Chemical Biology of Halogenated Antifouling Compounds

• Project/Area Number: 16H04975
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Aquatic life science
• Research Institution: Hokkaido University
• Principal Investigator: Okino Tatsufumi 北海道大学, 地球環境科学研究院, 教授 (30280910)
• Co-Investigator(Kenkyū-buntansha): 野方 靖行 一般財団法人電力中央研究所, 環境科学研究所, 上席研究員 (10371535) ; 梅澤 大樹 北海道大学, 地球環境科学研究院, 准教授 (20503618) ; 森本 善樹 大阪市立大学, 大学院理学研究科, 教授 (90244631)
• Project Period (FY): 2016-04-01 – 2020-03-31
• Project Status: Completed (Fiscal Year 2019)
• Budget Amount: ¥17,030,000 (Direct Cost: ¥13,100,000、Indirect Cost: ¥3,930,000); Fiscal Year 2019: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2018: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000); Fiscal Year 2017: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2016: ¥7,930,000 (Direct Cost: ¥6,100,000、Indirect Cost: ¥1,830,000)
• Keywords: フジツボ / 絶対立体配置 / 付着阻害 / 藍藻 / ブロモペルオキシダーゼ / ペプチド / 塩素 / 臭素 / 生合成 / 防汚塗料 / テルペノイド / ソゾ / 着生 / ラン藻 / 酵素 / 紅藻

Outline of Final Research Achievements

Reaction condition of vanadium-dependent bromoperoxidase from the red alga Laurencia saitoi was optimized to propose its products by MS. Chlorinated compounds were isolated from marine cyanobacteria.

Academic Significance and Societal Importance of the Research Achievements

臭素や塩素などのハロゲンを含む化合物は海洋天然物に多いことが知られているが、本研究においても海洋藍藻からそのようなユニークな化合物を発見することができた。また、海藻由来のハロゲンを導入する酵素についても、その性質を明らかにすることができ、医薬品の候補物質等にハロゲンを導入することに使える可能性がある。発見した化合物は船底防汚塗料として開発されることが期待される。

Research Products

• [Int'l Joint Research] マレーシアサバ大学(マレーシア)
• [Int'l Joint Research] キングアブドゥルアジーズ大学(サウジアラビア)
• [Int'l Joint Research] マレーシアサバ大学(マレーシア)
• [Int'l Joint Research] キングアブドゥルアジーズ大学(サウジアラビア)
• [Journal Article] Cytotoxicity and Antibacterial Potential of Halogenated Chamigrenes from Malaysian Red Alga, Laurencia majuscula (2019)
  • Author(s): Kamada Takashi、Phan Chin-Soon、Okino Tatsufumi、Vairappan Charles Santhanaraju
  • Journal Title: Planta Medica International Open Volume: 6 Issue: 02 Pages: e36-e40
  • DOI: 10.1055/a-0977-4418
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] 海洋生物由来の天然有機物質による付着生物阻害効果 (2019)
  • Author(s): 沖野龍文
  • Journal Title: 塗装工学 Volume: 54 Pages: 452-456
• [Journal Article] Environmentally Friendly Antifouling Metabolites from Red Sea Organisms (2019)
  • Author(s): Al-Lihaibi Sultan Semran、Abdel-Lateff Ahmed、Alarif Walied Mohamed、Alorfi Hajer Saeed、Nogata Yasuyuki、Okino Tatsufumi
  • Journal Title: Journal of Chemistry Volume: 2019 Pages: 1-15
  • DOI: 10.1155/2019/3278394
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Synthesis and Structure?Activity Relationship of Omaezallene Derivatives (2019)
  • Author(s): Umezawa Taiki、Prakoso Nurcahyo Iman、Kannaka Miho、Nogata Yasuyuki、Yoshimura Erina、Okino Tatsufumi、Matsuda Fuyuhiko
  • Journal Title: Chemistry & Biodiversity Volume: 16 Issue: 1 Pages: 1800451-1800451
  • DOI: 10.1002/cbdv.201800451
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] IN VITRO CYTOTOXIC ANTICANCER POTENTIAL OF BIOACTIVE FRACTION ISOLATED FROM INDONESIAN TIDAL SPONGE CALTHROPELLA SP. (2019)
  • Author(s): Susilowati Fitria、Tri Swasono Respati、Okino Tatsufumi、Haryadi Winarto
  • Journal Title: Asian Journal of Pharmaceutical and Clinical Research Volume: 12 Issue: 1 Pages: 380-380
  • DOI: 10.22159/ajpcr.2019.v12i1.23655
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] A study on synthesis of antifouling natural products and their derivatives (2018)
  • Author(s): Umezawa Taiki、Matsuda Fuyuhiko
  • Journal Title: Sessile Organisms Volume: 35 Issue: 2 Pages: 35-44
  • DOI: 10.4282/sosj.35.35
  • NAID: 130007495130
  • ISSN: 1342-4181, 1883-4701
  • Year and Date: 2018-10-05
  • Peer Reviewed / Open Access
• [Journal Article] Kakeromamide A, a new cyclic pentapeptide inducing astrocyte differentiation isolated from the marine cyanobacterium (2018)
  • Author(s): Nakamura F, Maejima H, Kawamura M, Arai D, Okino T, Zhao M, Ye T, Lee J, Chang Y-T, Fusetan N, Nakao Y
  • Journal Title: Bioorg.Med.Chem.Lett. Volume: - Issue: 12 Pages: 2206-2209
  • DOI: 10.1016/j.bmcl.2018.04.067
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Antioxidants from the Brown Alga Dictyopteris undulata (2018)
  • Author(s): Kumagai Momochika、Nishikawa Keisuke、Matsuura Hiroshi、Umezawa Taiki、Matsuda Fuyuhiko、Okino Tatsufumi
  • Journal Title: Molecules Volume: 23 Issue: 5 Pages: 1214-1214
  • DOI: 10.3390/molecules23051214
  • NAID: 120006522673
  • Peer Reviewed / Open Access
• [Journal Article] Adhesion force measurement of live cypris tentacles by scanning probe microscopy in seawater (2018)
  • Author(s): Shiomoto Shohei、Yamaguchi Yuka、Yamaguchi Kazuo、Nogata Yasuyuki、Kobayashi Motoyasu
  • Journal Title: Polymer Journal Volume: 51 Issue: 1 Pages: 51-59
  • DOI: 10.1038/s41428-018-0120-0
  • NAID: 40021935751
  • Peer Reviewed
• [Journal Article] Columbamides D and E: Chlorinated Fatty Acid Amides from the Marine Cyanobacterium Moorea bouillonii Collected in Malaysia (2017)
  • Author(s): J. A. V. Lopez, J. G. Petitbois, C. S. Vairappan, T. Umezawa, F. Matsuda, and T. Okino
  • Journal Title: Org. Lett. Volume: 19 Issue: 16 Pages: 4231-4234
  • DOI: 10.1021/acs.orglett.7b01869
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] New Marine Antifouling Compounds from the Red Alga Laurencia sp. (2017)
  • Author(s): Oguri Yuko、Watanabe Mami、Ishikawa Takafumi、Kamada Takashi、Vairappan Charles、Matsuura Hiroshi、Kaneko Kensuke、Ishii Takahiro、Suzuki Minoru、Yoshimura Erina、Nogata Yasuyuki、Okino Tatsufumi
  • Journal Title: Marine Drugs Volume: 15 Issue: 9 Pages: 267-267
  • DOI: 10.3390/md15090267
  • NAID: 120006360134
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Serinolamides and Lyngbyabellins from an Okeania sp. Cyanobacterium Collected from the Red Sea (2017)
  • Author(s): J. G. Petitbois, L. O. Casalme, J. A. V. Lopez, W. M. Alarif, A. Abdel-Lateff, S. S. Al-Lihaibi, E. Yoshimura, Y. Nogata, T. Umezawa, F. Matsuda, and T. Okino
  • Journal Title: J. Nat. Prod. Volume: 80 Issue: 10 Pages: 2708-2715
  • DOI: 10.1021/acs.jnatprod.7b00449
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] 海洋生物由来の天然有機化学物質による付着生物阻害効果 (2017)
  • Author(s): Petitbois, Julie, 沖野龍文
  • Journal Title: 日本マリンエンジニアリング学会誌 Volume: 52 Pages: 33-37
  • NAID: 130006496583
• [Journal Article] Total synthesis and biological activity of dolastatin 16 (2017)
  • Author(s): 1.Casalme, L. O., Yamauchi, A., Sato, A., Petitbois, J. G., Nogata, Y., Yoshimura, E., Okino, T., Umezawa, T., & Matsuda, F.
  • Journal Title: Org. Biomol. Chem. Volume: 15 Issue: 5 Pages: 1140-1150
  • DOI: 10.1039/c6ob02657e
  • NAID: 120006374983
  • Peer Reviewed
• [Presentation] 藍藻Moorea bouilloniiから得られたバイオサーファクタント (2020)
  • Author(s): Mehjabin J. J., Petitbois, 梅澤大樹、松田冬彦、沖野龍文
  • Organizer: 令和２年度日本水産学会春季大会
• [Presentation] Halogenated biosurfactants from Moorea bouillonii collected in Sabah Malaysia (2019)
  • Author(s): Mehjabin J. J., Lopez, J. A. V., Umezawa, T,., Matsuda, F., Okino, T.
  • Organizer: Marine Biotechnology Conference 2019
  • Int'l Joint Research
• [Presentation] Biosurfactants from Marine Cyanobacteria (2019)
  • Author(s): Mehjabin J. J., Petitbois, J. G., Liang W., Okino, T.
  • Organizer: ASP Annual Meeting
  • Int'l Joint Research
• [Presentation] Biosurfactants from Marine Cyanobacteria (2019)
  • Author(s): Mehjabin J. J., Petitbois, J. G., Liang W., Okino, T.
  • Organizer: 第１４回化学生態学研究会
• [Presentation] Isolation of Secondary Metabolites from Marine Cyanobacteria and their Biosurfactant Activity (2019)
  • Author(s): Mehjabin J. J., Petitbois, J. G., Liang W., Okino, T.
  • Organizer: 23rd International Seaweed Symposium
  • Int'l Joint Research
• [Presentation] Chemical and Biological Diversity of Marine Cyanobacteria (2018)
  • Author(s): Tatsufumi Okino
  • Organizer: 6th Biennial International Conference on New Developments in Drug Discovery from Natural Products and Traditional Medicines
  • Int'l Joint Research / Invited
• [Presentation] Total Synthesis of Antifouling Natural Products toward Development of Molecular Probe (2018)
  • Author(s): 梅澤大樹
  • Organizer: International Congress on Pure & Applied Chemistry Langkawi
  • Int'l Joint Research / Invited
• [Presentation] オマエザレン誘導体の合成研究 (2018)
  • Author(s): 水谷央・梅澤大樹・松田冬彦
  • Organizer: 第30回記念 万有札幌シンポジウム
• [Presentation] オマエザレン鏡像体の合成研究 (2018)
  • Author(s): 水谷央・梅澤大樹・松田冬彦
  • Organizer: 北海道支部2018年夏季研究発表会
• [Presentation] Antifouling Lyngbyabellins from an Okeania sp. Cyanobacterium (2018)
  • Author(s): Petitbois Julie, Casalme Loida, Lopez Julius, Alarif Walied, Abdel-Lateff Ahmed, Al-Lihaibi Sultan, 吉村えり奈、野方靖行、梅澤大樹、松田冬彦、沖野龍文
  • Organizer: 化学系学協会北海道支部2018年冬季研究発表会
• [Presentation] Isolation of Lyngbyabellins from Okeania sp. (2017)
  • Author(s): Julie Gabrielle Petitbois, Sultan S. Al-Lihaibi, Walied M. Alarif, AhmedAbdel-Lateff, Tatsufumi Okino
  • Organizer: 平成29年度日本水産学会春季大会
  • Place of Presentation: 東京海洋大学品川キャンパス（東京都港区）
  • Year and Date: 2017-03-27
• [Presentation] 付着阻害物質研究の進展 (2017)
  • Author(s): 沖野龍文
  • Organizer: ２０１７年度日本付着生物学会シンポジウム
  • Invited
• [Presentation] Antifouling Marine Natural Products---Secondary Metabolites from Red Algae Laurencia spp. and Cyanobacteria (2017)
  • Author(s): 沖野龍文
  • Organizer: 11th International Symposium on Marine Engineering
  • Int'l Joint Research
• [Presentation] Potential of Marine Cyanobacteria as Anti-Cancer Agent Sources (2017)
  • Author(s): 沖野龍文
  • Organizer: 8th Asian Pacific Phycological Forum
  • Int'l Joint Research / Invited
• [Presentation] Structure Elucidation of Cytotoxic Compounds from Marine Cyanobacteria (2016)
  • Author(s): Okino Tatsufumi
  • Organizer: 24th National Symposium of Natural Products Chemistry
  • Place of Presentation: ジョグジャカルタ（インドネシア）
  • Year and Date: 2016-10-18
  • Int'l Joint Research / Invited
• [Presentation] Acyl amides from the cyanobacteria Okeania sp. collected in theRed Sea and Moorea bouillonii in Malaysia (2016)
  • Author(s): Julie Gabrielle Petitbois, Julius Adam Velasco Lopez, Sultan S. Al-Lihaibi, Walied M. Alarif, Ahmed Abdel-Lateff, Charles S. Vairappan,Tatsufumi Okino
  • 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: 2016-09-15
• [Presentation] ラン藻のつくる機能性物質の多様性 (2016)
  • Author(s): 沖野龍文
  • Organizer: 平成２８年度 公益社団法人日本農芸化学会 北海道支部第１回講演会
  • Place of Presentation: ホテル函館ロイヤル（北海道函館市）
  • Year and Date: 2016-08-05
  • Invited
• [Presentation] Antifouling strategy compounds from Red Sea organisms (2016)
  • Author(s): Julie Gabrielle Petitbois, Ahmed Abdel-Lateff, Walied M. Alarif, Seif-Eldin N. Ayyad, Sultan S. Al-Lihaibi, Erina Yoshimura, Yasuyuki Nogata,Tatsufumi Okino
  • Organizer: 18th International Congress on Marine Corrosion and Fouling
  • Place of Presentation: トゥーロン（フランス）
  • Year and Date: 2016-06-23
  • Int'l Joint Research
• [Presentation] Cytotoxic Natural Products from Moorea bouillonii Collected from Malaysia (2016)
  • Author(s): Julius Adam Lopez, Charles S. Vairappan¸ Tatsufumi Okino
  • Organizer: 第18回マリンバイオテクノロジー学会大会
  • Place of Presentation: 北海道大学函館キャンパス（北海道函館市）
  • Year and Date: 2016-05-29