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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.
J Agric Food Chem 2006; 54(3):973-9JA

Abstract

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.

Authors+Show Affiliations

Cátedra de Química Agrícola, E.T.S.I. Agrónomos, Universidad Castilla-La Mancha, 02071 Albacete, Spain. Manuel.Carmona@uclm.esNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

16448211

Citation

Carmona, Manuel, et al. "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." Journal of Agricultural and Food Chemistry, vol. 54, no. 3, 2006, pp. 973-9.
Carmona M, Zalacain A, Sánchez AM, et al. 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. J Agric Food Chem. 2006;54(3):973-9.
Carmona, M., Zalacain, A., Sánchez, A. M., Novella, J. L., & Alonso, G. L. (2006). 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. Journal of Agricultural and Food Chemistry, 54(3), pp. 973-9.
Carmona M, et al. 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. J Agric Food Chem. 2006 Feb 8;54(3):973-9. PubMed PMID: 16448211.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 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. AU - Carmona,Manuel, AU - Zalacain,Amaya, AU - Sánchez,Ana M, AU - Novella,Jose Luis, AU - Alonso,Gonzalo Luis, PY - 2006/2/2/pubmed PY - 2006/3/29/medline PY - 2006/2/2/entrez SP - 973 EP - 9 JF - Journal of agricultural and food chemistry JO - J. Agric. Food Chem. VL - 54 IS - 3 N2 - 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. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/16448211/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_ L2 - https://dx.doi.org/10.1021/jf052297w DB - PRIME DP - Unbound Medicine ER -