Isolation, purification, and biological activity of a novel prostanoid from the red alga Gracilaria edulis collected in Philippines

• Project/Area Number: 19580119
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Tohoku University
• Principal Investigator: YAMASHITA Mari Tohoku University, 大学院・農学研究科, 教授 (50192430)
• Project Period (FY): 2007 – 2008
• Project Status: Completed (Fiscal Year 2008)
• Budget Amount: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2008: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2007: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
• Keywords: 紅藻 / プロスタグランジン / アラキドン酸 / 構造決定 / 代謝 / プロスタノイド / オゴノリ / エイコサノイド / カタオゴノリ / ESI-MS

Research Abstract

フィリピン産紅藻カタオゴノリGracilaria edulisに新規プロスタグランジン類の存在を認めたため、単離し平面構造を決定した。また、生理活性試験を実施し、生合成・代謝経路を推定した。本化合物の分子量を366と決定し、プロスタグランジンD2からレトロアルドール反応により開環した後、海藻中または付着生物の酸化反応を触媒する酵素が関与して生成すると考えられた。

Research Products

• [Journal Article] Two critical residues in p-loop regions of puffer fish Na+channels on TTX-sensitivity (2008)
  • Author(s): Satoshi Maruta, Kaoru Yamaoka and Mari Yotsu-Yamashita
  • Journal Title: Toxicon 51 Pages: 381-387
  • Peer Reviewed
• [Journal Article] Accumulation of tetrodotoxin and 4, 9-anhydrotetorodotoxin in cultured juvenile kusafugu Fugu niphobles by dietary administration of natural toxic komonfugu Fugu poecilonotus liver (2008)
  • Author(s): Michiko Kono, Takashi Matsui, Kiyoshi Furukawa, Mari Yotsu-Yamashita, Kunio Yamamori
  • Journal Title: Toxicon 51 Pages: 1269-1273
  • Peer Reviewed
• [Journal Article] Examination of transformation among tetrodotoxin and its analogs in the living cultured juvenile puffer fish, kusafugu, Fugu niphobles by intramuscular administration (2008)
  • Author(s): Michiko Kono, Takashi Matsui, Kiyoshi Furukawa, Takuhiko Takase, Kunio Yamamori, Hideko Kaneda, Daisuke Aoki, Jun-Ho Jang, Mari Yotsu-Yamashita
  • Journal Title: Toxicon 52 Pages: 714-720
  • Peer Reviewed
• [Journal Article] Tetrodotoxin and 5, 6, 11-trideoxytetrodotoxin in Tetraodon nigroviridis and T. biocellatus collected from Southeast Asia (2008)
  • Author(s): Jun-Ho Jang and Mari Yotsu-Yamashita
  • Journal Title: The proceedings of the 5th World Fisheries Congress 1 Pages: 1-2
  • Peer Reviewed
• [Journal Article] 紅藻オゴノリ属(Gracilaria)由来の新規エイコサノイドの単離と構造 (2008)
  • Author(s): 中島康賀、金井良和、廣木禎彦、谷口和也、山下まり
  • Journal Title: 第50回天然有機化合物討論会要旨集 1 Pages: 297-302
• [Journal Article] Two critical residues in p-loop regions of puffer fish Na+ channels on TTX-ensitivity (2008)
  • Author(s): Satoshi Maruta
  • Journal Title: Toxicon 51 Pages: 381-387
  • Peer Reviewed
• [Journal Article] Accumulation of tetrodotoxin and 4, 9-anhydrotetorodotoxin in cultured juvenile kusafugu Fugu niphobles by dietary administration of natural toxic komonfugu Fugu poecilonotus liver (2008)
  • Author(s): Michiko Kono
  • Journal Title: Toxicon 51 Pages: 1269-1273
  • Peer Reviewed
• [Journal Article] Examination of transformation among tetrodotoxin and its analogs in the living cultured juvenile puffer fish, kusafugu, Fugu niphobles by intramuscular administration (2008)
  • Author(s): Michiko Kono
  • Journal Title: Toxicon 52 Pages: 714-720
  • Peer Reviewed
• [Journal Article] 紅藻オゴノリ属(Gracilaria)由来の新規エイコサノイドの単離と構造 (2008)
  • Author(s): 中島康賀
  • Journal Title: 第50回天然有機化合物討論会講演要旨集 50 Pages: 297-302
• [Journal Article] Tetrodotoxin and 5, 6, 11-trideoxytetrodotoxin in Tetraodon nigroviridis and T. biocellatus collected from Southeast Asia (2008)
  • Author(s): Jun-Ho Jang
  • Journal Title: 5th World Fisheries Congress proceedings 1 Pages: 1-2
  • Peer Reviewed
• [Journal Article] Two critical residues in p-loop regions of puffer fish Na+channels on TTX-sensitivity (2008)
  • Author(s): Satoshi Maruta
  • Journal Title: Toxicon 51 Pages: 381-387
  • Peer Reviewed
• [Journal Article] Accumulation of tetrodotoxin and 4,9-anhydrotetorodotoxin in cultured juvenile kusafugu Fugu niphobles by dietary administration of natural toxic komonfugu Fugu poecilonotus liver (2008)
  • Author(s): Michiko Kono
  • Journal Title: Toxicon (accepted)
  • Peer Reviewed
• [Journal Article] Polycavernoside C and C_2, the new analogs of the human lethal toxin polycavernoside A, from thered alga, Gracilaria edulis (2007)
  • Author(s): Mari Yotsu-Yamashita, Kazumi Abe, Tetsuya Seki, Kenshu Fujiwara and Takeshi Yasumoto
  • Journal Title: Tetrahedron Lett. 48 Pages: 2255-2259
  • Peer Reviewed
• [Journal Article] Tetrodotoxin and its analogue 6-epitetrodotoxin in newts (Triturus spp. ; Urodela, Salamandridae) from southern Germany (2007)
  • Author(s): Mari Yotsu-Yamashita, Dietrich Mebs, Axel Kwed and Michael Schneider
  • Journal Title: Toxicon 50 Pages: 306-309
  • Peer Reviewed
• [Journal Article] Effects of a synthetic analog of polycavernoside a on human neuroblastoma cells (2007)
  • Author(s): E. Cagide, M.C. Louzao, I.R. Ares, M.R. Vieytes, M. Yotsu-Yamashita, L.A. Paquette, T. Yasumoto and L.M. Botana
  • Journal Title: Cell Physiol. Biochem. 19 Pages: 185-194
  • Peer Reviewed
• [Journal Article] 6, 11-Dideoxytetrodotoxin from the puffer fish, Fugu pardalis (2007)
  • Author(s): Jun-Ho Jang and Mari Yotsu-Yamashita
  • Journal Title: Toxicon 50 Pages: 947-951
  • Peer Reviewed
• [Journal Article] Polycavemoside C and C2,the new analogs of the human lethal toxin polycavernoside A,from the red alga, Gracitaria edulis (2007)
  • Author(s): Mari Yotsu-Yamashita
  • Journal Title: Tetrahedron Lett 48 Pages: 2255-2259
  • Peer Reviewed
• [Journal Article] Tetrodotoxin and its analogue 6-epiterodotoxin in newts (Triturus spp;Urodela, Salamandridae)from southern Germany (2007)
  • Author(s): Mari Yotsu-Yamashita
  • Journal Title: Toxicon 50 Pages: 306-309
  • Peer Reviewed
• [Journal Article] 6,11-Dideoxytetrodotoxin from the puffer fish,Fugu pardalis (2007)
  • Author(s): Jun-Ho Jang
  • Journal Title: Toxicon 50 Pages: 947-951
  • Peer Reviewed
• [Presentation] 紅藻カタオゴノリGracilaria edulis 由来の新規プロスタグランジンの構造と生成経路の推定 (2009)
  • Author(s): 金井良和、廣木禎彦、越野広雪、山下まり
  • Organizer: 日本農芸化学会2009年度大会
  • Place of Presentation: 福岡、マリンメッセ福岡
  • Year and Date: 2009-03-28
• [Presentation] 紅藻オゴノリ属(Gracilaria)由来の新規エイコサノイドの単離と構造 (2008)
  • Author(s): 中島康賀、金井良和、廣木禎彦、谷口和也、山下まり
  • Organizer: 第50回天然有機化合物討論会
  • Place of Presentation: 福岡、福岡国際会議場
  • Year and Date: 2008-09-30
• [Presentation] 紅藻オゴノリ属(Gracillaria)由来の新規エイコサノイドの単離と構造 (2008)
  • Author(s): 山下まり
  • Organizer: 第50回天然有機化合物討論会講演
  • Place of Presentation: 福岡国際会議場
  • Year and Date: 2008-09-30
• [Presentation] 紅藻オゴノリ (Gracilaria vermiculophylla) 由来新規エイコサノイドの単離と構造 (2008)
  • Author(s): 中島康賀、谷口和也、山下まり
  • Organizer: 第5回東北大学バイオサイエンスシンポジウム
  • Place of Presentation: 仙台、仙台国際センター
  • Year and Date: 2008-05-19
• [Presentation] 紅藻オゴノリ(Gracilaria vermiculophylla)由来新規エイコサノイドの単離と構造 (2008)
  • Author(s): 中島康賀
  • Organizer: 第5回東北大学バイオサイエンスシンポジウム
  • Place of Presentation: 仙台国際センター
  • Year and Date: 2008-05-19
• [Presentation] 紅藻オゴノリ(Gracilaria vermiculophylla)由来の新規エイコサノイドの単離と構造 (2008)
  • Author(s): 中島康賀、谷口和也、山下まり
  • Organizer: 日本農芸化学会2008年度大会
  • Place of Presentation: 名古屋、名城大学
  • Year and Date: 2008-03-29
• [Presentation] 紅藻カタオゴノリGracilaria edulis由来の新規プロスタグランジンの構造と生成経路の推定 (2008)
  • Author(s): 山下まり
  • Organizer: 2009年度日本農芸化学会大会
  • Place of Presentation: 福岡マリンメッセ
  • Year and Date: 2008-03-28
• [Presentation] 紅藻オゴノリ(Graciaria vermiculophylla)由来の新規エイコサノイドの単離と構造 (2008)
  • Author(s): 中島 康賀
  • Organizer: 日本農芸化学会
  • Place of Presentation: 名城大学(名古屋市)
  • Year and Date: 2008-03-28
• [Book] Polycavernosides and Gambierol : Chemistry, Pharmacology, Toxicology, and Detection, in Seafood and Freshwater Toxins : Pharmacology(Editor, Louis M. Botana, Crc Pr I Llc.) (2008)
  • Author(s): M. Carmen Louzao, Eva Cagide, Mari Yotsu-Yamashita and Makoto Sasaki
  • Publisher: Physiology and detection (Food Science and Technology)detection
• [Book] Seafood and Freshwater Toxins : Pharmacology, Physiology and detection (Food Science and Technology) (2008)
  • Author(s): M. Carmen Louzao
  • Total Pages: 960
  • Publisher: Crc Pr I Llc
• [Book] Polycavernosides, In "Phycotoxins : chemistry and biochemistry"(Captor 15) (2007)
  • Author(s): Leo A. Paquette and Mari Yotsu-Yamashita
  • Publisher: Ames, Iowa, USA. Blackwell Publ
• [Book] Polycavernosides, In "Phycotoxins:chemistry and biochemistry" Captor 15 (2007)
  • Author(s): Leo A. Paquette and Mari Yotsu-Yamashita
  • Publisher: Blackwell Publ