Betalamic acid, a new naturally occurring pigment

Kimler, Linda; Larson, Richard A.; Messenger, L J; Moore, John B.; Mabry, Tom J.

doi:10.1039/c29710001329

Cited by 44 publications

(23 citation statements)

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“…3c), II (tyrosine), III (glycine), vulgaxanthin I (glutamine), II (glutamic acid), dopaxanthin (3,4 -dihydroxyphenylalanine), miraxanthin I (methionine sulfoxide), indicaxanthin (proline), and humulixanthin (5-hydroxynorvaline) (Piattelli et al 1965;Adachi and Nakatsukasa 1983;Strack et al 1987;Böhm et al 1991;Trezzini and Zryd 1991). Free betalamic acid could be detected in P. grandiflora petals, especia1ly together with betaxanthins (Kimler et al 1971;Reznik 1978;Adachi and Nakatsukasa 1983), but its presence obviously depends on the genotype (Adachi and Nakatsukasa 1983;Böhm et al 1991;Rink and Böhm 1991). Betalain formation is preceded by an increase in tyrosine concentration in P. grandiflora flowers (Kishima et al 1991b).…”

Section: Betalains and Other Chemical Characteristicsmentioning

confidence: 92%

Portulaca grandiflora Hook. and P. oleracea L.: Formation of Betalains and Unsaturated Fatty Acids

Böhm

Böhm²

1996

Biotechnology in Agriculture and Forestry

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Section: Betalains and Other Chemical Characteristicsmentioning

confidence: 92%

Portulaca grandiflora Hook. and P. oleracea L.: Formation of Betalains and Unsaturated Fatty Acids

Böhm

Böhm²

1996

Biotechnology in Agriculture and Forestry

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“…The chiral centre from tyrosine is retained at C-6 of 1. Compound 1 was identified as a naturally occurring yellow pigment in Beta vulgaris, Celosia cristata and Portulaca grandiflora (Kimler et al, 1971). Based on chemical analysis, the structure was confirmed as the chromophore of all betalains.…”

Section: Structure Elucidationmentioning

confidence: 99%

Plant betalains: Chemistry and biochemistry

2015

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“…637,638 It forms spontaneously from 4,5- seco DOPA ( 1035 ), which arises from action of regiospecific plant dioxygenases on the abundant metabolite L-DOPA ( 528 ). 639 The enzyme is a member of the extradiol dioxygenase family, cleaving adjacent to one of the catechol-OH groups.…”

Section: Oxidative Ring Rearrangementmentioning

confidence: 99%

Oxidative Cyclization in Natural Product Biosynthesis

et al. 2016

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Oxidative cyclizations are important transformations that occur widely during natural product biosynthesis. The transformations from acyclic precursors to cyclized products can afford morphed scaffolds, structural rigidity and biological activities. Some of the most dramatic structural alterations in natural product biosynthesis occur through oxidative cyclization. In this review, we examine the different strategies used by Nature to create new intra-(inter-)-molecular bonds via redox chemistry. The review will cover both oxidation- and reduction-enabled cyclization mechanisms, with an emphasis on the former. Radical cyclizations catalyzed by P450, nonheme iron, α-KG dependent oxygenases and radical SAM enzymes are discussed to illustrate the use of molecular oxygen and S-adenosylmethionine to forge new bonds at unactivated sites via one-electron manifolds. Nonradical cyclizations catalyzed by flavin-dependent monooxygenases and NAD(P)H-dependent reductases are covered to show the use of two-electron manifolds in initiating cyclization reactions. The oxidative installation of epoxides and halogens into acyclic scaffolds to drive subsequent cyclizations are separately discussed as examples of “disappearing” reactive handles. Lastly, oxidative rearrangement of rings systems, including contractions and expansions will be covered.

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Betalamic acid, a new naturally occurring pigment

Cited by 44 publications

References 0 publications

Portulaca grandiflora Hook. and P. oleracea L.: Formation of Betalains and Unsaturated Fatty Acids

Portulaca grandiflora Hook. and P. oleracea L.: Formation of Betalains and Unsaturated Fatty Acids

Plant betalains: Chemistry and biochemistry

Oxidative Cyclization in Natural Product Biosynthesis

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