Discovery of a Dimeric Zinc Complex and Five Cyclopentenone Derivatives from the Sponge-Associated Fungus Aspergillus ochraceopetaliformis
In devotion to investigating structurally novel and biologically active marine natural products, a dimer of a zinc complex, dizinchydroxyneoaspergillin (1), aspernones A–E (2–6), five cyclopentenone derivatives together with known polyketides (7–10), and neoaspergillic acid analogues (11–14) were is...
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| Published in | ACS omega Vol. 6; no. 13; pp. 8942 - 8949 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
06.04.2021
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| Abstract | In devotion to investigating structurally novel and biologically active marine natural products, a dimer of a zinc complex, dizinchydroxyneoaspergillin (1), aspernones A–E (2–6), five cyclopentenone derivatives together with known polyketides (7–10), and neoaspergillic acid analogues (11–14) were isolated from the sponge-associated fungus Aspergillus ochraceopetaliformis SCSIO 41018. Their structures were elucidated on the basis of spectroscopic analysis, electronic circular dichroism (ECD) analysis, and X-ray diffraction. Dizinchydroxyneoaspergillin (1) displayed significant bactericide effects toward methicillin-resistant Staphyloccocus aureus, Staphyloccocus aureus, Enterococcus faecalis, Acinetobacter baumannii, and Klebsiella pneumonia with MIC values of 0.45–7.8 μg/mL and moderate in vitro cytotoxic activities against the K562, BEL-7402, and SGC-7901 cell lines with IC50 values of 12.88 ± 0.14, 15.83 ± 0.23, and 15.08 ± 0.62 μM, respectively. This is the first time to report the dimer of the zinc complex of hydroxyneoaspergillic acid conjunction at Zn–N-4 by a coordination bond. Additionally, compound 1 displayed significant antibacterial and cytotoxic activities, which would be a promising drug lead and could attract much attention from both chemists and pharmacists. |
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| AbstractList | In devotion to investigating structurally novel and biologically active marine natural products, a dimer of a zinc complex, dizinchydroxyneoaspergillin (
), aspernones A-E (
-
), five cyclopentenone derivatives together with known polyketides (
-
), and neoaspergillic acid analogues (
-
) were isolated from the sponge-associated fungus
SCSIO 41018. Their structures were elucidated on the basis of spectroscopic analysis, electronic circular dichroism (ECD) analysis, and X-ray diffraction. Dizinchydroxyneoaspergillin (
) displayed significant bactericide effects toward methicillin-resistant
,
,
,
, and
with MIC values of 0.45-7.8 μg/mL and moderate in vitro cytotoxic activities against the K562, BEL-7402, and SGC-7901 cell lines with IC
values of 12.88 ± 0.14, 15.83 ± 0.23, and 15.08 ± 0.62 μM, respectively. This is the first time to report the dimer of the zinc complex of hydroxyneoaspergillic acid conjunction at Zn-N-4 by a coordination bond. Additionally, compound
displayed significant antibacterial and cytotoxic activities, which would be a promising drug lead and could attract much attention from both chemists and pharmacists. In devotion to investigating structurally novel and biologically active marine natural products, a dimer of a zinc complex, dizinchydroxyneoaspergillin (1), aspernones A-E (2-6), five cyclopentenone derivatives together with known polyketides (7-10), and neoaspergillic acid analogues (11-14) were isolated from the sponge-associated fungus Aspergillus ochraceopetaliformis SCSIO 41018. Their structures were elucidated on the basis of spectroscopic analysis, electronic circular dichroism (ECD) analysis, and X-ray diffraction. Dizinchydroxyneoaspergillin (1) displayed significant bactericide effects toward methicillin-resistant Staphyloccocus aureus, Staphyloccocus aureus, Enterococcus faecalis, Acinetobacter baumannii, and Klebsiella pneumonia with MIC values of 0.45-7.8 μg/mL and moderate in vitro cytotoxic activities against the K562, BEL-7402, and SGC-7901 cell lines with IC50 values of 12.88 ± 0.14, 15.83 ± 0.23, and 15.08 ± 0.62 μM, respectively. This is the first time to report the dimer of the zinc complex of hydroxyneoaspergillic acid conjunction at Zn-N-4 by a coordination bond. Additionally, compound 1 displayed significant antibacterial and cytotoxic activities, which would be a promising drug lead and could attract much attention from both chemists and pharmacists.In devotion to investigating structurally novel and biologically active marine natural products, a dimer of a zinc complex, dizinchydroxyneoaspergillin (1), aspernones A-E (2-6), five cyclopentenone derivatives together with known polyketides (7-10), and neoaspergillic acid analogues (11-14) were isolated from the sponge-associated fungus Aspergillus ochraceopetaliformis SCSIO 41018. Their structures were elucidated on the basis of spectroscopic analysis, electronic circular dichroism (ECD) analysis, and X-ray diffraction. Dizinchydroxyneoaspergillin (1) displayed significant bactericide effects toward methicillin-resistant Staphyloccocus aureus, Staphyloccocus aureus, Enterococcus faecalis, Acinetobacter baumannii, and Klebsiella pneumonia with MIC values of 0.45-7.8 μg/mL and moderate in vitro cytotoxic activities against the K562, BEL-7402, and SGC-7901 cell lines with IC50 values of 12.88 ± 0.14, 15.83 ± 0.23, and 15.08 ± 0.62 μM, respectively. This is the first time to report the dimer of the zinc complex of hydroxyneoaspergillic acid conjunction at Zn-N-4 by a coordination bond. Additionally, compound 1 displayed significant antibacterial and cytotoxic activities, which would be a promising drug lead and could attract much attention from both chemists and pharmacists. In devotion to investigating structurally novel and biologically active marine natural products, a dimer of a zinc complex, dizinchydroxyneoaspergillin (1), aspernones A–E (2–6), five cyclopentenone derivatives together with known polyketides (7–10), and neoaspergillic acid analogues (11–14) were isolated from the sponge-associated fungus Aspergillus ochraceopetaliformis SCSIO 41018. Their structures were elucidated on the basis of spectroscopic analysis, electronic circular dichroism (ECD) analysis, and X-ray diffraction. Dizinchydroxyneoaspergillin (1) displayed significant bactericide effects toward methicillin-resistant Staphyloccocus aureus, Staphyloccocus aureus, Enterococcus faecalis, Acinetobacter baumannii, and Klebsiella pneumonia with MIC values of 0.45–7.8 μg/mL and moderate in vitro cytotoxic activities against the K562, BEL-7402, and SGC-7901 cell lines with IC50 values of 12.88 ± 0.14, 15.83 ± 0.23, and 15.08 ± 0.62 μM, respectively. This is the first time to report the dimer of the zinc complex of hydroxyneoaspergillic acid conjunction at Zn–N-4 by a coordination bond. Additionally, compound 1 displayed significant antibacterial and cytotoxic activities, which would be a promising drug lead and could attract much attention from both chemists and pharmacists. In devotion to investigating structurally novel and biologically active marine natural products, a dimer of a zinc complex, dizinchydroxyneoaspergillin ( 1 ), aspernones A–E ( 2 – 6 ), five cyclopentenone derivatives together with known polyketides ( 7 – 10 ), and neoaspergillic acid analogues ( 11 – 14 ) were isolated from the sponge-associated fungus Aspergillus ochraceopetaliformis SCSIO 41018. Their structures were elucidated on the basis of spectroscopic analysis, electronic circular dichroism (ECD) analysis, and X-ray diffraction. Dizinchydroxyneoaspergillin ( 1 ) displayed significant bactericide effects toward methicillin-resistant Staphyloccocus aureus , Staphyloccocus aureus , Enterococcus faecalis , Acinetobacter baumannii , and Klebsiella pneumonia with MIC values of 0.45–7.8 μg/mL and moderate in vitro cytotoxic activities against the K562, BEL-7402, and SGC-7901 cell lines with IC 50 values of 12.88 ± 0.14, 15.83 ± 0.23, and 15.08 ± 0.62 μM, respectively. This is the first time to report the dimer of the zinc complex of hydroxyneoaspergillic acid conjunction at Zn–N-4 by a coordination bond. Additionally, compound 1 displayed significant antibacterial and cytotoxic activities, which would be a promising drug lead and could attract much attention from both chemists and pharmacists. |
| Author | Guo, Cui Zhou, Xuefeng Pang, Xiaoyan Wang, Junfeng Liu, Yonghong Lin, Xiuping Liao, Shengrong Yang, Bin Wang, Pei |
| AuthorAffiliation | Chinese Academy of Sciences RNAM Center for Marine Microbiology Guangdong Key Laboratory of Marine Materia Medica Innovation Academy of South China Sea Ecology and Environmental Engineering Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) Institute of Tropical Bioscience and Biotechnology CAS Key Laboratory of Tropical Marine Bio-resources and Ecology University of Chinese Academy of Sciences |
| AuthorAffiliation_xml | – name: Innovation Academy of South China Sea Ecology and Environmental Engineering – name: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology – name: Institute of Tropical Bioscience and Biotechnology – name: RNAM Center for Marine Microbiology – name: Chinese Academy of Sciences – name: Guangdong Key Laboratory of Marine Materia Medica – name: Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) – name: University of Chinese Academy of Sciences |
| Author_xml | – sequence: 1 givenname: Cui surname: Guo fullname: Guo, Cui organization: Chinese Academy of Sciences – sequence: 2 givenname: Pei surname: Wang fullname: Wang, Pei organization: Institute of Tropical Bioscience and Biotechnology – sequence: 3 givenname: Xiaoyan surname: Pang fullname: Pang, Xiaoyan organization: Chinese Academy of Sciences – sequence: 4 givenname: Xiuping surname: Lin fullname: Lin, Xiuping organization: Chinese Academy of Sciences – sequence: 5 givenname: Shengrong orcidid: 0000-0003-4393-3823 surname: Liao fullname: Liao, Shengrong organization: Chinese Academy of Sciences – sequence: 6 givenname: Bin surname: Yang fullname: Yang, Bin organization: Chinese Academy of Sciences – sequence: 7 givenname: Xuefeng orcidid: 0000-0001-9601-4869 surname: Zhou fullname: Zhou, Xuefeng organization: Chinese Academy of Sciences – sequence: 8 givenname: Junfeng orcidid: 0000-0001-8914-5174 surname: Wang fullname: Wang, Junfeng email: wangjunfeng@scsio.ac.cn organization: Chinese Academy of Sciences – sequence: 9 givenname: Yonghong orcidid: 0000-0001-8327-3108 surname: Liu fullname: Liu, Yonghong email: yonghongliu@scsio.ac.cn organization: Chinese Academy of Sciences |
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| Title | Discovery of a Dimeric Zinc Complex and Five Cyclopentenone Derivatives from the Sponge-Associated Fungus Aspergillus ochraceopetaliformis |
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