Mirabiquinone, a new unsymmetrical binaphthoquinone from the sea urchin Scaphechinus mirabilis

Mishchenko, Natalia P.; Васильева, Е. А.; Fedoreyev, Sergey A.

doi:10.1016/j.tetlet.2014.09.018

Cited by 19 publications

(25 citation statements)

References 8 publications

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“…Previously, this compound was found in the holothurian Polycheria rufescens as its main pigment and was named namakochrome. [22] In addition, the S5 and S6 CHCl 3 extract contained trace amounts of unsymmetrical binaphthoquinone 10 [29] and two compounds 13 and 14 with m/z [M -H] À 279. Compounds with such a molecular mass could be echinochrome A monomethyl ethers.…”

Section: Resultsmentioning

confidence: 99%

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Diversity of Polyhydroxynaphthoquinone Pigments in North Pacific Sea Urchins

Васильева

Mishchenko

Fedoreyev

2017

Chemistry & Biodiversity

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Using high-performance liquid chromatography with diode-array detection and mass spectrometry (HPLC-DAD/MS) we investigated the composition of polyhydroxynaphthoquinone (PHNQ) pigments from sea urchins Strongylocentrotus pallidus, St. polyacanthus, St. droebachiensis, Brisaster latifrons and Echinarachnius parma, collected in the Sea of Okhotsk and the Bering Sea. Identification of PHNQ pigments from sea urchins St. polyacanthus, B. latifrons, and E. parma was performed for the first time. Among the usual PHNQ pigments, mono- and dimethoxy derivatives of spinochrome E, not previously found in other sea urchins, were discovered in St. polyacanthus and St. droebachiensis. In St. droebachiensis, two monomethoxy derivatives of echinochrome A were detected, isolated previously from only tropical sea urchins. It was found that the composition and total content of pigments of St. droebachiensis depends on the collection area of the sea urchins and its depth and varies from 88 to 331 μg/g of dry shells. Sea urchins St. pallidus, B. latifrons and E. parma had average values for PHNQ pigment content, approximately 30 μg/g, and St. polyacanthus had a low PHNQ content, 13 μg/g.

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Section: Resultsmentioning

confidence: 99%

“…Elyakov Pacific Institute of Bioorganic Chemistry (Vladivostok, Russia). Mirabiquinone [29] and echinamines A and B [33] were isolated previously from S. mirabilis. Spinochromes A, B, C, E and spinamine E were isolated from St. pallidus and M. nudus.…”

Section: Methodsmentioning

confidence: 99%

Diversity of Polyhydroxynaphthoquinone Pigments in North Pacific Sea Urchins

Васильева

Mishchenko

Fedoreyev

2017

Chemistry & Biodiversity

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“…26 It was established that these compounds predominantly exist as ethylidene-3,3 0 -bis(2,6,7trihydroxynaphthazarin) (23) and 7,7 0 -anhydroethylidene-6,6 0bis(2,3,7-trihydroxynaphthazarin) (26), respectively. 26 In addition to these two binaphthoquinones from sand dollar Scaphechinus mirabilis, the isomer of 26 was isolated, which was the rst unsymmetrical binaphthoquinone mirabiquinone (7,5 0 -anhydroethylidene-6,6 0 -bis(2,3,7-trihydroxynaphthazarin) (27). 27 Four novel compounds, spinazarin (28) and ethylspinazarin (29) that previously were not considered to be natural pigments, and echinamines A (30) and B (31), the rst representatives of aminated spinochromes, were all isolated from S. mirabilis.…”

Section: The Structure and Nomenclature Of Spinochromesmentioning

confidence: 99%

“…26 In addition to these two binaphthoquinones from sand dollar Scaphechinus mirabilis, the isomer of 26 was isolated, which was the rst unsymmetrical binaphthoquinone mirabiquinone (7,5 0 -anhydroethylidene-6,6 0 -bis(2,3,7-trihydroxynaphthazarin) (27). 27 Four novel compounds, spinazarin (28) and ethylspinazarin (29) that previously were not considered to be natural pigments, and echinamines A (30) and B (31), the rst representatives of aminated spinochromes, were all isolated from S. mirabilis. 15,16 A Chinese group using UPLC identied two new aminated quinonoid pigments, aminopentahydroxynaphthoquinone and acetylaminotrihydroxynaphthoquinone, in the sea urchin Mesocentrotus nudus.…”

Section: The Structure and Nomenclature Of Spinochromesmentioning

confidence: 99%

Naphthoquinones of the spinochrome class: occurrence, isolation, biosynthesis and biomedical applications

et al. 2018

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Quinones are widespread in nature and have been found in plants, fungi and bacteria, as well as in members of the animal kingdom. More than forty closely related naphthoquinones have been found in echinoderms, mainly in sea urchins but occasionally in brittle stars, sea stars and starfish. This review aims to examine controversial issues on the chemistry, biosynthesis, functions, stability and application aspects of the spinochrome class, a prominent group of secondary metabolites found in sea urchins. The emphasis of this review is on the isolation and structure of these compounds, together with evaluation of their relevant biological activities, source organisms, the location of origin and methods used for isolation and identification. In addition, the studies of their biosynthesis and ecological function, stability and chemical synthesis have been highlighted. This review aims to establish a focus for future spinochrome research and its potential for benefiting human health and well-being. Scheme 2 Synthesis of spinochrome E (6) as described by Borisova and Anufriev. 94 Reagents and conditions: (i) (EtO) 3 CH, reflux; (ii) NaNO 2 , EtOH, H 2 O, heating; (iii) Na 2 S 2 O 4 , H 2 O; (iv) AlCl 3 , PhNO 2 , heating, then 5% HCl, heating. Scheme 1 Synthesis of spinochromes as described by Singh et al. 90 Reagents and conditions: (i) AlCl 3 -NaCl, 195 C; (ii) MeONa, MeOH, reflux; (iii) conc. HBr, reflux.This journal is

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“…The sea urchin quinones are derivatives of either juglone (5-hydroxy-1,4-naphthoquinone) ( Figure 3, structure 1) or naphthazarin (5,8-dihydroxy-1,4-naphthoquinone) ( Figure 3, structure 2) with additional hydroxy, ethyl, acetyl, methoxy and amino substituents [150]. The first identification of naphthoquinone pigments was made by MacMunn in 1883 [149].…”

Section: Echinochrome and Spinochrome In Sea Urchinsmentioning

confidence: 99%

Marine shells: Potential opportunities for extraction of functional and health-promoting materials

Hou

Shavandi

Carne

et al. 2016

Critical Reviews in Environmental Science and Technology

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Marine shell waste is a very rich source of several bioactive compounds and materials, such as calcium, chitin, pigments and proteins. Currently, this waste material is greatly underutilized and contributes to significant environmental problems due to off odour and concentration of minerals in landfill. The main objective of this review is to highlight the potential to value-add to and maximize the utilization of this waste stream. Therefore, this review provides up to date Downloaded by [University of California Santa Barbara] at 06:53 25 June 2016 ACCEPTED MANUSCRIPT ACCEPTED MANUSCRIPT 2information on various compounds available in marine shells that are generated as waste co-product from commercial processing operations and their potential uses. Methods are described for extraction of these compounds for use in food and pharmaceutical applications.

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Mirabiquinone, a new unsymmetrical binaphthoquinone from the sea urchin Scaphechinus mirabilis

Cited by 19 publications

References 8 publications

Diversity of Polyhydroxynaphthoquinone Pigments in North Pacific Sea Urchins

Diversity of Polyhydroxynaphthoquinone Pigments in North Pacific Sea Urchins

Naphthoquinones of the spinochrome class: occurrence, isolation, biosynthesis and biomedical applications

Marine shells: Potential opportunities for extraction of functional and health-promoting materials

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