Epimeric 3,3′-dihydroxy-Îµ,Îµ-carotenes from the skin of the yellow Costa Rican frog, Atelopus chiriquiensis

Bingham, Alpheus; Mosher, Harry S.; Andrewes, A. G.

doi:10.1039/c39770000096

Cited by 28 publications

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“…(1) und 3', 0-Didehydrolutein (((Ketolutein)); 2) ist aus folgenden Grunden aktuell geworden: a) 3'-Epilutein, das erst vor kurzem rein dargestellt und voll charakterisiert worden ist [ l ] , lasst sich mit den alteren (und auch heute noch oft verwendeten) chromatographischen und spektroskopischen Nachweisverfahren kaum vom Lutein unterscheiden; b) die Chiralitat von C(3) in ccnormalem)) Lutein (= Xanthophyll) aus Chloroplasten ist derjenigen von Zeaxanthin entgegengesetzt (Chiralitat von Zeaxanthin s. [2], von Lutein s. [3]); c) das sog. Lutein in Gold- [6] und Tunaxanthin [7] beobachtet worden.…”

Section: Discussionunclassified

Eine Suche nach 3′‐Epilutein ( = (3R,3′S,6′R)‐β,ε‐Carotin‐3,3′‐diol) und 3′, O‐Didehydrolutein (=(3R, 6′R)‐3‐Hydroxy‐β,ε‐carotin‐3′‐on) in Eigelb, in Blüten von Caltha palustris und in Herbstblättern

Buchecker

Eugster

1979

Helvetica Chimica Acta

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Search for the Presence in Egg Yolk, in Flowers of Caltha palustris and in Autumn Leaves of 3′‐Epilutein ( =(3R,3′S,6′R)‐β,ε‐Carotene‐3,3′‐diol) and 3′,O‐Didehydrolutein ( =(3R,6′R)‐3‐Hydroxy‐β,ε‐carotene‐3′‐one) 3′.O‐Didehydrolutein ( =(3R, 6′R)‐3‐hydroxy‐β,ε‐carotene‐3′‐one; 2) has been detected in egg yolk and in flowers of Caltha palustris. This is the first record for its occurrence in a plant. The compound shows a remarkable lability towards base; therefore, it may have been overlooked til now, because it is destroyed under the usual conditions of saponification of the carotenoid‐esters. One of the many products formed from 2 with 1% KOH in methanol has been purified and identified as the diketone 3 ( =(3R)‐3‐hydroxy‐4′, 12′‐retro‐β,β‐carotene‐3′,12′‐dione). The identification of this transformation product from lutein might throw a new light on the metabolism of this important carotenoid in green plants. 3′‐Epilutein ( =(3R,3′S,6′R)‐β,ε‐carotene‐3,3′‐diol; 1) was not detected in egg yolk, but is present besides lutein in flowers of C. palustris, thus confirming an earlier report of the occurrence of an isomeric (possibly epimeric) lutein (‘calthaxanthin’) in that plant [21]. We were not able to detect even traces of 1 or 2 in the carotenoid fraction from autumn leaves of Prunus avium (cherry), Parrotia persica, Acer montanum (maple) and yellow needles of Larix europaea (larch). α‐Cryptoxanthin (4), a very rare carotenoid, was isolated in considerable quantity for the first time from flowers of C. palustris.

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Section: Discussionunclassified

Eine Suche nach 3′‐Epilutein ( = (3R,3′S,6′R)‐β,ε‐Carotin‐3,3′‐diol) und 3′, O‐Didehydrolutein (=(3R, 6′R)‐3‐Hydroxy‐β,ε‐carotin‐3′‐on) in Eigelb, in Blüten von Caltha palustris und in Herbstblättern

Buchecker

Eugster

1979

Helvetica Chimica Acta

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Absolute Konfiguration von α‐Doradexanthin und von Fritschiellaxanthin, einem neuen Carotinoid aus Fritschiella tuberosa IYENG

Buchecker

Eugster

Weber

1978

Helvetica Chimica Acta

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Absolute Configuration of a-Doradexanthin and of Fritschiellaxanthin, a New Carotenoid fromFritschiella tuberosa IYENC. SummaryFritschiellaxanthin, a new oxocarotenoid produced by the green alga Fritschiella tuberosa in a nitrogen-deficient medium is now shown to be (3 S , 3'R, 6'R)-3,3'-dihydroxy-P, c-caroten-4-one (4b). It is not identical with a-doradexanthin (5b) previously found in goldfish (Carassius auratus) and to which we assign the (3 S, 3'S, 6'R)-chirality. Consequently, fritschiellaxanthin and a-doradexanthin are C (3')-epimers of lutein-4-011. Furthermore, the so-called 'lutein' from goldfish has now been found to be identical with 3'-epilutein (3). Therefore, fritschiellaxanthin is probably biogenetically derived from lutein (2), whereas u-doradexanthin is formed from 3'-epilutein (3) with 3', 0-didehydrolutein (= ( 3 R , 6'R)-3-hydroxyji', c-caroten-3'-one 10) as a precursor. For comparison, optically active 10 and 3 have been prepared from lutein (2) and are fully characterised.

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T

Buckingham¹

1990

Dictionary of Organic Compounds

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Epimeric 3,3′-dihydroxy-Îµ,Îµ-carotenes from the skin of the yellow Costa Rican frog, Atelopus chiriquiensis

Cited by 28 publications

References 0 publications

Eine Suche nach 3′‐Epilutein ( = (3R,3′S,6′R)‐β,ε‐Carotin‐3,3′‐diol) und 3′, O‐Didehydrolutein (=(3R, 6′R)‐3‐Hydroxy‐β,ε‐carotin‐3′‐on) in Eigelb, in Blüten von Caltha palustris und in Herbstblättern

Eine Suche nach 3′‐Epilutein ( = (3R,3′S,6′R)‐β,ε‐Carotin‐3,3′‐diol) und 3′, O‐Didehydrolutein (=(3R, 6′R)‐3‐Hydroxy‐β,ε‐carotin‐3′‐on) in Eigelb, in Blüten von Caltha palustris und in Herbstblättern

Absolute Konfiguration von α‐Doradexanthin und von Fritschiellaxanthin, einem neuen Carotinoid aus Fritschiella tuberosa IYENG

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