Mycaperoxide H, a New Cytotoxic Norsesterterpene Peroxide from a Thai Marine Sponge Mycale sp.

Abstract

Mycaperoxide H, a new cyclic norsesterterpene peroxide, was isolated from a Thai marine sponge Mycalesp. The structure of mycaperoxide H was deduced by spectroscopic and chemical analysis. Mycaperoxide H was cytotoxic against HeLa cells with an IC(50) value of 0.8 microgram/mL.

Towards the Total Synthesis of Mycaperoxide B: Probing Biosynthetic Rationale

“…[1,4,17,18] In our case, the chemical shift of the C-2Ј methyl group in compounds 12a-d is between δ H = 1.23 and 1.25 ppm (Figure 1), which suggests that the stereochemistry of the C2Ј-C3Ј fragment is threo and lends support to our proposal of a stereoselective trans addition across the double bond.…”

Peroxy natural products

“…Its relative and absolute stereochemistries were established by standard methodology, including chemical interconversions. 70 Synthetic efforts towards mycaperoxide B, originally isolated from a Mycale sp. from Thailand 71 , have been reported using a biomimetic approach.…”

Relative and Absolute Stereochemistry of Diacarperoxides: Antimalarial Norditerpene Endoperoxides from Marine Sponge Diacarnus megaspinorhabdosa

“…It was fortunate that a closely related compound, diacarperoxide J ( 3 ), was purified in our hands with the gross structure elucidated by comparing the spectroscopic data with 2 . Notably, all of the 1 H and 13 C NMR chemical shifts of 3 were almost identical to 2 , except for the nuclei surround C-9 (Table 1 and Table 2), which suggested a different relative configuration, but we still cannot conclude that 3 was the C-9 epimer of 2 , since the opposite stereogenicity of each center on the marine-derived endoperoxide class has been reported before [6,23,24]. Theoretically, there were four possibilities regarding the absolute configurations, e.g., for the diastereomeric-pair Compounds 2 and 3 .…”