Bioactive Steroids from the Red Sea Soft Coral $\textit{Sinularia polydactyla}$.

Mohamed A Tammam; Lucie Rárová; Marie Kvasnicová; Gabriel Gonzalez; Ahmed M Emam; Aldoushy Mahdy; Miroslav Strnad; Efstathia Ioannou; Vassilios Roussis

doi:10.3390/md18120632

Bioactive Steroids from the Red Sea Soft Coral $\textit{Sinularia polydactyla}$.

Mohamed A Tammam, Lucie Rárová, Marie Kvasnicová, Gabriel Gonzalez, Ahmed M Emam, Aldoushy Mahdy, Miroslav Strnad, Efstathia Ioannou, Vassilios Roussis

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

Six new (1, 2, 6, 8, 13, and 20) and twenty previously isolated (3-5, 7, 9-12, 14-19, and 21-26) steroids featuring thirteen different carbocycle motifs were isolated from the organic extract of the soft coral $\textit{Sinularia polydactyla}$ collected from the Hurghada reef in the Red Sea. The structures and the relative configurations of the isolated natural products have been determined based on extensive analysis of their NMR and MS data. The cytotoxic, anti-inflammatory, anti-angiogenic, and neuroprotective activity of compounds 3-7, 9-12, 14-20, and 22-26, as well as their effect on androgen receptor-regulated transcription was evaluated in vitro in human tumor and non-cancerous cells. Steroids 22 and 23 showed significant cytotoxicity in the low micromolar range against the HeLa and MCF7 cancer cell lines, while migration of endothelial cells was inhibited by compounds 11, 12, 22, and 23 at 20 µM. The results of the androgen receptor (AR) reporter assay showed that compound 11 exhibited the strongest inhibition of AR at 10 µM, while it is noteworthy that steroids 10, 16, and 20 displayed increased inhibition of AR with decreasing concentrations. Additionally, compounds 11 and 23 showed neuroprotective activity on neuron-like SH-SY5Y cells.

Original language	English (US)
Pages (from-to)	632
Journal	Marine Drugs
Volume	18
Issue number	12
DOIs	https://doi.org/10.3390/md18120632
State	Published - Dec 16 2020
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2021-09-09
Acknowledgements: M.A.T. acknowledges support by the mission sector of the Ministry of Higher Education of the Arab Republic of Egypt (Egyptian Cultural Bureau in Athens), the Directorate of Education and Cultural Affairs, Ministry of Foreign Affairs of Greece and the non-profit organization “Kleon Tsetis”. We thank Jitka Ulrichová for the kind gift of HUVEC cells and Zdeněk Dvořák for the kind gift of 22Rv1-ARE14 cells. Authors also thank Anežka Šindlerová and Veronika Górová for excellent technical assistance. Assistance on the acquisition of some NMR data by Lukasz Jaremko (King Abdullah University of Science and Technology, Saudi Arabia) is gratefully acknowledged.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

ASJC Scopus subject areas

Drug Discovery

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/md18120632

Cite this

@article{d80929dfcaf949bdb82c2ecb99fd96f5,

title = "Bioactive Steroids from the Red Sea Soft Coral $\textit{Sinularia polydactyla}$.",

abstract = "Six new (1, 2, 6, 8, 13, and 20) and twenty previously isolated (3-5, 7, 9-12, 14-19, and 21-26) steroids featuring thirteen different carbocycle motifs were isolated from the organic extract of the soft coral $\textit{Sinularia polydactyla}$ collected from the Hurghada reef in the Red Sea. The structures and the relative configurations of the isolated natural products have been determined based on extensive analysis of their NMR and MS data. The cytotoxic, anti-inflammatory, anti-angiogenic, and neuroprotective activity of compounds 3-7, 9-12, 14-20, and 22-26, as well as their effect on androgen receptor-regulated transcription was evaluated in vitro in human tumor and non-cancerous cells. Steroids 22 and 23 showed significant cytotoxicity in the low micromolar range against the HeLa and MCF7 cancer cell lines, while migration of endothelial cells was inhibited by compounds 11, 12, 22, and 23 at 20 µM. The results of the androgen receptor (AR) reporter assay showed that compound 11 exhibited the strongest inhibition of AR at 10 µM, while it is noteworthy that steroids 10, 16, and 20 displayed increased inhibition of AR with decreasing concentrations. Additionally, compounds 11 and 23 showed neuroprotective activity on neuron-like SH-SY5Y cells.",

author = "Tammam, {Mohamed A} and Lucie R{\'a}rov{\'a} and Marie Kvasnicov{\'a} and Gabriel Gonzalez and Emam, {Ahmed M} and Aldoushy Mahdy and Miroslav Strnad and Efstathia Ioannou and Vassilios Roussis",

note = "KAUST Repository Item: Exported on 2021-09-09 Acknowledgements: M.A.T. acknowledges support by the mission sector of the Ministry of Higher Education of the Arab Republic of Egypt (Egyptian Cultural Bureau in Athens), the Directorate of Education and Cultural Affairs, Ministry of Foreign Affairs of Greece and the non-profit organization “Kleon Tsetis”. We thank Jitka Ulrichov{\'a} for the kind gift of HUVEC cells and Zden{\v e}k Dvo{\v r}{\'a}k for the kind gift of 22Rv1-ARE14 cells. Authors also thank Ane{\v z}ka {\v S}indlerov{\'a} and Veronika G{\'o}rov{\'a} for excellent technical assistance. Assistance on the acquisition of some NMR data by Lukasz Jaremko (King Abdullah University of Science and Technology, Saudi Arabia) is gratefully acknowledged. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

year = "2020",

month = dec,

day = "16",

doi = "10.3390/md18120632",

language = "English (US)",

volume = "18",

pages = "632",

journal = "Marine Drugs",

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T1 - Bioactive Steroids from the Red Sea Soft Coral $\textit{Sinularia polydactyla}$.

AU - Tammam, Mohamed A

AU - Rárová, Lucie

AU - Kvasnicová, Marie

AU - Gonzalez, Gabriel

AU - Emam, Ahmed M

AU - Mahdy, Aldoushy

AU - Strnad, Miroslav

AU - Ioannou, Efstathia

AU - Roussis, Vassilios

N1 - KAUST Repository Item: Exported on 2021-09-09 Acknowledgements: M.A.T. acknowledges support by the mission sector of the Ministry of Higher Education of the Arab Republic of Egypt (Egyptian Cultural Bureau in Athens), the Directorate of Education and Cultural Affairs, Ministry of Foreign Affairs of Greece and the non-profit organization “Kleon Tsetis”. We thank Jitka Ulrichová for the kind gift of HUVEC cells and Zdeněk Dvořák for the kind gift of 22Rv1-ARE14 cells. Authors also thank Anežka Šindlerová and Veronika Górová for excellent technical assistance. Assistance on the acquisition of some NMR data by Lukasz Jaremko (King Abdullah University of Science and Technology, Saudi Arabia) is gratefully acknowledged. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2020/12/16

Y1 - 2020/12/16

N2 - Six new (1, 2, 6, 8, 13, and 20) and twenty previously isolated (3-5, 7, 9-12, 14-19, and 21-26) steroids featuring thirteen different carbocycle motifs were isolated from the organic extract of the soft coral $\textit{Sinularia polydactyla}$ collected from the Hurghada reef in the Red Sea. The structures and the relative configurations of the isolated natural products have been determined based on extensive analysis of their NMR and MS data. The cytotoxic, anti-inflammatory, anti-angiogenic, and neuroprotective activity of compounds 3-7, 9-12, 14-20, and 22-26, as well as their effect on androgen receptor-regulated transcription was evaluated in vitro in human tumor and non-cancerous cells. Steroids 22 and 23 showed significant cytotoxicity in the low micromolar range against the HeLa and MCF7 cancer cell lines, while migration of endothelial cells was inhibited by compounds 11, 12, 22, and 23 at 20 µM. The results of the androgen receptor (AR) reporter assay showed that compound 11 exhibited the strongest inhibition of AR at 10 µM, while it is noteworthy that steroids 10, 16, and 20 displayed increased inhibition of AR with decreasing concentrations. Additionally, compounds 11 and 23 showed neuroprotective activity on neuron-like SH-SY5Y cells.

AB - Six new (1, 2, 6, 8, 13, and 20) and twenty previously isolated (3-5, 7, 9-12, 14-19, and 21-26) steroids featuring thirteen different carbocycle motifs were isolated from the organic extract of the soft coral $\textit{Sinularia polydactyla}$ collected from the Hurghada reef in the Red Sea. The structures and the relative configurations of the isolated natural products have been determined based on extensive analysis of their NMR and MS data. The cytotoxic, anti-inflammatory, anti-angiogenic, and neuroprotective activity of compounds 3-7, 9-12, 14-20, and 22-26, as well as their effect on androgen receptor-regulated transcription was evaluated in vitro in human tumor and non-cancerous cells. Steroids 22 and 23 showed significant cytotoxicity in the low micromolar range against the HeLa and MCF7 cancer cell lines, while migration of endothelial cells was inhibited by compounds 11, 12, 22, and 23 at 20 µM. The results of the androgen receptor (AR) reporter assay showed that compound 11 exhibited the strongest inhibition of AR at 10 µM, while it is noteworthy that steroids 10, 16, and 20 displayed increased inhibition of AR with decreasing concentrations. Additionally, compounds 11 and 23 showed neuroprotective activity on neuron-like SH-SY5Y cells.

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U2 - 10.3390/md18120632

DO - 10.3390/md18120632

M3 - Article

C2 - 33322046

SN - 1660-3397

VL - 18

SP - 632

JO - Marine Drugs

JF - Marine Drugs

IS - 12

ER -

Bioactive Steroids from the Red Sea Soft Coral $\textit{Sinularia polydactyla}$.

Abstract

Bibliographical note

ASJC Scopus subject areas

UN SDGs

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