Unusual withanolides from aeroponically grown Withania somnifera

Xu, Ya Ming; Gao, Song; Bunting, Daniel P.; Gunatilaka, A. A. Leslie

doi:10.1016/j.phytochem.2010.12.020

Cited by 55 publications

(60 citation statements)

References 43 publications

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“…W. somnifera possesses immense therapeutic potential and is known for its immunomodulatory (Malik et al, 2009;Rasool & Varalakshmi, 2006), anti-stress (Archana & Namasivayan, 1998), cardioprotective (Mohanty et al, 2004), anti-aging (Singh, Narsimhamurthy, & Singh, 2008), antioxidant, anti-inflammatory (Mishra et al, 2000), anti-tumor Widodo et al, 2007Widodo et al, , 2008, neuroprotective, and anti-brain cancer activities (Kataria, Shah, Kaul, Wadhwa, & Kaur, 2011;Kataria, Wadhwa, Kaul, & Kaur, 2012. The medicinal properties of W. somnifera are attributed to the presence of a wide array of secondary metabolites, including alkaloids [tropine, pseudotropine, hygrine, 3-trigloyloxytropine, cuscohygrine, choline, dl-isopelletierine, anaferine, anahygrine, and withanosomine (Schröter, Neumann, Katritzky, & Swinbourne, 1966;Schwarting et al, 1963)], flavanol glycosides [6,8-dihydroxykaempferol 3-rutinoside, quercetin and its 3-O-rutinoside and 3-rutinoside-7-glucoside (Kandil, El Sayed, Abou-Douh, Ishak, & Mabry, 1994)], glycowithanolides [sitoindoside VII to X (Bhattacharya, Satyan, & Ghosal, 1997)], steroidal lactones [withanolide A, withanolide D, withanone, withaferin A], sterols, and phenolics (Chatterjee et al, 2010;Chaurasiya, Sangwan, Misra, Tuli, & Sangwan, 2009;Chaurasiya, Sangwan, Sabir, Misra, & Sangwan, 2012;Ghosal, Kaur, & Shrivastava, 1988;Sangwan et al, 2008;Xu, Gao, Bunting, & Gunatilaka, 2011).…”

Section: Biotechnological Interventions Inmentioning

confidence: 99%

Biotechnological interventions inWithania somnifera(L.) Dunal

Singh

Guleri

Singh

et al. 2015

Biotechnology and Genetic Engineering Reviews

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Withania somnifera is one of the most valued plants and is extensively used in Indian, Unani, and African systems of traditional medicine. It possess a wide array of therapeutic properties including anti-arthritic, anti-aging, anti-cancer, anti-inflammatory, immunoregulatory, chemoprotective, cardioprotective, and recovery from neurodegenerative disorders. With the growing realization of benefits and associated challenges in the improvement of W. somnifera, studies on exploration of genetic and chemotypic variations, identification and characterization of important genes, and understanding the secondary metabolites production and their modulation has gained significant momentum. In recent years, several in vitro and in vivo preclinical studies have facilitated the validation of therapeutic potential of the phytochemicals derived from W. somnifera and have provided necessary impetus for gaining deeper insight into the mechanistic aspects involved in the mode of action of these important pharmaceutically active constituents. The present review highlights some of the current developments and future prospects of biotechnological intervention in this important medicinal plant.

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Section: Biotechnological Interventions Inmentioning

confidence: 99%

Biotechnological interventions inWithania somnifera(L.) Dunal

Singh

Guleri

Singh

et al. 2015

Biotechnology and Genetic Engineering Reviews

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“…On this basis compound 3 was determined to be 2,3-dihydrowithaferin A-3b-O-sulfate. This is the first report of this compound from W. frutescens and it was recently isolated from aeroponically grown W. somnifera (Xu et al, 2009(Xu et al, , 2011. The presence of a sulfate group in steroids is quite rare and reported so far only from Datura metel (Shingu et al, 1989) and W. somnifera (Misra et al, 2005).…”

Section: Chemistrymentioning

confidence: 80%

Cytotoxic withanolides from the leaves of MoroccanWithania frutescens

Bouzidi

Mahiou-Leddet

Bun

et al. 2013

Pharmaceutical Biology

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Context: Withania species are a rich source of interesting phytochemical substances (withanolides) which have shown several biological properties. Objective: To investigate the cytotoxic potential of Withania frutescens (L.) Pauquy (Solanaceae) leaf extracts and isolated active compounds against cultured tumor cell lines. Materials and methods: The crude methanol extract of W. frutescens leaves was partitioned with dichloromethane, ethyl acetate and n-butanol. MeOH extract and its fractions were tested for their cytotoxic activity against cancer cell lines (HepG2 and HT29) using the MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay. Bioassay-guided fractionation was performed for the active CH 2 Cl 2 fraction employing column chromatography and preparative high-performance liquid chromatography. Structural elucidation of the isolated active compounds was carried out mainly by 1D and 2D NMR and mass spectrometry. The compounds were then tested for their cytotoxic activity. Results: The CH 2 Cl 2 fraction was the most active against HT29 cell line. The fractionation procedure resulted in the isolation of 4b,17a,27-trihydroxy-1-oxo-22-R-witha-2,5,24-trienolide (1), 5b,6b-epoxy-4b,17a,27-trihydroxy-1-oxowitha-2,24-dienolide (2) and 2,3-dihydroxywithaferin A-3b-O-sulfate (3). The latter exhibited the strongest cytotoxic activity against HT29 cancer cell lines (IC 50 of 1.78 AE 0.09 mM) which was comparable to that of 5-fluorouracil (5-FU) used as the positive antimitotic control. Discussion and conclusion: Compounds 2 and 3 were isolated from W. frutescens for the first time. Data obtained suggest that the sulfated steroidal lactone (3) can be considered as a compound with potential application in the new anticancer drugs development field.

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“…At the present time, aeroponic culture provides opportunity for biomass production on a commercial scale and it is being mainly applied to the obtaining of medicinal compounds. 93,[614][615][616] As part of our ongoing studies on the sustainable production of natural biopesticides from endemic species, we have developed an aeroponic system for Persea indica. The aerial part and stems of this species are characterized by their content in insecticidal ryanodane and isoryanodane-type diterpenes.…”

Section: Sustainable Production: Culture Methodsmentioning

confidence: 99%