Metachromins U-W: cytotoxic merosesquiterpenoids from an Australian specimen of the sponge Thorecta reticulata.

@article{Ovenden2011MetachrominsUC,
  title={Metachromins U-W: cytotoxic merosesquiterpenoids from an Australian specimen of the sponge Thorecta reticulata.},
  author={Simon P. B. Ovenden and Jonathan L. Nielson and Catherine H. Liptrot and Richard H. Willis and Dianne M. Tapiolas and Anthony David Wright and Cherie A. Motti},
  journal={Journal of natural products},
  year={2011},
  volume={74 5},
  pages={
          1335-8
        }
}
Three new merosesquiterpenoids, metachromins U, V, and W (1-3), were isolated from a specimen of the marine sponge Thorecta reticulata collected off Hunter Island, Tasmania, Australia. Structures of the new compounds were elucidated through extensive NMR investigations and comparison with literature values. The cytotoxicities of 1-3 were assessed against a panel of human tumor cell lines (SF-268, H460, MCF-7, and HT-29) and a mammalian cell line (CHO-K1). All compounds were found to have 50… 
Tuaimenal A, a Meroterpene from the Irish Deep-Sea Soft Coral Duva florida, Displays Inhibition of the SARS-CoV-2 3CLpro Enzyme
TLDR
Cold water benthic environments are a prolific source of structurally diverse molecules with a range of bioactivities against human disease, and functional biochemical assays and in silico docking experiments found tuaimenal A selectively inhibits the viral main protease (3CLpro) of SARS-CoV-2.
Meroterpenes from Marine Invertebrates: Structures, Occurrence, and Ecological Implications
TLDR
The structures and bioactivities of meroterpenes from marine invertebrates, mainly sponges and tunicates, are summarized and the issue of a potential microbial link to their biosynthesis is outlined.
Meroterpenes from Marine Invertebrates: Chemistry and Application in Cancer
TLDR
The group of meroterpenes, molecules derived from mixed biosynthesis that include both a terpene and quinone/hydroquinone moiety, are particularly interesting because of their anticancer activity.
Anticancer agents from marine sponges
TLDR
This review highlights novel secondary metabolites in sponges which inhibited diverse cancer species in the recent 5 years.
First report of antioxidative 2H-chromenyl derivatives from the intertidal red seaweed Gracilaria salicornia as potential anti-inflammatory agents
Abstract Phytochemical investigation on biologically active compounds of an intertidal red seaweed Gracilaria salicornia (family Gracilariaceae) guided to the separation of two previously undisclosed
Cytotoxic and antioxidant marine prenylated quinones and hydroquinones.
TLDR
This review covers the literature of prenylated quinone, hydroquinone and naphthoquinone marine natural products with reported cytotoxic and/or antioxidant properties and recent biosynthetic studies of selected compounds are discussed.
Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin †
TLDR
The chemical diversity and bioactivity of those isolated from marine organisms in the last 10 years are summarized and aspects related to synthetic approaches towards the preparation of improved bioactive analogues from inactive terpenoids are outlined.
A General Synthetic Approach to Hydroquinone Meroterpenoids: Stereoselective Synthesis of (+)-(S)-Metachromin V and Alliodorol
TLDR
The marine meroterpenoid, (+)-(S)-metachromin V, was synthesized for the first time; its chemical structure was confirmed and its absolute configuration was unambiguously assigned.
Collective Synthesis of Natural Products Sharing the Dihydro-γ-Ionone Core
We decided to follow the so-called “collective total synthesis” approach to synthesize several structurally different molecules from a common intermediate possessing appropriate stereochemistry and
...
...

References

SHOWING 1-10 OF 21 REFERENCES
Metachromin C, a new cytotoxic sesquiterpenoid from the Okinawan marine sponge Hippospongia metachromia.
A new sesquiterpenoid quinone, metachromin C[1], with potent cytotoxic activity has been isolated together with a known terpenoid metachromin A[2] from the Okinawan marine sponge Hippospongia
The aignopsanes, a new class of sesquiterpenes from selected chemotypes of the sponge Cacospongia mycofijiensis.
TLDR
A survey of individual specimens of northern Papua New Guinea derived Cacospongia mycofijiensis has yielded novel sesquiterpenes, aignopsanoic acid A, methyl aignopanoate A, and isoaignopsanoa A, which were moderately active against Trypanosoma brucei, the parasite responsible for sleeping sickness.
Metachromins J and K, New Sesquiterpenoids from Marine Sponge Spongia Species
Two new cytotoxic sesquiterpenoids, metachromins J (1) and K (2), have been isolated from an Okinawan marine sponge Spongia sp. (SS-1037). The structures of 1 and 2 were elucidated on the basis of
Metachromins R--T, new sesquiterpenoids from marine sponge Spongia sp.
TLDR
Three new sesquiterpenoids, metachromins R--T (1--3), have been isolated from an Okinawan marine sponge and showed modest cytotoxicity.
Sesquiterpene benzoxazoles and sesquiterpene quinones from the marine sponge Dactylospongia elegans.
TLDR
All compounds isolated from the methanol extract of the marine sponge Dactylospongia elegans were found to have activities in the range 1.8-46 μM and lacked selectivity for tumor versus normal cell lines.
Conicaquinones A and B, Two Novel Cytotoxic Terpene Quinones from the Mediterranean Ascidian Aplidium conicum
Two new unique cytotoxic metabolites, conicaquinones A (1) and B (2), each possessing a 1,1-dioxo-1,4-thiazine ring, were isolated from the Mediterranean ascidian Aplidium conicum. Their structures
Dictazolines A and B, bisspiroimidazolidinones from the marine sponge Smenospongia cerebriformis.
TLDR
Two new bisspiroimidazolidinone derivatives, dictazolines A and B, are isolated from the marine sponge Smenospongia cerebriformis, along with the known soft coral metabolites tubastrindoles A, B, and 4.
...
...