Isolation and Bioactivity Evaluation of Sesquiterpenes from an Alcyonarian of the Genus Lemnalia from the Saudi Arabian Red Sea
Jazyk angličtina Země Švýcarsko Médium print-electronic
Typ dokumentu časopisecké články
Grantová podpora
OSR-2017-CPF-3627-2
Subaward Agreement
King Abdullah University of Science and Technology
Z.02.1.01/0.0/0.0/16_019/0000868
European Regional Developmental
23-05474S
Czech Grant Agency
PubMed
38412304
DOI
10.1002/cbdv.202400235
Knihovny.cz E-zdroje
- Klíčová slova
- Lemnalia, androgen receptor-regulated transcription, anti-inflammatory activity, neuroprotective activity, sesquiterpenes,
- MeSH
- korálnatci * chemie MeSH
- lidé MeSH
- protinádorové látky * farmakologie metabolismus MeSH
- seskviterpeny * chemie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Indický oceán MeSH
- Saudská Arábie MeSH
- Názvy látek
- protinádorové látky * MeSH
- seskviterpeny * MeSH
Over the last decades, soft corals have been proven a rich source of biologically active compounds, featuring a wide range of chemical structures. Herein, we investigated the chemistry of an alcyonarian of the genus Lemnalia (Neptheidae), specimens of which were collected from the coral reefs near Al Lith, on the south-west coast of Saudi Arabia. A series of chromatographic separations led to the isolation of 31 sesquiterpenes, featuring mainly the nardosinane and neolemnane carbon skeletons, among which three (13, 14 and 28) are new natural products. The metabolites isolated in sufficient amounts were evaluated in vitro in human tumor and non-cancerous cell lines for a number of biological activities, including their cytotoxic, anti-inflammatory, anti-angiogenic, and neuroprotective activities, as well as for their effect on androgen receptor (AR)-regulated transcription. Among the tested metabolites, compound 12 showed comparable neuroprotective activity to the positive control N-acetylcysteine, albeit at a 10-fold lower concentration.
Zobrazit více v PubMed
B. Haefner, Drug. Discov. Today 2003, 8, 536–544.
X. Yan, H. Ouyang, W. Wang, J. Liu, T. Li, B. Wu, X. Yan, S. He, Mar. Drugs 2021, 19, 294–305.
S. Y. Cheng, E. H. Lin, J. S. Huang, Z. H. Wen, C. Y. Duh, Chem. Pharm. Bull. 2010, 58, 381–385.
W. C. Wei, P. J. Sung, C. Y. Duh, B. W. Chen, J. H. Sheu, N.-S. Yang, Mar. Drugs 2013, 11, 4083–4126.
Q. Wu, J. Sun, J. Chen, H. Zhang, Y. W. Guo, H. Wang, Mar. Drugs 2018, 16, 320–334.
J. H. Churchill, A. S. Bower, D. C. McCorkle, Y. Abualnaja J. Mar. Res. 2014, 72, 165–181.
M. E. F. Hegazy, T. A. Mohamed, M. A. Alhammady, A. M. Shaheen, E. H. Reda, A. I. Elshamy, M. Aziz, P. W. Paré, Mar. Drugs 2015, 13, 3154–3181.
J. Liu, F. Xia, H. Ouyang, W. Wang, T. Li, Y. Shi, X. Yan, X. Yan, S. He, Phytochemistry 2022, 196, 113088.
F. Yang, S. W. Li, J. Zhang, L. F. Liang, Y. H. Lu, Y. W. Guo, Bioorg. Chem. 2020, 96, 103636.
G. H. Wang, H. C. Huang, J. H. Su, Y. C. Wu, J. H. Sheu, Chem. Pharm. Bull. 2010, 58, 30–33.
R. R. Izac, P. Schneider, M. Swain, W. Fenical, Tetrahedron Lett. 1982, 23, 817–820.
S. E. N. Ayyad, M. A. Deyab, T. Kosbar, W. M. Alarif, A. H. Eissa, Nat. Prod. Res. 2019, 35, 4303–4310.
D. Daloze, J. C. Braekman, P. Georget, B. Tursch, Bull. Soc. Chim. Belg. 1977, 86, 47–54.
B. F. Bowden, J. C. Coll, S. J. Mitchell, Aust. J. Chem. 1980, 33, 885–890.
H. Abe, M. Fujimaki, E. Goto, A. Yokosuka, Y. Mimaki, T. Kobayashi, H. Ito, Tetrahedron Lett. 2019, 60, 1604–1606.
H. C. Huang, C. H. Chao, J. H. Liao, Y. Michael, M. Y. Chiang, C. F. Dai, Y. C. Wu, J. H. Sheu, Tetrahedron Lett. 2005, 46, 7711–7714.
J. E. Dellar, M. D. Cole, A. I. Gray, S. Gibbons, P. G. Waterman, Phytochemistry 1994, 36, 957–960.
R. Lu, C. Paul, S. Basar, W. A. König, T. Hashimoto, Y. Asakawa, Phytochemistry 2003, 63, 581–587.
A. Ahond, J. C. Coil, J. D. Fourneron, Tetrahedron Lett. 1979, 20, 1879–1880.
J. Y. Su, Y. L. Zhong, L. M. Zeng, J. Nat. Prod. 1993, 56, 288–291.
M. Liu, P. Li, X. Tang, X. Luo, K. Liu, Y. Zhang, Q. Wang, G. Li, J. Org. Chem. 2021, 86, 970–979.
H. C. Huang, Z. H. Wen, C. H. Chao, A. F. Ahmed, M. Y. Chiang, Y. H. Kuo, C. H. Hsu, J. H. Sheu, Tetrahedron Lett. 2006, 47, 8751–8755.
H. C. Huang, C. H. Chao, J. H. Su, C. H. Hsu, S. P. Chen, Y. H. Kuo, J. H. Sheu, Chem. Pharm. Bull. 2007, 55, 876–880.
M. Liu, P. Li, X. Luo, L. van Ofwegen, X. Tang, G. Li, Nat. Prod. Res. 2020, 35, 3752–3756.
J. Jurek, P. J. Scheuer, J. Nat. Prod. 1993, 56, 508–513.
A. Bishara, D. Yeffet, M. Sisso, G. Shmul, M. Schleyer, Y. Benayahu, Y. Kashman J. Nat. Prod. 2008, 71, 375–380.
H. C. Morrogh-Bernard, I. Foitová, Z. Yeen, P. Wilkin, R. de Martin, L. Rárová, K. Doležal, W. Nurcahyo, M. Olšanský, Sci. Rep. 2017, 7, 16653.
K. Ito, Y. Eguchi, Y. Imagawa, S. Akai, H. Mochizuki, Y. Tsujimoto, Cell Death Dis. 2017, 3, 17013.
P. Risiglione, L. Leggio, S. A. M. Cubisino, S. Reina, G. Paternò, B. Marchetti, A. Magrì, N. Iraci, A. Messina, Int. J. Mol. Sci. 2020, 21, 7809.
D. Colle, D. B. Santos, J. M. Hartwig, M. Godoi, D. F. Engel, A. Fabro de Bem, A. L. Braga, M. Farina Mol. Neurobiol. 2016, 53, 1280–1295.
G. Gonzalez, M. Kvasnica, K. Svrčková, Š. Štěpánková, J. R. C. Santos, M. Peřina, R. Jorda, S. M. M. Lopes, T. M. V. D. Pinho e Melo, J. Steroid Biochem. Mol. Biol. 2023, 225, 106194.
K. F. Chang, X. F. Huang, J. T. Chang, Y. C. Huang, J. C. Weng, N. M. Tsai, Cancer Lett. 2020, 495, 180–190.
A. M. Steely, J. A. Sr. Willoughby, S. N. Sundar, V. I. Aivaliotis, G. L. Firestone, Anti-Cancer Drugs 2017, 28, 1018–1031.
L. Rárová, Z. Pakulski, M. Strnad, M. Kvasnicová, T. Štenclová, P. Cmoch, J. Steroid Biochem. Mol. Biol. 2022, 224,106161.
L. Rárová, D. Sedlák, J. Oklestkova, J. Steigerová, J. Liebl, S. Zahler, P. Bartůněk, Z. Kolář, L. Kohout, M. Kvasnica, M. Strnad, J. Steroid Biochem. Mol. Biol. 2018, 178, 263–271.
I. Bartonkova, A. Novotna, Z. Dvorak PLoS One 2015, 10, e0121316.
R. Jorda, E. Řezníčková, U. Kiełczewska, J. Maj, J. W. Morzycki, L. Siergiejczyk, V. Bazgier, K. Berka, L. Rárová, A. Wojtkielewicz, Eur. J. Med. Chem. 2019, 179, 483–492.
G. Gonzalez, J. Grúz, C. W. D'Acunto, P. Kaňovský, M. Strnad, Cytokinin Molecules 2021, 26(2), 361.
M. S. Aymerich, E. Rojo-Bustamante, C. Molina, M. Celorrio, J. A. Sánchez-Arias, R. Franco, Mol. Neurobiol. 2016, 53, 2312–2319.
Ø. Hammer, D. A. T. Harper, P. D. Ryan, Palaeontol. Electron. 2001, 4, 1–9.
