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Armochaetoglobins A-J: Cytochalasan Alkaloids from Chaetomium globosum TW1-1, a Fungus Derived from the Terrestrial Arthropod Armadillidium vulgare.
J Nat Prod. 2015 Jun 26; 78(6):1193-201.JN

Abstract

Ten new cytochalasan alkaloids, termed armochaetoglobins A-J (1-10), and four known chaetoglobosins (11-14) were isolated from a methanol extract of Chaetomium globosum TW1-1, a fungus isolated from the medicinal terrestrial arthropod Armadillidium vulgare. Their structures were elucidated by a combination of spectroscopy, single-crystal X-ray crystallography, and ECD calculations. Armochaetoglobins A-E (1-5) represented the first examples of seco-chaetoglobosins arising from an oxidative cleavage of C-19 and C-20. Among these compounds, armochaetoglobin A (1) features an unusual pyrrole ring. The cytotoxic activities of 2-10 were evaluated, and armochaetoglobin H (8) showed moderate inhibitory activities against five human cancer cell lines, with IC50 values ranging from 3.31 to 9.83 μM.

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Authors+Show Affiliations

Chen C
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Wang J
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Liu J
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Zhu H
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Sun B
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Wang J
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Zhang J
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Luo Z
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Yao G
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Xue Y
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Zhang Y
†Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, and ‡Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.

MeSH

AnimalsAntineoplastic AgentsChaetomiumChinaCrystallography, X-RayDrug Screening Assays, AntitumorHL-60 CellsHumansIndole AlkaloidsInhibitory Concentration 50IsopodaMolecular ConformationMolecular StructureNuclear Magnetic Resonance, Biomolecular

Pub Type(s)

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

Language

eng

PubMed ID

26068802

Citation

Chen, Chunmei, et al. "Armochaetoglobins A-J: Cytochalasan Alkaloids From Chaetomium Globosum TW1-1, a Fungus Derived From the Terrestrial Arthropod Armadillidium Vulgare." Journal of Natural Products, vol. 78, no. 6, 2015, pp. 1193-201.
Chen C, Wang J, Liu J, et al. Armochaetoglobins A-J: Cytochalasan Alkaloids from Chaetomium globosum TW1-1, a Fungus Derived from the Terrestrial Arthropod Armadillidium vulgare. J Nat Prod. 2015;78(6):1193-201.
Chen, C., Wang, J., Liu, J., Zhu, H., Sun, B., Wang, J., Zhang, J., Luo, Z., Yao, G., Xue, Y., & Zhang, Y. (2015). Armochaetoglobins A-J: Cytochalasan Alkaloids from Chaetomium globosum TW1-1, a Fungus Derived from the Terrestrial Arthropod Armadillidium vulgare. Journal of Natural Products, 78(6), 1193-201. https://doi.org/10.1021/np500626x
Chen C, et al. Armochaetoglobins A-J: Cytochalasan Alkaloids From Chaetomium Globosum TW1-1, a Fungus Derived From the Terrestrial Arthropod Armadillidium Vulgare. J Nat Prod. 2015 Jun 26;78(6):1193-201. PubMed PMID: 26068802.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Armochaetoglobins A-J: Cytochalasan Alkaloids from Chaetomium globosum TW1-1, a Fungus Derived from the Terrestrial Arthropod Armadillidium vulgare. AU - Chen,Chunmei, AU - Wang,Jianping, AU - Liu,Junjun, AU - Zhu,Hucheng, AU - Sun,Bin, AU - Wang,Jing, AU - Zhang,Jinwen, AU - Luo,Zengwei, AU - Yao,Guangmin, AU - Xue,Yongbo, AU - Zhang,Yonghui, Y1 - 2015/06/12/ PY - 2015/6/13/entrez PY - 2015/6/13/pubmed PY - 2015/9/16/medline SP - 1193 EP - 201 JF - Journal of natural products JO - J Nat Prod VL - 78 IS - 6 N2 - Ten new cytochalasan alkaloids, termed armochaetoglobins A-J (1-10), and four known chaetoglobosins (11-14) were isolated from a methanol extract of Chaetomium globosum TW1-1, a fungus isolated from the medicinal terrestrial arthropod Armadillidium vulgare. Their structures were elucidated by a combination of spectroscopy, single-crystal X-ray crystallography, and ECD calculations. Armochaetoglobins A-E (1-5) represented the first examples of seco-chaetoglobosins arising from an oxidative cleavage of C-19 and C-20. Among these compounds, armochaetoglobin A (1) features an unusual pyrrole ring. The cytotoxic activities of 2-10 were evaluated, and armochaetoglobin H (8) showed moderate inhibitory activities against five human cancer cell lines, with IC50 values ranging from 3.31 to 9.83 μM. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/26068802/Armochaetoglobins_A_J:_Cytochalasan_Alkaloids_from_Chaetomium_globosum_TW1_1_a_Fungus_Derived_from_the_Terrestrial_Arthropod_Armadillidium_vulgare_ DB - PRIME DP - Unbound Medicine ER -