Spongiapyridine and Related Spongians Isolated from an Indonesian Spongia sp.

  title={Spongiapyridine and Related Spongians Isolated from an Indonesian Spongia sp.},
  author={Stephen M. Parrish and Wesley. Yoshida and Tamara P. Kondratyuk and Eun-Jung Park and John M. Pezzuto and Michelle Kelly and Philip G Williams},
  journal={Journal of Natural Products},
  pages={1644 - 1649}
New compounds 18-nor-3,17-dihydroxyspongia-3,13(16),14-trien-2-one (1), 18-nor-3,5,17-trihydroxyspongia-3,13(16),14-trien-2-one (2), and spongiapyridine (3) and the known compound 17-hydroxy-4-epi-spongialactone A (4) were isolated from an Indonesian sponge of the genus Spongia. The structures of 1–3 were deduced by analyses of physical and spectroscopic data. Diterpene 3 is unusual, as the D-ring is a pyridyl ring system rather than the standard δ-lactone. The structure elucidation of this… 

Figures and Tables from this paper

An Anti-Inflammatory 2,4-Cyclized-3,4-Secospongian Diterpenoid and Furanoterpene-Related Metabolites of a Marine Sponge Spongia sp. from the Red Sea

Anti-inflammatory activity of these metabolites to inhibit superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophil cells and cytotoxicity of these compounds toward three cancer cell lines and one human dermal fibroblast cell line were assayed.

Sesquiterpene Quinones/Hydroquinones from the Marine Sponge Spongia pertusa Esper.

Nine new sesquiterpene quinones/hydroquinones (1-7, 10, and 12), three solvent-generated artifacts (8, 9, and 11), and three known compounds, 5-epi-smenospongine (13), smenospongine (14), and

Novel 3,4-seco-3,19-dinorspongian and 5,17-epoxy-19-norspongian diterpenes from the marine sponge Spongia sp.

Twelve new norspongian diterpenes, dinorspongians A–F (1–6) and epoxynorspongians A–F (7–12), were isolated from the marine sponge Spongia sp. Compounds 1–6 were the first examples of dinorspongian

(+)- and (−)-Spongiterpene, a pair of new valerenane sesquiterpene enantiomers from the marine sponge Spongia Sp.

These were the first examples of valerenane sesquiterpenes isolated from the marine sponges and the cytotoxic activities of (+)-1 and (−)-1 were also evaluated.

The Role of Spongia sp. in the Discovery of Marine Lead Compounds

The present review covers the literature from 1971 to 2015 and includes studies on the intraspecific diversity of a Mediterranean species, compounds isolated from associated sponge and nudibranch and compounds isolate from S. zimocca and the red seaweed Laurentia microcladia.

The chemical and chemo-ecological studies on Weizhou nudibranch Glossodoris atromarginata.

A detailed chemical investigation of the nudibranch Glossodoris atromarginata yielded a new spongian-type diterpene 1, together with the four known-related compounds 2-5, and evidence for the absolute stereochemistry of the known compound 2 was provided by the application of time-dependent density functional theory electronic circular dichroism calculation.

Construction of the isocopalane skeleton: application of a desulfinylative 1,7-hydrogen atom transfer strategy.

Two attractive chirons, aldehyde 6 and chloride 7, exhibiting functionalized ent-spongiane-type tricyclic skeletons (ABC ring system), have been constructed and their absolute configurations have

Marine Natural Products from Indonesian Waters

This review covers the literature on marine natural products discovered in Indonesian waters published from January 1970 to December 2017, and includes 732 original MNPs, 4 structures isolated for the first time but known to be synthetic entities, 34 structural revisions, 9 artifacts, and 4 proposed MNPs.

Chemical Diversity and Biological Activity of Secondary Metabolites Isolated from Indonesian Marine Invertebrates

This paper summarizes the structural diversity and biological function of the bioactive compounds isolated from Indonesian marine invertebrates as antimicrobial, antifungal, anticancer, and antiviral, while also presenting the opportunity for further investigation of novel compounds derived from Indonesian marines.



Absolute structures and conformations of the spongian diterpenes spongia-13(16),14-dien-3-one, epispongiadiol and spongiadiol.

The absolute configurations of spongia-13(16),14-dien-3-one and epispongiadiol were assigned by analysis of anomalous dispersion data collected at 130 K with Cu Kalpha radiation.

Spongian diterpenes with thyrotropin releasing hormone receptor 2 binding affinity from Spongia sp.

High-throughput screening of a plant and marine invertebrate extract library to find natural products with rat thyrotropin releasing hormorne (TRH) receptor 2 binding affinity led to the isolation of

A New Series of Diterpenes from Australian Spongia Species

Great Barrier Reef sponges of the genus Spongia have yielded eight closely related tetracyclic furanoditerpenes. The structures, assigned on the basis of spectral methods, have been confirmed by a

Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities.

The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.

The amyloid hypothesis for Alzheimer’s disease: a critical reappraisal

  • J. Hardy
  • Biology
    Journal of neurochemistry
  • 2009
It is suggested that a major scientific need is to understand the normal function of amyloid‐β precursor protein (APP) and think how this may relate to the cell death in the disease process.

Alzheimer's disease: the amyloid cascade hypothesis: an update and reappraisal.

  • J. Hardy
  • Biology
    Journal of Alzheimer's disease : JAD
  • 2006
Here I recap the scientific and personal background of the delineation of the amyloid cascade hypothesis for Alzheimer's disease that I wrote with Gerry Higgins and the events leading to the writing