Lutein 19-hydroxy

Chorionic gonadotropin. Follicle stimulating hormone Urea, Uric add. Bilirubin, Cortisol, n-Maimitol. n-Glucose, Sodium pyruvate, 4-hydroxy-3-methoxy mandelic add, 4-Nitro-phenol, 17 Amino adds in HQ, Angiotensin-I, Tripahnitin, Bone meal (8 elements), Bone ash (8 elements), lithium carbonate Luteinizing hormone. Thyroid stimulating hormone... 

Monarch epidermis. Peaks seen at 8.7, 10, and 82min are 3-hydroxy-10 -apo-P-carotenal, lutein, zeaxanthin, and P-carotene, respectively. The peak seen eluting at 22 min is the internal standard, monopropyl lutein ether, (b) The chromatogram obtained from an extract of the leaves of the milkweed plant. Peaks eluting prior to lutein are xanthophylls and epoxy xanthophylls, identified components include lutein, zeaxanthin, P-carotene, and its crT-isomer, eluting at 10, 11, 41, 77, and 79min, respectively. 

Nickel peroxide [1, 731-732, before references). The reagent proved effective for the selective oxidation of lutein (1) to 3-hydroxy-3 -keto-a-carotenc (2).8... 

Metabolism in Animals. The conversion of [ C]-/ -carotene into its 2-hydroxy-and 3-hydroxy-metabolites by two species of moths has been demonstrated. The sea anemone Metridium senile can utilize dietary canthaxanthin but not jS-carotene, echinenone (/3,/3-caroten-4-one), or zeaxanthin to produce asta-xanthin in its ovaries. The chirality (3 5) of the 3-hydroxy-e-ring carotenoids a-doradexanthin (14) and lutein (15) of goldfish suggests that these carotenoids... 

There is much current debate about the relevance of such carotenoid repair processes to hydrocarbon carotenoids such as 8-carotene and lycopene in vivo where the parent carotenoid is unhkely to encounter the polar ascorbic acid. However, the cation radical, with a positive charge, maybe sufficiently polar and long-lived for such interactions to be possible. For the carotenoids found in the macula, where an efficient anti-oxidant process is crucial, the hydroxy carotenoids zeaxanthin, meso zeaxanthin and lutein are likely to be in a membrane orientation such that the corresponding cation radicals are efficiently repaired by the vitamin C (cf. vitamin E, below). 

The antioxidative effect of capsanthin and lutein on the chlorophyll-sensitised photooxidation of 2-ethylfiiran, 2,4,.S-trimethyloxazole, and 2,5-dimetliyl 4-hydroxy-3 2H)-fliranone (DMHF) was studied using a spectropholQmetric method. Both capsanthin and lutein exhibited the anti photoox id alive effect on these flavor compounds. The... 

This paper reports the antioxidative effect of capsanthin on the chlorophyll-photosensitized oxidation of soybean oil and selected flavor compounds including 2-ethylfiiran, 2,4.5-trimethyloxazole. and 2,5-dimethyl-4-hydroxy-3(2H)-fiiranone (DMHF), which are unstable when exposed to light in the presence of sensitizer 3,20). The quenching mechanism and kintics of capsanthin on the photosensitized oxidation of soybean oil are also reported. J3-carotene and lutein were used as controls for comparing the antiphotooxidative activity with capsanthin. 

Figure 3. Antiphotooxidative efTeci of capsanthln and lutein on (A) 2-cthylfuran. (B) 2,4,5-trimethyloxazole, and (C) 2,5-dimethyl-5-hydroxy-3(2H)-furanone (DMHF) in absolute alcohol containing 10 ppm chlorophyll at 20 C.

The sensitivity of CD spectra to steric alterations in the polyene chain is also reflected by the CD of in-chain substituted carotenoids such as loroxanthin (of unknown configuration), which is the 19 -hydroxy derivative of lutein (14) (59). In-chain substituents are known to influence the geometry of the polyene chain 49, 54). 

The chirality of lutein (14) is now firmly established with the 3,3 -hydroxy functions in the P- and s-rings possessing opposite absolute configuration 4, 40). The stereochemistry of the hydroxylation step in zeaxanthin (26) biosynthesis in a Flavobacterium sp. has been determined by using (5/ )-[2- C, 5- Hi] mevalonate as substrate which demonstrated retention of the 5-pro-S hydrogen at C-3(3 ) (50), Scheme 9. Also in the case of lutein (14) it has been shown that the 5-pro-S hydrogen at C-3 is retained (81,171) and P,e-carotene (92) biosynthesized from (4/ )-[2- C, 4- Hi] mevalonate retains the tritium at C-6 (82). Any mechanistic interpretation of the biosynthetic evidence must be consistent with the established chirality. 

In 1992, a group of Nutrient Composition Laboratory, U.S. Department of Agriculture, ARS (Agricultural Research Service), Beltsville, Maryland eonfirmed the total 18 carotenoids such as 8,8-caroten-3,3 -dione (34 ), 3 -hydroxy-8,8-caroten-3-one (35 ), 5,6-dihydroxy-5,6-dihydrolycopene (36 ), 3-hydroxy-P,8-caroten-3 -one (37 ), lutein (6), zeaxanthin (9), 3 -epilutein... 

ACTH, adrenocorticotropin hormone FSH, follicle stimulating hormone LH, luteinizing hormone 170 HP, 17-hydroxy progesterone DHEA, dehy-droepiandrosterone, A4A, androstenedione T, testosterone DHT, dihydrotestosterone E2, estradiol Aldo, aldosterone DOC, deoxycorticosterone B> corticosterone F, cortisol,... 

Figure 4 Reversed-phase HPLC elution profiles of tocopherols (panel A), retinoids (B), and carotenoids (C) present in human plasma (200 pL). Blood was collected 3 h after an oral dose of retinoic acid. The chromatogram was obtained by use of gradient elution (Table 3). Peak identification 2, 4-oxo-retinoic acid 4, retinoyl P-glucuronide 7, retinoic acid 8, retinol 9, retinyl acetate (internal standard) 15, butylated hydroxy toluene 16, y-tocopherol 17, a-tocopherol 18, free bilirubin 19, lutein 20, zeaxanthin 21, 2, 3 -anhydrolutein 22, P-cryptoxanthin 23, lycopene 24, a-carotene 25, P-carotene. (From Ref. 73.)...

Hydroxy ionones and epoxy ionones arise by hssion of various xanthophylls. For example, (S)-3-hydroxy-P-ionone arises from P-cryptoxanthin, (3 R,3 J )-p,p-carotene-3,3 diol (zeaxanthin) and 3R, 3J, 6 J )-P,8-carotene-3,3 diol (lutein). 5,6-Epoxy- -ionone arises, for example, from (3J ,5S,6S,3 J )-5,6-epoxy-5,6-dihydro-P,P-carotene-3,3 -diol (antheraxanthin) and (3S,5R,6S,3 S,5 R,6 S)-5,6,5, 6 -diepoxy-5,6,5 6 -tetrahydro-P,p-caroten-3,3 -diol (vio-laxanthin). (3 R,6 R)-3-Hydroxy-a-ionone may arise from lutein, (3S,6S)-3-hydroxy-a-ionone from (3S,3 S,6S,6 S)-8,8-carotene-3,3 -diol (lactucaxanthin) and (3S,6 R)-3-hydroxy-a-ionone from (3J ,3S, 6 J )-P,s-carotene-3,3 -diol (3 -epilutein). 

Antheraxanthin, capsanthin, capsanthin-5, 6-epoxide, capsorubin, fj-carotene, fJ-carotene-S, 6-epoxide, hydroxy-a-carotene, cryptocapsin, fj-cryptoxanthin, lutein, neoxanthin, violaxanthin, and zeaxanthin (3-Carotene, (3-cryptoxanthin, lutein, neoxanthin, violaxanthin, neocrome, auroxanthin, zeaxanthin, capsanthin, capsorubin, and cucurbitaxanthin A (3-Carotene, (3-cryptoxanthin, zeaxanthin, capsanthin, and capsorubin Lycopene, prolycopene, violaxanthin, neoxanthin, c -mutatoxanthin, and lutein... 

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