ChemInform Abstract: Structure of Dinoflagellate Luciferin and Its Enzymatic and Nonenzymatic Air‐Oxidation Products

Nakamura, Hideshi; Kishi, Yoshito; Shimomura, Osamu; Morse, Danielle; Hastings, J. Woodland

doi:10.1002/chin.199002330

Cited by 31 publications

(50 citation statements)

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“…The same selectivity was also found in the red bilin from Chlorella protothecoides (Engel et al, 1991(Engel et al, , 1996, but another mechanism seems to be responsible for breakdown of Chl into the luciferin of the dinoflagellate Pyrocystis lunula, which is oxygenolytically cleaved at the C20/C1 mesoposition (Nakamura et al, 1989).…”

Section: Discussionsupporting

confidence: 52%

Chlorophyll Breakdown in Senescent Chloroplasts (Cleavage of Pheophorbide a in Two Enzymic Steps)

et al. 1997

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Section: Discussionsupporting

confidence: 52%

Chlorophyll Breakdown in Senescent Chloroplasts (Cleavage of Pheophorbide a in Two Enzymic Steps)

et al. 1997

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“…A third group of linear tetrapyrroles that is likely to be derived from Chls has been discovered in some lumines- cent compounds from the marine dinoflagellates Pyvocystis lunula and Euphausia pacifica (Nakamura et al, 1988(Nakamura et al, , 1989. However, in these cases the presumed ring opening occurs at the western mesoposition, i.e.…”

mentioning

confidence: 99%

Chlorophyll Breakdown in Senescent Leaves

Matile¹,

Hörtensteiner²,

Thomas³

et al. 1996

Plant Physiology

289

223

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“…Scheme 1, (A) (Nakamura et al, 1989). Non-enzymatic oxidation of luciferin produced a hydroxy adduct at a dipyrrole methane and this strongly supports the hydroperoxide intermediate (formed at dipyrrole methene) in bilirubin CL.…”

Section: Resultsmentioning

confidence: 69%

Weak chemiluminescence of bilirubin and its stimulation by aldehydes

Watanabe¹,

Usa²,

Kobayashi³

et al. 1992

J. Biolumin. Chemilumin.

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Bilirubin in an alkaline solution exhibits a weak chemiluminescence (CL) under aerobic conditions. This spontaneous CL was markedly enhanced by the addition of various aldehydes. The fluorescent emission spectrum of bilirubin, excited by weak intensity light at 350 nm, coincided with its CL emission spectrum (peak at 670 nm). CL emission from bilirubin was not quenched by active oxygen scavengers. This suggests that triplet oxygen reacts with bilirubin, and forms an oxygenated intermediate (hydroperoxide) as a primary emitter (oxidative scission of tetrapyrrole bonds in bilirubin is not involved in this CL). The Ehrlich reaction (test for monopyrroles) and hydrolsulphite reaction (test for dipyrroles) on the CL reaction mixture and unreacted bilirubin showed no differences. When the CL was initiated by singlet oxygen, rather than superoxide anion, monopyrrole, was detected in the reaction products by gel chromatography. The inhibitory effect of a scavenger of singlet oxygen on CL was eliminated in the presence of formaldehyde. Therefore, triplet carbonyl, formed by singlet oxygen through the dioxetane structure in bilirubin, is not an emitter. The reaction mechanism of bilirubin CL and the formation of a hydroperoxide intermediate is discussed in relation to the chemical structure of luciferin molecules from bioluminescent organisms.

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ChemInform Abstract: Structure of Dinoflagellate Luciferin and Its Enzymatic and Nonenzymatic Air‐Oxidation Products

Cited by 31 publications

References 1 publication

Chlorophyll Breakdown in Senescent Chloroplasts (Cleavage of Pheophorbide a in Two Enzymic Steps)

Chlorophyll Breakdown in Senescent Chloroplasts (Cleavage of Pheophorbide a in Two Enzymic Steps)

Chlorophyll Breakdown in Senescent Leaves

Weak chemiluminescence of bilirubin and its stimulation by aldehydes

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