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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.JA

Abstract

In preceding studies, cultivation of Chaetomium globosum, an endophytic fungus in Ginkgo biloba, produced five cytochalasan mycotoxins, chaetoglobosins A, G, V, Vb, and C (1-5), in three media. In the present work, five known chaetoglobosins, C, E, F, Fex, and 20-dihydrochaetoglobosin A (5-9), together with the four known compounds (11-14), were isolated from the MeOH extracts of the solid culture of the same endophyte. The structures of these metabolites were elucidated on the basis of spectroscopic analysis. Treatment of chaetoglobosin F (7) with (diethylamino)sulfur trifluoride (DAST) in dichloromethane afforded an unexpected fluorinated chaetoglobosin, named chaetoglobosin Fa (10), containing an oxolane ring between C-20 and C-23. The phytotoxic effects of compounds 1, 3-8, and 10 were assayed on radish seedlings; some of these compounds (1, 3, and 6-8) significantly inhibited the growth of radish (Raphanus sativus) seedlings with inhibitory rates of >60% at a concentration of 50 ppm, which was comparable or superior to the positive control, glyphosate. In addition, the cytotoxic activities against HCT116 human colon cancer cells were also tested, and compounds 1 and 8-10 showed remarkable cytotoxicity with IC50 values ranging from 3.15 to 8.44 μM, in comparison to the positive drug etoposide (IC50 = 2.13 μM). The epoxide ring between C-6 and C-7 or the double bond at C-6(12) led to a drastically increased cytotoxicity, and chaetoglobosin Fa (10) displayed a markedly increased cytotoxicity but decreased phytotoxicity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li H
Shaanxi Engineering Center of Bioresource Chemistry and Sustainable Utilization, College of Science, Northwest A&F University , Yangling 712100, Shaanxi, People's Republic of China.
Xiao J
No affiliation info available
Gao YQ
No affiliation info available
Tang JJ
No affiliation info available
Zhang AL
No affiliation info available
Gao JM
No affiliation info available

MeSH

Cell Line, TumorCell ProliferationChaetomiumCytotoxinsEndophytesGinkgo bilobaHumansIndole AlkaloidsMycotoxinsRaphanus

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24708412

Citation

Li, He, et al. "Chaetoglobosins From Chaetomium Globosum, an Endophytic Fungus in Ginkgo Biloba, and Their Phytotoxic and Cytotoxic Activities." Journal of Agricultural and Food Chemistry, vol. 62, no. 17, 2014, pp. 3734-41.
Li H, Xiao J, Gao YQ, et al. Chaetoglobosins from Chaetomium globosum, an endophytic fungus in Ginkgo biloba, and their phytotoxic and cytotoxic activities. J Agric Food Chem. 2014;62(17):3734-41.
Li, H., Xiao, J., Gao, Y. Q., Tang, J. J., Zhang, A. L., & Gao, J. M. (2014). Chaetoglobosins from Chaetomium globosum, an endophytic fungus in Ginkgo biloba, and their phytotoxic and cytotoxic activities. Journal of Agricultural and Food Chemistry, 62(17), 3734-41. https://doi.org/10.1021/jf500390h
Li H, et al. 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. PubMed PMID: 24708412.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chaetoglobosins from Chaetomium globosum, an endophytic fungus in Ginkgo biloba, and their phytotoxic and cytotoxic activities. AU - Li,He, AU - Xiao,Jian, AU - Gao,Yu-Qi, AU - Tang,Jiang Jiang, AU - Zhang,An-Ling, AU - Gao,Jin-Ming, Y1 - 2014/04/15/ PY - 2014/4/9/entrez PY - 2014/4/9/pubmed PY - 2014/10/2/medline SP - 3734 EP - 41 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 62 IS - 17 N2 - In preceding studies, cultivation of Chaetomium globosum, an endophytic fungus in Ginkgo biloba, produced five cytochalasan mycotoxins, chaetoglobosins A, G, V, Vb, and C (1-5), in three media. In the present work, five known chaetoglobosins, C, E, F, Fex, and 20-dihydrochaetoglobosin A (5-9), together with the four known compounds (11-14), were isolated from the MeOH extracts of the solid culture of the same endophyte. The structures of these metabolites were elucidated on the basis of spectroscopic analysis. Treatment of chaetoglobosin F (7) with (diethylamino)sulfur trifluoride (DAST) in dichloromethane afforded an unexpected fluorinated chaetoglobosin, named chaetoglobosin Fa (10), containing an oxolane ring between C-20 and C-23. The phytotoxic effects of compounds 1, 3-8, and 10 were assayed on radish seedlings; some of these compounds (1, 3, and 6-8) significantly inhibited the growth of radish (Raphanus sativus) seedlings with inhibitory rates of >60% at a concentration of 50 ppm, which was comparable or superior to the positive control, glyphosate. In addition, the cytotoxic activities against HCT116 human colon cancer cells were also tested, and compounds 1 and 8-10 showed remarkable cytotoxicity with IC50 values ranging from 3.15 to 8.44 μM, in comparison to the positive drug etoposide (IC50 = 2.13 μM). The epoxide ring between C-6 and C-7 or the double bond at C-6(12) led to a drastically increased cytotoxicity, and chaetoglobosin Fa (10) displayed a markedly increased cytotoxicity but decreased phytotoxicity. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/24708412/Chaetoglobosins_from_Chaetomium_globosum_an_endophytic_fungus_in_Ginkgo_biloba_and_their_phytotoxic_and_cytotoxic_activities_ DB - PRIME DP - Unbound Medicine ER -