Crocetin esters, picrocrocin and its related compounds present in Crocus sativus stigmas and Gardenia jasminoides fruits.: Tentative identification of seven new compounds by LC-ESI-MS
Crocetin esters, picrocrocin and its related compounds present in Crocus sativus stigmas and Gardenia jasminoides fruits.: Tentative identification of seven new compounds by LC-ESI-MS
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DOI：
10.1021/jf052297w
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发表时间：
2006-02-08
影响因子：
6.1
通讯作者：
Alonso, GL
中科院分区：
文献类型：
--
作者：
Carmona, M;Zalacain, A;Alonso, GL
藏红花中含有西红花素酯类化合物。柱头和栀子果实是决定其颜色的化合物。在所鉴定的15个藏红花酸酯中，初步鉴定了5个新化合物：藏红花素(β-D-三糖苷)-(β-D-龙胆糖基)酯的反式和顺式异构体，西红花素(β-D-新葡萄糖基)-(β-D-葡萄糖基)酯的反式和顺式异构体，以及顺式西红花素(β-D-新葡萄糖苷)-(β-D-龙胆生物糖基)酯。两种栀子之间最相关的差异是反式crocetin(beta-D-glucosyl)-(beta-D-gentibiosyl)酯含量较低，栀子中不存在反式西红花素二(β-D-葡萄糖基)酯，而其反式西红花素(β-D-龙胆糖基)酯和顺式西红花素二(β-D-龙胆糖基)酯含量较高。用同样的方法可以一次从藏红花提取物中鉴定出10个糖苷类化合物，其UV/Vis图谱与苦参素相似，其中5-hydroxy-7，7-dimethyl-4，5，6，7-tetrahydro-3H-isobenzofuranone 5-O-β-D-龙胆苦苷和4-hydroxymethyl-3，5，5-trimethyl-cyclohexen-2-one 4-O-β-D-龙胆苦苷为首次从藏红花中鉴定。在这10种糖苷中，只有2-甲基-6-氧代-2，4-七-2，4-二烯酸的O-β-D-龙胆糖酯在栀子中被发现，但可以鉴定出环烯醚萜糖苷京尼平苷。
Crocetin esters present in saffron (Crocus sativus L.) stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. Of the fifteen crocetin esters identified in this study, five new compounds were tentatively identified: trans and cis isomers of crocetin (beta-D-triglucoside)-(beta-D-gentibiosyl) ester, trans and cis isomers of crocetin (beta-D-neapolitanose)-(beta-D-glucosyl) ester, and cis crocetin (beta-D-neapolitanose)-(beta-D-gentibiosyl) ester. The most relevant differences between both species were a low content of the trans crocetin(beta-D-glucosyl)-(beta-D-gentibiosyl) ester, the absence of trans crocetin di-(beta-D-glucosyl) ester in gardenia, and its higher content of trans crocetin (beta-D-gentibiosyl) ester and cis crocetin di-(beta-D-gentibiosyl) ester. With the same chromatographic method it was possible to identify, in a single run, ten glycosidic compounds in saffron extracts with a UV/vis pattern similar to that of picrocrocin; among them, 5-hydroxy-7,7-dimethyl-4,5,6,7-tetrahydro-3H-isobenzofuranone 5-O-beta-D-gentibioside and 4-hydroxymethyl-3,5,5-trimethyl-cyclohexen-2-one 4-O-beta-D-gentibioside were tentatively identified for the first time in saffron. Of these ten glycosides, only the O-beta-D-gentibiosyl ester of 2-methyl-6-oxo-2,4-hepta-2,4-dienoic acid was found in gardenia samples, but it was possible to identify the iridoid glycoside, geniposide.