Synthesis, Cytotoxic and Contraceptive Activity of 6,8,9-Trihydroxy-2-methyl-2H-naphtho[2,3-b]pyran-5,10-dione, a Pigment of Echinothrix diadema, and its Analogs

Natalia D Pokhilo; Galina I Melman; Marina I Kiseleva; Vladimir A Denisenko; Victor Ph Anufriev

Synthesis, Cytotoxic and Contraceptive Activity of 6,8,9-Trihydroxy-2-methyl-2H-naphtho[2,3-b]pyran-5,10-dione, a Pigment of Echinothrix diadema, and its Analogs

Nat Prod Commun. 2015 Jul;10(7):1243-6.

Authors

Natalia D Pokhilo, Galina I Melman, Marina I Kiseleva, Vladimir A Denisenko, Victor Ph Anufriev

PMID: 26411021

Abstract

6,8,9-Trihydroxy-2-methyl-2H-naphtho[2,3-b]pyran-5,10-dion, a pigment of the sea urchin Echinothrix diadema, and six analogs were synthesized. The cytotoxic activity and contraceptive properties of the synthesized pyranonaphthazarins have been investigated using the sperm and eggs of the sea urchin Strongylocentrotus intermedius.

MeSH terms

Animals
Contraceptive Agents / chemical synthesis*
Contraceptive Agents / toxicity
Male
Naphthoquinones / chemistry*
Naphthoquinones / toxicity
Ovum / drug effects
Pigments, Biological / chemistry*
Pigments, Biological / toxicity
Pyrones / analysis
Pyrones / chemical synthesis*
Pyrones / toxicity
Sea Urchins / chemistry*
Spermatozoa / drug effects

Substances

6,8,9-trihydroxy-2-methyl-2H-naphtho(2,3-b)pyran-5,10-dione
Contraceptive Agents
Naphthoquinones
Pigments, Biological
Pyrones