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Yonghui Zhang - One of the best experts on this subject based on the ideXlab platform.
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two anti inflammatory chlorinated azaphilones from Chaetomium globosum tw1 1 cultured with 1 methyl l tryptophan and structure revision of chaephilone c
Tetrahedron Letters, 2020Co-Authors: Chunmei Chen, Hucheng Zhu, Jianping Wang, Yanyan Wang, Chenwei Chai, Weiguang Sun, Yonghui Zhang, Weixi GaoAbstract:Abstract By feeding 1-methyl- l -tryptophan (1-MT) into the inactivated rice cultures of an arthropod-derived fungus Chaetomium globosum TW1-1, two new chlorinated azaphilones (1 and 2) were isolated and identified. Their structures incorporating absolute configurations were determined by comprehensive spectroscopic analyses and single-crystal X-ray diffraction. Remarkably, chaephilone C, which was reported to possess an unprecedented 6-6-5-6-fused ring system with a chlorine substitution, was structurally revised to 1. Chaephilones C (1) and D (2) showed moderate anti-inflammatory activity against the NO production with IC50 values of 15.12 ± 1.48 and 20.65 ± 0.95 μM, respectively.
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antibacterial activity against drug resistant microbial pathogens of cytochalasan alkaloids from the arthropod associated fungus Chaetomium globosum tw1 1
Bioorganic Chemistry, 2019Co-Authors: Weixi Gao, Chunmei Chen, Hucheng Zhu, Jinwen Zhang, Jianping Wang, Chenwei Chai, Jieru Guo, Yonghui ZhangAbstract:Abstract By feeding 1-methyl- l -tryptophan (1-MT) into cultures of the arthropod-associated fungus Chaetomium globosum TW1-1, three novel cytochalasan alkaloids, termed as armochaetoglosins A–C (1–3), together with five known analogues, namely prochaetoglobosin I (4), chaetoglobosin T (5), chaetoglobosin C (6), armochaetoglobin Y (7), and chaetoglobosin Vb (8), were isolated and characterized. Their structures including absolute configurations were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of the experimental electronic circular dichroism (ECD) spectra. Structurally, compounds 1–3 represented the first examples of 1′-N-methyl-chaetoglobosins, which were possibly biosynthesized from the additive 1-MT rather than tryptophan. Additionally, compound 3 showed the highest antibacterial activity against K. pneumoniae and ESBL-E. coli with MIC values of 4.0 μg/mL and 16.0 μg/mL, respectively, wherein the inhibitory effect of 3 against K. pneumoniae was stronger than that of the clinically used antibiotic meropenem, with an MIC value of 8 μg/mL. Our findings may provide new chemical templates for the development of new antibacterial agents against drug-resistant microbial pathogens.
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armochaetoglasins a i cytochalasan alkaloids from fermentation broth of Chaetomium globosum tw1 1 by feeding l tyrosine
Phytochemistry, 2018Co-Authors: Weixi Gao, Chunmei Chen, Hucheng Zhu, Yongbo Xue, Jianping Wang, Chenwei Chai, Weiguang Sun, Yonghui ZhangAbstract:Abstract By feeding L-tyrosine into the culture medium, nine undescribed compounds, termed as armochaetoglasins A–I, together with three known analogues, namely armochaetoglobin E, chaetoglobosin V, and chaetoglobosin J, were isolated and identified from the medicinal terrestrial arthropod-derived fungus Chaetomium globosum TW1-1. Their structures were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of their electronic circular dichroism (ECD) spectra. Structurally, armochaetoglasin A represented the first tyrosine-derived cytochalasan alkaloid characterized by a 13-membered carbocyclic ring system; armochaetoglasins B and C possessed a rare 19,20-seco-chaetoglobosin skeleton. Armochaetoglasin B, chaetoglobosin V, and chaetoglobosin J showed weak cytotoxic activity with IC50 values ranging from 19.5 to 34.72 μM.
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armochaeglobines a and b two new indole based alkaloids from the arthropod derived fungus Chaetomium globosum
Organic Letters, 2015Co-Authors: Chunmei Chen, Qingyi Tong, Jianping Wang, Jing Yang, Xiaonian Li, Gentao Li, Yan Li, Yonghui ZhangAbstract:Armochaeglobines A (1) and B (2), two indole-based cytochalasan alkaloids with new carbon skeletons, were obtained from the fungus Chaetomium globosum TW1-1, which was first isolated from the arthropod Armadillidium vulgare. Their structures were elucidated by extensive spectroscopic analyses, ECD calculation, and single-crystal X-ray diffraction analysis. Interestingly, compound 1 featured a unique tetracyclic 5/6/7/5 fused ring system and 2 possessed a rare 12-membered carbon scaffold.
Chunmei Chen - One of the best experts on this subject based on the ideXlab platform.
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two anti inflammatory chlorinated azaphilones from Chaetomium globosum tw1 1 cultured with 1 methyl l tryptophan and structure revision of chaephilone c
Tetrahedron Letters, 2020Co-Authors: Chunmei Chen, Hucheng Zhu, Jianping Wang, Yanyan Wang, Chenwei Chai, Weiguang Sun, Yonghui Zhang, Weixi GaoAbstract:Abstract By feeding 1-methyl- l -tryptophan (1-MT) into the inactivated rice cultures of an arthropod-derived fungus Chaetomium globosum TW1-1, two new chlorinated azaphilones (1 and 2) were isolated and identified. Their structures incorporating absolute configurations were determined by comprehensive spectroscopic analyses and single-crystal X-ray diffraction. Remarkably, chaephilone C, which was reported to possess an unprecedented 6-6-5-6-fused ring system with a chlorine substitution, was structurally revised to 1. Chaephilones C (1) and D (2) showed moderate anti-inflammatory activity against the NO production with IC50 values of 15.12 ± 1.48 and 20.65 ± 0.95 μM, respectively.
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antibacterial activity against drug resistant microbial pathogens of cytochalasan alkaloids from the arthropod associated fungus Chaetomium globosum tw1 1
Bioorganic Chemistry, 2019Co-Authors: Weixi Gao, Chunmei Chen, Hucheng Zhu, Jinwen Zhang, Jianping Wang, Chenwei Chai, Jieru Guo, Yonghui ZhangAbstract:Abstract By feeding 1-methyl- l -tryptophan (1-MT) into cultures of the arthropod-associated fungus Chaetomium globosum TW1-1, three novel cytochalasan alkaloids, termed as armochaetoglosins A–C (1–3), together with five known analogues, namely prochaetoglobosin I (4), chaetoglobosin T (5), chaetoglobosin C (6), armochaetoglobin Y (7), and chaetoglobosin Vb (8), were isolated and characterized. Their structures including absolute configurations were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of the experimental electronic circular dichroism (ECD) spectra. Structurally, compounds 1–3 represented the first examples of 1′-N-methyl-chaetoglobosins, which were possibly biosynthesized from the additive 1-MT rather than tryptophan. Additionally, compound 3 showed the highest antibacterial activity against K. pneumoniae and ESBL-E. coli with MIC values of 4.0 μg/mL and 16.0 μg/mL, respectively, wherein the inhibitory effect of 3 against K. pneumoniae was stronger than that of the clinically used antibiotic meropenem, with an MIC value of 8 μg/mL. Our findings may provide new chemical templates for the development of new antibacterial agents against drug-resistant microbial pathogens.
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armochaetoglasins a i cytochalasan alkaloids from fermentation broth of Chaetomium globosum tw1 1 by feeding l tyrosine
Phytochemistry, 2018Co-Authors: Weixi Gao, Chunmei Chen, Hucheng Zhu, Yongbo Xue, Jianping Wang, Chenwei Chai, Weiguang Sun, Yonghui ZhangAbstract:Abstract By feeding L-tyrosine into the culture medium, nine undescribed compounds, termed as armochaetoglasins A–I, together with three known analogues, namely armochaetoglobin E, chaetoglobosin V, and chaetoglobosin J, were isolated and identified from the medicinal terrestrial arthropod-derived fungus Chaetomium globosum TW1-1. Their structures were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of their electronic circular dichroism (ECD) spectra. Structurally, armochaetoglasin A represented the first tyrosine-derived cytochalasan alkaloid characterized by a 13-membered carbocyclic ring system; armochaetoglasins B and C possessed a rare 19,20-seco-chaetoglobosin skeleton. Armochaetoglasin B, chaetoglobosin V, and chaetoglobosin J showed weak cytotoxic activity with IC50 values ranging from 19.5 to 34.72 μM.
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Cytochathiazines A–C: Three Merocytochalasans with a 2H‑1,4-Thiazine Functionality from Coculture of Chaetomium globosum and Aspergillus flavipes
2018Co-Authors: Wenjing Wang, Chunmei Chen, Qingyi Tong, Jianping Wang, Junjun Liu, Fanrong Zeng, Qiong Bie, Chong Dai, Yuan Zhou, Hucheng ZhuAbstract:Cytochathiazines A–C (1–3), which represent a new type of merocytochalasan, were isolated from coculture of Chaetomium globosum and Aspergillus flavipes. Compounds 1–3 are the first natural products featuring an unprecedented 2H-1,4-thiazine functionality. Plausible biosynthetic pathways for 1–3 with a chaetoglobosin and a dipeptide as the main constitutional units were proposed. Compound 2 induced apoptosis in leukemia cells through the activation of caspase-3 and the degradation of poly ADP-ribose polymerase
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chaephilones a and b two new azaphilone derivatives isolated from Chaetomium globosum
Chemistry & Biodiversity, 2016Co-Authors: Chunmei Chen, Hucheng Zhu, Dongdong Tan, Jinwen Zhang, Yongbo Xue, Jianping Wang, Jing Wang, Guangzheng Wei, Yi Guo, Chunping YinAbstract:Two new azaphilone derivatives, chaephilones A (1) and B (2), were isolated from the fungus Chaetomium globosum, together with four structurally related analogs 3 - 6. The structures of 1 and 2 were elucidated by comprehensive spectroscopic analyses including HR-ESI-MS and NMR. The known compounds were identified as chaetomugilin Q (3), chaetomugilin D (4), 11-epichaetomugilin A (5), and chaetomugilin S (6) by comparing their NMR data and optical rotation values with those reported. Compound 2 represents the first example of azaphilone with an open furan ring. Compounds 1 and 2 were evaluated for cytotoxic activities against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480) by the MTS method.
Jianping Wang - One of the best experts on this subject based on the ideXlab platform.
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two anti inflammatory chlorinated azaphilones from Chaetomium globosum tw1 1 cultured with 1 methyl l tryptophan and structure revision of chaephilone c
Tetrahedron Letters, 2020Co-Authors: Chunmei Chen, Hucheng Zhu, Jianping Wang, Yanyan Wang, Chenwei Chai, Weiguang Sun, Yonghui Zhang, Weixi GaoAbstract:Abstract By feeding 1-methyl- l -tryptophan (1-MT) into the inactivated rice cultures of an arthropod-derived fungus Chaetomium globosum TW1-1, two new chlorinated azaphilones (1 and 2) were isolated and identified. Their structures incorporating absolute configurations were determined by comprehensive spectroscopic analyses and single-crystal X-ray diffraction. Remarkably, chaephilone C, which was reported to possess an unprecedented 6-6-5-6-fused ring system with a chlorine substitution, was structurally revised to 1. Chaephilones C (1) and D (2) showed moderate anti-inflammatory activity against the NO production with IC50 values of 15.12 ± 1.48 and 20.65 ± 0.95 μM, respectively.
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antibacterial activity against drug resistant microbial pathogens of cytochalasan alkaloids from the arthropod associated fungus Chaetomium globosum tw1 1
Bioorganic Chemistry, 2019Co-Authors: Weixi Gao, Chunmei Chen, Hucheng Zhu, Jinwen Zhang, Jianping Wang, Chenwei Chai, Jieru Guo, Yonghui ZhangAbstract:Abstract By feeding 1-methyl- l -tryptophan (1-MT) into cultures of the arthropod-associated fungus Chaetomium globosum TW1-1, three novel cytochalasan alkaloids, termed as armochaetoglosins A–C (1–3), together with five known analogues, namely prochaetoglobosin I (4), chaetoglobosin T (5), chaetoglobosin C (6), armochaetoglobin Y (7), and chaetoglobosin Vb (8), were isolated and characterized. Their structures including absolute configurations were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of the experimental electronic circular dichroism (ECD) spectra. Structurally, compounds 1–3 represented the first examples of 1′-N-methyl-chaetoglobosins, which were possibly biosynthesized from the additive 1-MT rather than tryptophan. Additionally, compound 3 showed the highest antibacterial activity against K. pneumoniae and ESBL-E. coli with MIC values of 4.0 μg/mL and 16.0 μg/mL, respectively, wherein the inhibitory effect of 3 against K. pneumoniae was stronger than that of the clinically used antibiotic meropenem, with an MIC value of 8 μg/mL. Our findings may provide new chemical templates for the development of new antibacterial agents against drug-resistant microbial pathogens.
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armochaetoglasins a i cytochalasan alkaloids from fermentation broth of Chaetomium globosum tw1 1 by feeding l tyrosine
Phytochemistry, 2018Co-Authors: Weixi Gao, Chunmei Chen, Hucheng Zhu, Yongbo Xue, Jianping Wang, Chenwei Chai, Weiguang Sun, Yonghui ZhangAbstract:Abstract By feeding L-tyrosine into the culture medium, nine undescribed compounds, termed as armochaetoglasins A–I, together with three known analogues, namely armochaetoglobin E, chaetoglobosin V, and chaetoglobosin J, were isolated and identified from the medicinal terrestrial arthropod-derived fungus Chaetomium globosum TW1-1. Their structures were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of their electronic circular dichroism (ECD) spectra. Structurally, armochaetoglasin A represented the first tyrosine-derived cytochalasan alkaloid characterized by a 13-membered carbocyclic ring system; armochaetoglasins B and C possessed a rare 19,20-seco-chaetoglobosin skeleton. Armochaetoglasin B, chaetoglobosin V, and chaetoglobosin J showed weak cytotoxic activity with IC50 values ranging from 19.5 to 34.72 μM.
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cytochalasans produced by the coculture of aspergillus flavipes and Chaetomium globosum
Journal of Natural Products, 2018Co-Authors: Wenjing Wang, Yongbo Xue, Zengwei Luo, Jianping Wang, Yanyan Wang, Chong Dai, Yuan Zhou, Jiaojiao Gong, Xiaorui Liu, Hucheng ZhuAbstract:The cocultivation of Aspergillus flavipes and Chaetomium globosum, rich sources of cytochalasans, on solid rice medium, resulted in the production of 13 new, highly oxygenated cytochalasans, aspochalasinols A-D (1-4) and oxichaetoglobosins A-I (5-13), as well as seven known compounds (14-20). Of these compounds, 13 is a novel cytochalasan with an unexpected 2-norindole group. The isolated compounds were characterized by NMR spectroscopy, single-crystal X-ray crystallography, and ECD experiments. Compounds 1-4 represent the first examples of Asp-type cytochalasans with C-12 hydroxy groups, which may be a result of the coculture, as hydroxylated Me-12 groups are frequently found in Chae-type cytochalasans from C. globosum. In addition, 5-10 are unusual cytochalasans with an oxygenated C-10. Interestingly, 13 is the first example of a naturally occurring cytochalasan possessing a uniquely degraded indole ring that is derived from chaetoglobosin W, with 11 and 12 both serving as its biosynthetic intermediates. In the coculture of A. flavipes and C. globosum, most of these cytochalasans are more functionalized than normal cytochalasans, and the underlying causes may attract substantial attention from synthetic biologists. The cytotoxicities against five human cancer cell lines (SW480, HL-60, A549, MCF-7, and SMMC-7721) and the immunomodulatory activities of these new compounds were evaluated in vitro.
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Cytochathiazines A–C: Three Merocytochalasans with a 2H‑1,4-Thiazine Functionality from Coculture of Chaetomium globosum and Aspergillus flavipes
2018Co-Authors: Wenjing Wang, Chunmei Chen, Qingyi Tong, Jianping Wang, Junjun Liu, Fanrong Zeng, Qiong Bie, Chong Dai, Yuan Zhou, Hucheng ZhuAbstract:Cytochathiazines A–C (1–3), which represent a new type of merocytochalasan, were isolated from coculture of Chaetomium globosum and Aspergillus flavipes. Compounds 1–3 are the first natural products featuring an unprecedented 2H-1,4-thiazine functionality. Plausible biosynthetic pathways for 1–3 with a chaetoglobosin and a dipeptide as the main constitutional units were proposed. Compound 2 induced apoptosis in leukemia cells through the activation of caspase-3 and the degradation of poly ADP-ribose polymerase
Hucheng Zhu - One of the best experts on this subject based on the ideXlab platform.
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two anti inflammatory chlorinated azaphilones from Chaetomium globosum tw1 1 cultured with 1 methyl l tryptophan and structure revision of chaephilone c
Tetrahedron Letters, 2020Co-Authors: Chunmei Chen, Hucheng Zhu, Jianping Wang, Yanyan Wang, Chenwei Chai, Weiguang Sun, Yonghui Zhang, Weixi GaoAbstract:Abstract By feeding 1-methyl- l -tryptophan (1-MT) into the inactivated rice cultures of an arthropod-derived fungus Chaetomium globosum TW1-1, two new chlorinated azaphilones (1 and 2) were isolated and identified. Their structures incorporating absolute configurations were determined by comprehensive spectroscopic analyses and single-crystal X-ray diffraction. Remarkably, chaephilone C, which was reported to possess an unprecedented 6-6-5-6-fused ring system with a chlorine substitution, was structurally revised to 1. Chaephilones C (1) and D (2) showed moderate anti-inflammatory activity against the NO production with IC50 values of 15.12 ± 1.48 and 20.65 ± 0.95 μM, respectively.
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antibacterial activity against drug resistant microbial pathogens of cytochalasan alkaloids from the arthropod associated fungus Chaetomium globosum tw1 1
Bioorganic Chemistry, 2019Co-Authors: Weixi Gao, Chunmei Chen, Hucheng Zhu, Jinwen Zhang, Jianping Wang, Chenwei Chai, Jieru Guo, Yonghui ZhangAbstract:Abstract By feeding 1-methyl- l -tryptophan (1-MT) into cultures of the arthropod-associated fungus Chaetomium globosum TW1-1, three novel cytochalasan alkaloids, termed as armochaetoglosins A–C (1–3), together with five known analogues, namely prochaetoglobosin I (4), chaetoglobosin T (5), chaetoglobosin C (6), armochaetoglobin Y (7), and chaetoglobosin Vb (8), were isolated and characterized. Their structures including absolute configurations were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of the experimental electronic circular dichroism (ECD) spectra. Structurally, compounds 1–3 represented the first examples of 1′-N-methyl-chaetoglobosins, which were possibly biosynthesized from the additive 1-MT rather than tryptophan. Additionally, compound 3 showed the highest antibacterial activity against K. pneumoniae and ESBL-E. coli with MIC values of 4.0 μg/mL and 16.0 μg/mL, respectively, wherein the inhibitory effect of 3 against K. pneumoniae was stronger than that of the clinically used antibiotic meropenem, with an MIC value of 8 μg/mL. Our findings may provide new chemical templates for the development of new antibacterial agents against drug-resistant microbial pathogens.
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armochaetoglasins a i cytochalasan alkaloids from fermentation broth of Chaetomium globosum tw1 1 by feeding l tyrosine
Phytochemistry, 2018Co-Authors: Weixi Gao, Chunmei Chen, Hucheng Zhu, Yongbo Xue, Jianping Wang, Chenwei Chai, Weiguang Sun, Yonghui ZhangAbstract:Abstract By feeding L-tyrosine into the culture medium, nine undescribed compounds, termed as armochaetoglasins A–I, together with three known analogues, namely armochaetoglobin E, chaetoglobosin V, and chaetoglobosin J, were isolated and identified from the medicinal terrestrial arthropod-derived fungus Chaetomium globosum TW1-1. Their structures were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of their electronic circular dichroism (ECD) spectra. Structurally, armochaetoglasin A represented the first tyrosine-derived cytochalasan alkaloid characterized by a 13-membered carbocyclic ring system; armochaetoglasins B and C possessed a rare 19,20-seco-chaetoglobosin skeleton. Armochaetoglasin B, chaetoglobosin V, and chaetoglobosin J showed weak cytotoxic activity with IC50 values ranging from 19.5 to 34.72 μM.
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cytochalasans produced by the coculture of aspergillus flavipes and Chaetomium globosum
Journal of Natural Products, 2018Co-Authors: Wenjing Wang, Yongbo Xue, Zengwei Luo, Jianping Wang, Yanyan Wang, Chong Dai, Yuan Zhou, Jiaojiao Gong, Xiaorui Liu, Hucheng ZhuAbstract:The cocultivation of Aspergillus flavipes and Chaetomium globosum, rich sources of cytochalasans, on solid rice medium, resulted in the production of 13 new, highly oxygenated cytochalasans, aspochalasinols A-D (1-4) and oxichaetoglobosins A-I (5-13), as well as seven known compounds (14-20). Of these compounds, 13 is a novel cytochalasan with an unexpected 2-norindole group. The isolated compounds were characterized by NMR spectroscopy, single-crystal X-ray crystallography, and ECD experiments. Compounds 1-4 represent the first examples of Asp-type cytochalasans with C-12 hydroxy groups, which may be a result of the coculture, as hydroxylated Me-12 groups are frequently found in Chae-type cytochalasans from C. globosum. In addition, 5-10 are unusual cytochalasans with an oxygenated C-10. Interestingly, 13 is the first example of a naturally occurring cytochalasan possessing a uniquely degraded indole ring that is derived from chaetoglobosin W, with 11 and 12 both serving as its biosynthetic intermediates. In the coculture of A. flavipes and C. globosum, most of these cytochalasans are more functionalized than normal cytochalasans, and the underlying causes may attract substantial attention from synthetic biologists. The cytotoxicities against five human cancer cell lines (SW480, HL-60, A549, MCF-7, and SMMC-7721) and the immunomodulatory activities of these new compounds were evaluated in vitro.
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Cytochathiazines A–C: Three Merocytochalasans with a 2H‑1,4-Thiazine Functionality from Coculture of Chaetomium globosum and Aspergillus flavipes
2018Co-Authors: Wenjing Wang, Chunmei Chen, Qingyi Tong, Jianping Wang, Junjun Liu, Fanrong Zeng, Qiong Bie, Chong Dai, Yuan Zhou, Hucheng ZhuAbstract:Cytochathiazines A–C (1–3), which represent a new type of merocytochalasan, were isolated from coculture of Chaetomium globosum and Aspergillus flavipes. Compounds 1–3 are the first natural products featuring an unprecedented 2H-1,4-thiazine functionality. Plausible biosynthetic pathways for 1–3 with a chaetoglobosin and a dipeptide as the main constitutional units were proposed. Compound 2 induced apoptosis in leukemia cells through the activation of caspase-3 and the degradation of poly ADP-ribose polymerase
Weixi Gao - One of the best experts on this subject based on the ideXlab platform.
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two anti inflammatory chlorinated azaphilones from Chaetomium globosum tw1 1 cultured with 1 methyl l tryptophan and structure revision of chaephilone c
Tetrahedron Letters, 2020Co-Authors: Chunmei Chen, Hucheng Zhu, Jianping Wang, Yanyan Wang, Chenwei Chai, Weiguang Sun, Yonghui Zhang, Weixi GaoAbstract:Abstract By feeding 1-methyl- l -tryptophan (1-MT) into the inactivated rice cultures of an arthropod-derived fungus Chaetomium globosum TW1-1, two new chlorinated azaphilones (1 and 2) were isolated and identified. Their structures incorporating absolute configurations were determined by comprehensive spectroscopic analyses and single-crystal X-ray diffraction. Remarkably, chaephilone C, which was reported to possess an unprecedented 6-6-5-6-fused ring system with a chlorine substitution, was structurally revised to 1. Chaephilones C (1) and D (2) showed moderate anti-inflammatory activity against the NO production with IC50 values of 15.12 ± 1.48 and 20.65 ± 0.95 μM, respectively.
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antibacterial activity against drug resistant microbial pathogens of cytochalasan alkaloids from the arthropod associated fungus Chaetomium globosum tw1 1
Bioorganic Chemistry, 2019Co-Authors: Weixi Gao, Chunmei Chen, Hucheng Zhu, Jinwen Zhang, Jianping Wang, Chenwei Chai, Jieru Guo, Yonghui ZhangAbstract:Abstract By feeding 1-methyl- l -tryptophan (1-MT) into cultures of the arthropod-associated fungus Chaetomium globosum TW1-1, three novel cytochalasan alkaloids, termed as armochaetoglosins A–C (1–3), together with five known analogues, namely prochaetoglobosin I (4), chaetoglobosin T (5), chaetoglobosin C (6), armochaetoglobin Y (7), and chaetoglobosin Vb (8), were isolated and characterized. Their structures including absolute configurations were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of the experimental electronic circular dichroism (ECD) spectra. Structurally, compounds 1–3 represented the first examples of 1′-N-methyl-chaetoglobosins, which were possibly biosynthesized from the additive 1-MT rather than tryptophan. Additionally, compound 3 showed the highest antibacterial activity against K. pneumoniae and ESBL-E. coli with MIC values of 4.0 μg/mL and 16.0 μg/mL, respectively, wherein the inhibitory effect of 3 against K. pneumoniae was stronger than that of the clinically used antibiotic meropenem, with an MIC value of 8 μg/mL. Our findings may provide new chemical templates for the development of new antibacterial agents against drug-resistant microbial pathogens.
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armochaetoglasins a i cytochalasan alkaloids from fermentation broth of Chaetomium globosum tw1 1 by feeding l tyrosine
Phytochemistry, 2018Co-Authors: Weixi Gao, Chunmei Chen, Hucheng Zhu, Yongbo Xue, Jianping Wang, Chenwei Chai, Weiguang Sun, Yonghui ZhangAbstract:Abstract By feeding L-tyrosine into the culture medium, nine undescribed compounds, termed as armochaetoglasins A–I, together with three known analogues, namely armochaetoglobin E, chaetoglobosin V, and chaetoglobosin J, were isolated and identified from the medicinal terrestrial arthropod-derived fungus Chaetomium globosum TW1-1. Their structures were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of their electronic circular dichroism (ECD) spectra. Structurally, armochaetoglasin A represented the first tyrosine-derived cytochalasan alkaloid characterized by a 13-membered carbocyclic ring system; armochaetoglasins B and C possessed a rare 19,20-seco-chaetoglobosin skeleton. Armochaetoglasin B, chaetoglobosin V, and chaetoglobosin J showed weak cytotoxic activity with IC50 values ranging from 19.5 to 34.72 μM.