Confomational analysis and antiallergic activity of triterpenes

三萜类化合物的构象分析及抗过敏活性

• 批准号: 05671870
• 负责人: TANAKA Shigeo
• 金额: $ 1.28万
• 依托单位: KYOTO UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1993
• 资助国家: 日本
• 起止时间: 1993 至 1994
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-05671870/
• 关键词: Cucurbitaceae; Luffa cylindrica; Plant cell culture; Triterpene; Bryonolic acid; Confomational analysis; Anti-allergic activity; Structure-activity relationship; ウリ科植物; 植物培養細胞; バイオテクノロジー; 物質生産; アレルギー

Cell suspension cultures of Luffa cylindrica accumulate large quantities of bryonolic acid (BA,D : C-friedoolean-8-en-3beta-ol-29-oic acid) , an acidic, pentacyclic tritepene found exclusively in the roots of the intact plant. Pharmacological tests using mice demonstrated that BA or its derivative is active against at least three types of allergies and that its activity could be increased significantly by preparing synthetic derivatives, in particular a potassium salt of its succinate ester (BS) . To study the relationship between conformation and antiallergic activity of triterpenes, synthetic BS derivatives that differ in the conformation of D/E rings (Fold type, Stretch type, and Equilibrium type) were subjected to an antiallergic test (passive cutaneous anaphylaxis) . The results of experiments suggested that not only Fold type conformation but also a functional group containing oxygen at C-29 is needed for the potentiation of antiallergic activity. A succinate ester (K salt) of D : C-friedoolean-7,9 (11) -dien-3beta-ol-29-oic acid was less effective than BS,suggesting that the conformation between B and C rings is also of importance in modulating the biological activity.

丝瓜的细胞悬浮培养物积累了大量的bryonolic acid（BA，D：C-friedocyanoic-8-en-3beta-ol-29-oic acid），这是一种只在完整植物的根中发现的酸性五环三烯。使用小鼠进行的药理学试验表明，BA或其衍生物对至少三种类型的变态反应具有活性，并且其活性可以通过制备合成衍生物，特别是其琥珀酸酯（BS）的钾盐而显著增加。为了研究三萜的构象和抗过敏活性之间的关系，对D/E环构象不同（折叠型、拉伸型和平衡型）的合成BS衍生物进行抗过敏试验（被动皮肤过敏反应）。实验结果表明，Fold型构象和C-29位含氧官能团是增强抗过敏活性的必要条件。D：C-无萜-7，9（11）-二烯-3 β-醇-29-酸的琥珀酸酯（K盐）比BS效果差，表明B和C环之间的构象在调节生物活性中也是重要的。

项目成果

J.Shimakura, H.J.Cho, S.Tanaka, H.Fukui and M.Tabata: "Intracellular distribution of the hydrophobic triterpene, bryonolic acid, in cultured cells of Luffa cylindrica L." Plant Cell Rep.12. 264-267 (1993)

J.Shimakura、H.J.Cho、S.Tanaka、H.Fukui 和 M.Tabata：“疏水性三萜、苔藓酸在丝瓜培养细胞中的细胞内分布。”

J.Shimakura: "Intracellular distribution of the hydrophobic triterpene,bryonolic acid,in cultured cells of Luffa cylindrica L." Plant Cell Rep.12. 264-267 (1993)

J.Shimakura：“丝瓜培养细胞中疏水性三萜、苔藓酸的细胞内分布。”

M.Tabata: "Production of anti-allergic triterpene,bryonolic acid,by plant cell cultures" J.Nat.Prod.56. 165-174 (1993)

M.Tabata：“通过植物细胞培养物生产抗过敏三萜、苔藓酸”J.Nat.Prod.56。

M.Tabata, S.Tanaka, H.J.Cho, C.Uno, J.Shimakura, M.Ito, W.Kamisako and C.Honda: "Production of anti-allergic triterpene, bryonolic acid, by plant cell cultures" J.Nat.Prod.56. 165-174 (1993)

M.Tabata、S.Tanaka、H.J.Cho、C.Uno、J.Shimakura、M.Ito、W.Kamisako 和 C.Honda：“通过植物细胞培养生产抗过敏三萜、苔藓酸” J.Nat

Hi Jae Cho: "Biosynthesis of bryonolic acid in cultured cells of watermelon" Phytochemistry. 33. 1407-1413 (1993)

Hi Jae Cho：“西瓜培养细胞中苔藓酸的生物合成”植物化学。