosylation of butyric acid by Nicotiana plumbaginifolia (Kamel et al 1992), 3-demethylthiocolchiside by Centella asiatica (Bouhouche et al 1998), and cannabinoids by Pinellia ternata (Tanaka et al 1996).…”

Section: Resultsmentioning

confidence: 95%

“…The formation of glucosides and other sugar conjugates upon feeding of foreign substrates to tobacco and other plants is not uncommon and has been used to produce pharmacologically active compounds (Ushiyama et al 1989;Kamel et al 1992;Tanaka et al 1996;Bouhouche et al 1998;Kraemer et al 1999). In studies involving legume tissues such as soybean (Glycine max) (Knops et al 1995) and Pueraria lobata (Park et al 1995), the glucosides were further processed to the glucoside-malonates, consistent with the tendency of these species to accumulate glucoside-malonate derivatives of their endogenous isoflavonoids.…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of an exogenously supplied isoflavonoid by transgenic tobacco cells expressing alfalfa isoflavone reductase

2002

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Isoflavone reductase (IFR) from alfalfa catalyzes the NADPH-dependent reduction of 2′-hydroxy isoflavones to 2′-hydroxyisoflavanones such as vestitone, thereby performing a key step in isoflavonoid phytoalexin biosynthesis. Tobacco (Nicotiana tabacum L. cv. Xanthi) was transformed with an alfalfa cDNA encoding IFR regulated by an enhanced cauliflower mosaic virus 35S promoter and used to generate cell suspension cultures. Transformed cells expressed high levels of IFR activity and could take up 2′-hydroxyformononetin (2′OHF; IFR substrate) and convert it to vestitone. Both 2′OHF and vestitone were each converted to two sugar conjugates. The structure of the most abundant vestitone conjugate was determined using NMR spectroscopic analysis to be a novel vestitone 2′-O-glucoside. Liquid chromatography-mass spectroscopy (LC-MS) indicated that the molecular weights of the three less abundant conjugates were consistent with hexose conjugates of vestitone and 2′OHF. The IFR reduction and conjugation reactions were complete within 4 h, with the net percentage conversion of 2′OHF to vestitone ranging as high as 60%.

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Conversion of 3-demethylthiocolchicine into thiocolchicoside by Centella asiatica suspension cultures

Cited by 9 publications

References 25 publications

Characterisation of two phenotypes of Centella asiatica in Southern Africa through the composition of four triterpenoids in callus, cell suspensions and leaves

Characterisation of two phenotypes of Centella asiatica in Southern Africa through the composition of four triterpenoids in callus, cell suspensions and leaves

Pentacyclic Triterpenoids from the Medicinal Herb, Centella asiatica (L.) Urban

Biotransformation of an exogenously supplied isoflavonoid by transgenic tobacco cells expressing alfalfa isoflavone reductase

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