A new bis-γ-pyrone polypropionate from a marine pulmonate mollusc Onchidium struma

Abstract

A new bis-γ-pyrone polypropionate compound onchidione II (1), together with three known compounds, was isolated from a marine pulmonate mollusc Onchidium struma, collected at Hainan Island of China. The structure of new compound was determined by extensive spectroscopic analyses including IR, 1D and 2D NMR techniques, and chemical methods. Compounds 1-4 were evaluated for their cytotoxicity against human tumor cell lines HepG-2, A549, and MCF-2. The results showed that compounds 1 and 2 were moderate cytotoxic against HepG-2, A549, and MCF-2 cell lines, with IC values from 13.2 to 22.4 μM.

From Persian Gulf to Indonesia: interrelated phylogeographic distance and chemistry within the genus Peronia (Onchidiidae, Gastropoda, Mollusca)

“…Compounds that were found in both species also included a diverse mixture of polypropionate esters as the most common and prominent chemical features. Polypropionates are reported from various Onchidiidae, including Onchidium reevesii 17 , partly described under the former name Onchidium struma (nomen nudum) 40 , various unidentified Onchidium species 18 , 19 , 41 , and also P. verruculata 42 . Polypropionates with different carbon skeleton were also described from genus Siphonaria (Gastropoda: Tectipleura) such as Siphonaria baconi Reeve, 1856 (now accepted as Siphonaria zelandica Quoy and Gaimard, 1833) 43 , and Siphonaria diemenensis Quoy and Gaimard, 1833 44 .…”

A Review on Metabolites from Onchidium Genus: Chemistry and Bioactivity

“…While the other three compounds ( 27 – 29 ) showed the further enhanced inhibitory activity against the PC‐3 cell line in vitro , under the same conditions [19] . Onchidione ( 19 ) and onchidione II ( 32 ) were evaluated moderate cytotoxic against HepG‐2 (hepatocellular carcinoma), A549, and MCF‐2 cell lines using MTT assay, with IC 50 values from 13.2 to 22.4 μ m [24] . In a bioassay, the isolated compounds 4,16‐di‐ epi ‐onchidiol ( 34 ), onchidiol ( 20 ), 4‐ epi ‐onchidiol ( 21 ) and 16‐epi‐onchidiol were tested in 96‐well plates by the method of sulforhodamine B (SRB).…”

“…According to extensive spectroscopic analyses and chemical methods, not only three known compounds (onchidione, onchidiol, 4‐ epi ‐onchidiol), but also a new compound called onchidione II ( 32 ) that possessed bis‐γ‐pyrone rings co‐occurring was analyzed by our research group in 2018; among such four chemical compounds were from the muscular tissue and mucus of Onchidium struma , in the coast of Hainan Island's intertidal zone along (in the South China Sea) [24] . At the same period, besides six previously reported polypropionates closely‐related with onchidione, two new members of the onchidione family respectively named 16‐ epi ‐onchidione ( 33 ) and 4‐ epi ‐onchidione ( 32 ) were also isolated from the Onchidium sp [25] .…”

Recent advances on marine mollusk-derived natural products: chemistry, chemical ecology and therapeutical potential

“…Further, membranolide (196), which was previously isolated from the sponge Dendrilla membranosa, 122 together with a new oxeatamide-related derivative, oxeatamide I (197), were detected from the mantle of the nudibranch Felimida grahami using UPLC-QTOF analysis by Berlinck et al 123 Although only the RC of 197 was determined, 197 represents the rst nitrogenous spongian-related diterpenoid from the mantle of a nudibranch. Sixteen palmadorins (198)(199)(200)(201)(202)(203)(204)(205)(206)(207)(208)(209)(210)(211)(212)(213) were isolated from the Antarctic nudibranch Doris (formerly Austrodoris) kerguelenensis by Baker et al, 124 and 206 represents the rst halogenated diterpene from A. kerguelenensis. These diterpenoids belong to three classes, clerodane (198)(199)(200)(201)(202)(203)(204)(205)(206), labdane (207)(208)(209)(210)(211) and halimane (212 and 213).…”