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Identification of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside, a postulated intermediate in the biosynthesis of ternatin C5 in the blue petals of Clitoria ternatea (butterfly pea).
Chem Biodivers. 2004 Nov; 1(11):1762-70.CB

Abstract

Ternatins are blue anthocyanins found in the petals of Clitoria ternata (butterfly pea). Among them, ternatin C5 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3',5'-di-O-beta-glucoside; 2) has the structure common to all the ternatins, which is characterized by its glucosylation pattern: a 3,3',5'-triglucosylated anthocyanidin. In the course of studying biosynthetic pathways of ternatins, the key enzymatic activities to produce ternatin C5 were discovered in a crude enzyme preparation from the petals of a blue petal line of C. ternatea. When this preparation was tested for activity against several delphinidin glycosides, delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside (6), a postulated intermediate, was found in the reaction mixture, together with three known anthocyanins, which were spectroscopically structurally identified. As a result of structural identification, the following enzymatic activities were identified: UDP-glucose :delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside 5'-O-glucosyltransferase (5'GT), UDP-glucose :delphinidin 3-O-(6''-O-malonyl)-beta-glucoside 3'-O-glucosyltransferase (3'GT), UDP-glucose :delphinidin 3-O-glucosyltransferase, and malonyl-CoA :delphinidin 3-O-beta-glucoside 6''-malonyltransferase. In a mauve petal line, which did not accumulate ternatins but delphinidin 3-O-(6''-O-malonyl)-beta-glucoside in its petal, there were neither 5'GT nor 3'GT activities. Thus, the early biosynthetic pathway of ternatins may be characterized by the stepwise transfer of two glucose residues to 3'- and 5'-position of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside (1; Scheme) from UDP-glucose.

Authors+Show Affiliations

Division of Cell Engineering, Aomori Green BioCenter, 221-10 Nogi-Yamaguchi, Aomori, Aomori 030-0142, Japan. kohei_kazuma@pref.aomori.jpNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17191814

Citation

Kazuma, Kohei, et al. "Identification of Delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside, a Postulated Intermediate in the Biosynthesis of Ternatin C5 in the Blue Petals of Clitoria Ternatea (butterfly Pea)." Chemistry & Biodiversity, vol. 1, no. 11, 2004, pp. 1762-70.
Kazuma K, Kogawa K, Noda N, et al. Identification of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside, a postulated intermediate in the biosynthesis of ternatin C5 in the blue petals of Clitoria ternatea (butterfly pea). Chem Biodivers. 2004;1(11):1762-70.
Kazuma, K., Kogawa, K., Noda, N., Kato, N., & Suzuki, M. (2004). Identification of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside, a postulated intermediate in the biosynthesis of ternatin C5 in the blue petals of Clitoria ternatea (butterfly pea). Chemistry & Biodiversity, 1(11), 1762-70.
Kazuma K, et al. Identification of Delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside, a Postulated Intermediate in the Biosynthesis of Ternatin C5 in the Blue Petals of Clitoria Ternatea (butterfly Pea). Chem Biodivers. 2004;1(11):1762-70. PubMed PMID: 17191814.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Identification of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside, a postulated intermediate in the biosynthesis of ternatin C5 in the blue petals of Clitoria ternatea (butterfly pea). AU - Kazuma,Kohei, AU - Kogawa,Koichiro, AU - Noda,Naonobu, AU - Kato,Naoki, AU - Suzuki,Masahiko, PY - 2006/12/29/pubmed PY - 2007/2/23/medline PY - 2006/12/29/entrez SP - 1762 EP - 70 JF - Chemistry & biodiversity JO - Chem Biodivers VL - 1 IS - 11 N2 - Ternatins are blue anthocyanins found in the petals of Clitoria ternata (butterfly pea). Among them, ternatin C5 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3',5'-di-O-beta-glucoside; 2) has the structure common to all the ternatins, which is characterized by its glucosylation pattern: a 3,3',5'-triglucosylated anthocyanidin. In the course of studying biosynthetic pathways of ternatins, the key enzymatic activities to produce ternatin C5 were discovered in a crude enzyme preparation from the petals of a blue petal line of C. ternatea. When this preparation was tested for activity against several delphinidin glycosides, delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside (6), a postulated intermediate, was found in the reaction mixture, together with three known anthocyanins, which were spectroscopically structurally identified. As a result of structural identification, the following enzymatic activities were identified: UDP-glucose :delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside 5'-O-glucosyltransferase (5'GT), UDP-glucose :delphinidin 3-O-(6''-O-malonyl)-beta-glucoside 3'-O-glucosyltransferase (3'GT), UDP-glucose :delphinidin 3-O-glucosyltransferase, and malonyl-CoA :delphinidin 3-O-beta-glucoside 6''-malonyltransferase. In a mauve petal line, which did not accumulate ternatins but delphinidin 3-O-(6''-O-malonyl)-beta-glucoside in its petal, there were neither 5'GT nor 3'GT activities. Thus, the early biosynthetic pathway of ternatins may be characterized by the stepwise transfer of two glucose residues to 3'- and 5'-position of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside (1; Scheme) from UDP-glucose. SN - 1612-1880 UR - https://www.unboundmedicine.com/medline/citation/17191814/Identification_of_delphinidin_3_O__6''_O_malonyl__beta_glucoside_3'_O_beta_glucoside_a_postulated_intermediate_in_the_biosynthesis_of_ternatin_C5_in_the_blue_petals_of_Clitoria_ternatea__butterfly_pea__ L2 - https://doi.org/10.1002/cbdv.200490132 DB - PRIME DP - Unbound Medicine ER -