Untersuchungen über den Paprika‐Farbstoff. V. Natürliche und synthetische Ester des Capsanthins

Ƶechmeister, L.; Cholnoky, L. v.

doi:10.1002/jlac.19314870114

Cited by 17 publications

(3 citation statements)

References 8 publications

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“…Capsanthin and capsorubin were isolated and purified from red paprika in the 1930s. 20,45 The mechanisms underlying κend group formation via the pinacollic rearrangement were proposed in 1970. 8,19 The CaCCS gene was identified and characterized in the 1990s.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Reconstruction of the Native Biosynthetic System of Carotenoids in E. coli─Biosynthesis of a Series of Carotenoids Specific to Paprika Fruit

et al. 2023

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Capsanthin, capsorubin, cucurbitaxanthin A, and capsanthin 3,6-epoxide, a series of carotenoids specific to the red fruit of paprika (Capsicum annuum), were produced in pathway-engineered Escherichia coli cells. These cells functionally expressed multiple genes for eight carotenogenic enzymes, two of which, paprika capsanthin/ capsorubin synthase (CaCCS) and zeaxanthin epoxidase (CaZEP), were designed to be located adjacently. The biosynthesis of these carotenoids, except for capsanthin, was the first successful attempt in E. coli. In a previous study, the levels of capsanthin synthesized were low despite the high expression of the CaCCS gene, which may have been due to the dual activity of CaCCS as a lycopene β-cyclase and CCS. An enhanced interaction between CaCCS and CaZEP that supplies antheraxanthin and violaxanthin, substrates for CaCCS, was considered to be crucial for an efficient reaction. To achieve this, we adapted S•tag and S-protein binding. The S•tag Thrombin Purification Kit (Novagen) is merchandized for in vitro affinity purification, and S•tag-fused proteins in the E. coli lysate are specifically trapped by Sproteins fixed on the agarose carrier. Furthermore, S-proteins have been reported to oligomerize via C-terminal swapping. In the present study, CaCCS and CaZEP were individually fused to the S•tag and designed to interact on oligomerized S-protein scaffolds in E. coli, which led to the biosynthesis of not only capsanthin and capsorubin but also cucurbitaxanthin A and capsanthin 3,6epoxide. The latter reaction by CaCCS was assigned for the first time. This approach reinforces the scaffold's importance for multienzyme pathways when native biosynthetic systems are reconstructed in microorganisms.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Reconstruction of the Native Biosynthetic System of Carotenoids in E. coli─Biosynthesis of a Series of Carotenoids Specific to Paprika Fruit

et al. 2023

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“…Based on their own methods, they reported many novel findings: the isolation and structure elucidation of paprika dyes capsanthin and capsorubin [14][15][16][17][18][19][20][21], lycophyll, and lycoxanthin [22,23]; alkaline degradation of capsanthin to β-citraurin [24] (Figure S1); photometric and colorimetric determination of carotenoids [25]; and the investigation of different flowers and fruits (Solanum dulcamara [26], Tamus communis [27], Lycium halimifolium [28], Calendula officinalis [29]). They established the occurrence of zeaxanthin dipalmitate (physalien) in Physalien berries, and the occurrence of different capsanthin esters in paprika [18]. After the leaving of Zechmeister in the 1940s, the intensity of publication slackened, and the next articles were published only in the 1950s [30].…”

Section: Open-column Chromatographymentioning

confidence: 99%

Isolation and Analysis of Carotenoids in Hungary from Zechmeister until Today

et al. 2022

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László Zechmeister, one of the most important pioneers of carotenoid chemistry, died 50 years ago. He founded a carotenoid research group in Pécs (Hungary), which is the only place in the world where carotenoid research has been conducted continuously over the past 95 years. This review presents the life of Zechmeister and gives a summary about the evolution of the methods of analysis, isolation, and structure elucidation of carotenoids from the 1930s until today, based on the results of the research group founded by Zechmeister.

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“…Zechmeister and Cholnoky (83), by the use of suitable solvents, extracted from the fruit hard red waxes which, when hydrolyzed by 10 per cent potassium hydroxide in methyl alcohol, gave capsanthin, a yellow dye, and various acids. From capsanthin, by the action of the acid chlorides and pyridine, a number of esters were prepared-the diacetate, dipalmitate, dioleate, etc.…”

Section: Physaliene C72h116o4mentioning

confidence: 99%

Recent Isoprene Chemistry.

Bogert¹

1932

Chem. Rev.

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Untersuchungen über den Paprika‐Farbstoff. V. Natürliche und synthetische Ester des Capsanthins

Cited by 17 publications

References 8 publications

Reconstruction of the Native Biosynthetic System of Carotenoids in E. coli─Biosynthesis of a Series of Carotenoids Specific to Paprika Fruit

Reconstruction of the Native Biosynthetic System of Carotenoids in E. coli─Biosynthesis of a Series of Carotenoids Specific to Paprika Fruit

Isolation and Analysis of Carotenoids in Hungary from Zechmeister until Today

Recent Isoprene Chemistry.

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