Toxic substance in red tides, Heterocapsa circularisquama, appeared in Seto inland sea

濑户内海出现赤潮有毒物质Heterocapsacircularisquama

• 批准号: 11558077
• 负责人: HIRAGA Yoshikazu
• 金额: $ 4.35万
• 依托单位: Hiroshima University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (B)
• 财政年份: 1999
• 资助国家: 日本
• 起止时间: 1999 至 2001
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-11558077/
• 关键词: Red Tide Plankton; Dinoflagellate; Heterocapsa circularisquama; Bivalves; Fatty Acids; Sterols; Galactolipids; Cytolytic Activity; ガラクトース; 遊離脂肪酸; トリアシルグリセライド; ディノステロール; 7-デヒドロコレステロール; 培養; 殺二枚貝活性; 魚毒活性

The compositions of fatty acids and sterols were determined in laboratory cultures of the marine dinoflagellate Heterocapsa circularisquama. In the free fatty acids, C_<22 : 6>,C_<16 : 0> and C_<18 : 4> were major components. Polyunsaturated fatty acids account for a substantial portion of the total free fatty acids (63.6 %) and include C_<18>, C_<20> and C_<22> acids. The fraction containig the free fatty acid exhibited potent cytotoxicity towards primary cultured gill cells of oyster. The major components in the fatty acids consisted of triacylglycerols were C_<18 : 2>, C_<16 : 0> and C_<14 : 0>.Ten kinds of the sterol in H. circularisquama were identified by capillary gas chromatography-mass spectrometry. The major sterol was a 4-methyl sterol, 4α, 23, 24-trimethyl-5α-cholest-22E-en-3β-ol (dinosterol) which is the common sterol in many dinoflagellates. On the other hand, 5, 8α-epidioxy-5α-cholest-6-en-3β-ol was isolated as potent cytotoxic substance.A novel digalactosyl diacylglycerol has been isolated from H. circularisquama together with two known monogalactosyl diacylglycerols, and their structures were elucidated by spectroscopic methods. The isolated monogalactosyl and digalactosyl diacylglycerols showed potent cytolytic activity towards heart cells of oyster.

对实验室培养的海洋甲藻Heterocapsa circuliquama的脂肪酸和甾醇组成进行了测定。在游离脂肪酸中，C_（22：6）、C_（16：0）和C_（18：4）为主要成分。多不饱和脂肪酸占总游离脂肪酸的相当大的部分（63.6%），并且包括C_<18>、C_<20>和C_<22>酸。游离脂肪酸组分对原代培养的牡蛎鳃细胞具有较强的细胞毒性。脂肪酸主要由C_（18：2）、C_（16：0）、C_（14：0）三种脂肪酸组成。采用毛细管气相色谱-质谱联用技术对其中的类胡萝卜素进行了鉴定。主要的甾醇是4-甲基甾醇，4α，23，24-三甲基-5 α-胆甾-22 E-en-3β-醇（dinosterol），这是许多甲藻中常见的甾醇。另一方面，5，8α-环氧-5 α-胆甾-6-烯-3 β-醇是一种强细胞毒性物质。与两个已知的单半乳糖基甘油二酯化合物，并通过光谱方法鉴定了它们的结构。分离的单半乳糖和双半乳糖二酰基甘油对牡蛎心脏细胞具有较强的细胞溶解活性。

项目成果

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Y. Shinohara 等人：“取代环己酮与 α-氯乙酸酯的 Darzens 缩合反应中的立体选择性”杂环化合物 55(1)。

H. Nishitani et al.: "Asymmetric Synthesis of Rhopaloic Acid A Analogues and Their Biological Propaties"Heterocycles. 50(1). 35-38 (1999)

H. Nishitani 等人：“Rhopaloic Acid A 类似物及其生物特性的不对称合成”杂环。

Y. Hiraga et al: "Ion-transport Activity of Phenylpentanoic Acids Occurring in the Roots of Athyrium yokoscense"Biosci. Biotechnol. Biochem.. 63(5). 958-960 (1999)

Y. Hiraga 等人：“Athyrium yokoscense 根部发生的苯基戊酸的离子传输活性”Biosci。

T. Kanchanapoom, R. Kasai, P. Chumsri, Y. Hiraga, and K. Yamasaki: "Canthin-6-one and beta-carboline alkaloids from Eurycoma harmandiana"Phytochemistry. 56. 383-386 (2001)

T. Kanchanapoom、R. Kasai、P. Chumsri、Y. Hiraga 和 K. Yamasaki：“来自 Eurycoma Harmandiana 的 Canthin-6-one 和 β-咔啉生物碱”植物化学。

T.kanchanapoom et al.: "Lignan glucosides from Acanthus ilicifolius"Phytochemistry. 56. 369-372 (2001)

T.kanchanapoom 等人：“来自 Acanthus ilicifolius 的木脂素糖苷”植物化学。