Spongiains A-C: Three new spongian diterpenes with ring A rearrangement from the marine sponge Spongia sp.

Liang, Yong-Qian; Liao, Xiaojian; Lin, Jia; Xü, Wei; Chen, Guodong; Zhao, Bing-Xin; Xu, Shi‐Hai

doi:10.1016/j.tet.2019.06.001

Cited by 20 publications

(11 citation statements)

References 20 publications

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“…In total, the NMR spectroscopic data of 1 ( Table 1 ) displayed signals for an α-hydroxy- γ -lactone (δ C 183.3 C, 90.2 C, 75.3 CH 2 , and 48.6 C; δ H 4.40 and 3.83, each 1H, d, J = 10.0 Hz,) [ 12 ] and an unsaturated γ -lactone (δ C 174.7 C, 172.2 C, 123.5 C, and 68.8 CH 2 ; δ H 4.82, 1H, tt, J = 17.0, 2.5 Hz and 4.51, 1H, dd, J = 17.0, 2.5 Hz) [ 14 , 15 ]. Further, the 1 H– 1 H COSY experiment revealed the presence of two partial structures ( Figure 2 ), which were connected by the HMBC correlations of 1 ( Figure 2 ) to establish the 5,5,6,6,5-pentacyclic structure of 1 [ 3 , 4 , 12 ].…”

Section: Resultsmentioning

confidence: 99%

“…The CD spectrum of 1 ( Figure 3 ) showed positive and negative Cotton effects at 214.5 and 234.0 nm, respectively, which was found to be well consistent with the calculated ECD of 1a (212.5 and 230.4 nm, Figure 3 ), and the absolute configuration of 1 was thus elucidated as 1 S ,2 R ,4 S ,5 R ,8 R ,9 S , and 10 R . Based on the above observations, the structure of 1 was identified as a new compound possessing the recently discovered 5,5,6,6,5-pentacyclic-based skeleton [ 3 , 4 , 12 ], but with a characteristic 1β-OH and named spongenolactone A.…”

Section: Resultsmentioning

confidence: 99%

“…Sponges of the genus Spongia have been proven to be rich sources of structurally diversified secondary metabolites [ 1 , 2 ]. A series of previous studies for the discovery of versatile molecular structures and bioactivities of compounds from sponges of the genus Spongia have been reported [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ]. Our recent investigation on the secondary metabolites of a Red Sea sponge Spongia sp.…”

Section: Introductionmentioning

confidence: 99%

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Spongenolactones A–C, Bioactive 5,5,6,6,5-Pentacyclic Spongian Diterpenes from the Red Sea Sponge Spongia sp.

et al. 2022

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Three new 5,5,6,6,5-pentacyclic spongian diterpenes, spongenolactones A–C (1–3), were isolated from a Red Sea sponge Spongia sp. The structures of the new metabolites were elucidated by extensive spectroscopic analysis and the absolute configurations of 1–3 were determined on the basis of comparison of the experimental circular dichroism (CD) and calculated electronic circular dichroism (ECD) spectra. Compounds 1–3 are the first 5,5,6,6,5-pentacyclic spongian diterpenes bearing an β-hydroxy group at C-1. These metabolites were assayed for their cytotoxic, antibacterial, and anti-inflammatory activities. All three compounds were found to exert inhibitory activity against superoxide anion generation in fMLF/CB-stimulated human neutrophils. Furthermore, 1 showed a higher activity against the growth of Staphylococcus aureus in comparison to 2.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Spongenolactones A–C, Bioactive 5,5,6,6,5-Pentacyclic Spongian Diterpenes from the Red Sea Sponge Spongia sp.

et al. 2022

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“…Sponge belongs to Porifera and is distributed in the ocean, lakes and streams. Terpenoids and terpenoids extracted from sponges play an important role in combating malaria, anti-inflammatory, antibacterial, antiviral 45 . Schmitz and Bloor 46 isolated halenaquinone (7) from Adocia sp.…”

Section: Spongementioning

confidence: 99%

An overview on natural farnesyltransferase inhibitors for efficient cancer therapy

Dai

Sun

Zhang

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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As one of the world's five terminally ills, tumours can cause important genetic dysfunction. However, some current medicines for tumours usually have strong toxic side effects and are prone to drug resistance. Studies have found that farnesyltransferase inhibitors (FTIs) extracted from natural materials have a good inhibiting ability on tumours with fewer side effects. This article describes several FTIs extracted from natural materials and clarifies the current research progress, which provides a new choice for the treatment of tumours.

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“…In our ongoing search for biological marine natural products, three new butenolides, caulerpalide A ( 1 ), (+)‐caulerpalide B ((+)‐ 2 ) and (−)‐caulerpalide B ((−)‐ 2 ), together with seven known compounds ( 3 – 9 ), had been isolated from the alga C. racemosa var. turbinata , the chemical investigation of which had never been reported before ( Figure ).…”

Section: Introductionmentioning

confidence: 99%

Three New Butenolides from the Green Alga Caulerpa racemosa var. turbinata

Yang

Zhang

et al. 2020

Chemistry & Biodiversity

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Three new butenolides, caulerpalide A and a pair of enantiomers, (+)-caulerpalide B and (À )-caulerpalide B, together with seven known compounds, have been isolated from the green alga Caulerpa racemosa var. turbinata. All these structures were determined by spectroscopic techniques. The absolute configurations of caulerpalide A, (+)-caulerpalide B and (À )-caulerpalide B were elucidated by the method of ECD calculation. This is the first separation of butenolides from the algae of genus Caulerpa. Additionally, the antibacterial activities of the nine isolated compounds were also evaluated.[a][b] Data can be exchanged freely.

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Spongiains A-C: Three new spongian diterpenes with ring A rearrangement from the marine sponge Spongia sp.

Cited by 20 publications

References 20 publications

Spongenolactones A–C, Bioactive 5,5,6,6,5-Pentacyclic Spongian Diterpenes from the Red Sea Sponge Spongia sp.

Spongenolactones A–C, Bioactive 5,5,6,6,5-Pentacyclic Spongian Diterpenes from the Red Sea Sponge Spongia sp.

An overview on natural farnesyltransferase inhibitors for efficient cancer therapy

Three New Butenolides from the Green Alga Caulerpa racemosa var. turbinata

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