Neopetrosiquinones A and B, sesquiterpene benzoquinones isolated from the deep-water sponge Neopetrosia cf. proxima

Abstract

Two new marine-derived sesquiterpene benzoquinones which we designate as neopetrosiquinone A (1) and B (2), have been isolated from a deep-water sponge of the family Petrosiidae. The structures were elucidated on the basis of their spectroscopic data. Compounds 1 and 2 inhibit the in vitro proliferation of the DLD-1 human colorectal adenocarcinoma cell line with IC50 values of 3.7 and 9.8 μM, respectively, and the PANC-1 human pancreatic carcinoma cell line with IC50 values of 6.1 and 13.8 μM, respectively. Neopetrosiquinone A (1) also inhibited the in vitro proliferation of the AsPC-1 human pancreatic carcinoma cell line with an IC50 value of 6.1 μM. The compounds are structurally related to alisiaquinone A, cyclozonarone and xestoquinone.

Marine natural products

“…Meroterpenoids that had initial total syntheses are panicein A 2 , 774,775 dictyoceratins A 776 and C, [777][778][779] and neopetrosiquinones A and B. 780,781 The structure of siphondictyal B 782 has been revised to 1112, based upon total synthesis. The biomimetic conversion of siphondictyal B to liphagal 783 via a stable o-quinone methide supports a novel biogenetic proposal.…”

Cytotoxic Terpene-Purines and Terpene-Quinones from the Sea

“…Neopetrosiquinones A 76 and B 77 inhibit the in vitro proliferation of the DLD-1 human colorectal adenocarcinoma cell line with IC 50 values of 3.7 and 9.8 μM, respectively, and the PANC-1 human pancreatic carcinoma cell line with IC 50 values of 6.1 and 13.8 μM, respectively. Neopetrosiquinone A also inhibited the in vitro proliferation of the AsPC-1 human pancreatic carcinoma cell line with an IC 50 value of 6.1 μM [32]. Bolinaquinone 78 (Fig.…”

Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin †

“…The same carbon skeleton was also present in neopetrosiquinones A and B ( 269 and 270 ) ( Figure 24 ), isolated from the deep-water sponge Neopetrosia cf. proxima , collected off the north coast of Jamaica [ 114 ]. Their enantiospecific synthesis have been performed by Chayboun et al from the labdane diterpenoid trans -communic acid.…”