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Structure Database (LMSD)

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Common Name

24-epi-brassinolide

Systematic Name

(22R,23R)-2α,3α,22,23-tetrahydroxy-7a-homo-7-oxa-5α-ergostan-6-one

Synonyms

24-epi-Brassinolide

LM ID

LMST01140002

Formula

C₂₈H₄₈O₆

Exact Mass

Calculate m/z

480.345091

Sum Composition

ST 28:1;O6

Status

Curated

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Classification

Biological Context

Epibrassinolide is a brassinosteroid that can be isolated from various plants and has been shown to decrease toxicity and stimulate healthy plant growth in plants under stress.¹ Epibrassinolide is also reported to be a potential apoptotic inducer in various cancer cells without affecting the non-tumor cell growth.² It has also been shown to protect neuronal PC12 cells from 1-methyl-4-phenylpyridinium-induced oxidative stress and consequent apoptosis in dopaminergic neurons.³

This information has been provided by Cayman Chemical

References

1. Carange, J., Longpré, F., Daoust, B., et al. 24-Epibrassinolide, a phytosterol from the brassinosteroid family, protects dopaminergic cells against MPP-induced oxidative stress and apoptosis. J. Toxicol. 392859 (2011).

2. Obakan, P., Barrero, C., Coker-Gurkan, A., et al. SILAC-based mass pectrometry analysis reveals that epibrassinolide induces apoptosis via activating endoplasmic reticulum stress in prostate cancer cells. PLoS One 10(9), (2015).

3. Sondhi, N., Bhardwaj, R., Kaur, S., et al. Isolation of 24-epibrassinolide from leaves of Aegle marmelos and evaluation of its antigenotoxicity employing Allium cepa chromosomal aberration assay. Plant Growth Regul. 54(3), 217-224 (2008).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Vicia faba (#3906)

Magnoliopsida (#3398)

Identification of 24-Epibrassinolide in Bee Pollen of the Broad Bean, Vicia faba L.,
Chem Pharm Bull, 1987

DOI: 10.1248/cpb.36.405

String Representations

InChiKey (Click to copy)

IXVMHGVQKLDRKH-QHBHMFGVSA-N

InChi (Click to copy)

InChI=1S/C28H48O6/c1-14(2)15(3)24(31)25(32)16(4)18-7-8-19-17-13-34-26(33)21-11-22(29)23(30)12-28(21,6)20(17)9-10-27(18,19)5/h14-25,29-32H,7-13H2,1-6H3/t15-,16+,17+,18-,19+,20+,21-,22+,23-,24-,25-,27-,28-/m1/s1

SMILES (Click to copy)

C1C[C@]([H])([C@H](C)[C@@H](O)[C@H](O)[C@H](C)C(C)C)[C@@]2(C)CC[C@@]3([H])[C@](COC(=O)[C@@]4([H])C[C@H](O)[C@H](O)C[C@]34C)([H])[C@@]21[H]