Chaetoglobosin C

1. Core Information[1]

English Name: Chaetoglobosin C
Chinese Name (pinyin): Mao Qiu Jun Su C
CAS No.: 50645-76-6
Molecular Formula: C32H36N2O5
Molecular Weight: 528.6 g/mol
SMILES:CC1CC=CC2C3C(O3)(C(C4C2(C(=O)CCC(=O)C(=O)C(=C1)C)C(=O)NC4CC5=CNC6=CC=CC=C65)C)C

 

2. International Nomenclature & Identifiers

2.1 IUPAC Name

(7Z,9S,11E,13R,14S,16R,17S,18R,19S)-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-2,5,6,21-tetrone

2.2 InChI

InChI=1S/C32H36N2O5/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/h5-7,9-11,14,16-17,19,22,24,27,29,33H,8,12-13,15H2,1-4H3,(H,34,38)/b10-7+,18-14-/t17-,19-,22-,24-,27-,29-,31+,32?/m0/s1

2.3 InChlKey

RIZAHVBYKWUPHQ-JZDGHNCDSA-N

2.4 Canonical SMILES

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

2.5 Isomeric SMILES

C[C@H]/1C/C=C/[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]4C2(C(=O)CCC(=O)C(=O)/C(=C1)/C)C(=O)N[C@H]4CC5=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. Biological Activities of Chaetoglobosin C

Chaetoglobosin C, a secondary metabolite from Chaetomium globosum, exhibits antifungal, anticancer, and phytotoxic properties.[2]

4.1 Antifungal Activity

It inhibits multiple fungi, including Rhizoctonia solani (MIC 11.79–23.66 μM) and Mucor miehei.[3]

4.2 Antitumor Activity

Chaetoglobosin C displays cytotoxicity against various cancer cell lines—IC₅₀ 6.27–20.0 μM for human breast cancer BC1 cells—and shows moderate potency against KB, K562, MCF7, and HepG2 cells.[4]

4.3 Phytotoxicity

At 50 ppm, chaetoglobosin C suppresses radish root growth by 26.4–67.5% and hypocotyl elongation by 33.3–71.6%; at 200 ppm inhibition reaches 60.7–71.2%, comparable to glyphosate.[4] It also impairs alfalfa seedling growth.[5]

4.4 Antitubercular Potential

Reports indicate activity against Mycobacterium tuberculosis, suggesting utility as an antitubercular lead.[6]

Chaetoglobosin C’s spectrum—from antifungal to cytotoxic and phytotoxic effects—underscores its potential in medicine and agriculture. Future work will further elucidate mechanisms and applications.

 

References