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Penochalasin K, a new unusual chaetoglobosin from the mangrove endophytic fungus Penicillium chrysogenum V11 and its effective semi-synthesis.
Fitoterapia. 2017 Nov; 123:23-28.F

Abstract

A new chaetoglobosin, penochalasin K (1) bearing an unusual six-cyclic 6/5/6/5/6/13 fused ring system, along with the known analogues, chaetoglobosin C (2), penochalasin I (3), and chaetoglobosin A (4) were isolated from the solid culture of the mangrove endophytic fungus Penicillium chrysogenum V11. Their structures were elucidated by 1D, 2D NMR spectroscopic analysis and high resolution mass spectroscopic data. The absolute configuration of compound 1 was determined by comparing the theoretical and experimental electronic circular dichroism curves. Compound 1 displayed significant inhibitory activities against Colletotrichum gloeosporioides and Rhizoctonia solani (MICs=6.13, 12.26μM, respectively), which was better than those of carbendazim, and exhibited potent cytotoxicity against MDA-MB-435, SGC-7901 and A549 cells (IC50<10μM). An effective biomimetic transformation of chaetoglobosin C (2)/chaetoglobosin A (4) into penochalasin K (1)/penochalasin I (3) was developed, which provided a simple method for the semi-synthesis of chaetoglobosins with a six-cyclic 6/5/6/5/6/13 fused system formed by the connectivity of C-5 and C-2' from their corresponding epoxide analogues.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhu X
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China.
Zhou D
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China.
Liang F
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China.
Wu Z
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China.
She Z
School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China.
Li C
College of Materials and Energy, South China Agricultural University, Guangzhou 510642, China. Electronic address: chunyuanli@scau.edu.cn.

MeSH

Antifungal AgentsCell Line, TumorColletotrichumEndophytesHumansIndole AlkaloidsMicrobial Sensitivity TestsMolecular StructurePenicillium chrysogenumRhizoctonia

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28958956

Citation

Zhu, Xinwei, et al. "Penochalasin K, a New Unusual Chaetoglobosin From the Mangrove Endophytic Fungus Penicillium Chrysogenum V11 and Its Effective Semi-synthesis." Fitoterapia, vol. 123, 2017, pp. 23-28.
Zhu X, Zhou D, Liang F, et al. Penochalasin K, a new unusual chaetoglobosin from the mangrove endophytic fungus Penicillium chrysogenum V11 and its effective semi-synthesis. Fitoterapia. 2017;123:23-28.
Zhu, X., Zhou, D., Liang, F., Wu, Z., She, Z., & Li, C. (2017). Penochalasin K, a new unusual chaetoglobosin from the mangrove endophytic fungus Penicillium chrysogenum V11 and its effective semi-synthesis. Fitoterapia, 123, 23-28. https://doi.org/10.1016/j.fitote.2017.09.016
Zhu X, et al. Penochalasin K, a New Unusual Chaetoglobosin From the Mangrove Endophytic Fungus Penicillium Chrysogenum V11 and Its Effective Semi-synthesis. Fitoterapia. 2017;123:23-28. PubMed PMID: 28958956.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Penochalasin K, a new unusual chaetoglobosin from the mangrove endophytic fungus Penicillium chrysogenum V11 and its effective semi-synthesis. AU - Zhu,Xinwei, AU - Zhou,Danli, AU - Liang,Fengyan, AU - Wu,Zhihui, AU - She,Zhigang, AU - Li,Chunyuan, Y1 - 2017/09/27/ PY - 2017/08/29/received PY - 2017/09/14/revised PY - 2017/09/25/accepted PY - 2017/9/30/pubmed PY - 2018/1/11/medline PY - 2017/9/30/entrez KW - Antifungal activity KW - Chaetoglobosin KW - Cytotoxicity KW - Mangrove endophytic fungus KW - Penicillium chrysogenum SP - 23 EP - 28 JF - Fitoterapia JO - Fitoterapia VL - 123 N2 - A new chaetoglobosin, penochalasin K (1) bearing an unusual six-cyclic 6/5/6/5/6/13 fused ring system, along with the known analogues, chaetoglobosin C (2), penochalasin I (3), and chaetoglobosin A (4) were isolated from the solid culture of the mangrove endophytic fungus Penicillium chrysogenum V11. Their structures were elucidated by 1D, 2D NMR spectroscopic analysis and high resolution mass spectroscopic data. The absolute configuration of compound 1 was determined by comparing the theoretical and experimental electronic circular dichroism curves. Compound 1 displayed significant inhibitory activities against Colletotrichum gloeosporioides and Rhizoctonia solani (MICs=6.13, 12.26μM, respectively), which was better than those of carbendazim, and exhibited potent cytotoxicity against MDA-MB-435, SGC-7901 and A549 cells (IC50<10μM). An effective biomimetic transformation of chaetoglobosin C (2)/chaetoglobosin A (4) into penochalasin K (1)/penochalasin I (3) was developed, which provided a simple method for the semi-synthesis of chaetoglobosins with a six-cyclic 6/5/6/5/6/13 fused system formed by the connectivity of C-5 and C-2' from their corresponding epoxide analogues. SN - 1873-6971 UR - https://www.unboundmedicine.com/medline/citation/28958956/Penochalasin_K_a_new_unusual_chaetoglobosin_from_the_mangrove_endophytic_fungus_Penicillium_chrysogenum_V11_and_its_effective_semi_synthesis_ DB - PRIME DP - Unbound Medicine ER -