Chaetoglobosin Fex

1. Core Information[1]

English Name: Chaetoglobosin Fex
CAS No.: 149457-95-4
Molecular Formula: C32H38N2O5
Molecular Weight: 530.7 g/mol
SMILES:CC1CC=CC2C(C(=C)C(C3C2(C(=O)CCC(C(=O)C(=C1)C)O)C(=O)NC3CC4=CNC5=CC=CC=C54)C)O

 

2. International Nomenclature & Identifiers

2.1 IUPAC Name

(1R,5S,7Z,9S,11E,13R,14S,16S,17R,18S)-5,14-dihydroxy-18-(1H-indol-3-ylmethyl)-7,9,16-trimethyl-15-methylidene-19-azatricyclo[11.7.0.01,17]icosa-7,11-diene-2,6,20-trione

2.2 InChI

InChI=1S/C32H38N2O5/c1-17-8-7-10-23-30(38)20(4)19(3)28-25(15-21-16-33-24-11-6-5-9-22(21)24)34-31(39)32(23,28)27(36)13-12-26(35)29(37)18(2)14-17/h5-7,9-11,14,16-17,19,23,25-26,28,30,33,35,38H,4,8,12-13,15H2,1-3H3,(H,34,39)/b10-7+,18-14-/t17-,19+,23-,25-,26-,28-,30+,32+/m0/s1

2.3 InChlKey

UFMHUKPYQLJSOB-BOTXPQCZSA-N

2.4 Canonical SMILES

CC1CC=CC2C(C(=C)C(C3C2(C(=O)CCC(C(=O)C(=C1)C)O)C(=O)NC3CC4=CNC5=CC=CC=C54)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(=O)CC[C@@H](C(=O)/C(=C1)/C)O)C(=O)N[C@H]3CC4=CNC5=CC=CC=C54)C)O

 

 

 

3. Spectroscopic Data

3.1 ¹³C Nuclear Magnetic Resonance (¹³C NMR)

 

3.2 ¹H Nuclear Magnetic Resonance (¹H NMR)

 

4. Bioactivity Summary

Chaetoglobosin Fex (Cha Fex) is a cytochalasin-based alkaloid derived from marine endophytic Chaetomium globosum QEN-14.[2] Although structurally characterized, its biological profile is still emerging; recent work highlights anti-inflammatory and immunomodulatory potential.

4.1 Anti-inflammatory Activity

Cha Fex shows pronounced anti-inflammatory effects in macrophages by suppressing TLR4 signaling. It reduces LPS-induced TNF-α, IL-6, and MCP-1 production and downregulates corresponding mRNA expression.[2] Mechanistically, it inhibits NF-κB activation and dampens phosphorylation of ERK1/2, p38, and JNK1/2.

4.2 Immunomodulation

Cha Fex also limits CpG-DNA–driven dendritic cell maturation by suppressing surface markers (CD40, CD80, CD86, MHC-II), reducing IL-12 and CXCL-10 production, and inhibiting activation of MAPKs, NF-κB, and STAT1.[3]

 

Collectively, Chaetoglobosin Fex’s anti-inflammatory and immunomodulatory activities provide a strong foundation for therapeutic exploration. Future studies should examine additional mechanisms, efficacy across systems, and safety as a potential lead compound.

 

References

• [1] http://www.kehuaai.com/productInfo/174969
• [2] Dou H ,Song Y ,Liu X , et al.Chaetoglobosin Fex from the Marine-Derived Endophytic Fungus Inhibits Induction of Inflammatory Mediators via Toll-Like Receptor 4 Signaling in Macrophages[J].Biological and Pharmaceutical Bulletin,2011,34(12):1864-1873.
• [3] Hua C, Yang Y, Sun L, Dou H, Tan R, Hou Y. Chaetoglobosin F, a small molecule compound, possesses immunomodulatory properties on bone marrow-derived dendritic cells via TLR9 signaling pathway. Immunobiology. 2013 Mar;218(3):292-302.