曾广方, 赵志远. 中药黄酮类的研究 Ⅸ.南岭蕘花成分的研究新黄酮甙南蕘素的分离及其化学结构J. 药学学报, 1963, 10(5): 286-292.
引用本文: 曾广方, 赵志远. 中药黄酮类的研究 Ⅸ.南岭蕘花成分的研究新黄酮甙南蕘素的分离及其化学结构J. 药学学报, 1963, 10(5): 286-292.
TSENG KWONG-FONG .AND CHAO TSE-YUAN, . STUDIES ON THE FLAVONOIDS PRESENT IN CHINESE DRUGS Ⅸ. A NEW FLAVONE GLYCOSIDE ISOLATED FROM WIKSTROEMIA VIRIDIFLORAJ. Acta Pharmaceutica Sinica, 1963, 10(5): 286-292.
Citation: TSENG KWONG-FONG .AND CHAO TSE-YUAN, . STUDIES ON THE FLAVONOIDS PRESENT IN CHINESE DRUGS Ⅸ. A NEW FLAVONE GLYCOSIDE ISOLATED FROM WIKSTROEMIA VIRIDIFLORAJ. Acta Pharmaceutica Sinica, 1963, 10(5): 286-292.

中药黄酮类的研究 Ⅸ.南岭蕘花成分的研究新黄酮甙南蕘素的分离及其化学结构

STUDIES ON THE FLAVONOIDS PRESENT IN CHINESE DRUGS Ⅸ. A NEW FLAVONE GLYCOSIDE ISOLATED FROM WIKSTROEMIA VIRIDIFLORA

  • 摘要: 自瑞香科(Thymelaeceae)植物南岭荛花(Wikstroemia viridiflora Meisen,一种民間植物药,俗名海底龙)中分得一种新黄酮甙結晶,命名为南荛素(wikstroemin),分子式C28F32O15,具有双熔点200—202℃,270—272℃。由紫外吸收光譜及紙上层析知属于黄酮类。水解后得甙元,分子式C16H12O5,熔点290—293℃,經乙酰化、甲基化产物的制备以及甙元及衍生物的各种物理化学性貭比較,証明甙元为芫花素(genkwanin)。所連接的糖为葡萄糖,經测定为2分子葡萄糖,并証实接在5位上,糖型为α型。因此南荛素的結构应为(Ib)所示。

     

    Abstract: The Chinese folk medicine called Nan-Lin-Yao-Hua is a botanical drug (Wikstroemia viridiflora Meisen) family Thymelaeceae, which has been used as a remedy for ascites of the late stage Schistosomiasis. From its root bark or cortex radicis, a yellowish needle crystalline substance was isolated, and it is a new flavone glycoside and hence named wikstroemin. The new glycoside showed a diuretic action when intravenously injected at a dosage of 2—4mg/kg on anaesthetized dogs. This may respond a part of its effectiveness. The wikstroemin (C28H32O15) was obtained in light yellow needles and possesses a characteristic double melting point, melting at 200—202℃ into transparent yellow liquid and resolidified at 210℃ and finally decomposed at 270—272℃. The pure substance was obtained in 0.05%. It is insoluble in ordinary organic solvents, but sparingly soluble in hot water or warmed ethanol and methanol. It exhibits no color reaction with FeCl3, but developes a deep red coloration with Mg-HCl. It gave a positive color test with Molisch's reagent and produced a golden yellow coloration in alkali solution. Its paper chromatography showed Rf=0.46 (BuOH:HOAc:H2O=4:1:5). U. V. spectra in absolute ethanol shows peaks λmax 262 and 333mμ (log ε=4.45 and 4.50). On acid hydrolysis, the wikstroemin gave an aglycone (C16H12O5 m. p. 290—293°) and two moles of glucose. Although the wikseroemin gave a negative color reaction with FeCl3, but its aglycone developed a violet brown coloration. This proves that the 5-position hydroxy group has been opened on hydrolysis. From the above properties, wikstroemin has been identified as a flavone glycoside and its aglycone as genkwanin by the comparison of U. V. spectra and mixed melting point with authentic sample. The digluconide has been proved to be linked on the 5-position in A ring as a known compound genkwanin-4'-methylether (C17H14O5, m. p. 169—171℃) which was successively isolated on mild methylation and then hydrolysis. From this fact, there is ample reason to explain that the aglycone is not linked separately both in 5 and 4'-positions. Wikstroemin will not be hydrolysed by the emulsin which was freshly prepared from bitter almond. The structure formula, therefore, has been confirmed to be (Ib), as genkwanin-5-α-D-glucosido-α-D-glucose.

     

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