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Structure Database (LMSD)

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Common Name

Withanolide A

Systematic Name

15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^{2,4}.0^{5,10}.0^{14,18}]octadec-7-en-9-one

Synonyms

LM ID

LMST01160019

Formula

C₂₈H₃₈O₆

Exact Mass

Calculate m/z

470.266841

Sum Composition

ST 28:6;O6

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Withanolide A is a natural product isolated from the medicinal plant W. somnifera that has antioxidant and neuroprotective activity.¹ It helps to promote neurite outgrowth at 1 µM in cultured neurons and in rodents injected with Aβ(25-35), and also recovers Aβ(25-35)-induced memory deficit in mice (10 µmol/kg/day).^2,3 Withanolide A reverses hypoxia-mediated neurodegeneration by restoring hypoxia-induced glutathione depletion in the hippocampus of mice.⁴

This information has been provided by Cayman Chemical

References

1. Baitharu, I., Jain, V., Deep, S.N., et al. Withanolide A prevents neurodegeneration by modulating hippocampal glutathione biosynthesis during hypoxia. PLoS One 9(10), 1-17 (2014).

2. Kuboyama, T., Tohda, C., and Komatsu, K. Neuritic regeneration and synaptic reconstruction induced by withanolide A. Br. J. Pharmacol. 144(7), 961-971 (2005).

3. Zhao, J., Nakamura, N., Hattori, M., et al. Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities. Chem. Pharm. Bull. (Tokyo) 50(6), 760-765 (2002).

4. Kurapati, K.R.V., Samikkannu, T., Atluri, V.S.R., et al. β-Amyloid1-42, HIV-1Bα-L (clade B) infection and drugs of abuse induced degeneration in human neuronal cells and protective effects of ashwagandha (Withania somnifera) and its constituent Withanolide A. PLoS One 9(11), 1-23 (2014).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Withania somnifera (#126910)

Magnoliopsida (#3398)

Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities.,
Chem Pharm Bull (Tokyo), 2002

Pubmed ID: 12045329

String Representations

InChiKey (Click to copy)

DXWHOKCXBGLTMQ-SFQAJKIESA-N

InChi (Click to copy)

InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3/t16-,17-,18-,20+,21-,22-,23-,25-,26-,27+,28-/m0/s1

SMILES (Click to copy)

O1C(=O)C(C)=C(C)C[C@]1([H])[C@](O)([C@]1([H])[C@@]2(C)CC[C@@]3([H])[C@@]([H])([C@@H]4O[C@@H]4[C@@]4(O)CC=CC(=O)[C@@]43C)[C@]2([H])CC1)C