Analysis of apocarotenoid volatiles during the development of Ficus carica fruits and characterization of carotenoid cleavage dioxygenase genes

Nawade, Bhagwat; Shaltiel‐Harpaz, Liora; Yahyaa, Mosaab; Bosamia, Tejas C.; Kabaha, Anas; Kedoshim, Rika; Zohar, Matat; Isaacson, Tal; Ibdah, Mwafaq

doi:10.1016/j.plantsci.2019.110292

Cited by 29 publications

(16 citation statements)

References 86 publications

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“…Cell decoloration after the expression of CCD enzymes in E. coli cells that produce pigmented carotenoids indicates that they are metabolized to new cleaved colorless compounds (Schwartz et al, 2001;Huang et al, 2009;Nawade et al, 2020). In BoCCD1-1, BoCCD1-3, and BoCCD4-3, we observed a decolored pellet after its expression in lycopene-producing E. coli cells.…”

Section: Bixin Aldehyde Biosynthesis Is Performed By Different Member...mentioning

confidence: 77%

“…Pellet decoloration intensity is an indication that lycopene is being cleaved by the activity of the expressed CCD proteins, generating new colorless compounds (Carballo-Uicab et al, 2019;Gómez-Gómez et al, 2020;Nawade et al, 2020). Mass spectrometry analysis by direct injection of lycopene-producing E. coli cell extracts expressing the BoCCD1 and BoCCD4 proteins revealed a decrease in the lycopene peak (m/z 536.3) compared to the control, even in BoCCD4-4, which has a red orange color (Supplementary Figure 7).…”

Section: Boccd1 and Boccd4 Enzymes Are Involved In Bixin Aldehyde Bio...mentioning

confidence: 99%

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Identifying Bixa orellana L. New Carotenoid Cleavage Dioxygenases 1 and 4 Potentially Involved in Bixin Biosynthesis

et al. 2022

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Carotene cleavage dioxygenases (CCDs) are a large family of Fe2+ dependent enzymes responsible for the production of a wide variety of apocarotenoids, such as bixin. Among the natural apocarotenoids, bixin is second in economic importance. It has a red-orange color and is produced mainly in the seeds of B. orellana. The biosynthesis of bixin aldehyde from the oxidative cleavage of lycopene at 5,6/5′,6′ bonds by a CCD is considered the first step of bixin biosynthesis. Eight BoCCD (BoCCD1-1, BoCCD1-3, BoCCD1-4, CCD4-1, BoCCD4-2, BoCCD4-3 and BoCCD4-4) genes potentially involved in the first step of B. orellana bixin biosynthesis have been identified. However, the cleavage activity upon lycopene to produce bixin aldehyde has only been demonstrated for BoCCD1-1 and BoCCD4-3. Using in vivo (Escherichia coli) and in vitro approaches, we determined that the other identified BoCCDs enzymes (BoCCD1-3, BoCCD1-4, BoCCD4-1, BoCCD4-2, and BoCCD4-4) also participate in the biosynthesis of bixin aldehyde from lycopene. The LC-ESI-QTOF-MS/MS analysis showed a peak corresponding to bixin aldehyde (m/z 349.1) in pACCRT-EIB E. coli cells that express the BoCCD1 and BoCCD4 proteins, which was confirmed by in vitro enzymatic assay. Interestingly, in the in vivo assay of BoCCD1-4, BoCCD4-1, BoCCD4-2, and BoCCD4-4, bixin aldehyde was oxidized to norbixin (m/z 380.2), the second product of the bixin biosynthesis pathway. In silico analysis also showed that BoCCD1 and BoCCD4 proteins encode functional dioxygenases that can use lycopene as substrate. The production of bixin aldehyde and norbixin was corroborated based on their ion fragmentation pattern, as well as by Fourier transform infrared (FTIR) spectroscopy. This work made it possible to clarify at the same time the first and second steps of the bixin biosynthesis pathway that had not been evaluated for a long time.

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Section: Bixin Aldehyde Biosynthesis Is Performed By Different Member...mentioning

confidence: 77%

Section: Boccd1 and Boccd4 Enzymes Are Involved In Bixin Aldehyde Bio...mentioning

confidence: 99%

Identifying Bixa orellana L. New Carotenoid Cleavage Dioxygenases 1 and 4 Potentially Involved in Bixin Biosynthesis

et al. 2022

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“…On the other hand, the SlCCD1A enzyme may mainly cleave cyclic lutein, zeaxanthin, and α-carotene, producing α-ionone and β-ionone, but with less cleavage than linear lycopene. Escherichia coli showed that the recombinant FcCCD1A enzyme of Ficus carica L. was specific for the C9=C10 (C9 =C10 ) double bond of cyclic carotenoid, producing α-ionone and β-ionone, while FcCCD1B cleaved the acyclic parts of lycopene and β-carotene to produce 6-methyl-5-heptene-2-one [64].…”

Section: Discussionmentioning

confidence: 99%

SlCCD1A Enhances the Aroma Quality of Tomato Fruits by Promoting the Synthesis of Carotenoid-Derived Volatiles

Cheng

et al. 2021

Foods

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The loss of volatiles results in the deterioration of flavor in tomatoes. Volatiles are mainly derived from fatty acid, carotenoid, phenylpropane, and branched chain amino acids. In this study, the tomato accession CI1005 with a strong odor and accession TI4001 with a weak odor were analyzed. The volatile contents were measured in tomato fruits using gas chromatography-mass spectrometry. The scores of tomato taste and odor characteristics were evaluated according to hedonistic taste and olfaction. It was found that the content of fatty acid-derived volatiles accounted for more than half of the total volatiles that had grassy and fatty aromas. Phenylpropane-derived volatiles had irritation and floral aromas. Branched-chain amino acid-derived volatiles had a caramel aroma. Carotenoid-derived volatiles had floral, fruity, fatty, and sweet-like aromas, preferred by consumers. A lack of carotenoid-derived volatiles affected the flavor quality of tomato fruits. The accumulation of carotenoid-derived volatiles is regulated by carotenoid cleavage oxygenases (CCDs). A tissue-specific expression analysis of the SlCCD genes revealed that the expression levels of SlCCD1A and SlCCD1B were higher in tomato fruits than in other tissues. The expression levels of SlCCD1A and SlCCD1B were consistent with the trend of the carotenoid-derived volatile contents. The expression of SlCCD1A was higher than that for SlCCD1B. A bioinformatics analysis revealed that SlCCD1A was more closely linked to carotenoid metabolism than SlCCD1B. The overexpression of SlCCD1A indicated that it could cleave lycopene, α-carotene, and β-carotene to produce 6-methyl-5-hepten-2-one, geranylacetone, α-ionone, and β-ionone, increasing the floral, fruity, fatty, and sweet-like aromas of tomato fruits. The flavor quality of tomato fruits could be improved by overexpressing SlCCD1A.

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“…Orthologs of AtCCD1 have been identified in a number of species, including tomato (Solanum lycopersicum) [40], strawberry (Fragaria vesca) [205], petunia (Petunia hybrida) [41], pepper (Capsicum annum L.) [206], coffee (Coffea canephora/C. arabica) [46,191], carrot (Daucus carota L.) [207], rice (Oryza sativa) [208], melon (Cucumis melo) [209], fig (Ficus carica) [210], grape (Vitis vinifera) [211][212][213], rapeseed (Brassica napus) [214], and roses (Rosa damascena) [215]. CCD1 has been shown to cleave both cyclic and acyclic carotenoids [40,44,208,216] forming apocarotenoid aldehydes and ketones, indicating that CCD1 may have a more complex reaction tunnel than other CCDs that cleave either cyclic carotenoids or apocarotenoids alone.…”

Section: Carotenoid Cleavage Dioxygenase 1 (Ccd1) Enzymes Cleave a Broad Category Of Carotenoids And Apocarotenoids At Multiple Double Bomentioning

confidence: 99%

Carotenoids and Apocarotenoids in Planta: Their Role in Plant Development, Contribution to the Flavour and Aroma of Fruits and Flowers, and Their Nutraceutical Benefits

Simkin

2021

Plants

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Carotenoids and apocarotenoids are diverse classes of compounds found in nature and are important natural pigments, nutraceuticals and flavour/aroma molecules. Improving the quality of crops is important for providing micronutrients to remote communities where dietary variation is often limited. Carotenoids have also been shown to have a significant impact on a number of human diseases, improving the survival rates of some cancers and slowing the progression of neurological illnesses. Furthermore, carotenoid-derived compounds can impact the flavour and aroma of crops and vegetables and are the origin of important developmental, as well as plant resistance compounds required for defence. In this review, we discuss the current research being undertaken to increase carotenoid content in plants and research the benefits to human health and the role of carotenoid derived volatiles on flavour and aroma of fruits and vegetables.

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Analysis of apocarotenoid volatiles during the development of Ficus carica fruits and characterization of carotenoid cleavage dioxygenase genes

Cited by 29 publications

References 86 publications

Identifying Bixa orellana L. New Carotenoid Cleavage Dioxygenases 1 and 4 Potentially Involved in Bixin Biosynthesis

Identifying Bixa orellana L. New Carotenoid Cleavage Dioxygenases 1 and 4 Potentially Involved in Bixin Biosynthesis

SlCCD1A Enhances the Aroma Quality of Tomato Fruits by Promoting the Synthesis of Carotenoid-Derived Volatiles

Carotenoids and Apocarotenoids in Planta: Their Role in Plant Development, Contribution to the Flavour and Aroma of Fruits and Flowers, and Their Nutraceutical Benefits

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