|
UPSI Digital Repository (UDRep)
|
|
| ||||||||||||||||||||||||||
| Abstract : Universiti Pendidikan Sultan Idris |
| As part of our ongoing study of the specialised metabolites present in brown algae belonging to the Cystophora genus, eight new steroids including three pairs of diastereoisomers were isolated from Cystophora xiphocarpa (Harvey) (Sargassacea, Fucales). The metabolites identified by standard spectrometric methods are (16S,22S)-16,22-dihydroxyergosta-4,24(28)-dien-3-one and (16S,22R)-16,22-dihydroxyergosta-4,24(28)-dien-3-one, (16S,22S,24R)-16,22,24-trihydroxyporifera-4,28-dien-3-one and (16S,22S,24S)-16,22,24-trihydroxystigma-4,28-dien-3-one along with (16S,22S,24E)-16,22-dihydroxystigma-4,24(28)-dien-3-one and (16S,20S)-16,20-dihydroxyergosta-4,24(28)-dien-3-one. (16S,22S,24E)-16,22-Dihydroxystigma-4,24(28)-dien-3-one possessed the most potent cytotoxicity of the steroids in this series with cell growth inhibitions of GI50 8.7 � 0.7 ?M against colon cancer HT29, GI50 5.6 � 0.8 ?M against the breast cancer line MCF-7 and GI50 4.5 � 0.2 ?M against the ovarian cancer cell line A2780. (16S,22R)-16,22-dihydroxyergosta-4,24(28)-dien-3-one was found to be active against the ovarian cancer cell line A2780 with a GI50 of 6.2 � 0.1 ?M. ? 2021 Elsevier Ltd |
| References |
Achenbach, H., Hübner, H., & Reiter, M. (1996). Cholestane- and pregnane-type glycosides from the roots of tribulus cistoides. Phytochemistry, 41(3), 907-917. doi:10.1016/0031-9422(95)00622-2 Akihisa, T., Kimura, Y., Koike, K., Kokke, W. C. M. C., Ohkawa, T., & Nikaido, T. (1999). (24R)- and (24S)-24-hydroxy-24-vinyllathosterols and other sterols from the aerial part of bryonia dioica. Phytochemistry, 52(8), 1601-1605. doi:10.1016/S0031-9422(99)00400-8 Alarif, W. M., Ayyad, S. -. N., El-Assouli, S. M., & Al-Lihaibi, S. S. (2012). Antigenotoxic ketosteroid from the red algae jania adhaerens. Natural Product Research, 26(9), 785-791. doi:10.1080/14786419.2010.548336 Balacco, G. (1996). A desktop calculator for the karplus equation. Journal of Chemical Information and Computer Sciences, 36(4), 885-887. doi:10.1021/ci950227r Benvegnù, R., Cimino, G., De Rosa, S., & De Stefano, S. (1982). Guggulsterol-like steroids from the mediterranean gorgonian leptogorgia sarmentosa. Experientia, 38(12), 1443-1444. doi:10.1007/BF01955758 Bian, B., & Van Altena, I. A. (1998). Four new compounds from the australian brown alga cystophora brownii. Australian Journal of Chemistry, 51(12), 1157-1165. doi:10.1071/C98008 Douanla, P. D., Tabopda, T. K., Tchinda, A. T., Cieckiewicz, E., Frédérich, M., Boyom, F. F., . . . Tchuendem, M. H. K. (2015). Antrocarines A-F, antiplasmodial ergostane steroids from the stem bark of antrocaryon klaineanum. Phytochemistry, 117, 521-526. doi:10.1016/j.phytochem.2015.07.011 El-Mekkawy, S., Meselhy, M. R., Nkobole, N., & Lall, N. (2013). Three new α-glucosidase inhibitors from guggul, the oleogum resin of commiphora wightii. Natural Product Research, 27(2), 146-154. doi:10.1080/14786419.2012.662651 Harding, W. W., Jacobs, H., Lewis, P. A., McLean, S., & Reynolds, W. F. (2001). Cycloartanes, protolimonoids, a pregnane and a new ergostane from trichilia reticulata. Natural Product Letters, 15(4), 253-260. doi:10.1080/10575630108041289 Harwood, L. M. (1985). Aldrichimica Acta, 18, 25-25. Retrieved from www.scopus.com Holland, I. P., McCluskey, A., Sakoff, J. A., Gilbert, J., Chau, N., Robinson, P. J., . . . Van Altena, I. A. (2009). Steroids from an australian sponge psammoclema sp. Journal of Natural Products, 72(1), 102-106. doi:10.1021/np800688f Laird, D. W., Bennett, S., Bian, B., Sauer, B., Wright, K., Hughes, V., & van Altena, I. A. (2010). Chemical investigation of seven australasian cystophora species: New chemistry and taxonomic insights. Biochemical Systematics and Ecology, 38(2), 187-194. doi:10.1016/j.bse.2009.12.010 Laird, D. W., Poole, R., Wikström, M., & Van Altena, I. A. (2007). Pycnanthuquinone C, an unusual 6,6,5-tricyclic geranyltoluquinone from the western australian brown alga cystophora harveyi. Journal of Natural Products, 70(4), 671-674. doi:10.1021/np060566m Laird, D. W., & van Altena, I. A. (2006). Tetraprenyltoluquinols from the brown alga cystophora fibrosa. Phytochemistry, 67(10), 944-955. doi:10.1016/j.phytochem.2006.03.011 Miyaoka, H., Shinohara, M., Shimomura, M., Mitome, H., Yano, A., Iguchi, K., & Yamada, Y. (1997). Aragusterols E-H, new 26,27-cyclosterols from the okinawan marine sponge of the genus xestospongia and absolute configurations of xestokerols A and B. Tetrahedron, 53(15), 5403-5412. doi:10.1016/S0040-4020(97)00231-7 Saez, J., Cardona, W., Espinal, D., Blair, S., Mesa, J., Bocar, M., & Jossang, A. (1998). Five new steroids from solanum nudum. Tetrahedron, 54(36), 10771-10778. doi:10.1016/S0040-4020(98)00632-2 Sheu, J. -., Wang, G. -., Sung, P. -., & Duh, C. -. (1999). New cytotoxic oxygenated fucosterols from the brown alga turbinaria conoides. Journal of Natural Products, 62(2), 224-227. doi:10.1021/np980233s Steinberg, P. D., & Van Altena, I. (1992). Tolerance of marine invertebrate herbivores to brown algal phlorotannins in temperate australasia. Ecological Monographs, 62(2), 189-222. doi:10.2307/2937093 van Altena, I. A. (1988). Terpenoids from the brown alga cystophora moniliformis. Australian Journal of Chemistry, 41(1), 49-56. doi:10.1071/CH9880049 Womersley, H. B. S. (1987). The Marine Benthic Flora of Southern Australia.Part II, Retrieved from www.scopus.com Wu, S. -., Ji, Y. -., Zhu, J. -., Zhao, Y., Xia, G., Hu, Y. -., & Hu, J. -. (2009). Steroids from the leaves of chinese melia azedarach and their cytotoxic effects on human cancer cell lines. Steroids, 74(9), 761-765. doi:10.1016/j.steroids.2009.04.005 |
| This material may be protected under Copyright Act which governs the making of photocopies or reproductions of copyrighted materials. You may use the digitized material for private study, scholarship, or research. |