4-Hydroxyretinal, a new visual pigment chromophore found in the bioluminescent squid, Watasenia scintillans

Matsui, Shinji; Seidou, Masatsugu; Uchiyama, Isamu; Sekiya, Noriko; Hiraki, Kenji; Yoshihara, Kazuo; Kito, Yuji

doi:10.1016/0304-4165(88)90087-6

Cited by 50 publications

(20 citation statements)

References 10 publications

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“…8–12 As a result, visual pigments containing A 1 -retinal are called as rhodopsins, A 2 -retinal as porphyropsins, A 3 -retinal as xanthopsins. 13,14 Firefly squid ( Watasenia scintillians ), which exhibits intense bioluminescence from large photophores, was found to be the only animal utilizing three visual pigments 11,15–17 with three different chromophores for color vision, namely, A 1 -, A 2 - and 4-hydroxyretinal or A 4 -retinal (Scheme I). …”

Section: Introductionmentioning

confidence: 99%

Quantum Mechanical/Molecular Mechanical Structure, Enantioselectivity, and Spectroscopy of Hydroxyretinals and Insights into the Evolution of Color Vision in Small White Butterflies

Sekharan

Yokoyama²,

Morokuma

2011

J. Phys. Chem. B

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Since Vogt’s discovery of A3-retinal or 3-hydroxyretinal in insects in 1983 and Matsui’s discovery of A4-retinal or 4-hydroxyretinal in firefly squid in 1988, hydroxyretinal-protein interactions mediating vision remains largely unexplored. In the present study, A3- and A4-retinals are theoretically incorporated into squid and bovine visual pigments using the hybrid quantum mechanics/molecular mechanics (SORCI+Q//B3LYP/6-31G(d):Amber96) method and insights into the structure, enantioselectivity and spectroscopy are gathered and presented for the first time. Contrary to general perception, our findings rule out the formation of hydrogen bond between the hydroxyl-bearing β-ionone ring part of retinal and opsin. Compared to A1-pigments, A3- and A4-pigments exhibit slightly blue-shifted absorption maxima due to increase in bond-length alternation of the hydroxyretinal. We suggest that, (i) The binding site of firefly squid (Watasenia scintillians) opsin is very similar to that of the Japanese common squid (Todarodes pacificus) opsin, (ii) Molecular mechanism of spectral tuning in the small white butterflies involve sites S116, T185 and breaking of hydrogen bond between sites E180 and T185; and finally, (iii) A3-retinal may have occurred during the conversion of A1- to A2-retinal and insects may have acquired them, in order to absorb light in the blue-green wavelength region and to speed up the G-protein signaling cascade.

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Section: Introductionmentioning

confidence: 99%

Quantum Mechanical/Molecular Mechanical Structure, Enantioselectivity, and Spectroscopy of Hydroxyretinals and Insights into the Evolution of Color Vision in Small White Butterflies

Sekharan

Yokoyama²,

Morokuma

2011

J. Phys. Chem. B

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“…Most of them are bioluminescent, and some of them can even emit red light from the photophore as a searchlight (Denton et al 1970;O'Day and Fernandez 1974). Recently, we demonstrated that a deep-sea bioluminescent squid, Watasenia seintillans, has three kinds of visual pigments (Matsui et al 1988a): A major one with 2max=484 nm based on retinal and two others with 2max of about 500 nm and about 470 nm based on 3-dehydroretinal and 4-hydroxyretinal, respectively (Matsui et al 1988b). Recently, we demonstrated that a deep-sea bioluminescent squid, Watasenia seintillans, has three kinds of visual pigments (Matsui et al 1988a): A major one with 2max=484 nm based on retinal and two others with 2max of about 500 nm and about 470 nm based on 3-dehydroretinal and 4-hydroxyretinal, respectively (Matsui et al 1988b).…”

Section: Introductionmentioning

confidence: 99%

On the three visual pigments in the retina of the firefly squid, Watasenia scintillans

et al. 1990

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The deep-sea bioluminescent squid, Watasenia scintillans, has three visual pigments: The major one (A1 pigment) is based on retinal and has 2max=484 nm, the second one (A2 pigment) is based on 3-dehydroretinal and has 2m~x = 500 rim, and the third one (A4 pigment) is based on 4-hydroxyretinal and has )[m.x = 470 nm. The distribution of these 3 visual pigments in the retina was studied by HPLC analysis of the retinals in retina slices obtained by microdissection. It was found that A1 pigment was not located in the specific region of the ventral retina receiving the down-welling light which contains very long photoreceptor cells, forming two strata. A2 and A4 pigment were found exclusively in the proximal pinkish stratum and in the distal yellowish stratum. The role of these pigments in the retina is hypothesized to involve spectral discrimination. The extraction and analysis of retinoids to determine the origin of 3-dehydroretinal and 4-hydroxyretinal in the mature squid showed only a trace amount of 4-hydroxyretinol in the eggs. Similar analysis of other cephalopods collected near Japan showed the absence of A2 or A4 pigment in their eyes.

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“…The pigment with retinal as chromophore has k max at 484 nm; the pigment with 4-hydroxyretinal, at 470 nm (Matsui et al, 1988). Assuming the opsin is the same in both pigments, this 14-nm blueshift is caused by the difference in chromophore.…”

Section: Why the Hydroxyl Group?mentioning

confidence: 98%

Evolutionary tinkering with visual photoreception

Goldsmith

2012

Vis Neurosci

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Eyes have evolved many times, and arthropods and vertebrates share transcription factors for early development. Moreover, the photochemistry of vision in all eyes employs an opsin and the isomerization of a retinoid from the 11-cis to the all-trans configuration. The opsins, however, have associated with several different G proteins, initiating hyperpolarizing and depolarizing conductance changes at the photoreceptor membrane. Beyond these obvious instances of homology, much of the evolutionary story is one of tinkering, producing a great variety of morphological forms and variation within functional themes. This outcome poses a central issue in the convergence of evolutionary and developmental biology: what are the heritable features in the later stages of development that give natural selection traction in altering phenotypic outcomes? This paper discusses some results of evolutionary tinkering where this question arises and, in some cases, where the reasons for particular outcomes and the role of adaptation may not be understood. Phenotypic features include: the exploitation of microvilli in rhabdomeric photoreceptors for detecting the plane of polarized light; different instances of retinoid in the visual pigment; examples of the many uses of accessory pigments in tuning the spectral sensitivity of photoreceptors; selection of opsins in tuning sensitivity in aquatic environments; employing either reflection or refraction in the optics of compound eyes; the multiple ways of constructing images in compound eyes; and the various ways of regenerating 11-cis retinals to maintain visual sensitivity. Evolution is an irreversible process, but tinkering may recover some lost functions, albeit by new mutational routes. There is both elegance and intellectual coherence to the natural processes that produce such variety and functional complexity. But marginalizing the teaching of evolution in public education is a continuing social and political problem that contributes to the reckless capacity of humans to alter the planet without trying to understand how nature works.

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4-Hydroxyretinal, a new visual pigment chromophore found in the bioluminescent squid, Watasenia scintillans

Cited by 50 publications

References 10 publications

Quantum Mechanical/Molecular Mechanical Structure, Enantioselectivity, and Spectroscopy of Hydroxyretinals and Insights into the Evolution of Color Vision in Small White Butterflies

Quantum Mechanical/Molecular Mechanical Structure, Enantioselectivity, and Spectroscopy of Hydroxyretinals and Insights into the Evolution of Color Vision in Small White Butterflies

On the three visual pigments in the retina of the firefly squid, Watasenia scintillans

Evolutionary tinkering with visual photoreception

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