Identification and antioxidant of polyhydroxylated naphthoquinone pigments from sea urchin pigments of Echinometra mathaei

Soleimani, Samira; Yousefzadi, Morteza; Moein, Soheila; Rezadoost, Hassan; Bioki, Narges Amrollahi

doi:10.1007/s00044-016-1586-y

Cited by 24 publications

(14 citation statements)

References 23 publications

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“…Hence, the reducing power could mainly be imputed to the bioactive compounds associated with antioxidant activity (5). Our previous study on the shell and spine pigments of purple sea urchin E. mathaei showed that reducing power of both pigments extractions (shell and spine) increased as the concentrations increased (15). Results from previous studies have shown that dicholoromethan extract of sea cucumber Holoturia leucospilota increases absorbance with increasing dose dependent manner (16).…”

Section: Discussionmentioning

confidence: 95%

Determination of In Vitro Antioxidant Properties, Anti-inflammatory Effects and A-Amylase Inhibition of Purple Sea Urchin Extract of Echinometra mathaei from the Persian Gulf

Soleimani

Moein

Yousefzadi

et al. 2016

Jundishapur J Nat Pharm Prod

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Section: Discussionmentioning

confidence: 95%

Determination of In Vitro Antioxidant Properties, Anti-inflammatory Effects and A-Amylase Inhibition of Purple Sea Urchin Extract of Echinometra mathaei from the Persian Gulf

Soleimani

Moein

Yousefzadi

et al. 2016

Jundishapur J Nat Pharm Prod

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“…For example, earlier ndings by Anderson and co-authors did not describe echinochrome A as being present in E. mathaei, H. crassispina, P. milliaris, T. gratilla, 7 but recent reports have found this compound in all of these species. 6,28,35,61 It was likely more challenging to identify spinochromes earlier because of a lack of modern instrumentation such as LC-MS and high-resolution NMR. It is also well known that the composition of secondary metabolites in marine organisms may differ signicantly due to geographic, ecological, seasonal, gender and other variables.…”

Section: Family Schizasteridaementioning

confidence: 99%

“…28 Currently, HPLC coupled with UV and mass detection is being used as a rapid and accurate method for the identication of spinochrome pigments. 5,6,23,35,51,61…”

Section: Extraction Fractionation and Identification Of Spinochromesmentioning

confidence: 99%

“…A number of investigations have reported that spinochromes are strong antioxidants that can block a number of free radical reactions, inhibit lipid peroxidation, and reduce and chelate metal ions. 5,6,28,50,51,[73][74][75][76] The antioxidant effect in vitro of spinochromes depends on the number and mutual positions of the chemical substituents in the molecule. 75,76 Substitution of hydroxyl groups with methoxyls in the naphthoquinone molecule leads to the loss of antioxidant activity.…”

Section: Bioactivities Of Spinochromesmentioning

confidence: 99%

“…This shell material is rich in bioactive quinonoid pigments, principally spinochromes. [4][5][6] Although this class of compounds has been known for over 100 years, 7,8 there is still some controversy in relation to their structures, stability, biosynthesis and ecological functions. In this review, a critical evaluation of existing data on spinochrome structures, biosynthesis, distribution, isolation and identication techniques, stability, synthesis and biomedical applications is presented.…”

Section: Introductionmentioning

confidence: 99%

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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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Electrochemical Sulphenylation/Cyclization of Quinones: A Rapid, Green, and Efficient Access to Cytotoxic Compounds

Diogo,

Delolo,

Graça

et al. 2023

Eur J Org Chem

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Undivided electrochemical cells enable economical preparation of sulphur‐containing naphthoquinones via electrochemical sulphenylation of quinoidal compounds. The environmentally friendly and efficient protocol eliminates the use of chemical oxidants and facilitates the synthesis of the desired molecules. This approach offers an efficient and versatile method to synthesize quinones that exhibit cytotoxic against cancer cell lines.

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Identification and antioxidant of polyhydroxylated naphthoquinone pigments from sea urchin pigments of Echinometra mathaei

Cited by 24 publications

References 23 publications

Determination of In Vitro Antioxidant Properties, Anti-inflammatory Effects and A-Amylase Inhibition of Purple Sea Urchin Extract of Echinometra mathaei from the Persian Gulf

Determination of In Vitro Antioxidant Properties, Anti-inflammatory Effects and A-Amylase Inhibition of Purple Sea Urchin Extract of Echinometra mathaei from the Persian Gulf

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

Electrochemical Sulphenylation/Cyclization of Quinones: A Rapid, Green, and Efficient Access to Cytotoxic Compounds

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