Cytochalasin H

1. Core Information[1]

Chinese Name (pinyin): Xibao Songchisu H
English Name: Cytochalasin H
CAS No.: 53760-19-3
Molecular Formula: C30H39NO5
Molecular Weight: 493.6 g/mol
SMILES:CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O

 

2. International Nomenclature & Identifiers

2.1 IUPAC Name

[(1R,2R,3E,5R,7S,9E,11R,12S,14S,15R,16S)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-18-oxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate

2.2 InChI

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

2.3 InChlKey

NAEWXXDGBKTIMN-OWTACEMYSA-N

2.4 Canonical SMILES

CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O

2.5 Isomeric SMILES

C[C@H]1C/C=C/[C@H]2[C@@H](C(=C)[C@H]([C@@H]3[C@@]2([C@@H](/C=C/[C@](C1)(C)O)OC(=O)C)C(=O)N[C@H]3CC4=CC=CC=C4)C)O

 

 

 

3. Spectroscopic Data

3.1 ¹³C Nuclear Magnetic Resonance (¹³C NMR)

 

3.2 ¹H Nuclear Magnetic Resonance (¹H NMR)

 

4. Bioactivity Overview

Cytochalasin H is a fungal metabolite of the cytochalasin family, featuring a hydrogenated isoindole linked to a macrocycle.[2] Documented activities include inhibition of actin polymerization, anticancer effects, and modulation of apoptosis.

4.1 Mechanism of Action

Cytochalasin H binds the barbed ends of actin filaments, preventing actin monomer addition or loss and destabilizing the cytoskeleton.[3]

4.2 Biological Activities

4.2.1 Inhibition of Actin Polymerization

As an actin polymerization inhibitor, cytochalasin H disrupts cell motility, growth, phagocytosis, degranulation, and secretion by preventing filament formation.[3]

 

4.2.2 Anticancer Activity

Cytochalasin H induces apoptosis and impairs proliferation/migration in tumor cells. In MCF-7 breast cancer cells, co-treatment with zinc oxide nanoparticles dramatically increases apoptosis.[4]

4.2.3 Modulation of Apoptosis

In Parkinson’s disease models, cytochalasin H lowers MPP⁺-induced apoptosis in PC12 cells by reducing intracellular ROS and shielding against oxidative stress.[5]

Together, these findings position cytochalasin H as a valuable probe for cytoskeletal biology and a promising lead for novel anticancer strategies.

 

References

• [1] http://www.kehuaai.com/productInfo/174970
• [2] Zhu H, Chen C, Tong Q, Zhou Y, Ye Y, Gu L, Zhang Y. Progress in the Chemistry of Cytochalasans. Prog Chem Org Nat Prod. 2021;114:1-134.
• [3] Lambert, C.; Schmidt, K.; Karger, M.; Stadler, M.; Stradal, T.E.B.; Rottner, K. Cytochalasans and Their Impact on Actin Filament Remodeling. Biomolecules 2023, 13, 1247.
• [4] Baghbani-Arani, F., Sadat Shandiz, S. Combination of Cytochalasin H and zinc oxide nanoparticles in human breast cancer: an insight into apoptosis study. Biologia 76, 763–772 (2021).
• [5] Yan Yuwen, Wei Zhongqi, Ju Jingjing, et al. Protective effects of cytochalasin H on MPP+-induced apoptosis in PC12 cells. Journal of Yangzhou University (Agriculture and Life Science Edition), 2014, 35(01):16-21.