Spongian diterpenes from Chinese marine sponge Spongia officinalis

Han, Guorong; Sun, Degang; Liang, Lin-Fu; Yao, Li‐Gong; Chen, Kaixian; Guo, Yue‐Wei

doi:10.1016/j.fitote.2018.02.010

Cited by 20 publications

(14 citation statements)

References 25 publications

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“…Among compounds 1 – 5 , compound 5 is a scalarane‐type sesterterpene; whereas, compounds 1 – 4 belong to spongian‐type diterpenes. Because spongian‐type diterpenes normally originate from sponges of Genus Spongia , such as Spongia officinalis and Spongia ceylonensis [ 16 ] , combining this research with previous investigation [ 17 ] , the prey–predator relationship between Spongia officinalis and G . atromarginata could be illustrated.…”

Section: Discussionmentioning

confidence: 99%

The chemical and chemo‐ecological studies on Weizhou nudibranch Glossodoris atromarginata

Yao

et al. 2019

Magnetic Reson in Chemistry

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A detailed chemical investigation of the nudibranch Glossodoris atromarginata collected from Weizhou Island, South China Sea, yielded a new spongian‐type diterpene 1, together with the four known‐related compounds 2–5. The structure of the new compound 1 was elucidated by the detailed spectroscopic analysis, the comparison of the spectroscopic data with the known diterpene isoagatholactone, and the 13C chemical shift calculation. In addition, evidence for the absolute stereochemistry of the known compound 2 was, for the first time, provided by the application of time‐dependent density functional theory electronic circular dichroism calculation.

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Section: Discussionmentioning

confidence: 99%

The chemical and chemo‐ecological studies on Weizhou nudibranch Glossodoris atromarginata

Yao

et al. 2019

Magnetic Reson in Chemistry

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“…A broad range of biological activities, such as antifungal, anti-inflammatory, and antiviral effects among others, have been reported for spongian diterpenes stimulating further efforts on synthesis and modifications of these molecules and their derivatives 1 , 2 . In contrast, hardly any cytotoxic effects have been demonstrated for the majority of the molecules belonging to this family of natural compounds, including a virtually non-existent effect on malignant cells 1 – 5 . However, following a chemical modification the newly developed semisynthetic derivates revealed pronounced anticancer activity in vitro 6 , 7 .…”

Section: Introductionmentioning

confidence: 98%

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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“…However, the overall match of the experimental and calculated ECD curves was only partial (Figure S36). Interestingly, compound 1 represents a new pentacyclic skeleton that could be derived from 6−8 via a series of oxidation, nucleophilic addition, and rearrangement reactions, 10 and it was named sponalactone.…”

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confidence: 99%

“…To date, about 200 spongian diterpenes and rearranged derivatives have been reported since the first spongian diterpene, named isoagatholactone, was isolated from the sponge Spongia officinalis (family Spongiidae) collected in the Mediterranean . Some of these compounds were reported to possess a variety of pharmaceutical bioactivities, such as cytotoxic, anti-inflammatory, and antiviral properties. − Spongia species of the South China Sea have been rarely chemically investigated, with only three studies reporting three new spongian diterpenes and two novel trinorsesquiterpenoids from the title species and nine sesquiterpene quinones/hydroquinones from S. pertusa , making them an understudied resource of chemical diversity for potential drug discovery efforts. In the course of our continuing research on bioactive molecules from marine invertebrates of the South China Sea, − a specimen of the previously investigated sponge, S. officinalis , was re-collected.…”

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confidence: 99%

Spongian Diterpenes Including One with a Rearranged Skeleton from the Marine Sponge Spongia officinalis

et al. 2019

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Five new diterpenes, including an unprecedented 5,5,6,6,5-pentacyclic diterpene, sponalactone (1), two new spongian diterpenes, 17-O-acetylepispongiatriol (2) and 17-O-acetylspongiatriol (3), and two new spongian diterpene artifacts, 15α,16α-dimethoxy-15,16-dihydroepispongiatriol (4) and 15α-ethoxyepispongiatriol-16(15H)-one (5), were isolated from a South China Sea collection of the marine sponge Spongia of f icinalis, together with three known analogues (6−8). The structures of the new diterpenes were elucidated by extensive spectroscopic analysis. The absolute configurations were established on the basis of ECD data. Compounds 1−5 and 7 exhibited moderate inhibition against LPS-induced NO production in RAW264.7 macrophages with IC 50 values of 12−32 μM.

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Spongian diterpenes from Chinese marine sponge Spongia officinalis

Cited by 20 publications

References 25 publications

The chemical and chemo‐ecological studies on Weizhou nudibranch Glossodoris atromarginata

The chemical and chemo‐ecological studies on Weizhou nudibranch Glossodoris atromarginata

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

Spongian Diterpenes Including One with a Rearranged Skeleton from the Marine Sponge Spongia officinalis

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