Chaetoglobosin A

1. Core Information[1]

English Name: Chaetoglobosin A
Chinese Name (pinyin): Mao Qiu Jun Su A
CAS No.: 50335-03-0
Molecular Formula: C32H36N2O5
Molecular Weight: 528.6 g/mol
SMILE:CC1CC=CC2C3C(O3)(C(C4C2(C(=O)C=CC(=O)C(C(=C1)C)O)C(=O)NC4CC5=CNC6=CC=CC=C65)C)C

 

2. International Nomenclature & Identifiers

2.1 IUPAC Name

(1R,3E,6R,7E,9S,11E,13R,14S,16R,17S,18R,19S)-6-hydroxy-19-(1H-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.01,18.014,16]henicosa-3,7,11-triene-2,5,21-trione

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/h5-7,9-14,16-17,19,22,24,27-29,33,37H,8,15H2,1-4H3,(H,34,38)/b10-7+,13-12+,18-14+/t17-,19-,22-,24-,27-,28+,29-,31+,32+/m0/s1

2.3 InChlKey

OUMWCYMRLMEZJH-VOXRAUTJSA-N

2.4 Canonical SMILES

CC1CC=CC2C3C(O3)(C(C4C2(C(=O)C=CC(=O)C(C(=C1)C)O)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]4[C@@]2(C(=O)/C=C/C(=O)[C@@H](/C(=C1)/C)O)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. Research Progress on Chaetoglobosin A

4.1 Biosynthesis & Regulation

Chaetoglobosin A is a macrocyclic alkaloid with antifungal, antiparasitic, and anticancer properties.[2] Low yields and production costs have limited broader adoption. Recent work identified the _CgMfs1_ gene encoding a major facilitator superfamily transporter that influences biosynthesis and secretion; deletion reduces titers whereas overexpression raises output to 298.77 mg/L.[2]

4.2 Fermentation Optimization

Optimizing fermentation media via uniform design yielded a carbon/nitrogen combination of sucrose 17 g/L, starch 6 g/L, peptone 0.5 g/L with a 13-day culture time.[3] Ethyl acetate extraction (3-day soak) followed by silica gel chromatography provided efficient isolation, with optimal eluent and developing systems defined.

4.3 Straw-Based Fermentation

To reduce costs, a corn-straw-based fermentation/purification system was developed. Optimal conditions (straw 11.66 g, NH₄Cl 0.67 g, 25.5 °C) produced 3.7647 mg of chaetoglobosin A.[4] This approach lowers expense while enhancing yield.

4.4 Genetic Engineering

Overexpressing the polyketide synthase chain-extension gene _Cger_ significantly boosts production, whereas disruption of _CghdI_—a negative regulator—further elevates final titers.[4]

4.5 Application Potential

Chaetoglobosin A suppresses numerous plant pathogens and exhibits antitumor activity, indicating promise in biopesticide and pharmaceutical applications.[5] In vivo tests demonstrate effective control of potato dry rot, underscoring agricultural value.[4]

In summary, advances in biosynthetic regulation, fermentation optimization, straw-based production, and strain engineering provide a solid foundation for agricultural and biomedical deployment. Continued exploration of mechanistic and process innovations will support efficient manufacturing.

 

References

• [1] http://www.kehuaai.com/productInfo/174966
• [2] Zhao S, Lin C, Cheng M, Zhang K, Wang Z, Zhao T, Yang Q. New insight into the production improvement and resource generation of chaetoglobosin A in Chaetomium globosum. Microb Biotechnol. 2022 Oct;15(10):2562-2577.
• [3] Ruan Lulu, Cheng Jingli, Lu Yifu, et al. Optimization of chaetoglobosin A fermentation and extraction. Agrochemicals, 2011, 50(12):4.
• [4] Jiang Cheng. Regulation of chaetoglobosin A biosynthesis and fermentation optimization. Harbin Institute of Technology, 2025.
• [5] Lu Yifu. Extraction, isolation, and bioactivity of Chaetomium fermentation products. Zhejiang University of Technology, 2010.