Withaferin A
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Withaferin A
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CAS No:
5119-48-2
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Formula:
C28H38O6
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Chemical Name:
Withaferin A
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Synonyms:
Ergosta-2,24-dien-26-oic acid,5,6-epoxy-4,22,27-trihydroxy-1-oxo-,δ-lactone,(4β,5β,6β,22R)-;Withaferin A;5β-Ergosta-2,24-dien-26-oic acid,5,6β-epoxy-4β,22,27-trihydroxy-1-oxo-,δ-lactone,(20S,22R)-;5,6-Epoxy-5H-cyclopenta[a]phenanthrene,ergosta-2,24-dien-26-oic acid deriv.;Withaferine;Withaferine A;NSC 101088;NSC 273757;5196-55-4;22848-77-7;47738-04-5;1246849-97-7
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CAS No:
Description
Withaferin A is a steroidal lactone isolated from Withania somnifera, inhibits NF-kB activation and targets vimentin, with potent antiinflammatory and anticancer activities.
Withaferin A is a withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity. It has a role as an antineoplastic agent and an apoptosis inducer. It is a delta-lactone, a 4-hydroxy steroid, an enone, an ergostanoid, a secondary alcohol, a withanolide, a 27-hydroxy steroid, a primary alcohol and an epoxy steroid.|Ashwagandha is a popular Ayurvedic herb used as a general tonic, to increase energy and reduce stress. Ashwagandha has not been implicated in causing serum enzyme elevations during therapy, but recently has been implicated in rare cases of clinically apparent liver injury.
Characteristics
96.36000
3.80
1.3±0.1 g/cm3
230-232 °C
680.7±55.0 °C at 760 mmHg
226℃
1.599
Desiccate at -20°C
D28 +125° (c = 1.30 in CHCl3)
Toxicity
Despite widescale use, ashwagandha is considered generally safe and without major adverse effects. In clinical trials, there have been no reports of serum enzyme elevations occurring during therapy and no mention of serious adverse events or hepatotoxicity. Recently, however, several cases of clinically apparent liver injury have been reported in patients taking commercial herbal products that are labelled as containing ashwagandha. The liver injury presented 2 to 12 weeks after starting ashwagandha with a cholestatic or mixed pattern of injury, jaundice and pruritus. Immunoallergic and autoimmune features were not prominent. Jaundice tended to be protracted but ultimately resolved without fatalities or chronic injury. Because commercial herbal preparations are often mixtures of herbs and nutritional products and can be mislabeled and contain unknown herbs and medications, it is not always clear whether the reported cases were due to ashwagandha and one of its components or to a contaminant. In several reported cases, however, the commercial product being taken was tested and found to have ashwagandha without other contaminants. Thus, clinically apparent liver injury attributable to ashwagandha appears to occur, but is rare.
Drug Information
Ashwagandha is a popular Ayurvedic herb used as a general tonic, to increase energy and reduce stress. Ashwagandha has not been implicated in causing serum enzyme elevations during therapy, but recently has been implicated in rare cases of clinically apparent liver injury.
Herbal and Dietary Supplements
5,6-epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dienoic acid delta-lactone
Withaferin A Use and Manufacturing
Withaferin A is a promising anticancer constituent of Ayurvedic medicinal plant Withania somnifera. Withaferin A showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986).
Computed Properties
Molecular Weight:470.6
XLogP3:3.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:470.26683893
Monoisotopic Mass:470.26683893
Topological Polar Surface Area:96.4
Heavy Atom Count:34
Complexity:999
Defined Atom Stereocenter Count:11
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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