Three New Spongian Diterpenes from the Marine Sponge Dendrilla rosea

Hayton, Joshua B.; Grant, Gary; Carroll, Anthony R.

doi:10.1071/ch19299

Cited by 7 publications

(5 citation statements)

References 16 publications

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“…Dendrilla terpenoids have been previously tested for different biological activities, and some of these compounds showed potent activity against the parasite Leishmania donovani , [9–16] Certain terpenoids also inhibited the formation of methicillin‐resistant Staphylococcus aureus (MRSA) biofilms [5] . At the same time, the cytotoxicity of these compounds was very low.…”

Section: Discussionmentioning

confidence: 99%

“…Although marine sponges of the genus Dendrilla have a widespread geographical distribution, from polar to tropical seas, [1] they are particularly abundant in Antarctic waters, and are probably amongst the most chemically studied Antarctic benthic invertebrates. The chemistry associated with sponges of this genus is very diverse, and includes lamellarins, bastadins and other alkaloids, [2–7] as well as spongiane‐related diterpenoids and seco diterpenoids, [8–16] among other classes of compounds. However, the presence of seco and nor‐spongiane derived diterpenes seems to be restricted mainly to Antarctic species, typically to Dendrilla antarctica (although there are several publications on D. membranosa , which has recently been revised to D. antarctica ).…”

Section: Introductionmentioning

confidence: 99%

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Antifouling Diterpenoids from the Sponge Dendrilla antarctica

Prieto

Paola

Pérez

et al. 2021

Chemistry & Biodiversity

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Two nor‐diterpenes, 9,11‐dihydrogracilin A (1) and the previously unreported 9,11‐dihydrogracillinone A (2), were isolated from the sponge Dendrilla antarctica. The sponge was collected by trawling at a depth of 49 m, from the research vessel Puerto Deseado, near the coast of Tierra del Fuego, farther north than the reported habitat for this species. Since these compounds were particularly abundant and the sponge was free from epibionts, both 1 and 2 were included in soluble‐matrix paints and tested for antifouling activity in the ocean. The results obtained from these experiments clearly indicated a potent antifouling activity for both compounds against a variety of colonizing organisms, and established a probable role as natural antifoulants for these abundant secondary metabolites and other structurally related compounds previously isolated from Dendrilla spp.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antifouling Diterpenoids from the Sponge Dendrilla antarctica

Prieto

Paola

Pérez

et al. 2021

Chemistry & Biodiversity

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“…effect on malignant cells [1][2][3][4][5] . However, following a chemical modification the newly developed semisynthetic derivates revealed pronounced anticancer activity in vitro 6,7 .…”

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confidence: 99%

New diterpenes from the marine sponge Spongionella sp. overcome drug resistance in prostate cancer by inhibition of P-glycoprotein

Dyshlovoy

Shubina

Makarieva

et al. 2022

Sci Rep

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Spongian diterpenes are a group of marine natural compounds possessing various biological activities. However, their anticancer activity is still poorly studied and understood. We isolated six spongian diterpenes from the marine sponge Spongionella sp., including one new spongionellol A and five previously known molecules. The structures were elucidated using a detailed analysis MS and NMR spectra as well as by comparison with previously reported data. Two of them, namely, spongionellol A and 15,16-dideoxy-15α,17β-dihydroxy-15,17-oxidospongian-16-carboxylate-15,17-diacetate exhibited high activity and selectivity in human prostate cancer cells, including cells resistant to hormonal therapy and docetaxel. The mechanism of action has been identified as caspase-dependent apoptosis. Remarkably, both compounds were able to suppress expression of androgen receptor (AR) and AR-splice variant 7, as well as AR-dependent signaling. The isolated diterpenes effectively inhibited drug efflux mediated by multidrug-resistance protein 1 (MDR1; p-glycoprotein). Of note, a synergistic effect of the compounds with docetaxel, a substrate of p-glycoprotein, suggests resensitization of p-glycoprotein overexpressing cells to standard chemotherapy. In conclusion, the isolated spongian diterpenes possess high activity and selectivity towards prostate cancer cells combined with the ability to inhibit one of the main drug-resistance mechanism. This makes them promising candidates for combinational anticancer therapy.

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“…of the region. To date, we have collected over 500 mens from reefs from this region, and a systemat has been initiated [7][8][9][10][11][12]. Herein, we report on th biological activity of two new alkaloids, tedaniop novel skeleton ( Figure 1) that we have isolated fro oceanic waters adjacent to Cook Island in far nor is the first report on the chemistry of sponges fro…”

Section: Introductionmentioning

confidence: 99%

“…Due to the paucity of chemical data reported for species from this region, we have initiated a project to investigate the chemical diversity in relation to the sessile marine invertebrate biodiversity of the region. To date, we have collected over 500 sponges, ascidian, and bryozoan specimens from reefs from this region, and a systematic analysis of the chemistry they contain has been initiated [ 7 , 8 , 9 , 10 , 11 , 12 ]. Herein, we report on the isolation, structure determination, and biological activity of two new alkaloids, tedaniophorbasins A ( 1 ) and B ( 2 ), possessing a novel skeleton ( Figure 1 ) that we have isolated from Tedaniophorbas ceratosis collected from oceanic waters adjacent to Cook Island in far northern New South Wales, Australia.…”

Section: Introductionmentioning

confidence: 99%

Tedaniophorbasins A and B—Novel Fluorescent Pteridine Alkaloids Incorporating a Thiomorpholine from the Sponge Tedaniophorbas ceratosis

et al. 2021

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Two new fluorescent pteridine alkaloids, tedaniophorbasins A (1) and B (2), together with the known alkaloid N-methyltryptamine, were isolated, through application of mass directed purification, from the sponge Tedaniophorbas ceratosis collected from northern New South Wales, Australia. The structures of tedaniophorbasins A and B were deduced from the analysis of 1D/2D NMR and MS data and through application of 13C NMR DFT calculations. Tedaniophorbasin A possesses a novel 2-imino-1,3-dimethyl-2,3,7,8-tetrahydro-1H-[1,4]thiazino[3,2-g]pteridin-4(6H)-one skeleton, while tedaniophorbasin B is its 2-oxo derivative. The compounds show significant Stokes shifts (~14,000 cm−1) between excitation and emission wavelengths in their fluorescence spectra. The new compounds were tested for bioactivity against chloroquine-sensitive and chloroquine-resistant strains of the malaria parasite Plasmodium falciparum, breast and pancreatic cancer cell lines, and the protozoan parasite Trypanosoma brucei brucei but were inactive against all targets at 40 µM.

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Three New Spongian Diterpenes from the Marine Sponge Dendrilla rosea

Cited by 7 publications

References 16 publications

Antifouling Diterpenoids from the Sponge Dendrilla antarctica

Antifouling Diterpenoids from the Sponge Dendrilla antarctica

New diterpenes from the marine sponge Spongionella sp. overcome drug resistance in prostate cancer by inhibition of P-glycoprotein

Tedaniophorbasins A and B—Novel Fluorescent Pteridine Alkaloids Incorporating a Thiomorpholine from the Sponge Tedaniophorbas ceratosis

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