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Structure Database (LMSD)

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Common Name

Cytochalasin H

Systematic Name

Synonyms

LM ID

LMPK11000013

Formula

C₃₀H₃₉NO₅

Exact Mass

Calculate m/z

493.282824

Status

Curated

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Classification

Biological Context

Cytochalasin H is a potent inhibitor of actin incorporation into filaments.^1,2 Like cytochalasin D , it also increases the steady-state diffusion coefficients of filaments, suggesting that it stimulates filament shortening.¹ Cytochalasin H suppresses the production of reactive oxygen species by stimulated human neutrophils, blocks endocytosis of CD59 in lymphocytes, and shows anti-angiogenic activity both in vitro and in vivo.^3,4,5

This information has been provided by Cayman Chemical

References

1. Yahara, I., Harada, F., Sekita, S., et al. Correlation between effects of 24 different cytochalasins on cellular structures and cellular events and those on actin in vitro. J. Cell Biol. 92(1), 69-78 (1982).

2. Lee, J., Yi, J.M., Kim, H., et al. Cytochalasin H, an active anti-angiogenic constituent of the ethanol extract of Gleditsia sinensis thorns. Biol. Pharm. Bull. 37(1), 6-12 (2014).

3. Deckert, M., Ticchioni, M., and Bernard, A. Endocytosis of GPI-anchored proteins in human lymphocytes: Role of glycolipid-based domains, actin cytoskeleton, and protein kinases. J. Cell Biol. 133(4), 791-799 (1996).

4. Chapla, V.M., Zeraik, M.L., Ximenes, V.F., et al. Bioactive secondary metabolites from Phomopsis sp., and endophytic fungus from Senna spectabilis. Molecules 19, 6597-6608 (2014).

5. Walling, E.A., Krafft, G.A., and Ware, B.R. Actin assembly activity of cytochalasins and cytochalasin analogs assayed using fluorescence photobleaching recovery. Arch. Biochem. Biophys. 264(1), 321-332 (1988).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Phomopsis sp. (#1715245)

Sordariomycetes (#147550)

Cytochalasins from an Australian Marine Sediment-Derived Phomopsis sp. (CMB-M0042F): Acid-Mediated Intramolecular Cycloadditions Enhance Chemical Diversity.,
J Org Chem, 2017

Pubmed ID: 28831797

String Representations

InChiKey (Click to copy)

NAEWXXDGBKTIMN-OWTACEMYSA-N

InChi (Click to copy)

InChI=1S/C30H39NO5/c1-18-10-9-13-23-27(33)20(3)19(2)26-24(16-22-11-7-6-8-12-22)31-28(34)30(23,26)25(36-21(4)32)14-15-29(5,35)17-18/h6-9,11-15,18-19,23-27,33,35H,3,10,16-17H2,1-2,4-5H3,(H,31,34)/b13-9+,15-14+/t18-,19+,23-,24-,25+,26-,27+,29-,30+/m0/s1

SMILES (Click to copy)

[C@@H]1(C)C(=C)[C@@H](O)[C@]2([H])C=CC[C@H](C)C[C@](O)(C)C=C[C@@H](OC(C)=O)[C@@]32C(=O)N[C@@H](CC2C=CC=CC=2)[C@]13[H]