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Acylated pelargonidin glycosides from the red-purple flowers of Iberis umbellata L. and the red flowers of Erysimum × cheiri (L.) Crantz (Brassicaceae)
Phytochemistry ( IF 3.2 ) Pub Date : 2019-03-01 , DOI: 10.1016/j.phytochem.2018.12.010
Fumi Tatsuzawa

Five previously undescribed acylated pelargonidin 3-sophoroside-5-glucosides (pigments 2-6) were isolated from the red-purple flowers of Iberis umbellata L. 'Candycane Rose' and 'Candycane Red', in addition to a known one (pigment 1). The structures of five undescribed acylated anthocyanins were determined by chemical and spectroscopic methods to be pelargonidin 3-O-[2-O-(2-O-("acyl-A")-β-glucopyranosyl)-6-O-("acyl-B")-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside], in which the "acyl-A" group was either trans-sinapic (2), trans-ferulic (3), trans-sinapic (4), trans-ferulic (5), or trans-ferulic acid (6), and "acyl-B" was either glucosyl-trans-p-coumaric acid (2), glucosyl-trans-p-coumaric acid (3), trans-feruloyl-glucosyl-trans-p-coumaric acid (4), trans-feruloyl-glucosyl-trans-p-coumaric acid (5), or glucosyl-trans-feruloyl-glucosyl-trans-p-coumaric acid (6). Moreover, three previously undescribed acylated pelargonidin 3-sambubioside-5-glucosides (pigments 7, 8, and 10) and one undescribed acylated pelargonidin 3-(3X-glucosylsambubioside)-5-glucoside (pigment 9) were isolated from the red flowers of Erysimum × cheiri (L.) Crantz 'Aurora' as major anthocyanins. The structures of the three undescribed acylated pelargonidin 3-sambubioside-5-glucosides were determined to be pelargonidin 3-O-[2-O-(2-O-("acyl-C")-β-xylopyranosyl)-6-O-("acyl-D")-β-glucopyranoside]-5-O-(β-glucopyranoside), in which the "acyl-C" group was either non (7), non (8), or trans-p-coumaric acid (10) and "acyl-D" was either trans-p-coumaric (7), trans-ferulic (8), or trans-p-coumaric acid (10). Moreover, a previously undescribed acylated pelargonidin 3-(3X-glucosylsambubioside)-5-glucoside was identified to be pelargonidin 3-O-[2-O-(2-O-(trans-p-coumaroyl)-3-O-(β-glucopyranosyl)-β-xylopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-O-(β-glucopyranoside) (9). In addition, the distribution of anthocyanidins structural elements in 24 Brassicaceous species is compared.

中文翻译:

来自 Iberis umbellata L. 的红紫色花和 Erysimum × cheiri (L.) Crantz (Brassicaceae) 的红色花的酰化天竺葵苷糖苷

从 Iberis umbellata L. 'Candycane Rose' 和 'Candycane Red' 的红紫色花中分离出五种先前未描述的酰化天竺葵素 3-sophoroside-5-glucosides(颜料 2-6),以及一种已知的(颜料 1 )。五种未描述的酰化花青素的结构通过化学和光谱方法确定为天竺葵素 3-O-[2-O-(2-O-("acyl-A")-β-吡喃葡萄糖基)-6-O-("酰基-B")-β-吡喃葡萄糖苷]-5-O-[6-O-(丙二酰)-β-吡喃葡萄糖苷],其中“酰基-A”基团为反式-sinapic (2)、反式-阿魏酸(3)、反式阿魏酸 (4)、反式阿魏酸 (5) 或反式阿魏酸 (6),并且“酰基-B”是葡糖基-反式-对香豆酸 (2)、葡糖基-反式-p-香豆酸 (3), 反式-阿魏酰-葡萄糖基-反式-p-香豆酸 (4), 反式阿魏酰-葡糖基-反式-对香豆酸(5),或葡糖基-反式-阿魏酰-葡糖基-反式-对香豆酸(6)。此外,三种先前未描述的酰化天竺葵素 3-sambubioside-5-glucosides(颜料 7、8 和 10)和一种未描述的酰化天竺葵素 3-(3X-glucosylsambubioside)-5-glucoside(颜料 9)从红花中分离出来。 Erysimum × cheiri (L.) Crantz 'Aurora' 作为主要的花青素。三种未描述的酰化天竺葵素 3-sambubioside-5-glucosides 的结构被确定为天竺葵素 3-O-[2-O-(2-O-("acyl-C")-β-xylopyranosyl)-6-O -(“酰基-D”)-β-吡喃葡萄糖苷]-5-O-(β-吡喃葡萄糖苷),其中“酰基-C”基团为非(7)、非(8)或反式-p-香豆酸 (10) 和“酰基-D”是反式对香豆酸 (7)、反式阿魏酸 (8)、或反式对香豆酸 (10)。此外,先前未描述的酰化天竺葵素 3-(3X-glucosylsambubioside)-5-glucoside 被鉴定为天竺葵素 3-O-[2-O-(2-O-(trans-p-coumaroyl)-3-O-( β-吡喃葡萄糖基)-β-吡喃木糖基)-6-O-(反式-对香豆酰基)-β-吡喃葡萄糖苷]-5-O-(β-吡喃葡萄糖苷) (9)。此外,还比较了24种芸苔属植物中花青素结构元素的分布。
更新日期:2019-03-01
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