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Transformation of naturally occurring (3R,3'R,6'R)-lutein and its fatty acid esters to (3 R)-β-cryptoxanthin and (3R,6'R)-α-cryptoxanthin.
Arch Biochem Biophys. 2018 09 01; 653:107-112.AB

Abstract

The objective of this study was to develop straightforward processes that could be applied to the large-scale production of β-cryptoxanthin in an attempt to facilitate investigation of its biological activity. An oleoresin obtained from crude extracts of marigold flowers (Tagetes erecta) with approximately 24% total lutein fatty acid ester content was directly used as starting material for partial synthesis of (3 R)-β-cryptoxanthin under mild reaction conditions at ambient temperature. Therefore, acid-catalyzed deoxygenation of lutein esters from marigold oleoresin followed by hydrogenation in the presence of catalytic amount of platinum (Pt) supported on alumina (5%) at ambient temperature gave a mixture of (3 R)-β-cryptoxanthin fatty acid esters (major) and (3 R,6'R)-α-cryptoxanthin fatty acid esters (minor). Saponification and Z-to-E isomerization of the product followed by crystallization gave a mixture of (3 R)-β-cryptoxanthin as the major product. Similarly, acid-catalyzed hydrogenation of unesterified (3 R,3'R,6'R)-lutein with Pt/alumina in ethyl acetate gave a mixture of (3 R,6'R)-α-cryptoxanthin acetate (minor) in a one-pot reaction. Alkaline hydrolysis and Z-to-E isomerization of the mixture followed by crystallization provided (3 R)-β-cryptoxanthin.

Authors+Show Affiliations

Kemin Foods, L.C., 1900 Scott Street, Des Moines, IA, 50317, USA. Electronic address: fred.khachik@kemin.com.

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

29990480

Citation

Khachik, Frederick. "Transformation of Naturally Occurring (3R,3'R,6'R)-lutein and Its Fatty Acid Esters to (3 R)-β-cryptoxanthin and (3R,6'R)-α-cryptoxanthin." Archives of Biochemistry and Biophysics, vol. 653, 2018, pp. 107-112.
Khachik F. Transformation of naturally occurring (3R,3'R,6'R)-lutein and its fatty acid esters to (3 R)-β-cryptoxanthin and (3R,6'R)-α-cryptoxanthin. Arch Biochem Biophys. 2018;653:107-112.
Khachik, F. (2018). Transformation of naturally occurring (3R,3'R,6'R)-lutein and its fatty acid esters to (3 R)-β-cryptoxanthin and (3R,6'R)-α-cryptoxanthin. Archives of Biochemistry and Biophysics, 653, 107-112. https://doi.org/10.1016/j.abb.2018.06.012
Khachik F. Transformation of Naturally Occurring (3R,3'R,6'R)-lutein and Its Fatty Acid Esters to (3 R)-β-cryptoxanthin and (3R,6'R)-α-cryptoxanthin. Arch Biochem Biophys. 2018 09 1;653:107-112. PubMed PMID: 29990480.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Transformation of naturally occurring (3R,3'R,6'R)-lutein and its fatty acid esters to (3 R)-β-cryptoxanthin and (3R,6'R)-α-cryptoxanthin. A1 - Khachik,Frederick, Y1 - 2018/07/07/ PY - 2018/02/28/received PY - 2018/06/08/revised PY - 2018/06/23/accepted PY - 2018/7/11/pubmed PY - 2019/7/6/medline PY - 2018/7/11/entrez KW - Acid-catalyzed catalytic hydrogenation KW - Deoxygenation KW - Lutein fatty acid esters KW - Partial synthesis KW - α- and β-Cryptoxanthin SP - 107 EP - 112 JF - Archives of biochemistry and biophysics JO - Arch. Biochem. Biophys. VL - 653 N2 - The objective of this study was to develop straightforward processes that could be applied to the large-scale production of β-cryptoxanthin in an attempt to facilitate investigation of its biological activity. An oleoresin obtained from crude extracts of marigold flowers (Tagetes erecta) with approximately 24% total lutein fatty acid ester content was directly used as starting material for partial synthesis of (3 R)-β-cryptoxanthin under mild reaction conditions at ambient temperature. Therefore, acid-catalyzed deoxygenation of lutein esters from marigold oleoresin followed by hydrogenation in the presence of catalytic amount of platinum (Pt) supported on alumina (5%) at ambient temperature gave a mixture of (3 R)-β-cryptoxanthin fatty acid esters (major) and (3 R,6'R)-α-cryptoxanthin fatty acid esters (minor). Saponification and Z-to-E isomerization of the product followed by crystallization gave a mixture of (3 R)-β-cryptoxanthin as the major product. Similarly, acid-catalyzed hydrogenation of unesterified (3 R,3'R,6'R)-lutein with Pt/alumina in ethyl acetate gave a mixture of (3 R,6'R)-α-cryptoxanthin acetate (minor) in a one-pot reaction. Alkaline hydrolysis and Z-to-E isomerization of the mixture followed by crystallization provided (3 R)-β-cryptoxanthin. SN - 1096-0384 UR - https://www.unboundmedicine.com/medline/citation/29990480/Transformation_of_naturally_occurring__3R3'R6'R__lutein_and_its_fatty_acid_esters_to__3_R__β_cryptoxanthin_and__3R6'R__α_cryptoxanthin_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0003-9861(18)30166-8 DB - PRIME DP - Unbound Medicine ER -