Isolation and biological activity of marine natural compounds with bone-resorbing and bone forming properties

• Project/Area Number: 15K01803
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Biomolecular chemistry
• Research Institution: University of the Ryukyus
• Principal Investigator: TERUYA Toshiaki 琉球大学, 教育学部, 教授 (90375428)
• Co-Investigator(Renkei-kenkyūsha): Woo Je-Tae 中部大学, 応用生物学部・応用生物科学科 (20272693)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2017: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2016: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000); Fiscal Year 2015: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
• Keywords: 破骨細胞 / 骨芽細胞 / アルカリホスファターゼ / 海洋ラン藻 / アルカリ性ホスファターゼ / 石灰化 / 海洋シアノバクテリア / リポペプチド

Outline of Final Research Achievements

Two new pyrrolinone-containing lipopeptides, ypaoamides B and C, were isolated from an Okeania sp. marine cyanobacterium collected in Okinawa. Their structures were determined by spectroscopic analysis and Marfey’s analysis of acid hydrolysates. Ypaoamides C inhibited receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclastogenesis in mouse monocytic RAW264 cells. Aplysin is a known compound derived from Red Alga Laurencia nidifica collected in Okinawa. Aplysin enhanced the Alkaline Phosphatase (ALP) activity, an early osteoblast marker.

Research Products

• [Journal Article] Evaluation of raw nepodin extraction from Rumex japonicus and R. obtusifolius and their DNA polymorphisms. (2018)
  • Author(s): Minami M, Mori T, Yonezawa T, Saito Y, Teruya T, Woo JT.
  • Journal Title: J Nat Med. Volume: 72 Issue: 1 Pages: 369-374
  • DOI: 10.1007/s11418-017-1143-0
  • Peer Reviewed
• [Journal Article] Three New Malyngamides from the Marine Cyanobacterium Moorea producens (2017)
  • Author(s): Kosuke Sueyoshi, Aki Yamano, Kaori Ozaki, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya
  • Journal Title: Marine drugs Volume: 15 Issue: 1 Pages: 367-367
  • DOI: 10.1080/14786419.2017.1338282
  • Peer Reviewed
• [Journal Article] Leptolyngbyolides, Cytotoxic Macrolides from the Marine Cyanobacterium Leptolyngbya sp.: Isolation, Biological Activity, and Catalytic Asymmetric Total Synthesis (2017)
  • Author(s): Cui, J.; Morita, M.; Ohno, O.; Kimura, T.; Teruya, T.; Watanabe, T.; Suenaga, K.; Shibasaki, M.
  • Journal Title: Chem. Eur. J. Volume: 23 Issue: 35 Pages: 8500-8509
  • DOI: 10.1002/chem.201701183
  • Peer Reviewed
• [Journal Article] Biseokeaniamides A, B, and C, Sterol O-Acyltransferase Inhibitors from an Okeania sp. Marine Cyanobacterium. (2017)
  • Author(s): Iwasaki A, Tadenuma T, Sumimoto S, Ohshiro T, Ozaki K, Kobayashi K, Teruya T, Tomoda H, Suenaga K.
  • Journal Title: J Nat Prod. Volume: 80 Issue: 4 Pages: 1161-1166
  • DOI: 10.1021/acs.jnatprod.7b00137
  • Peer Reviewed
• [Journal Article] Odobromoamide, a Terminal Alkynyl Bromide-Containing Cyclodepsipeptide from the Marine Cyanobacterium Okeania sp. (2017)
  • Author(s): Kosuke Sueyoshi,Takafumi Kudo,Aki Yamano,Shimpei Sumimoto,Arihiro Iwasaki,Kiyotake Suenaga, Toshiaki Teruya
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 60 Issue: 4 Pages: 436-440
  • DOI: 10.1246/bcsj.20160417
  • NAID: 130006770729
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii. (2016)
  • Author(s): Shimpei Sumimoto, Arihiro Iwasaki, Osamu Ohno, Kosuke Sueyoshi, Toshiaki Teruya, and Kiyotake Suenaga
  • Journal Title: Organic Letters Volume: 18 Issue: 19 Pages: 9886-9894
  • DOI: 10.1021/acs.orglett.6b02364
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Total synthesis of odoamide, a novel cyclic depsipeptide from an Okinawan marine cyanobacterium (2016)
  • Author(s): Masato Kaneda, Kosuke Sueyoshi, Toshiaki Teruya, Ohno Hiroaki, Nobutaka Fujii, Shinya Oishi
  • Journal Title: Organic & Biomolecular Chemistry Volume: 14 Issue: 38 Pages: 9093-9104
  • DOI: 10.1039/c6ob01583b
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp. (2016)
  • Author(s): Kosuke Sueyoshi, Masato Kaneda, Shinpei Sumimoto, Shinya Oishi, Nobutaka Fujii, Kiyotake Suenaga, Toshiaki Teruya
  • Journal Title: Tetrahedron Volume: 72 Issue: 35 Pages: 5472-5478
  • DOI: 10.1016/j.tet.2016.07.031
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Honokiol, magnolol, and a combination of both compounds improve glucose metabolism in high-fat diet-induced obese mice (2015)
  • Author(s): Young-Sil Lee, Sun-Sil Choi, Takayuki Yonezawa, Toshiaki Teruya, Je-Tae Woo, Hyo Jung Kim, Byung-Yoon Cha
  • Journal Title: Food Science and Biotechnology Volume: 24 Issue: 4 Pages: 1467-1474
  • DOI: 10.1007/s10068-015-0189-6
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Antiproliferative Activity of Acerogenin C, a Macrocyclicdiarylheptanoid, on PDGF-Induced Human Aortic Smooth Muscle Cells Proliferation (2015)
  • Author(s): Byung-Yoon Cha, Wen Lei Shi, Kotaro Watanabe, Takayuki Yonezawa, Toshiaki Teruya, Kiyotake Kiyotake, Yuichi Ishikawa, Shigeru Nishiyama, Kazuo Nagai, Je-Tae Woo
  • Journal Title: Pharmacology & Pharmacy Volume: 6 Issue: 02 Pages: 47-55
  • DOI: 10.4236/pp.2015.62007
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Presentation] 海洋産リポペプチドMinnamide Aの合成研究と立体化学の決定 (2018)
  • Author(s): 小林正幸、澄本慎平、四宮誠一、照屋俊明、岩﨑有紘、末永 聖武
  • Organizer: 日本化学会第98春季年会
• [Presentation] 沖縄県産海洋生物における糖取り込み物質の探索 (2018)
  • Author(s): 尾崎香織、山野亜紀、末吉康佑、澄本慎平、岩﨑有紘、末永聖武、照屋俊明
  • Organizer: 日本化学会第98春季年会
• [Presentation] 沖縄県産海洋シアノバクテリア由来チアゾール含有ペプチドの 単離と構造 (2017)
  • Author(s): 岩崎有紘、蓼沼隆人、大城太一、尾崎香織、澄本慎平、照屋俊明、供田 洋、末永聖武
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶應義塾大学（神奈川県横浜市）
  • Year and Date: 2017-03-16
• [Presentation] 沖縄県産海洋生物における骨代謝調節物質の探索 (2017)
  • Author(s): 尾崎香織、山野亜紀、石井貴広、照屋俊明
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶應義塾大学（神奈川県横浜市）
  • Year and Date: 2017-03-16
• [Presentation] 沖縄県産海洋生物由来筋管細胞糖取り込み活性物質の探索 (2017)
  • Author(s): 山野亜紀・尾崎香織、山田美希、末吉康佑、澄本慎平、岩崎有紘、末永聖武、照屋俊明
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶應義塾大学（神奈川県横浜市）
  • Year and Date: 2017-03-16
• [Presentation] 海洋シアノバクテリア由来新規リポペプチド Minnamide 類の単 離と構造決定 (2017)
  • Author(s): 澄本慎平、四宮誠一、岩崎有紘、犬塚 俊康、照屋俊明、末永聖武
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶應義塾大学（神奈川県横浜市）
  • Year and Date: 2017-03-16
• [Presentation] 沖縄県備瀬産海洋シアノバクテリア由来の新規類縁体 Jahanyne B,C の構造と生物活性 (2017)
  • Author(s): 工藤隆文、尾崎香織、山野亜紀、末吉康佑、澄本慎平、岩崎有紘、末永聖武、照屋俊明
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶應義塾大学（神奈川県横浜市）
  • Year and Date: 2017-03-16
• [Presentation] 海洋シアノバクテリア由来のリポペプチドの構造 (2016)
  • Author(s): 澄本慎平、四宮誠一、岩崎有紘、大野修、犬塚 俊康、照屋俊明、末永聖武
  • Organizer: 第58回天然有機化合物討論会
  • Place of Presentation: 東北大学（宮城県仙台市）
  • Year and Date: 2016-09-14
• [Presentation] Structures and bioactivities of okeaniamide and chlorookeaniamide from marine cyanobacterium Okeania sp. (2015)
  • Author(s): Miki Yamada, Kosuke Sueyoshi, Takayuki Yonezawa, Byung-Yoon Cha, Je-Tae Woo, Shinpei Sumimoto, Shoichiro Suda, Toshiaki Teruya.
  • Organizer: 2015 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Odoamide, a novel cyclodepsipeptide from marine cyanobacterium Symploca sp. (2015)
  • Author(s): Kosuke Sueyoshi, Masato Kaneda, Shinya Oishi, Nobutaka Fujii, Shinpei Sumimoto, Shoichiro Suda, Toshiaki Teruya
  • Organizer: 2015 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Isolation and structure of a novel potent cytotoxic peptide from the marine cyanobacterium Symploca sp. (2015)
  • Author(s): Takafumi Kudo, Kosuke Sueyoshi, Kozo Fukumoto, Shinpei Sumimoto, Shoichiro Suda, Toshiaki Teruya
  • Organizer: 2015 International Chemical Congress of Pacific Basin Societies
  • Place of Presentation: Honolulu
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Novel Bioactive Substances from Okinawan Marine Cyanobacteria (2015)
  • Author(s): 照屋 俊明
  • Organizer: 済州水産加工産業育成のシンポジウムや品評会 -済州水産加工業の現在と未来-
  • Place of Presentation: オーシャンスイーツ済州ホテル
  • Year and Date: 2015-12-15