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Chlorinated Withanolides from Withania somnifera.

TLDR
All structures were elucidated on the basis of spectroscopic methods (IR, HRESIMS, 1D/2D NMR) and X-ray crystallography confirmed the absolute configuration of 1.5-methoxy-2,3-dihydrowithaferin A.
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This article is published in Phytochemistry Letters.The article was published on 2011-12-01 and is currently open access. It has received 40 citations till now. The article focuses on the topics: Withania somnifera & Withanolide.

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Citations
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Are plants used for skin care in South Africa fully explored

TL;DR: The present review discusses the ethnopharmacological values, pharmacological and toxicological evidence of 117 plant species grown in South Africa, which are used traditionally for skin care purposes and almost 35 out of the 117 species are totally unexplored in the area of skin care.
Journal ArticleDOI

Identification of bioactive molecule from Withania somnifera (Ashwagandha) as SARS-CoV-2 main protease inhibitor.

TL;DR: The study suggests that Withanoside V in Ashwagandha may be serve as a potential inhibitor against Mpro of SARS-CoV-2 to combat COVID-19 and may have an antiviral effect on nCoV.
Journal ArticleDOI

Antiproliferative withanolides from the Solanaceae: A structure–activity study

TL;DR: The structure–activity relationship analysis (SARA) confirmed the importance of the presence of a ∆2-1-oxo-functionality in ring A, a 5β, 6β-epoxy or 5α-chloro-6β-hydroxy grouping in ring B, and nine-carbon side chain with a lactone moiety for cytotoxic activity.
Journal ArticleDOI

Cytotoxic withanolide constituents of Physalis longifolia.

TL;DR: Using a MTS viability assay, eight withanolides and four acetylated derivatives showed potent cytotoxicity against human head and neck squamous cell carcinoma, melanoma, and normal fetal fibroblast cells with IC₅₀ values in the range between 0.067 and 9.3 μM.
References
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Journal ArticleDOI

Steroidal lactones from Withania somnifera, an ancient plant for novel medicine.

TL;DR: An overview of the chemical structures of triterpenoid components and their biological activity is presented, focusing on two novel activities, tumor inhibition and antiangiogenic properties of withaferin A and the effects of withanolide A on Alzheimer's disease.
Journal ArticleDOI

Immunomodulatory activity of Withania somnifera.

TL;DR: The results confirm the immunomodulatory activity of W. somnifera extract, which is a known immunosorbent in indigenous medicine, and Administration of Withania extract inhibited delayed type hypersentivity reaction in mice.
Journal Article

Antioxidant activity of glycowithanolides from Withania somnifera.

TL;DR: Antioxidant effect of active principles of W. somnifera may explain, at least in part, the reported antistress, immunomodulatory, cognition-facilitating, anti-inflammatory and anti-aging effects produced by them in experimental animals, and in clinical situations.
Journal ArticleDOI

Anxiolytic-antidepressant activity of Withania somnifera glycowithanolides: an experimental study.

TL;DR: Investigation of the anxiolytic and antidepressant actions of the bioactive glycowithanolides of Withania somnifera, isolated from WS roots, in rats support the use of WS as a mood stabilizer in clinical conditions of anxiety and depression in Ayurveda.
Journal ArticleDOI

Antibacterial efficacy of Withania somnifera (ashwagandha) an indigenous medicinal plant against experimental murine salmonellosis

TL;DR: Oral administration of the aqueous extracts successfully obliterated salmonella infection in Balb/C mice as revealed by increased survival rate as well as less bacterial load in various vital organs of the treated animals.
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Frequently Asked Questions (11)
Q1. What contributions have the authors mentioned in the paper "Chlorinated withanolides from withania somnifera" ?

Timmer and Timmermann this paper used spectroscopic methods ( IR, HRESIMS, 1D/2D NMR ) and X-ray crystallography confirmed the absolute configuration of 1. 

W. somnifera, commonly known as “ashwagandha” and widely cultivated in the drier parts of India, is well known for its use in Ayurvedic medicine. 

The four methyl groups resonated at δ0.99 (3H, d, J = 7.0 Hz), δ0.78 (3H, s), δ1.27 (3H, s), and δ2.03 (3H, s), corresponding to the secondary methyl of C-21 and the quaternary methyls C-18, 19 and 28 of a withanolide. 

Previous research supports its pharmacological uses, confirming antioxidant, anti-inflammatory (Sumantran et al., 2008), immunomodulatory, anticarcinogenic, antibacterial (Owais et al., 2005), antiparkinsonism (Sankar et al., 2007) and antistress (Geetha and Harish, 2006) properties. 

The major withanolide in fraction E7 was obtained as a white powder yielding 3-methoxy-2,3dihydrowithaferin A (22 mg) by recystallization from CHCl3–CH3COCH3 (1:1). 

The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. 

The ethyl acetate-soluble fraction of the crude extract acquired for this study was subjected to repeated column chromatography to yield compound 1. 

With the exception of 27-acetoxy-5β-chloro-6α-hydroxywithaferin A and withanolide Z, all the reported chlorinated withanolides contain a 6α-chloro-5β-hydroxy system. 

E12 was separated over a C-18 reverse phase SPE column (5 g, 20 mL, Phenoment strata C-18), eluted with MeOH-H2O (1:1), to give a mixture of two compounds. 

Normal phase TLC was performed on Sorbent Technologies Silica G TLC plates (200 μm, w/UV 254) using the solvent system CH2Cl2–EtOAc–MeOH (1:8:1), and reverse phase TLC was performed on Sorbent Technologies C18 TLC plates (150 μm, w/UV 254) using H2O-MeOH (1:1). 

1H and 13C spectra were recorded using the residual protonated signal in the CDCl3 solvent (δH 7.24) or the central peak of the CDCl3 triplet (δC 77.00) as the internal standard.