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Identification and characterization of organic and glycosidic acids in crude resin glycoside fraction from Calystegia hederacea.
Journal of Natural Medicines ( IF 2.5 ) Pub Date : 2019-11-05 , DOI: 10.1007/s11418-019-01366-9
Masateru Ono 1 , Yoshino Ichihara 1 , Nao Saito 1 , Minami Yamada 1 , Kana Yuuki 1 , Masami Nawata 1 , Shuhei Tsutsumi 1 , Shin Yasuda 1 , Ryota Tsuchihashi 2 , Masafumi Okawa 2 , Junei Kinjo 2 , Hiroyuki Miyashita 3 , Hitoshi Yoshimitsu 3 , Toshihiro Nohara 3
Affiliation  

Resin glycosides are well known as the purgative ingredients, which are characteristic of convolvulaceous plants. Calystegia hederacea Wall. is a perennial herbaceous vine that is widespread throughout India and East Asia. All parts of this plant are used for the treatment of menoxenia, gonorrhea, etc. Alkaline hydrolysis of the crude resin glycoside fraction of the whole plants of C. hederacea yielded four new glycosidic acids, calyhedic acids A, B, C, and D, along with two known glycosidic acids, calysolic acids A and C, and three known organic acids, 2S-methylbutyric, tiglic, and 2R,3R-nilic acids. Their structures were characterized on the basis of spectroscopic data and chemical evidence. Calyhedic acids A, B, and D were penta-, hexa-, and hepta-glycosides of 12S-hydroxyhexadecanoic acid, respectively, and cayhedic acid C was an isomer of calyhedic acid D, in which the 12S-hydroxyhexadecanoyl residue of calyhedic acid D was replaced by a 11S-hydroxyhexadecanoyl residue. Additionally, cytotoxic activity toward HL-60 human promyelocytic leukemia cells of the crude resin glycoside fraction, the glycosidic acid fraction, calyhedic acid A, and calysolic acid A from C. hederacea was evaluated. Furthermore, to clarify the structure–activity relationship of resin glycosides, the activities of six genuine resin glycosides with calysolic acid A or calysolic acid C as the glycosidic acid, which were isolated from C. soldanella, were examined. Among them, the crude resin glycoside fraction and five genuine resin glycosides with macrolactone structures demonstrated clear cytotoxic activities, while the glycosidic acid fraction, calyhedric acid A, calysolic acid A, and a genuine non-macrolactone-type resin glycoside were either inactive or exhibited weaker activity than the tested macrolactone-type resin glycosides.

中文翻译:

硬皮花萼粗制树脂糖苷馏分中有机酸和糖苷酸的鉴定和表征。

树脂苷是众所周知的泻药成分,是旋花植物的特征。Calystegia hederacea墙。是多年生草本藤蔓,遍布印度和东亚。该植物的所有部分都用于治疗月经不调的,淋病等碱性的整个植物的粗树脂糖苷馏分的水解C. hederacea产生四个新的糖苷酸,calyhedic酸A,B,C,和d,以及两种已知的糖苷酸,凯撒酸A和C,以及三种已知的有机酸2 S-甲基丁酸,tiglic和2 R,3 R-硝酸。根据光谱数据和化学证据对它们的结构进行了表征。乙二酸A,B和D分别是12 S-羟基十六烷酸的五,六和七糖苷,而乙二酸C是乙二酸D的异构体,其中乙二酸的12 S-羟基十六烷酰基残基酸D被11 S-羟基十六烷酰基残基代替。此外,粗枝glyco木中的粗树脂糖苷级分,糖苷酸级分,calyhedic acid A和calysolic acid A对HL-60人早幼粒细胞白血病细胞具有细胞毒活性被评估。此外,为了澄清树脂糖苷的结构-活性关系,与calysolic酸A或calysolic酸C作为糖苷酸,将其分离自6节真正树脂苷活动C. soldanella,进行了研究。其中,粗树脂糖苷级分和五个具有大内酯结构的真正树脂苷具有明显的细胞毒活性,而糖苷酸级分,calyhedric acid A,calysolic acid A和真正的非大内酯型树脂糖苷则无活性或表现出活性比被测试的大内酯型树脂糖苷弱。
更新日期:2019-11-05
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