Lingaoamide, a cyclic heptapeptide from a Chinese freshwater cyanobacterium Oscillatoria sp.

Arihiro Iwasaki; Naoaki Kurisawa; Tingting Wang; Xiaohui Li; Haixi Luo; Chengcong Zhu; Gaurav Patial; Xiaojun Yan; Shan He; Tal Luzzatto-Knaan; Fuli Tian; C. Benjamin Naman; Kiyotake Suenaga

doi:10.1016/j.tetlet.2021.153214

Lingaoamide, a cyclic heptapeptide from a Chinese freshwater cyanobacterium Oscillatoria sp.

Arihiro Iwasaki, Naoaki Kurisawa, Tingting Wang, Xiaohui Li, Haixi Luo, Chengcong Zhu, Gaurav Patial, Xiaojun Yan, Shan He, Tal Luzzatto-Knaan, Fuli Tian, C. Benjamin Naman, Kiyotake Suenaga

Department of Marine Biology

Research output: Contribution to journal › Article › peer-review

Abstract

Lingaoamide (1), a new cyclic heptapeptide natural product, was isolated from a freshwater Oscillatoria cyanobacterium. The producing organism was collected in Chinese water spinach paddy farm fields in Lingao County, Hainan, China. The structure of 1 was determined by conventional mass spectrometry, NMR spectroscopy, and chemical degradation studies. Lingaoamide concentration-dependently up-regulates the biogenesis of pro-pathogenic melanin pigments (melanogenesis) in the rice blast fungus, Magnaporthe grisea, when tested in vitro. This molecule also exhibits weak in vitro inhibition (MIC 32 μg/mL) of Gram-negative Pseudomonas aeruginosa and Gram-positive Bacillus pumilus, and does not appear to impact plant growth or immune response in vivo using the model organism, Arabidopsis thaliana.

Original language	English
Article number	153214
Journal	Tetrahedron Letters
Volume	75
DOIs	https://doi.org/10.1016/j.tetlet.2021.153214
State	Published - 6 Jul 2021

Bibliographical note

Funding Information:
This work was supported by the National Key Research and Development Program of China, funded through MOST (the Ministry of Science and Technology of China; grant 2018YFC0310900 to X.Y., S.H., and C.B.N.), NSFC (the National Natural Science Foundation of China; grants 81850410553 and 82050410451 to C.B.N.), Japan Society for the Promotion of Science (JSPS; KAKENHI grant 18 K14346), the National 111 Project of China (D16013), and the Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Development Fund of Ningbo University. W. Zhou and P. Shao (College of Fisheries, Tianjin Agricultural University, Tianjin, China) are thanked for providing the aquatic Pseudomonas and Vibrio pathogens used for biological testing in this study.

Funding Information:
This work was supported by the National Key Research and Development Program of China, funded through MOST (the Ministry of Science and Technology of China; grant 2018YFC0310900 to X.Y. S.H. and C.B.N.), NSFC (the National Natural Science Foundation of China; grants 81850410553 and 82050410451 to C.B.N.), Japan Society for the Promotion of Science (JSPS; KAKENHI grant 18 K14346), the National 111 Project of China (D16013), and the Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Development Fund of Ningbo University. W. Zhou and P. Shao (College of Fisheries, Tianjin Agricultural University, Tianjin, China) are thanked for providing the aquatic Pseudomonas and Vibrio pathogens used for biological testing in this study.

Publisher Copyright:
© 2021 Elsevier Ltd

Keywords

Cyanobacteria
Lingaoamide
Natural product
Oscillatoria
Rice blast fungus

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2021.153214

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@article{76e3260a1b094d978f07a101d4f939fa,

title = "Lingaoamide, a cyclic heptapeptide from a Chinese freshwater cyanobacterium Oscillatoria sp.",

abstract = "Lingaoamide (1), a new cyclic heptapeptide natural product, was isolated from a freshwater Oscillatoria cyanobacterium. The producing organism was collected in Chinese water spinach paddy farm fields in Lingao County, Hainan, China. The structure of 1 was determined by conventional mass spectrometry, NMR spectroscopy, and chemical degradation studies. Lingaoamide concentration-dependently up-regulates the biogenesis of pro-pathogenic melanin pigments (melanogenesis) in the rice blast fungus, Magnaporthe grisea, when tested in vitro. This molecule also exhibits weak in vitro inhibition (MIC 32 μg/mL) of Gram-negative Pseudomonas aeruginosa and Gram-positive Bacillus pumilus, and does not appear to impact plant growth or immune response in vivo using the model organism, Arabidopsis thaliana.",

keywords = "Cyanobacteria, Lingaoamide, Natural product, Oscillatoria, Rice blast fungus",

author = "Arihiro Iwasaki and Naoaki Kurisawa and Tingting Wang and Xiaohui Li and Haixi Luo and Chengcong Zhu and Gaurav Patial and Xiaojun Yan and Shan He and Tal Luzzatto-Knaan and Fuli Tian and Naman, {C. Benjamin} and Kiyotake Suenaga",

note = "Funding Information: This work was supported by the National Key Research and Development Program of China, funded through MOST (the Ministry of Science and Technology of China; grant 2018YFC0310900 to X.Y., S.H., and C.B.N.), NSFC (the National Natural Science Foundation of China; grants 81850410553 and 82050410451 to C.B.N.), Japan Society for the Promotion of Science (JSPS; KAKENHI grant 18 K14346), the National 111 Project of China (D16013), and the Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Development Fund of Ningbo University. W. Zhou and P. Shao (College of Fisheries, Tianjin Agricultural University, Tianjin, China) are thanked for providing the aquatic Pseudomonas and Vibrio pathogens used for biological testing in this study. Funding Information: This work was supported by the National Key Research and Development Program of China, funded through MOST (the Ministry of Science and Technology of China; grant 2018YFC0310900 to X.Y. S.H. and C.B.N.), NSFC (the National Natural Science Foundation of China; grants 81850410553 and 82050410451 to C.B.N.), Japan Society for the Promotion of Science (JSPS; KAKENHI grant 18 K14346), the National 111 Project of China (D16013), and the Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Development Fund of Ningbo University. W. Zhou and P. Shao (College of Fisheries, Tianjin Agricultural University, Tianjin, China) are thanked for providing the aquatic Pseudomonas and Vibrio pathogens used for biological testing in this study. Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

year = "2021",

month = jul,

day = "6",

doi = "10.1016/j.tetlet.2021.153214",

language = "English",

volume = "75",

journal = "Tetrahedron Letters",

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T1 - Lingaoamide, a cyclic heptapeptide from a Chinese freshwater cyanobacterium Oscillatoria sp.

AU - Iwasaki, Arihiro

AU - Kurisawa, Naoaki

AU - Wang, Tingting

AU - Li, Xiaohui

AU - Luo, Haixi

AU - Zhu, Chengcong

AU - Patial, Gaurav

AU - Yan, Xiaojun

AU - He, Shan

AU - Luzzatto-Knaan, Tal

AU - Tian, Fuli

AU - Naman, C. Benjamin

AU - Suenaga, Kiyotake

N1 - Funding Information: This work was supported by the National Key Research and Development Program of China, funded through MOST (the Ministry of Science and Technology of China; grant 2018YFC0310900 to X.Y., S.H., and C.B.N.), NSFC (the National Natural Science Foundation of China; grants 81850410553 and 82050410451 to C.B.N.), Japan Society for the Promotion of Science (JSPS; KAKENHI grant 18 K14346), the National 111 Project of China (D16013), and the Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Development Fund of Ningbo University. W. Zhou and P. Shao (College of Fisheries, Tianjin Agricultural University, Tianjin, China) are thanked for providing the aquatic Pseudomonas and Vibrio pathogens used for biological testing in this study. Funding Information: This work was supported by the National Key Research and Development Program of China, funded through MOST (the Ministry of Science and Technology of China; grant 2018YFC0310900 to X.Y. S.H. and C.B.N.), NSFC (the National Natural Science Foundation of China; grants 81850410553 and 82050410451 to C.B.N.), Japan Society for the Promotion of Science (JSPS; KAKENHI grant 18 K14346), the National 111 Project of China (D16013), and the Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Development Fund of Ningbo University. W. Zhou and P. Shao (College of Fisheries, Tianjin Agricultural University, Tianjin, China) are thanked for providing the aquatic Pseudomonas and Vibrio pathogens used for biological testing in this study. Publisher Copyright: © 2021 Elsevier Ltd

PY - 2021/7/6

Y1 - 2021/7/6

N2 - Lingaoamide (1), a new cyclic heptapeptide natural product, was isolated from a freshwater Oscillatoria cyanobacterium. The producing organism was collected in Chinese water spinach paddy farm fields in Lingao County, Hainan, China. The structure of 1 was determined by conventional mass spectrometry, NMR spectroscopy, and chemical degradation studies. Lingaoamide concentration-dependently up-regulates the biogenesis of pro-pathogenic melanin pigments (melanogenesis) in the rice blast fungus, Magnaporthe grisea, when tested in vitro. This molecule also exhibits weak in vitro inhibition (MIC 32 μg/mL) of Gram-negative Pseudomonas aeruginosa and Gram-positive Bacillus pumilus, and does not appear to impact plant growth or immune response in vivo using the model organism, Arabidopsis thaliana.

AB - Lingaoamide (1), a new cyclic heptapeptide natural product, was isolated from a freshwater Oscillatoria cyanobacterium. The producing organism was collected in Chinese water spinach paddy farm fields in Lingao County, Hainan, China. The structure of 1 was determined by conventional mass spectrometry, NMR spectroscopy, and chemical degradation studies. Lingaoamide concentration-dependently up-regulates the biogenesis of pro-pathogenic melanin pigments (melanogenesis) in the rice blast fungus, Magnaporthe grisea, when tested in vitro. This molecule also exhibits weak in vitro inhibition (MIC 32 μg/mL) of Gram-negative Pseudomonas aeruginosa and Gram-positive Bacillus pumilus, and does not appear to impact plant growth or immune response in vivo using the model organism, Arabidopsis thaliana.

KW - Cyanobacteria

KW - Lingaoamide

KW - Natural product

KW - Oscillatoria

KW - Rice blast fungus

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U2 - 10.1016/j.tetlet.2021.153214

DO - 10.1016/j.tetlet.2021.153214

M3 - Article

AN - SCOPUS:85107534040

SN - 0040-4039

VL - 75

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153214

ER -

Lingaoamide, a cyclic heptapeptide from a Chinese freshwater cyanobacterium Oscillatoria sp.

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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