Absolute Configuration and Biological Activities of Meroterpenoids from an Endophytic Fungus of Lycium barbarum
Eleven new meroterpenoids, bipolahydroquinones A–C (1–3), cochlioquinones I–N (4–8 and 11), and isocochlioquinones F and G (9 and 10), together with six known ones, were obtained from an endophytic fungus Bipolaris sp. L1-2 from Lycium barbarum. Compound 2 is the first example of cochlioquinone deri...
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| Published in | Journal of natural products (Washington, D.C.) Vol. 82; no. 8; pp. 2229 - 2237 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society and American Society of Pharmacognosy
23.08.2019
Amer Chemical Soc |
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| Abstract | Eleven new meroterpenoids, bipolahydroquinones A–C (1–3), cochlioquinones I–N (4–8 and 11), and isocochlioquinones F and G (9 and 10), together with six known ones, were obtained from an endophytic fungus Bipolaris sp. L1-2 from Lycium barbarum. Compound 2 is the first example of cochlioquinone derivatives possessing a benzofuran moiety. The structures and absolute configurations of the new compounds were elucidated by spectroscopic data interpretation, single-crystal X-ray diffraction analysis, chemical transformations, and biosynthetic considerations. Compounds 3, 4, and 6–8 showed cytotoxicity against NCI-H226 and/or MDA-MB-231 with IC50 values ranging from 5.5 to 9.5 μM. |
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| AbstractList | Eleven new meroterpenoids, bipolahydroquinones A-C (1-3), cochlioquinones I-N (4-8 and 11), and isocochlioquinones F and G (9 and 10), together with six known ones, were obtained from an endophytic fungus Bipolaris sp. L1-2 from Lycium barbarum. Compound 2 is the first example of cochlioquinone derivatives possessing a benzofuran moiety. The structures and absolute configurations of the new compounds were elucidated by spectroscopic data interpretation, single-crystal X-ray diffraction analysis, chemical transformations, and biosynthetic considerations. Compounds 3, 4, and 6-8 showed cytotoxicity against NCI-H226 and/or MDA-MB-231 with IC50 values ranging from 5.5 to 9.5 μM.Eleven new meroterpenoids, bipolahydroquinones A-C (1-3), cochlioquinones I-N (4-8 and 11), and isocochlioquinones F and G (9 and 10), together with six known ones, were obtained from an endophytic fungus Bipolaris sp. L1-2 from Lycium barbarum. Compound 2 is the first example of cochlioquinone derivatives possessing a benzofuran moiety. The structures and absolute configurations of the new compounds were elucidated by spectroscopic data interpretation, single-crystal X-ray diffraction analysis, chemical transformations, and biosynthetic considerations. Compounds 3, 4, and 6-8 showed cytotoxicity against NCI-H226 and/or MDA-MB-231 with IC50 values ranging from 5.5 to 9.5 μM. Eleven new meroterpenoids, bipolahydroquinones A–C (1–3), cochlioquinones I–N (4–8 and 11), and isocochlioquinones F and G (9 and 10), together with six known ones, were obtained from an endophytic fungus Bipolaris sp. L1-2 from Lycium barbarum. Compound 2 is the first example of cochlioquinone derivatives possessing a benzofuran moiety. The structures and absolute configurations of the new compounds were elucidated by spectroscopic data interpretation, single-crystal X-ray diffraction analysis, chemical transformations, and biosynthetic considerations. Compounds 3, 4, and 6–8 showed cytotoxicity against NCI-H226 and/or MDA-MB-231 with IC50 values ranging from 5.5 to 9.5 μM. Eleven new meroterpenoids, bipolahydroquinones A-C (1-3), cochlioquinones I-N (4-8 and 11), and isocochlioquinones F and G (9 and 10), together with six known ones, were obtained from an endophytic fungus Bipolaris sp. L1-2 from Lycium barbarum. Compound 2 is the first example of cochlioquinone derivatives possessing a benzofuran moiety. The structures and absolute configurations of the new compounds were elucidated by spectroscopic data interpretation, single-crystal X-ray diffraction analysis, chemical transformations, and biosynthetic considerations. Compounds 3, 4, and 6-8 showed cytotoxicity against NCI-H226 and/or MDA-MB-231 with IC50 values ranging from 5.5 to 9.5 mu M. Eleven new meroterpenoids, bipolahydroquinones A-C ( - ), cochlioquinones I-N ( - and ), and isocochlioquinones F and G ( and ), together with six known ones, were obtained from an endophytic fungus sp. L1-2 from . Compound is the first example of cochlioquinone derivatives possessing a benzofuran moiety. The structures and absolute configurations of the new compounds were elucidated by spectroscopic data interpretation, single-crystal X-ray diffraction analysis, chemical transformations, and biosynthetic considerations. Compounds , , and - showed cytotoxicity against NCI-H226 and/or MDA-MB-231 with IC values ranging from 5.5 to 9.5 μM. Eleven new meroterpenoids, bipolahydroquinones A–C (1–3), cochlioquinones I–N (4–8 and 11), and isocochlioquinones F and G (9 and 10), together with six known ones, were obtained from an endophytic fungus Bipolaris sp. L1-2 from Lycium barbarum. Compound 2 is the first example of cochlioquinone derivatives possessing a benzofuran moiety. The structures and absolute configurations of the new compounds were elucidated by spectroscopic data interpretation, single-crystal X-ray diffraction analysis, chemical transformations, and biosynthetic considerations. Compounds 3, 4, and 6–8 showed cytotoxicity against NCI-H226 and/or MDA-MB-231 with IC₅₀ values ranging from 5.5 to 9.5 μM. |
| Author | Wang, Li-Ying Long, Yi Tang, Ting He, Bin Gao, Kun |
| AuthorAffiliation | State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering Ningxia Senmiao Goji Technology and Development Co., Ltd |
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| Cites_doi | 10.1016/j.tet.2015.05.044 10.1584/jpestics.23.281 10.1039/c29710000164 10.1039/c1np00030f 10.7164/antibiotics.48.1076 10.1271/bbb.58.1143 10.1016/j.tetlet.2007.05.151 10.1271/bbb.60.724 10.1021/np3007556 10.1039/b100918o 10.1021/acs.jafc.5b06107 10.1002/cbdv.201400106 10.1021/acs.jnatprod.8b00650 10.1039/p19800002686 10.1021/acs.jnatprod.8b00544 10.1016/j.fitote.2016.02.005 10.1002/anie.201804317 10.1055/s-0029-1186218 10.1038/ja.2005.95 10.1038/ja.2008.59 10.1007/s13225-011-0139-4 |
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| References | ref9/cit9 ref17/cit17 ref6/cit6 ref10/cit10 ref3/cit3 ref18/cit18 ref19/cit19 ref21/cit21 ref11/cit11 ref12/cit12 ref15/cit15 ref16/cit16 ref22/cit22 ref23/cit23 ref13/cit13 ref14/cit14 ref8/cit8 ref5/cit5 ref2/cit2 ref1/cit1 ref24/cit24 Chen Y. L. (ref4/cit4) 2017; 52 ref20/cit20 ref7/cit7 Phuwapraisirisan, P (WOS:000248155000005) 2007; 48 CANONICA, L (WOS:A1980KV25200012) 1980 Tan, RX (WOS:000170086100006) 2001; 18 Arayama, M (WOS:000357348100012) 2015; 71 Manamgoda, DS (WOS:000298007100002) 2011; 51 Brumley, D (WOS:000454962500014) 2018; 81 CARRUTHE.JR (WOS:A1971I502500036) 1971 Jiang, YJ (WOS:000446276600027) 2018; 81 Zhang, X (WOS:000436402100045) 2018; 57 Silverstein, R. M (000483435000020.18) 2005 Oj, Q Y (000483435000020.15) 2014; 11 MIYAGAWA, H (WOS:A1994NU98000034) 1994; 58 Kusari, S (WOS:000291946500001) 2011; 28 MACHIDA, T (WOS:A1995TB78500005) 1995; 48 Koyama, N (WOS:000233770400003) 2005; 58 Chen Yalin (CSCD:6134109) 2017; 52 Wang, M (WOS:000375739400012) 2016; 110 Potterat, O (WOS:000273762100001) 2010; 76 Lim, CH (WOS:000076449900010) 1998; 23 Oj, J (000483435000020.14) 2013; 76 Wang, TY (WOS:000371454000001) 2016; 64 Lim, CH (WOS:A1996UH21400046) 1996; 60 Yamazaki, H (WOS:000258668900003) 2008; 61 31691563 - J Nat Prod. 2019 Nov 22;82(11):3205 |
| References_xml | – ident: ref17/cit17 doi: 10.1016/j.tet.2015.05.044 – ident: ref20/cit20 – ident: ref8/cit8 doi: 10.1584/jpestics.23.281 – ident: ref16/cit16 doi: 10.1039/c29710000164 – ident: ref2/cit2 doi: 10.1039/c1np00030f – ident: ref12/cit12 doi: 10.7164/antibiotics.48.1076 – ident: ref6/cit6 doi: 10.1271/bbb.58.1143 – ident: ref11/cit11 doi: 10.1016/j.tetlet.2007.05.151 – ident: ref7/cit7 doi: 10.1271/bbb.60.724 – ident: ref18/cit18 doi: 10.1021/np3007556 – ident: ref1/cit1 doi: 10.1039/b100918o – ident: ref22/cit22 doi: 10.1021/acs.jafc.5b06107 – ident: ref9/cit9 doi: 10.1002/cbdv.201400106 – ident: ref24/cit24 doi: 10.1021/acs.jnatprod.8b00650 – ident: ref21/cit21 doi: 10.1039/p19800002686 – ident: ref19/cit19 – ident: ref23/cit23 doi: 10.1021/acs.jnatprod.8b00544 – ident: ref10/cit10 doi: 10.1016/j.fitote.2016.02.005 – ident: ref13/cit13 doi: 10.1002/anie.201804317 – ident: ref3/cit3 doi: 10.1055/s-0029-1186218 – volume: 52 start-page: 358 year: 2017 ident: ref4/cit4 publication-title: Chin. Pharm. J. – ident: ref14/cit14 doi: 10.1038/ja.2005.95 – ident: ref15/cit15 doi: 10.1038/ja.2008.59 – ident: ref5/cit5 doi: 10.1007/s13225-011-0139-4 – volume: 52 start-page: 358 year: 2017 ident: CSCD:6134109 article-title: Research Progress in Leaves of Lycium chinese Mill and Lycium barbarum L publication-title: Chinese Pharmaceutical Journal – start-page: 220 year: 2005 ident: 000483435000020.18 publication-title: Spectrometric Identification of Organic Compounds – volume: 81 start-page: 2716 year: 2018 ident: WOS:000454962500014 article-title: Isolation and Characterization of Anaephenes A-C, Alkylphenols from a Filamentous Cyanobacterium (Hormoscilla sp., Oscillatoriales) publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/acs.jnatprod.8b00650 – volume: 61 start-page: 426 year: 2008 ident: WOS:000258668900003 article-title: Structure-activity relationships of stemphones, potentiators of imipenern activity against methicillin-resistant Staphylococcus aureus publication-title: JOURNAL OF ANTIBIOTICS – volume: 76 start-page: 571 year: 2013 ident: 000483435000020.14 publication-title: J. Nat. Prod – volume: 60 start-page: 724 year: 1996 ident: WOS:A1996UH21400046 article-title: Cochlioquinol: A new cochlioquinone derivative produced by the plant pathogenic fungus Bipolaris cynodontis publication-title: BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY – volume: 28 start-page: 1203 year: 2011 ident: WOS:000291946500001 article-title: Are we ready for industrial production of bioactive plant secondary metabolites utilizing endophytes? publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/c1np00030f – start-page: 164 year: 1971 ident: WOS:A1971I502500036 article-title: STRUCTURES OF COCHLIOQUINONES-A AND B, NEW METABOLITES OF COCHLIOBOLUS-MIYABEANUS - CHEMICAL AND X-RAY CRYSTALLOGRAPHIC DETERMINATION publication-title: JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS – volume: 58 start-page: 1143 year: 1994 ident: WOS:A1994NU98000034 article-title: PHYTOTOXINS PRODUCED BY THE PLANT-PATHOGENIC FUNGUS BIPOLARIS BICOLOR EL-1 publication-title: BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY – volume: 11 start-page: 1892 year: 2014 ident: 000483435000020.15 publication-title: Chem. Biodiversity – volume: 57 start-page: 8184 year: 2018 ident: WOS:000436402100045 article-title: Genome Mining and Comparative Biosynthesis of Meroterpenoids from Two Phylogenetically Distinct Fungi publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201804317 – volume: 110 start-page: 77 year: 2016 ident: WOS:000375739400012 article-title: Cytotoxic cochlioquinone derivatives from the endophytic fungus Bipolaris sorokiniana derived from Pogostemon cablin publication-title: FITOTERAPIA doi: 10.1016/j.fitote.2016.02.005 – volume: 64 start-page: 1649 year: 2016 ident: WOS:000371454000001 article-title: New Alkaloids from Green Vegetable Soybeans and Their Inhibitory Activities on the Proliferation of Concanavalin A-Activated Lymphocytes publication-title: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY doi: 10.1021/acs.jafc.5b06107 – volume: 76 start-page: 7 year: 2010 ident: WOS:000273762100001 article-title: Goji (Lycium barbarum and L-chinense): Phytochemistry, Pharmacology and Safety in the Perspective of Traditional Uses and Recent Popularity publication-title: PLANTA MEDICA doi: 10.1055/s-0029-1186218 – volume: 51 start-page: 3 year: 2011 ident: WOS:000298007100002 article-title: Cochliobolus: an overview and current status of species publication-title: FUNGAL DIVERSITY doi: 10.1007/s13225-011-0139-4 – start-page: 2686 year: 1980 ident: WOS:A1980KV25200012 article-title: BIOSYNTHESIS OF COCHLIOQUINONES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 – volume: 81 start-page: 2120 year: 2018 ident: WOS:000446276600027 article-title: Medermycin-Type Naphthoquinones from the Marine-Derived Streptomyces sp XMA39 publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/acs.jnatprod.8b00544 – volume: 71 start-page: 4788 year: 2015 ident: WOS:000357348100012 article-title: Isolation, ECD assisted structural analyses, biosynthetic discussions, and biological activities of epi-cochlioquinones D and its derivatives publication-title: TETRAHEDRON doi: 10.1016/j.tet.2015.05.044 – volume: 48 start-page: 5193 year: 2007 ident: WOS:000248155000005 article-title: Anhydrocochlioquinone A, a new antitumor compound from Bipolaris oryzae publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2007.05.151 – volume: 23 start-page: 281 year: 1998 ident: WOS:000076449900010 article-title: Structures and biological activities of phytotoxins produced by the plant pathogenic fungus Bipolaris cynodontis cynA publication-title: JOURNAL OF PESTICIDE SCIENCE – volume: 48 start-page: 1076 year: 1995 ident: WOS:A1995TB78500005 article-title: COCHLIOQUINONE-A, AN INHIBITOR OF DIACYLGLYCEROL KINASE publication-title: JOURNAL OF ANTIBIOTICS – volume: 58 start-page: 695 year: 2005 ident: WOS:000233770400003 article-title: Stemphones, novel potentiators of imipenem activity against methicillin-resistant Staphylococcus aureus, produced by Aspergillus sp FKI-2136 publication-title: JOURNAL OF ANTIBIOTICS – volume: 18 start-page: 448 year: 2001 ident: WOS:000170086100006 article-title: Endophytes: a rich source of functional metabolites publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/b100918o – reference: 31691563 - J Nat Prod. 2019 Nov 22;82(11):3205 |
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| SubjectTerms | benzoquinones biosynthesis Bipolaris Chemistry, Medicinal cytotoxicity endophytes fungi hydroquinone inhibitory concentration 50 Life Sciences & Biomedicine Lycium barbarum meroterpenoids moieties Pharmacology & Pharmacy Plant Sciences Science & Technology spectral analysis X-ray diffraction |
| Title | Absolute Configuration and Biological Activities of Meroterpenoids from an Endophytic Fungus of Lycium barbarum |
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