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Chemistry, Organic
Joon Soo An, Bora Shin, Tae Ho Kim, Sunghoon Hwang, Yern-Hyerk Shin, Jinsheng Cui, Young Eun Du, Jungwoo Yi, Sang-Jip Nam, Suckchang Hong, Jongheon Shin, Jichan Jang, Yeo Joon Yoon, Dong-Chan Oh
Summary: Dumulmycin, isolated from Streptomyces sp. DM28 found in a riverine sediment sample, is a bicyclic macrolide with 19-membered and 5-membered rings. The compound exhibits in vitro antitubercular activity with MIC50 of 27.1 mu M.
Article
Chemistry, Organic
Tatyana N. Makarieva, Lyudmila A. Romanenko, Konstantin S. Mineev, Larisa K. Shubina, Elena B. Guglya, Natalia I. Kalinovskaya, Natalia V. Ivanchina, Alla G. Guzii, Olga A. Belozerova, Sergey I. Kovalchuk, Roman S. Popov, Vladimir A. Denisenko, Valery V. Mikhailov, Vladislav V. Babenko, Elena N. Ilina, Maja V. Malakhova, Stanislav S. Terekhov, Arsen M. Kudzhaev, Pavel S. Dmitrenok, Ilia V. Yampolsky, Valentin A. Stonik
Summary: This article describes a new structural class of highly chlorinated antibiotics, streptocinnamides A and B, produced by the bacterium Streptomyces sp. KMM 9044 isolated from a sample of marine sediment collected in the northwestern part of the Sea of Japan. The structures of streptocinnamides A and B were determined using nuclear magnetic resonance and mass spectrometry studies and their inhibitory activity against various bacteria was demonstrated.
Article
Chemistry, Organic
Li Wang, Zhi Zhou, Jian-Ping Huang, Liang Zhang, Xiaotao Tuo, Zhiyin Yu, Sheng-Xiong Huang, Yang Liu, Jing Yang
Summary: Strepyrrolins A-E, isolated from an endophytic Streptomyces sp. KIB 015, are five pyrrole-sesquiterpene hybrids with a 1,2,3-trisubstituted cyclopentanol terpene end-group. Their structures were determined through X-ray diffraction and spectroscopic methods. Feeding experiments revealed that the terpene moiety in strepyrrolins is biosynthesized via the MEP pathway, and the pyrrole ring is formed using free ammonia and two C3 units as potential substrates. Compound 3 exhibited immunosuppressive activity, inhibiting T cell proliferation and inducing cell cycle arrest in the G(0)/G(1) phase.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Biotechnology & Applied Microbiology
Rubin Thapa Magar, Van Thuy Thi Pham, Purna Bahadur Poudel, Hue Thi Nguyen, Adzemye Fovennso Bridget, Jae Kyung Sohng
Summary: In this study, a new macrolide called 25-hydroxy peucemycin was successfully identified from Streptomyces peucetius ATCC 27,952, which exhibited antibacterial effects on certain pathogens. By inactivating a polyketide synthase gene, the biosynthetic gene cluster for the compound was identified, which is considered to be cryptic. The biosynthetic pathway of peucemycin involves five type I polyketide synthase genes encoding eight modules and utilizes unusual extender units.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Constanze Paulus, Oleksandr Gromyko, Andriy Luzhetskyy
Summary: During the screening of new streptomycete strains, the strain Streptomyces sp. Cl 58-27 was found to produce a novel ansamycin natural product, kendomycin E, structurally similar to kendomycins. The structure of kendomycin E was elucidated using NMR spectroscopy, and its biosynthetic gene cluster was identified through genome sequencing and bioinformatic analysis of Streptomyces sp. Cl 58-27.
Article
Plant Sciences
Gwi Ja Hwang, Mina Jang, Sangkeun Son, Byeongsan Lee, Jun-Pil Jang, Jung-Sook Lee, Sung-Kyun Ko, Young-Soo Hong, Jong Seog Ahn, Jae-Hyuk Jang
Summary: Three new trichostatin analogues, ulleunganilines A-C, and seven known trichostatins were isolated from Streptomyces sp. 13F051 cultures. The structures and activities of these compounds were determined through experiments, with compounds 1 and 3 displaying moderate histone deacetylase inhibitory activity. This suggests that the hydroxamate group and the N,N-dimethyl group are both essential for inhibitory activity.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Plant Sciences
Kristiina Vind, Sonia Maffioli, Blanca Fernandez Ciruelos, Valentin Waschulin, Cristina Brunati, Matteo Simone, Margherita Sosio, Stefano Donadio
Summary: This study describes the discovery of two new N-acetyl-cysteinylated streptophenazines produced by a soil-derived Streptomyces sp. ID63040 using metabolomics. These compounds exhibit broad-spectrum antibacterial activity and are mainly derived from cellular functions according to the biosynthetic gene cluster analysis.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Biochemistry & Molecular Biology
Julie B. Nielsen, Tetiana Gren, Omkar S. Mohite, Tue S. Jorgensen, Andreas K. Klitgaard, Anna-Sophie Mourched, Kai Blin, Daniel Oves-Costales, Olga Genilloud, Thomas O. Larsen, David Tanner, Tilmann Weber, Charlotte H. Gotfredsen, Pep Charusanti
Summary: Actinomycetes produce a wealth of complex natural products. Researchers have identified the biosynthetic gene cluster for pyracrimycin A and proposed a complete biosynthesis pathway based on feeding experiments and isotope labeling analysis.
ACS CHEMICAL BIOLOGY
(2022)
Article
Chemistry, Organic
Bin Zhou, Gauri Shetye, Nina M. Wolf, Shao-Nong Chen, Mallique Qader, G. Joseph Ray, David C. Lankin, Sanghyun Cho, Jinhua Cheng, Joo-Won Suh, Scott G. Franzblau, James B. McAlpine, Guido F. Pauli
Summary: This study identified four new rufomycins compounds from Streptomyces atratus strain MJM3502. Compounds 1 and 2 possess a unique skeletal structure, while compounds 3 and 4 showed remarkable anti-Mycobacterium tuberculosis activity.
Article
Chemistry, Medicinal
Huaran Zhang, Yingying Chen, Yanqing Li, Yongxiang Song, Junying Ma, Jianhua Ju
Summary: The study on Streptomyces sp. SCSIO ZS0520 revealed new secondary metabolites and conducted bioinformatic analysis to lay foundations for solving remaining biosynthetic issues.
Article
Chemistry, Organic
Xin He, Jinqiu Ren, Li Wang, Jianying Luo, Jing Yang, Yu-Cheng Gu, Yijun Yan, Sheng-Xiong Huang
Summary: Quinolizidomycins A (1) and B (2), novel quinolizidine alkaloids, were discovered from Streptomyces sp. KIB-1714. Their structures were determined using spectroscopic methods and X-ray diffraction. Isotope labeling experiments revealed that compounds 1 and 2 are assembled from lysine, ribose 5-phosphate, and acetate units, representing an unprecedented biosynthetic pathway for the quinolizidine scaffold. Quinolizidomycin A (1) exhibited activity in an acetylcholinesterase inhibitory assay.
Article
Chemistry, Medicinal
Ya-Hui Zhang, Hui-Fang Du, Wen-Bin Gao, Wan Li, Fei Cao, Chang-Yun Wang
Summary: Three new polyketides were isolated from a marine-derived fungus, and their structures and configurations were determined. These compounds showed anti-inflammatory activities, with compounds 5 and 6 exhibiting the strongest effects.
Article
Plant Sciences
Isabelle Pouny, Christophe Long, Muriel Batut, Yannick Aussagues, Naubron Jean Valere, Gaston Achoundong, Bruno David, Catherine Lavaud, Georges Massiot
Summary: Five new quinolizidine alkaloids, named cylicomorphins A-E, were isolated from the leaves of Cylicomorpha solmstii. They are all ester derivatives of the same basic quinolizidine skeleton and exhibit cytotoxicity against HCT-116 cell line.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Organic
Qin Li, Meijia Zheng, Fengli Li, Yongqi Li, Chunmei Chen, Zijian Huang, Junjun Liu, Weiguang Sun, Ying Ye, Hucheng Zhu, Yonghui Zhang
Summary: Seven novel alpha-pyrone adducts, Talarolactones A-G, were isolated from Talaromyces adpressus, along with two pairs of alpha-pyrone monomers (+/-)-8 and (+/-)-9. Compounds 5 and 6 exhibited significant inhibition of NO production. Plausible biosynthetic pathways were proposed and supported by heterologous expression experiments.
Article
Chemistry, Organic
Mingyu Liu, Pinglin Li, Xuli Tang, Xiangchao Luo, Kechun Liu, Yun Zhang, Qi Wang, Guoqiang Li
Summary: New rearranged nardosinane sesquiterpenoids with unique carbon skeletons were isolated from the soft coral Lemnalia sp. collected from Xisha Islands of the South China Sea. Compound 1 and 10 exhibited in vivo angiogenesis promoting activity, while compounds 3 and 4 showed antiviral activity against the H1N1 virus.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biotechnology & Applied Microbiology
Ryota Hagihara, Yohei Katsuyama, Yoshinori Sugai, Hiroyasu Onaka, Yasuo Ohnishi
JOURNAL OF ANTIBIOTICS
(2018)
Article
Plant Sciences
Shotaro Hoshino, Masahiro Ozeki, Takayoshi Awakawa, Hiroyuki Morita, Hiroyasu Onaka, Ikuro Abe
JOURNAL OF NATURAL PRODUCTS
(2018)
Review
Biotechnology & Applied Microbiology
Shotaro Hoshino, Hiroyasu Onaka, Ikuro Abe
JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY
(2019)
Article
Chemistry, Organic
Yulu Jiang, Shan Lu, Go Hirai, Taira Kato, Hiroyasu Onaka, Hideaki Kakeya
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Multidisciplinary
Ryosuke Sugiyama, Takahiro Nakatani, Shinichi Nishimura, Kei Takenaka, Taro Ozaki, Shumpei Asamizu, Hiroyasu Onaka, Hideaki Kakeya
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Microbiology
Lu-Min Vaario, Shumpei Asamizu, Tytti Sarjala, Norihisa Matsushita, Hiroyasu Onaka, Yan Xia, Hiroyuki Kurokochi, Shin-Ichi Morinaga, Jian Huang, Shijie Zhang, Chunlan Lian
Article
Multidisciplinary Sciences
Alexander A. Vinogradov, Morito Shimomura, Yuki Goto, Taro Ozaki, Shumpei Asamizu, Yoshinori Sugai, Hiroaki Suga, Hiroyasu Onaka
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Alexander A. Vinogradov, Morito Shimomura, Naokazu Kano, Yuki Goto, Hiroyasu Onaka, Hiroaki Suga
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Chengqian Pan, Takefumi Kuranaga, Xun Cao, Takehiro Suzuki, Naoshi Dohmae, Naoya Shinzato, Hiroyasu Onaka, Hideaki Kakeya
Summary: Two nonapeptide natural products with a 22-membered cyclic depsipeptide skeleton, beta-hydroxytyrosine, and a highly modified side chain were discovered in a combined-culture of rare actinomycete Amycolatopsis sp. 26-4 with Tsukamurella pulmonis TP-B0596. The planar structures were elucidated through spectroscopic analyses, and the absolute configurations of component amino acids were determined using the advanced Marfey's method. Unstable/unusual moieties in the structures were corroborated by chemical synthesis and CD analysis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Alexander A. Vinogradov, Emiko Nagai, Jun Shi Chang, Kakeru Narumi, Hiroyasu Onaka, Yuki Goto, Hiroaki Suga
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Letter
Chemistry, Multidisciplinary
Naoya Oku, Shion Takemura, Hiroyasu Onaka, Yasuhiro Igarashi
MAGNETIC RESONANCE IN CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Yoshiki Asai, Tomoshige Hiratsuka, Miyu Ueda, Yumi Kawamura, Shumpei Asamizu, Hiroyasu Onaka, Manabu Arioka, Shinichi Nishimura, Minoru Yoshida
Summary: A. persicinum MF-347833 produces two ferrichrome-type siderophores with distinct biological properties, allowing it to adapt to different iron conditions.
ACS CHEMICAL BIOLOGY
(2022)
Article
Chemistry, Medicinal
Shinta Ijichi, Shotaro Hoshino, Shumpei Asamizu, Hiroyasu Onaka
Summary: We discovered solabiomycins, a new class of lipopeptides with polar-functionalized fatty acyl groups, through genome mining and stable isotope labeling. These solabiomycins contain a sulfoxide group in the labionin moiety called solabionin. Our study demonstrated that the sulfoxide is critical for the antibacterial activity of solabiomycins against Gram-positive bacteria. We also characterized the catalytic activity of SolS, which is involved in the sulfoxidation of solabionin, and determined its role in converting deoxysolabiomycins to solabiomycins.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Shotaro Hoshino, Shinta Ijichi, Shumpei Asamizu, Hiroyasu Onaka
Summary: Recently, the unique bioactivities of arsenic-containing secondary metabolites have been discovered, but studies on arsenic secondary metabolism in microorganisms are limited. In this study, we focused on an unknown arsenic metabolite called bisenarsan, produced by well-studied actinomycetes, and elucidated its structure through feeding experiments and detailed NMR analyses. Bisenarsan is the first characterized arsenic secondary metabolite derived from actinomycetes and could potentially serve as a prototoxin or a detoxification product. We also confirmed the genes responsible for bisenarsan biosynthesis, particularly the (2-hydroxyethyl)arsonic acid moiety. Notably, we proposed a novel mechanism for the formation of a C-As bond in bisenarsan through intramolecular rearrangement by a phosphoglycerate mutase homologue, which is distinct from the conventional As-alkylation mechanism. Our findings will accelerate the development of arsenic natural product biosynthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Taro Ozaki, Ryosuke Sugiyama, Morito Shimomura, Shinichi Nishimura, Shumpei Asamizu, Yohei Katsuyama, Hideaki Kakeya, Hiroyasu Onaka
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)