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MetaCyc Pathway: anthocyanidin sophoroside metabolism

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Phenylpropanoid Derivatives Biosynthesis Flavonoids Biosynthesis Anthocyanins Biosynthesis
Metabolic Clusters

Some taxa known to possess this pathway include ? : Ipomoea nil , Ipomoea purpurea

Expected Taxonomic Range: Magnoliophyta

Summary:
General Background

Diverse structures of anthocyanins significantly contribute to flower color, an important floricultural trait in ornamental plants. The 3-O-glucosylated anthocyanins represent the first stable molecules which are further decorated through glycosylation, acylation and methylation involved in fine adjustment and color variation and stabilization [Heller94].

Antocyanidins often occur as sophoroside, i.e. a diglucoside that consists of glucose attached to the 2''-O-position of the 3-O-glucose moiety of anthocyanidins. Such sophoroside, frequently acylated and methylated, are widely found in such plant families as Lamiacea [Terahara01], Convolvulaceae [Terahara04] [Lu92c] [Saito93] [Saito95] [Saito05] and Ranunculacea [Saito96] [Saito02]. The anthocyanidin that confers the bright blue color to Ipomoea nil (a member of the Convolvulacea) is a sophoroside that forms a complex with several caffeoyl residues, known as Heavenly Blue antocyanin (HBA). Reddish-brown flowers of dusky mutants of Ipomoea nil contain Wedding Bells anthocyanin (WBA) representing the most favorite flower hue for Japanese floriculturists [Morita05].

Anthocyanidin sophoroside and their derivatives have been demonstrated to exhibit a strong inhibition of maltase when subjected to an α-glucosidase (AGH) inhibitory assay. Acylation of the anthocyanidin sophoroside increased the inhibitory action substantially [Matsui01a]. Acylation as a promoting agent has also been shown for the antimutagenicity effect against Salmonella enterica enterica serovar Typhimurium TA 98 caused by anthocyanidin sophoroside [Yoshimoto99] [Yoshimoto01a]. Although anthocyanidin sophoroside and derivatives are induced by UV-B (290-320 nm) and act as protectants UV-A irradiation (320-400 nm) produces a down regulation of those anthocyanins implying complex interactions between UVA and UVB responses that remain to be addressed [Wilson01].

About This Pathway

The crucial step in the formation of anthocyanidin sophoroside as precursors for HBA and WBA in Ipomoea is catalyzed by the anthocyanidin 3-O-glucoside 2-O''-glucosyltransferase (3GGT). The enzyme adds glucose to anthocyanidin 3-glucosides at the 2''-O-position of the glucose moiety forming the corresponding sophorosides. Although the enzyme accepts all three major anthocyanidin 3-O-glucoside, anthocyanidin 3,5-diglucoside are not suitable substrates for the 3GGT [Morita05].

The reddish-brown hue of the flowers (WBA) in mutants of Ipomoea is based on pelargonidin- based anthocyanins whereas the blue flower color (HBA) in this plant has been synthesized from cyanidin-based anthocyanins. It has been found that all the mutants are deficient in a gene that encodes flavonoid 3'-hydroxylase (compare leucopelargonidin and leucocyanidin biosynthesis), involved in the earlier steps towards the biosynthesis of anthocyanins [Hoshino03].

Credits:
Created 21-Aug-2006 by Foerster H , TAIR


References

Heller94: Heller W, Forkmann G (1994). "Biosynthesis of flavonoids." In: Harborne JB (editor) The flavonoids. Advances in research since 1986. Chapman & Hall, London Glasgow New York Tokyo Melbourne Madras, 499-537.

Hoshino03: Hoshino A, Morita Y, Choi JD, Saito N, Toki K, Tanaka Y, Iida S (2003). "Spontaneous mutations of the flavonoid 3'-hydroxylase gene conferring reddish flowers in the three morning glory species." Plant Cell Physiol 44(10);990-1001. PMID: 14581624

Lu92c: Lu TS, Saito N, Yokoi M, Shigihara A, Honda T (1992). "Acylated pelargonidin glycosides in the red-purple flowers of Pharbitis nil." Phytochemistry 31(1);289-95. PMID: 1367882

Matsui01a: Matsui T, Ueda T, Oki T, Sugita K, Terahara N, Matsumoto K (2001). "alpha-Glucosidase inhibitory action of natural acylated anthocyanins. 2. alpha-Glucosidase inhibition by isolated acylated anthocyanins." J Agric Food Chem 49(4);1952-6. PMID: 11308352

Morita05: Morita Y, Hoshino A, Kikuchi Y, Okuhara H, Ono E, Tanaka Y, Fukui Y, Saito N, Nitasaka E, Noguchi H, Iida S (2005). "Japanese morning glory dusky mutants displaying reddish-brown or purplish-gray flowers are deficient in a novel glycosylation enzyme for anthocyanin biosynthesis, UDP-glucose:anthocyanidin 3-O-glucoside-2''-O-glucosyltransferase, due to 4-bp insertions in the gene." Plant J 42(3);353-63. PMID: 15842621

Saito02: Saito N, Toki K, Moriyama H, Shigihara A, Honda T (2002). "Acylated anthocyanins from the blue-violet flowers of Anemone coronaria." Phytochemistry 60(4);365-73. PMID: 12031427

Saito05: Saito N, Toki K, Morita Y, Hoshino A, Iida S, Shigihara A, Honda T (2005). "Acylated peonidin glycosides from duskish mutant flowers of Ipomoea nil." Phytochemistry 66(15);1852-60. PMID: 16045946

Saito93: Saito N, Lu TS, Yokoi M, Shigihara A, Honda T (1993). "An acylated cyanidin 3-sophoroside-5-glucoside in the violet-blue flowers of Pharbitis nil." Phytochemistry 33(1);245-7. PMID: 7763602

Saito95: Saito N, Tatsuzawa F, Yoda K, Yokoi M, Kasahara K, Iida S, Shigihara A, Honda T (1995). "Acylated cyanidin glycosides in the violet-blue flowers of Ipomoea purpurea." Phytochemistry 40(4);1283-9. PMID: 7492373

Saito96: Saito N, Toki K, Ozden S, Honda T (1996). "Acylated delphinidin glycosides in the blue-violet flowers of Consolida armeniaca." Phytochemistry 41(6);1599-605. PMID: 8722091

Terahara01: Terahara N, Callebaut A, Ohba R, Nagata T, Ohnishi-Kameyama M, Suzuki M (2001). "Acylated anthocyanidin 3-sophoroside-5-glucosides from Ajuga reptans flowers and the corresponding cell cultures." Phytochemistry 58(3);493-500. PMID: 11557083

Terahara04: Terahara N, Konczak I, Ono H, Yoshimoto M, Yamakawa O (2004). "Characterization of Acylated Anthocyanins in Callus Induced From Storage Root of Purple-Fleshed Sweet Potato, Ipomoea batatas L." J Biomed Biotechnol 2004(5);279-286. PMID: 15577190

Wilson01: Wilson KE, Thompson JE, Huner NP, Greenberg BM (2001). "Effects of ultraviolet-A exposure on ultraviolet-B-induced accumulation of specific flavonoids in Brassica napus." Photochem Photobiol 73(6);678-84. PMID: 11421075

Yoshimoto01a: Yoshimoto M, Okuno S, Yamaguchi M, Yamakawa O (2001). "Antimutagenicity of deacylated anthocyanins in purple-fleshed sweetpotato." Biosci Biotechnol Biochem 65(7);1652-5. PMID: 11515552

Yoshimoto99: Yoshimoto M, Okuno S, Yoshinaga M, Yamakawa O, Yamaguchi M, Yamada J (1999). "Antimutagenicity of sweetpotato (Ipomoea batatas) roots." Biosci Biotechnol Biochem 63(3);537-41. PMID: 10227139

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lazarowski03: Lazarowski ER, Shea DA, Boucher RC, Harden TK (2003). "Release of cellular UDP-glucose as a potential extracellular signaling molecule." Mol Pharmacol 63(5);1190-7. PMID: 12695547


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, BIOCYC13B.