Scopranones with Two Atypical Scooplike Moieties Produced by Streptomyces sp. BYK-11038
- Ryuji Uchida
- ,
- Daiki Lee
- ,
- Ibuki Suwa
- ,
- Masaki Ohtawa
- ,
- Nozomu Watanabe
- ,
- Ayumu Demachi
- ,
- Satoshi Ohte
- ,
- Takenobu Katagiri
- ,
- Tohru Nagamitsu
- , and
- Hiroshi Tomoda
View Author Information
† Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
‡ Research Center for Genomic Medicine, Saitama Medical University, 1397-1 Yamane, Hidaka-shi, Saitama 350-1298, Japan
*E-mail: [email protected]
Abstract
Three new compounds, designated scopranones A–C, were isolated from the culture broth of a soil isolate, Streptomyces sp. BYK-11038, and shown to be inhibitors of bone morphogenetic protein (BMP) induced alkaline phosphatase activity in a BMP receptor mutant cell line. The structures were elucidated using NMR and other spectral data. The scopranones have an unusual structure with two atypical scooplike moieties linked at the tails to form part of a unique 3-furanone ring.
Cited By
This article is cited by 15 publications.
- Ganesh S. Ghotekar, Ravi A. Shinde, Sagar S. Saswade, M. Muthukrishnan. Palladium-Catalyzed Oxidative Cyclization of α-Allenols in the Presence of TBN: Access to 3(2H)-Furanones. The Journal of Organic Chemistry 2023, 88 (7) , 4112-4122. https://doi.org/10.1021/acs.joc.2c02457
- Debojyoti Bag, Harpreet Kour, Nirjhar Saha, Kamal, Harish Holla, Prasad V. Bharatam, Sanghapal D. Sawant. Iodocycloisomerization/Nucleophile Addition Cascade Transformations of 1,2-Alkynediones. The Journal of Organic Chemistry 2023, 88 (4) , 2377-2384. https://doi.org/10.1021/acs.joc.2c02790
- Debojyoti Bag, Sanghapal D. Sawant. Gold(I)-Catalyzed Cycloisomerization–Indole Addition Cascade: Synthesis of 3(2H)-Furanone-Incorporated Unsymmetrical 3,3′- Bis(indolyl)methanes. Organic Letters 2022, 24 (27) , 4930-4934. https://doi.org/10.1021/acs.orglett.2c01845
- Ayumu Demachi, Ryuji Uchida, Shiho Arima, Tohru Nagamitsu, Junko Hashimoto, Mamoru Komatsu, Ikuko Kozone, Kazuo Shin-ya, Hiroshi Tomoda, Haruo Ikeda. An Unusual Extender Unit Is Incorporated into the Modular Polyketide Synthase of Scopranones Biosynthesis. Biochemistry 2019, 58 (50) , 5066-5073. https://doi.org/10.1021/acs.biochem.9b00908
- Sho Inagaki, Kai Saito, Soichiro Suto, Hiromi Aihara, Aoi Sugawara, Satoru Tamura, Tomikazu Kawano. Synthesis of 5-Aryl-3(2H)-furanones Using Intramolecular Cyclization of Sulfonium Salts. The Journal of Organic Chemistry 2018, 83 (22) , 13834-13846. https://doi.org/10.1021/acs.joc.8b02153
- Masaki Ohtawa. Comprehensive Studies on the Synthetic Organic Chemistry of Unique Bioactive Natural Products; Total Synthesis, Drug Discovery, and Development of New Reactions. YAKUGAKU ZASSHI 2022, 142 (10) , 1067-1075. https://doi.org/10.1248/yakushi.22-00118
- Ayumu Demachi, Satoshi Ohte, Ryuji Uchida, Kazuo Shin-ya, Taichi Ohshiro, Hiroshi Tomoda, Haruo Ikeda. Discovery of prescopranone, a key intermediate in scopranone biosynthesis. The Journal of Antibiotics 2022, 75 (6) , 305-311. https://doi.org/10.1038/s41429-022-00521-x
- Xiangwen Kong, Fang Yu, Zhizhou Chen, Fan Gong, Shuang Yang, Jinggong Liu, Benlong Luo, Xinqiang Fang. Catalytic chemodivergent annulations between α-diketones and alkynyl α-diketones. Science China Chemistry 2021, 64 (6) , 991-998. https://doi.org/10.1007/s11426-021-9972-3
- Satoshi Ohte, Hiroyuki Yamazaki, Ohgi Takahashi, Henki Rotinsulu, Defny S. Wewengkang, Deiske A. Sumilat, Delfly B. Abdjul, Wilmar Maarisit, Magie M. Kapojos, Huiping Zhang, Fumiaki Hayashi, Michio Namikoshi, Takenobu Katagiri, Hiroshi Tomoda, Ryuji Uchida. Inhibitory effects of sesquiterpene lactones from the Indonesian marine sponge Lamellodysidea cf. herbacea on bone morphogenetic protein-induced osteoblastic differentiation. Bioorganic & Medicinal Chemistry Letters 2021, 35 , 127783. https://doi.org/10.1016/j.bmcl.2021.127783
- Hiroyuki Yamazaki, Satoshi Ohte, Henki Rotinsulu, Defny S. Wewengkang, Deiske A. Sumilat, Delfly B. Abdjul, Wilmar Maarisit, Magie M. Kapojos, Michio Namikoshi, Takenobu Katagiri, Hiroshi Tomoda, Ryuji Uchida. Screening for Small Molecule Inhibitors of BMP-Induced Osteoblastic Differentiation from Indonesian Marine Invertebrates. Marine Drugs 2020, 18 (12) , 606. https://doi.org/10.3390/md18120606
- Nobuhiro Koyama, Yasuhiro Otoguro, Satoshi Ohte, Takenobu Katagiri, Hiroshi Tomoda. Penicillic Acid Congener, a New Inhibitor of BMP-Induced Alkaline Phosphatase Activity in Myoblasts, Produced by the Fungus Penicillium sp. BF-0343. Natural Product Communications 2020, 15 (9) , 1934578X2094265. https://doi.org/10.1177/1934578X20942653
- Satoshi Ohte, Takehiro Shiokawa, Nobuhiro Koyama, Takenobu Katagiri, Chiaki Imada, Hiroshi Tomoda. A new diketopiperazine-like inhibitor of bone morphogenetic protein-induced osteoblastic differentiation produced by marine-derived Aspergillus sp. BFM-0085. The Journal of Antibiotics 2020, 73 (8) , 554-558. https://doi.org/10.1038/s41429-020-0316-3
- Ikuma Shiota, Arihiro Iwasaki, Shimpei Sumimoto, Hiroshi Tomoda, Kiyotake Suenaga. Caldorin, a new polyketide from the marine cyanobacterium Caldora penicillata. Tetrahedron Letters 2018, 59 (13) , 1261-1263. https://doi.org/10.1016/j.tetlet.2018.02.046
- Robert A. Hill, Andrew Sutherland. Hot off the press. Natural Product Reports 2018, 35 (2) , 132-136. https://doi.org/10.1039/C7NP90051A
- Takenobu Katagiri, Sho Tsukamoto, Yutaka Nakachi, Mai Kuratani. Recent Topics in Fibrodysplasia Ossificans Progressiva. Endocrinology and Metabolism 2018, 33 (3) , 331. https://doi.org/10.3803/EnM.2018.33.3.331