Diverse bioactive compounds from <i>Sarcophtyton glaucom</i>: structure elucidation and cytotoxic activity studies

Shaaban, Mohamed; El-Hagrassi, Ali M.; Abdelghani, Mohamed A.; Osman, Abeer F.

doi:10.1515/znc-2017-0106

Cited by 9 publications

(7 citation statements)

References 23 publications

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“…Selected 1 H-NMR (500 MHz, CDCl 3 ) δ H : 1.03 (3H, s, H-8), 0.83 (3H, s, H-9), 1.16 (3H, s, H-10), 0.91 (3H, d, J = 7.5 Hz, H-11). 13 C-NMR (125 MHz, CDCl 3 ) δ C : 18.4 (C-1), 28.7 (C-1a), 18.8 (C-2) 25.7 (C-3), 58.0 (C-3a), 74.4 (C-4), 37.7 (C-5), 29.1 (C-6), 38.4 (C-7), 39.7 (C-7a), 22.3 (C-7b), 28.6 (C-8), 16.1 (C-9), 32.1 (C-10), 16.4 (C-11) [ 39 ].…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic metabolites from Sinularia levi supported by network pharmacology

Sun,

Abdelwahab,

Zhang

et al. 2024

PLoS ONE

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The in-vitro anti-proliferative evaluation of Sinularia levi total extract against three cell lines revealed its potent effect against Caco-2 cell line with IC50 3.3 μg/mL, followed by MCF-7 and HepG-2 with IC50 6.4 μg/mL and 8.5 μg/mL, respectively, in comparison to doxorubicin. Metabolic profiling of S. levi total extract using liquid chromatography coupled with high-resolution electrospray ionization mass spectrometry (LC-HR-ESI-MS) revealed the presence of phytoconstituents clusters consisting mainly of steroids and terpenoids (1–20), together with five metabolites 21–25, which were additionally isolated and identified through the phytochemical investigation of S. levi total extract through various chromatographic and spectroscopic techniques. The isolated metabolites included one sesquiterpene, two steroids and two diterpenes, among which compounds prostantherol (21) and 12-hydroperoxylsarcoph-10-ene (25) were reported for the first time in Sinularia genus. The cytotoxic potential evaluation of the isolated compounds revealed variable cytotoxic effects against the three tested cell lines. Compound 25 was the most potent with IC50 value of 2.13 ± 0.09, 3.54 ± 0.07 and 5.67 ± 0.08 μg/mL against HepG-2, MCF-7 and Caco-2, respectively, followed by gorgosterol (23) and sarcophine (24). Additionally, network analysis showed that cyclin-dependent kinase 1 (CDK1) was encountered in the mechanism of action of the three cancer types. Molecular docking analysis revealed that CDK1 inhibition could possibly be the reason for the cytotoxic potential.

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Section: Methodsmentioning

confidence: 99%

Cytotoxic metabolites from Sinularia levi supported by network pharmacology

Sun,

Abdelwahab,

Zhang

et al. 2024

PLoS ONE

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“…The compounds were tested against HepG2 cancer cell lines. Sarcophinone ( 118) and 8-epi-sarcophinone (119) were tested together and exhibited an EC 50 value of 11.32 µg/mL, while (+)-7α,8β-dihydroxydeepoxysarcophine (114), sinumaximol G (120), sarcophine (121), and prostantherol (122) showed EC 50 values of 17.84, 9.97, 10.32, and 12.22 µg/mL, respectively [65].…”

Section: Cytotoxic Compounds From the Genus Sarcophytonmentioning

confidence: 99%

Cytotoxic Compounds from Alcyoniidae: An Overview of the Last 30 Years

et al. 2022

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The octocoral family Alcyoniidae represents a rich source of bioactive substances with intriguing and unique structural features. This review aims to provide an updated overview of the compounds isolated from Alcyoniidae and displaying potential cytotoxic activity. In order to allow a better comparison among the bioactive compounds, we focused on molecules evaluated in vitro by using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, by far the most widely used method to analyze cell proliferation and viability. Specifically, we surveyed the last thirty years of research, finding 153 papers reporting on 344 compounds with proven cytotoxicity. The data were organized in tables to provide a ranking of the most active compounds, to be exploited for the selection of the most promising candidates for further screening and pre-clinical evaluation as anti-cancer agents. Specifically, we found that (22S,24S)-24-methyl-22,25-epoxyfurost-5-ene-3β,20β-diol (16), 3β,11-dihydroxy-24-methylene-9,11-secocholestan-5-en-9-one (23), (24S)-ergostane-3β,5α,6β,25 tetraol (146), sinulerectadione (227), sinulerectol C (229), and cladieunicellin I (277) exhibited stronger cytotoxicity than their respective positive control and that their mechanism of action has not yet been further investigated.

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“…A new pyrane-based cembranoid diterpene, 9-hydroxy-10,11-dehydro-sarcotrocheliol 16, was isolated from S. trocheliophorum. However, this compound showed no anti-bacterial activity against multiple microorganisms (Table 1 Sarcophyton glaucom from the same area was reported to yields five new diterpenes, sarcophinone 27, 8-epi-sarcophinone 28, (+)-7α,8β-dihydroxydeepoxysarcophine 29, sinumaximol G 30, and sarcophine 31 [26]. Several new cembranoids, (+)-(1E,3E,11E)-7,8-epoxycembra-1,3,11,15-tetraene 32 from Sarcophyton stellatum in Inner reef of Mahambo, Tamatave, Madagascar [27], and sarcophytrols M-U 33-41 from S. trocheliophorum in Yalong Bay, Hainan Province, China [28], was discovered but their activities have not been tested (Table 1, entries 32-41).…”

Section: Sarcophyton Cherbonnierimentioning

confidence: 99%

“…Sarcoehrenbergilids A was found as a white crystal with a molecular formula of C 21 H 32 O 5 (m/z at [M+Na] + of 387.2142) while Sarcoehrenbergilids B and C were isomers observed as a white powder with a molecular formula of C 20 H 30 O 5 (m/z at [M+Na] + of 373.1986). Another species Sarcophyton glaucom from the same area was reported to yields five new diterpenes, sarcophinone 27 , 8- epi -sarcophinone 28 , (+)-7α,8β-dihydroxydeepoxysarcophine 29 , sinumaximol G 30 , and sarcophine 31 [ 26 ]. Several new cembranoids, (+)-(1 E ,3 E ,11 E )-7,8-epoxycembra-1,3,11,15-tetraene 32 from Sarcophyton stellatum in Inner reef of Mahambo, Tamatave, Madagascar [ 27 ], and sarcophytrols M-U 33–41 from S. trocheliophorum in Yalong Bay, Hainan Province, China [ 28 ], was discovered but their activities have not been tested (Table 1 , entries 32–41).…”

Section: Cembranoidsmentioning

confidence: 99%

“…In addition, the known compounds 27–31 isolated from Sarcophyton glaucom also exerted moderate to potent activity against HepG2. Compound 27 and 28 were tested together and exerted effective concentration 50 (EC 50 ) value of 11.32 µg/mL, while compound 29 – 31 possessed EC 50 values of 17.84; 9.97; and 10.32 µg/mL, respectively [ 26 ]. Another study reported anti-cancer activity against MCF-7 human breast cancer cells from compounds 30 and 31 with IC 50 values of 24.97 and 22.39 μg/mL, respectively [ 32 ].…”

Section: Biological Activitiesmentioning

confidence: 99%

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Cembranoids of Soft Corals: Recent Updates and Their Biological Activities

Nurrachma

Sakaraga

Nugraha

et al. 2021

Nat. Prod. Bioprospect.

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Soft corals are well-known as excellent sources of marine-derived natural products. Among them, members of the genera Sarcophyton, Sinularia, and Lobophytum are especially attractive targets for marine natural product research. In this review, we reported the marine-derived natural products called cembranoids isolated from soft corals, including the genera Sarcophyton, Sinularia, and Lobophytum. Here, we reviewed 72 reports published between 2016 and 2020, comprising 360 compounds, of which 260 are new compounds and 100 are previously known compounds with newly recognized activities. The novelty of the organic molecules and their relevant biological activities, delivered by the year of publication, are presented. Among the genera presented in this report, Sarcophyton spp. produce the most cembranoid diterpenes; thus, they are considered as the most important soft corals for marine natural product research. Cembranoids display diverse biological activities, including anti-cancer, anti-bacterial, and anti-inflammatory. As cembranoids have been credited with a broad range of biological activities, they present a huge potential for the development of various drugs with potential health and ecological benefits. Graphic Abstract

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Diverse bioactive compounds from Sarcophtyton glaucom: structure elucidation and cytotoxic activity studies

Cited by 9 publications

References 23 publications

Cytotoxic metabolites from Sinularia levi supported by network pharmacology

Cytotoxic metabolites from Sinularia levi supported by network pharmacology

Cytotoxic Compounds from Alcyoniidae: An Overview of the Last 30 Years

Cembranoids of Soft Corals: Recent Updates and Their Biological Activities

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