Discovery and Development of Antitumor Compounds from Marine Dinoflagellates

• Project/Area Number: 21590011
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Kochi University
• Principal Investigator: TSUDA Masashi 高知大学, 教育研究部・総合科学系, 教授 (10261322)
• Project Period (FY): 2009 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2011: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 渦鞭毛藻 / 殺細胞活性 / 二次代謝産物

Research Abstract

Our investigation for new anticancer drug leads from the dinoflagellate Amphidinium sp., we have resulted in the isolation of several cytotoxic polyketide, amphirionins-2 and-3 and caribenolide-I from a marine dinoflagellate Amphidinium sp. Their structure elucidation were carried out using detailed analyses of spectroscopic data such as 2D NMR spectra and MS data.

Research Products

• [Journal Article] Hyrtioseragamines A and B, New Alkaloids from the Sponge Hyrtios Species (2011)
  • Author(s): Takahashi, Y. Iinuma, Y.; Kubota, T.; Tsuda, M.; Sekiguchi, M.; Mikami, Y.; Fromont, J.; Kobayashi, J
  • Journal Title: Organic Letters Volume: 13 Pages: 621-631
  • Peer Reviewed
• [Presentation] Biologically Active Substances from Marine Dinoflagellates Amphidinium Species (2011)
  • Author(s): Masashi Tsuda
  • Organizer: VII^<th> U.S.-Japan Seminar on Marine Natural Products : Cross-Disciplinary Expansions in Marine Bioorganic Chemistry
  • Place of Presentation: 沖縄、ラグナガーデンホテル(招待講演)
  • Year and Date: 2011-12-11
• [Presentation] Biologically Active Substances from Marine Dinoflagellates Amphidinium Species (2011)
  • Author(s): Tsuda M., Kumagai K.
  • Organizer: VII^<th> U. S.-Japan Seminar on Marine Natural Products : Cross-Disciplinary Expansions in Marine Bioorganic Chemistry
  • Place of Presentation: Okinawa Convention Center, Okinawa, Japan
• [Presentation] 渦鞭毛藻由来マクロリドCalibenolide Iの構造研究 (2011)
  • Author(s): 熊谷慶子,赤壁麻依,南田美佳,西坂太樹,津田正史,小西裕子,富永明
  • Organizer: 第53回天然物有機化合物討論会
  • Place of Presentation: 大阪国際交流センター
• [Presentation] Highly sensitive NMR system for discovery and structure elucidation of natural drug leads (2011)
  • Author(s): Tsuda M., Kumagai K.
  • Organizer: 2nd World Conference on Physico-Chemical Methods in Drug Discovery and Development
  • Place of Presentation: Falkensteiner Borik Hotel Complex, Zadar, Croatia
• [Presentation] EXTRACTION AND SEPARATION OF ANTICANCER DRUG LEADS FROM MICROALGAE BY USING SUPERCRITICAL FLUIED CARBON DIOXIDE (2011)
  • Author(s): Kumagai K., Tsuda M.
  • Organizer: 16th European Conference on Analytical Chemistry, Congress Center SAVA
  • Place of Presentation: Belgrade, Serbia
• [Presentation] Iriomoteolide-12a, a 12-membered macrolide from dinoflagellate Amphidinium species (2011)
  • Author(s): Kumagai K., Akakabe M., Minamida M., Tsuda M.
  • Organizer: 59th In Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research
  • Place of Presentation: Maritim Pine Beach Hotel, Antalya, Turkey
• [Presentation] CARIBENOLIDE REVISITED. REISOLATION OF CARIBENOLIDE-I TOGETHER WITH NEW CONGENERS (2011)
  • Author(s): Kumagai K., Minamida M., Akakabe M., Tsuda M., Konishi Y., Tominaga A.
  • Organizer: The 4th In Symposium on Advances in Synthetic and Medicinal Chemistryon
  • Place of Presentation: Holiday Inn ST. Petersburg-Moskovskye, St. Petersburg, Russia
• [Presentation] Iriomoteolide-10a, a new 20-membered macrolide from dinoflagellate Amphidinium species (2011)
  • Author(s): Kumagai K., Akakabe M., Minamida M., Tsuda M.
  • Organizer: The 7th Euoropean Conference on Marine Natural Products
  • Place of Presentation: Laholmen Hotel, Stramstad, Sweden
• [Presentation] Kiloliter-scale cultivation of microalgae producing anticancer drug leads (2011)
  • Author(s): Tsuda M., Kumagai K.
  • Organizer: The 7th Euoropean Conference on Marine Natural Products
  • Place of Presentation: Laholmen Hotel, Stramstad, Sweden
• [Presentation] CARIBENOLIDE REVISITED. REISOLATION OF CARIBENOLIDE-I TOGETHER WITH NEW CONGENERS (2011)
  • Author(s): Kumagai K., Akakabe M., Minamida M., Nishisaka T., Tsuda M., Konishi Y., Tsuda M., Tominaga A.
  • Organizer: 27Th In Symposium on The Chemistry of Natural Products 7Th In Conference on Biodiversity
  • Place of Presentation: Brisbane Convention & Exhibition Centre, Brisbane, Australia
• [Presentation] IRIOMOTEOLIDE-12A, a 12-membered macrolide from dinoflagellate Amphidinium species (2011)
  • Author(s): Akakabe M., Kumagai K., Tsuda M.
  • Organizer: 27Th In Symposium on The Chemistry of Natural Products 7Th In Conference on Biodiversity
  • Place of Presentation: Brisbane Convention & Exhibition Centre, Brisbane, Australia
• [Presentation] Neocaribenolide-I, a cytotoxic 26-membered macrolide from dinoflagellate Amphidinium species (2011)
  • Author(s): Kumagai K., Minamida M., Akakabe M., Tsuda M., Konishi Y., Tominaga A.
  • Organizer: 27Th In Symposium on The Chemistry of Natural Products 7Th In Conference on Biodiversity
  • Place of Presentation: Brisbane Convention & Exhibition Centre, Brisbane, Australia
• [Presentation] 海洋微細藻由来の生物活性天然分子 (2011)
  • Author(s): 津田正史
  • Organizer: 国際バイオEXPOバイオアカデミソクフォーラム
  • Place of Presentation: 東京ビッグサイト
• [Presentation] Isocaribenolide-1, a Cytotoxic 26-Memberd Macrolide from Dinoflagellate Amphidinium Species," AatAarma : Nature Aided Drug Discovery"(NADD) (2011)
  • Author(s): Akakabe M., Kumagai K., Tsuda M., Konishi Y., Tominaga A.
  • Organizer: Conference Centre of the University" Federico II"
  • Place of Presentation: Aula Magna Partenope, Napoli, Italy
• [Presentation] Amphirionin-2, a Novel Cytotoxic Polyketide from Dinofragellate Amphiclinium Species," Nataarma : Naure Aided Drug Aisovery"(NADD), (2011)
  • Author(s): Kumagai K., Akakabe M., Minamida M., Tsuda M., Konishi Y., Tominaga A.
  • Organizer: Conference Centre of the University" Federico II"
  • Place of Presentation: Aula Magna Partenope, Napoli, Italy
• [Presentation] Kiloliter-Scale Cultivation of Microalgae Producing Anticancer Drug Leads (2011)
  • Author(s): Tsuda M., Kumagai K.
  • Organizer: 4th Congress of the In Society for Applied Phycology
  • Place of Presentation: Marriott Harbourfront Hotel, Halifax, Canada
• [Presentation] 海洋性渦鞭毛藻Amphidinium sp.から新規12員環マクロリドIriomoteolide-12aの構造 (2011)
  • Author(s): 赤壁麻依,熊谷慶子,津田正史
  • Organizer: 第14回マリンバイ才テクノ々ジー学会大会
  • Place of Presentation: グランシップ(静岡県コンベンションアーツセンター)
• [Presentation] 海洋性渦鞭毛藻Amphidinium sp.からの新規ポリケチド化合物Amphirionin-3の構造 (2011)
  • Author(s): 南田美佳,熊谷慶子,津田正史
  • Organizer: 第14回マリンバイオテクノロジー学会大会
  • Place of Presentation: グランシップ(静岡県コンベンションアーツセンター)
• [Presentation] KILOLITER-SCALE CULTIVATION OF AMPHIDINIUM DINOFLAGELLATES TO SEARCH NEW BIOACTIVE METABOLITES TO SEARCH NEW BIOACTIVE METABOLITES (2010)
  • Author(s): Masashi Tsuda
  • Organizer: The 13th International Symposium on Marine Natural Products
  • Place of Presentation: Hilton Phuket Arcadia Resort & Spa タイ
  • Year and Date: 2010-10-18
• [Presentation] AMPHIDINIUM-2, A NOVEL CYTOTOXIC POLYKETIDE FROM DINO FLAGELLATE AMPHIDINIUM SPECIES (2010)
  • Author(s): Keiko Kumagai
  • Organizer: The 13th International Symposium on Marine Natural Products
  • Place of Presentation: Hilton Phuket Arcadia Resort & Spa タイ
  • Year and Date: 2010-10-18
• [Presentation] Novel Cytotoxic Substance from Amphidinium Dinoflagellates (2010)
  • Author(s): Masashi Tsuda
  • Organizer: 9th International Marine Biotechnology Conference
  • Place of Presentation: Huanghai Hotel 中国
  • Year and Date: 2010-10-12
• [Presentation] 渦鞭毛藻由来の抗がん剤シーズの探索と製造技術 (2010)
  • Author(s): 津田正史
  • Organizer: 四国地区四大学 新技術説明会
  • Place of Presentation: 科学技術振興機構 JSTホール(東京都)
  • Year and Date: 2010-04-02
• [Presentation] 海洋性渦鞭毛藻Amphidinium sp.からの新規マクロリドIsocaribenolide-1の構造 (2010)
  • Author(s): 赤壁麻依,熊谷慶子,津田正史,小西裕子,富永明
  • Organizer: 日本薬学会・日本薬剤師会・日本病院薬剤師会中四国支部学術大会
  • Place of Presentation: 米子コンベンションセンター
• [Presentation] 海洋性渦鞭毛藻Amphidinium sp.からの新規ポリケチドAmphirionin-3の構造 (2010)
  • Author(s): 南田美佳,熊谷慶子,津田正史
  • Organizer: 日本薬学会・日本薬剤師会・日本病院薬剤師会中四国支部学術大会
  • Place of Presentation: 米子コンベンションセンター
• [Presentation] KILOLITER-SCALE CULTIVATION OF AMPHIDINIUM DINOFLAGELLATES TO SEARCH NEW BIOACTIVE METABOLITES TO SEARCH NEW BIOACTIVE METABOLITES (2010)
  • Author(s): Masashi T
  • Organizer: The 13^<th> International Symposium on Marine Natural Products, Hilton Phuket Arcadia Resort & Spa
  • Place of Presentation: Phuket, Thailand
• [Presentation] ISOCARIBENOLIDE-1, A CYTOTOXIC 26-MEMBERD MACROLIDE FROM DINOFLAGELLATE AMPHIDINIUM SPECIES (2010)
  • Author(s): Akakabe M., Kumagai K., Tsuda M., Konishi, Y., Tominaga, A.
  • Organizer: The 13^<th> International Symposium on Marine Natural Products, Hilton Phuket Arcadia Resort & Spa
  • Place of Presentation: Phuket, Thailand
• [Presentation] AMPHIDINIUM-2, A NOVEL CYTOTOXIC POLYKETIDE FROM DINOFLAGELLATE AMPHIDINIUM SPECIES (2010)
  • Author(s): Keiko K., Mai A., Mika M., Masashi T., Yuko K., Akira T.
  • Organizer: The 13^<th> International Symposium on Marine Natural Products, Hilton Phuket Arcadia Resort & Spa
  • Place of Presentation: Phuket, Thailand
• [Presentation] Amphidinium属渦鞭毛藻より単離した新規ポリケチド化合物Amphidinium-2の構造 (2010)
  • Author(s): 熊谷慶子,赤壁麻依,南田美佳,津田正史,小西裕子,富永明,福士江里,川端潤
  • Organizer: 52^<nd> Symposium on The Chemistry of Natural Products
  • Place of Presentation: グランシップ(静岡コンベンションアーツセンター)
• [Presentation] AMPHIDINIUM-3 NEW POLYKETIDE FROM DINOFLAGELLATE AMPHIDINIUM SPECIES (2010)
  • Author(s): Mika M. Keiko K., Masashi T
  • Organizer: The 13^<th> International Symposium on Marine Natural Products, Hilton Phuket Arcadia Resort & Spa
  • Place of Presentation: Phuket, Thailan
• [Presentation] COMPARATIVE PROTEOMICS OF MARINE DINOFLAGELLATES AMPHIDINIUM SPECIES PRODUCING ANTITUMOR SUBSTANCES (2010)
  • Author(s): Masashi T., Keiko K.
  • Organizer: 14th International Biotechnology Symposium and Exhibition
  • Place of Presentation: Alma Mater Studiorum. University of Bologna, Palacongressi, Rimini, Ital
• [Presentation] Novel Cytotoxic Substance from Amphidinium Dinoflagellates (2010)
  • Author(s): Masashi, T. Keiko, K
  • Organizer: International Marine Biotechnology Conference
  • Place of Presentation: Huanghai Hotel, Qingdao, China
• [Presentation] Amphirionin-1, a novel cytotoxic poliketide from dinoflagellate Amphidinium species (2009)
  • Author(s): Kumagai K, Tsuda M.
  • Place of Presentation: Porte, Portugal
  • Year and Date: 2009-07-19
• [Presentation] Iriomotelide-8a, a novel 25-membered macrolide from dinoflagellate Amphidinium species (2009)
  • Author(s): Tsuda M., Kumagai K
  • Place of Presentation: Porte, Portugal
  • Year and Date: 2009-07-19
• [Presentation] Iriomotelide-8a, a novel 25-membered macrolide from dinoflagellate Amphidinium species (2009)
  • Author(s): TSUDA, M.
  • Organizer: 6^<th> European Conference on Marine Natural Products
  • Place of Presentation: HF Hotel Tuela ポルトガル
  • Year and Date: 2009-07-19
• [Presentation] Amphirionin-1, a novel cytotoxic poliketide from dinoflagellate Amphidinium species (2009)
  • Author(s): Kumagai K.
  • Organizer: 6^<th> European Conference on Marine Natural Products
  • Place of Presentation: HF Hotel Tuela ポルトガル
  • Year and Date: 2009-07-19
• [Patent(Industrial Property Rights)] 抗腫瘍活性を有するポリケチド化合物 (2010)
  • Inventor(s): 津田正史、熊谷慶子、赤壁麻依、富永明、小西裕子、津田雅之
  • Industrial Property Rights Holder: 高知大学
  • Industrial Property Number: 2010-029372
  • Filing Date: 2010-02-12
• [Patent(Industrial Property Rights)] 抗腫瘍性を有するポリケチド化合物 (2009)
  • Inventor(s): 津田正史
  • Industrial Property Rights Holder: 高知大学
  • Industrial Property Number: 2009-162977
  • Filing Date: 2009-07-09