Chaetoglobosin F

1. Core Information[1]

English Name: Chaetoglobosin F
Chinese Name (pinyin): Mao Jun Qiu Su F
CAS No.: 55945-75-0
Molecular Formula: C32H38N2O5
Molecular Weight: 530.7 g/mol
SMILES:CC1CC=CC2C3C(O3)(C(C4C2(C(=O)CCC(C(=O)C(=C1)C)O)C(=O)NC4CC5=CNC6=CC=CC=C65)C)C

 

2. International Nomenclature & Identifiers

2.1 IUPAC Name

(7Z,11E)-5-hydroxy-19-(1H-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.01,18.014,16]henicosa-7,11-diene-2,6,21-trione

2.2 InChI

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

2.3 InChlKey

KTFGDHPTDQFFRL-YWAYREADSA-N

2.4 Canonical SMILES

CC1CC=CC2C3C(O3)(C(C4C2(C(=O)CCC(C(=O)C(=C1)C)O)C(=O)NC4CC5=CNC6=CC=CC=C65)C)C

2.5 Isomeric SMILES

CC/1C/C=C/C2C3C(O3)(C(C4C2(C(=O)CCC(C(=O)/C(=C1)/C)O)C(=O)NC4CC5=CNC6=CC=CC=C65)C)C

 

 

 

3. Spectroscopic Data

3.1 ¹³C Nuclear Magnetic Resonance (¹³C NMR)

 

3.2 ¹H Nuclear Magnetic Resonance (¹H NMR)

 

4. Overview of Chaetoglobosin F Bioactivity

Chaetoglobosin F (Cha F) is a 10-indolyl cytochalasin from endophytic Chaetomium globosum with diverse physiological impacts.

4.1 Immunomodulatory Activity

Cha F modulates bone-marrow-derived dendritic cells (DCs) by suppressing CpG-triggered maturation via TLR9 signaling. It downregulates surface molecules (CD40, CD80, CD86, MHC-II), reduces cytokine/chemokine production (IL-12, CXCL-10), limits allogeneic T-cell proliferation, and impairs chemokine-directed migration.[2]

4.2 Phytotoxicity

At 50 ppm, Cha F suppresses radish seedling growth by over 60%, matching or surpassing glyphosate. [3]

4.3 Antitumor Activity

Cha F is cytotoxic to HCT116 human colorectal cancer cells with IC₅₀ values of 3.15–8.44 μM, comparable to etoposide (IC₅₀=2.13 μM).[3]

In sum, Chaetoglobosin F’s immunomodulatory, phytotoxic, and antitumor properties illustrate promising prospects in therapeutic and agricultural applications.

 

References

• [1] http://www.kehuaai.com/productInfo/174968
• [2] 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. \
• [3] Li H, Xiao J, Gao YQ, Tang JJ, Zhang AL, Gao JM. Chaetoglobosins from Chaetomium globosum, an endophytic fungus in Ginkgo biloba, and their phytotoxic and cytotoxic activities. J Agric Food Chem. 2014 Apr 30;62(17):3734-41.