Structural transformation of saikosaponins by intestinal flora and structure - activity relationship between their derivatives in anti - inflammatory action

肠道菌群对柴胡皂苷的结构转化及其抗炎作用衍生物的构效关系

• 批准号: 59570901
• 负责人: OGIHARA Yukio
• 金额: $ 1.02万
• 依托单位: Nagoya City 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: 1984
• 资助国家: 日本
• 起止时间: 1984 至 1986
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-59570901/
• 关键词: saikosaponin a; saikosaponin c; saikosaponin d; intestinal flora; structure-activity relationship; pituitary - adrenocortical axis function; corticosterone; アルカリ反解反応

Saikosaponin a (sa) and c (sc) were treated with rat or artificial gastric juice to produce saikosaponin <b_1> ( <sb_1> ) and h (sh), possessing heteroannular diene at C-11, 13(18), and saikosaponin g (sg) and i (si), possessing homoannular diene at C-9(11), 12. On the other hand, saikosaponin d (sd) gave only saikosaponin <b_2> ( <sb_2> ), possessing heteroannulardiene, by the same treatment. Then,the incubation of sa, <sb_1> , sg, sd and <sb_2> with mouse intestinal flora gave the partial hydrolysis compounds, prosaikogenin F, A, H, G and D (PSF, PSA, PSH, PSG and PSD) and saikogenin F, A, H, G and D (SF, SA, SH, SG and SD). Although, sc, sh and si gave saikogenin E, C and B (SE, SC and SB), by the treatment with intestinal flora, prosaikogenins were not detected due to their complexity. Therefore, the new cleavage reaction of the glycosidic bond of saponin in alkoholic metal solution containing a trace of water. This reaction never cleaved the ether ring of sc and and gave 9 kinds o … More f prosaikogenins, prosaikogenin <E_1> (PS <E_1> :glc-glc-SE), <E_2> (PS <E_2> :rham-glc-SE) and <E_3> (PS <E_3> :glc-SE), prosaikogenin <C_1> (PS <C_1> :glc-glc-SE), <C_2> (PS <C_2> :rham-glc-SE) and <C_3> (PS <C_3> :glc-SE), and prosaikogenin <B_1> (PS <B_1> :glc-glc-SE), <B_2> (PS <B_2> :rham-glc-SE) and <B_3> (PS <B_3> :glc-SE). The 30 kinds of saikosaponin derivatives those were derived from the oral administration of sa, sc and sd in the alimentary tract were absorbed into the blood stream. Then, the effects of these derivatives on the corticosterone (endogenous glucocorticoid) secretion was investigated. Among sa and sd metabolites, sa and sd showed the strong increasing activity. However, sc was inactive and PS <E_1> and PS <E_2> stimulated the corticosterone secretion among sc derivatives. These results show that the stimulation of pituitary-adrenocortical axis function by saikosaponin metabolites could be due to the differencese of the molar polarity which depends uppon the existence of ether ring and the diffent glycosidic chain. Less

用大鼠胃液或人工胃液处理柴草皂苷a （sa）和c (sc)，产生c -11、13位具有异环二烯的柴草皂苷<b_1> (<sb_1>)和h (sh)，以及c -9位具有同环二烯的柴草皂苷g （sg）和i （si)（11）、12位具有同环二烯）。而同样处理的柴草皂苷d （sd）只得到具有异环二烯的柴草皂苷<b_2> (<sb_2>)。然后，sa、<sb_1>、sg、sd和<sb_2>与小鼠肠道菌群孵育，得到部分水解化合物：素F、A、H、G和D （PSF、PSA、PSH、PSG和PSD）和素F、A、H、G和D （SF、sa、SH、sg和sd）。sc、sh和si虽然给予了赛根素E、C和B (SE、sc和SB)，但通过肠道菌群处理，由于其复杂性，未检测到原赛根素。因此，皂苷糖苷键在含微量水的酒精金属溶液中发生了新的裂解反应。该反应未使sc和的醚环断裂，得到了9种不同类型的prosaikogenin， prosaikogenin <E_1> (PS <E_1>:glc-glc-SE), <E_2> (PS <E_2>:rham-glc-SE)和<E_3> (PS <E_3>:glc-SE), prosaikogenin <C_1> (PS <C_1>:glc-glc-SE), <C_2> (PS <C_2>:rham-glc-SE)和<C_3> (PS <C_3>:glc-SE), prosaikogenin <B_1> (PS <B_1>:glc-glc-SE), <B_2> (PS <B_2>:rham-glc-SE)和<B_3> (PS <B_3>:glc-SE)。经消化道口服sa、sc和sd得到的30种柴草皂苷衍生物均被血液吸收。然后，研究了这些衍生物对内源性糖皮质激素分泌的影响。在sa和sd代谢产物中，sa和sd表现出较强的增加活性。sc无活性，PS <E_1>和PS <E_2>刺激sc衍生物皮质酮分泌。这些结果表明，柴胡皂苷代谢物对垂体-肾上腺皮质轴功能的刺激可能是由于醚环和不同糖苷链的存在导致的摩尔极性的差异。少

项目成果

Kenji Fujiwara;Yukio Ogihara: Life Sciences. 39. 297-301 (1986)

藤原健二；荻原幸男：生命科学。

Yukio Ogihara and Mitsuhiko Nose: "Novel cleavage of the glycosidic bond of saponins in alcoholic metal solution containing a trace of water." J. C. S. Chem. Commun.1417 (1986)

Yukio Ogihara 和 Mitsuhiko Nose：“在含有微量水的酒精金属溶液中皂苷糖苷键的新断裂。”

Kenji Fujiwara and Yukio Ogihara: "Pharmacological effects of oral saikosaponin a may differ depending on conditions of the gastrointestinal tract" Life Sciences. 39. 297-301 (1986)

Kenji Fujiwara 和 Yukio Ogihara：“口服柴胡皂苷 a 的药理作用可能会因胃肠道状况而异”生命科学。