Chemical constituents and bioactive secondary metabolites from soft corals
Soft corals (phylum Cnidaria, class Anthozoa, subclass Octocorallia) are found worldwide, more in tropical coral reefs as compared to the temperate coral reefs. Unlike Scleractinian coral, soft coral does not have internal calcium carbonate skeleton. Therefore, soft coral contains chemical compounds...
Saved in:
Main Author: | |
---|---|
Format: | Thesis |
Language: | English English |
Published: |
2010
|
Subjects: | |
Online Access: | https://eprints.ums.edu.my/id/eprint/6526/1/mt0000000176.pdf https://eprints.ums.edu.my/id/eprint/6526/7/Chemical%20Constituents%20And%20Bioactive%20Secondary%20Metabolites%20From%20Soft%20Corals.pdf |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
id |
my-ums-ep.6526 |
---|---|
record_format |
uketd_dc |
institution |
Universiti Malaysia Sabah |
collection |
UMS Institutional Repository |
language |
English English |
topic |
QL Zoology |
spellingShingle |
QL Zoology Lim, Chen Fong Chemical constituents and bioactive secondary metabolites from soft corals |
description |
Soft corals (phylum Cnidaria, class Anthozoa, subclass Octocorallia) are found worldwide, more in tropical coral reefs as compared to the temperate coral reefs. Unlike Scleractinian coral, soft coral does not have internal calcium carbonate skeleton. Therefore, soft coral contains chemical compounds in their body tissues, which are known as secondary metabolites that play an important role in their defense, and some of them also exhibited pharmacological activity. Research was carried out on four populations of Dendronephthya sp. from Sepanggar Island and one population of Lobophytum sp. from Banggi Island. Samples were extracted to obtain their crude extracts and chemical profiling of these extracts were carried out. Dendronephthya sp. with spiky morphology was found to contain very little secondary metabolites, with morphology similarity among the species and was not easily identified in the field. Further, microscopy studies were done using stereomicroscope and Scanning Electron Microscope (SEM). Observation showed differences in arrangement of spikes among the species. Dendronephthya Spl and Sp2 had similar morphology while spike arrangement of Dendronephthya Sp3 and Sp4 were different from Spl and Sp2. Samples were also subjected to extraction and only the primary metabolites were successfully isolated. Sterols isolated from every sample showed the same HPLC spectrum. Fatty acids, which were another isolate of these specimens, were analyzed using cluster analyses and presented in dendrogram. Dendrograms of monounsaturated fatty acids (MUFAs), polyunsaturated fatty acids (PUFAs) and selected fatty acids biomarker (C15: 1, C18:1n9t, C18:1n9c, C24:1, C18:2n6t, C18:3n3, C22:6n3) showed that Dendronephthya Spl and Sp2 had the closest correlation followed by Sp3 and then Sp4. These results were similar to the findings from microscopy observation. Therefore, fatty acids can be used as chemotaxonomy biomarker for these particular four populations of Dendronephthya sp. Sterols isolated from these Dendronephthya sp could be used as a "finger-print" profile in identification of this genus. Meanwhile, the Lobophytum sp. showed numerous secondary metabolites from the chemical profile. Based on the chemical profiles, extracts of Lobophytum were subjected to isolation of their pure metabolites. Four pure metabolites were isolated and each of the metabolites was tested for their antibacterial activities. Three metabolites from Lobophytum sp. showed positive results against five marine environmental bacteria and two human pathogenic bacterium. Apart from that, all the metabolites tested showed insignificant antioxidant activities. Isolated metabolites were subjected to spectroscopic analysis and their structures were determined to be cembrene. Out of the four cembrenes from this Lobophytum sp., three were found to be novel. |
format |
Thesis |
qualification_level |
Master's degree |
author |
Lim, Chen Fong |
author_facet |
Lim, Chen Fong |
author_sort |
Lim, Chen Fong |
title |
Chemical constituents and bioactive secondary metabolites from soft corals |
title_short |
Chemical constituents and bioactive secondary metabolites from soft corals |
title_full |
Chemical constituents and bioactive secondary metabolites from soft corals |
title_fullStr |
Chemical constituents and bioactive secondary metabolites from soft corals |
title_full_unstemmed |
Chemical constituents and bioactive secondary metabolites from soft corals |
title_sort |
chemical constituents and bioactive secondary metabolites from soft corals |
granting_institution |
Universiti Malaysia Sabah |
granting_department |
Borneo Marine Research Institute |
publishDate |
2010 |
url |
https://eprints.ums.edu.my/id/eprint/6526/1/mt0000000176.pdf https://eprints.ums.edu.my/id/eprint/6526/7/Chemical%20Constituents%20And%20Bioactive%20Secondary%20Metabolites%20From%20Soft%20Corals.pdf |
_version_ |
1747836326354354176 |
spelling |
my-ums-ep.65262020-12-02T07:32:43Z Chemical constituents and bioactive secondary metabolites from soft corals 2010 Lim, Chen Fong QL Zoology Soft corals (phylum Cnidaria, class Anthozoa, subclass Octocorallia) are found worldwide, more in tropical coral reefs as compared to the temperate coral reefs. Unlike Scleractinian coral, soft coral does not have internal calcium carbonate skeleton. Therefore, soft coral contains chemical compounds in their body tissues, which are known as secondary metabolites that play an important role in their defense, and some of them also exhibited pharmacological activity. Research was carried out on four populations of Dendronephthya sp. from Sepanggar Island and one population of Lobophytum sp. from Banggi Island. Samples were extracted to obtain their crude extracts and chemical profiling of these extracts were carried out. Dendronephthya sp. with spiky morphology was found to contain very little secondary metabolites, with morphology similarity among the species and was not easily identified in the field. Further, microscopy studies were done using stereomicroscope and Scanning Electron Microscope (SEM). Observation showed differences in arrangement of spikes among the species. Dendronephthya Spl and Sp2 had similar morphology while spike arrangement of Dendronephthya Sp3 and Sp4 were different from Spl and Sp2. Samples were also subjected to extraction and only the primary metabolites were successfully isolated. Sterols isolated from every sample showed the same HPLC spectrum. Fatty acids, which were another isolate of these specimens, were analyzed using cluster analyses and presented in dendrogram. Dendrograms of monounsaturated fatty acids (MUFAs), polyunsaturated fatty acids (PUFAs) and selected fatty acids biomarker (C15: 1, C18:1n9t, C18:1n9c, C24:1, C18:2n6t, C18:3n3, C22:6n3) showed that Dendronephthya Spl and Sp2 had the closest correlation followed by Sp3 and then Sp4. These results were similar to the findings from microscopy observation. Therefore, fatty acids can be used as chemotaxonomy biomarker for these particular four populations of Dendronephthya sp. Sterols isolated from these Dendronephthya sp could be used as a "finger-print" profile in identification of this genus. Meanwhile, the Lobophytum sp. showed numerous secondary metabolites from the chemical profile. Based on the chemical profiles, extracts of Lobophytum were subjected to isolation of their pure metabolites. Four pure metabolites were isolated and each of the metabolites was tested for their antibacterial activities. Three metabolites from Lobophytum sp. showed positive results against five marine environmental bacteria and two human pathogenic bacterium. Apart from that, all the metabolites tested showed insignificant antioxidant activities. Isolated metabolites were subjected to spectroscopic analysis and their structures were determined to be cembrene. Out of the four cembrenes from this Lobophytum sp., three were found to be novel. 2010 Thesis https://eprints.ums.edu.my/id/eprint/6526/ https://eprints.ums.edu.my/id/eprint/6526/1/mt0000000176.pdf text en public https://eprints.ums.edu.my/id/eprint/6526/7/Chemical%20Constituents%20And%20Bioactive%20Secondary%20Metabolites%20From%20Soft%20Corals.pdf text en validuser masters Universiti Malaysia Sabah Borneo Marine Research Institute Aceret, T. L., Brown, L., Miller, J., Coli, J. C. and Sammarco, P. W. 1996. Cardiac and Vascular Responses of Isolated Rat Tissues Treated with Diterpenes from Sinularia flexibilis (Coelenterata:Octocorallia). Toxicon. 34:10, 1165- 1171. Aceret, T. L, Coli, J. C., Uchio, Y. and Sammarco, P. W. 1998. Antimicrobial activity of the diterpenes flexibilide and sinulariolide derived from Sinularia flexibilis QUoy and Gaimard 1833 (Coelenterata: Alcyonacea, Octocorallia). Comparative Biochemistry and Physiology Part C 120, 121-126. Ahmed, A. F., Shiue, R. T., Wang, G. H., Dai, C. F., Kuo, Y. H. and Sheu, J. H. 2003. Five novel noecembranoids from Sinularia leptoclados and s.parva. Tetrahedron. 59, 7337-7344. Ahmed, A. F., Su, J. H., Shiue, r. T., Pan, X. J., Dai, C. F., Kuo, Y. H. and Sheu, J. H. 2004. New I3-Caryophyllene-derived Terpenoids from the Soft Coral Sinularia nanolobata. Journal of Natural Product. 67, 592-597. Anjaneyulu, A. S. R., Sagar, K. S. and Venugopal, M. J. R. V. 1995. Terpenoid and Steroid Constiuents of the Indian Ocean Soft Coral Sinularia maxima. Tetrahedron. 51:40, 10997-11010. Badria, F. A., Guirguis, A. N., Perovic, S. Steffen, R., Muller, W. E. G. and Schroder, H. C. 1998. Sarcophytolide: a new neuroprotective compound from the soft coral Sarcophyton glaucum. Toxicology. 131, 133-143. Berge, J. P. and Barnatham, G. 2005. Fatty acids from lipids of marine organisms: molecular biodiversity, roles as biomakers, biologically active compounds and economical aspects. Advance Biochemical Engineering/Biotechnology. 96,49-125. Bowden, B. F., Coli, J. c., Costa, M. S. lo, Mackay, M. F., Mahendran, M., Silva, E. D. and Willis, R. H. 1984. The Structure Determination of a New Cembranolide Diterpene from the Soft Coral Lobophytum cristigalli (Coelentrata, Octocorallia, Alcyonacea). Australia Journal of Chemistry. 31, 545-552. Bowden, B. F., Coli, J. c., Liyanage, N., Mitchell, S. J., Stokie, G. J. and Van Altena, I. A. 1978. Studies of Australian Soft Corals IV from Lobophytum hedley;' Australia Journal of Chemistry. 31, 163-170. Christian, G.D. 1994. Analytical Chemistry. 5th edition. John Wiley & Sons, New York. Coli, J. c., Mitchell, S. J. and Stokie, G. J. 1977. Studies of Australia Soft Crals. II* A Novel Cembrenoid Diterpene from Lobophytum michaelae. Australia Journal Chemical. 30, 1859-1863. Dahan, M. and Benayahu, Y. 1997. Clonal propagation of the azooxanthellate octocoral Dendronephthya hemprichi. Coral Reefs. 16, 5-12. Donia, M. and Hamann, M. T. 2003. Marine natural products and their potential applications as antiinfective agents. The Lancet 3, 338-348. Duh, C. Y., Chien, S. c., Song, P. Y., Wang, S. K., EI-Gamal, A. a. H. and Dai, C. F. 2002a. New Cadinene Sesquiterpenoids from the Formosan Soft Coral Xenia Puerto-galarae. Jounal of Natural Product. 65, 1853-1856. Duh, C. Y., EI-Gamal, A. A. H., Chiang, C. Y., Chu, C. J., Wang, S. K. and Dai, C. F. 2002. New Cytotoxic Xenia Diterpenoids from the Formosan Soft Coral Xenia umbellate. Journal of Natural Product. 65,1882-1885. EI-Gamal, A. A. H., Wang, S. K. and Duh, C. Y. 2005. Xenibellal, a novel norditerpenoid from the Formosan soft coral Xenia umbellate. Tetrahedron Letters. 46, 4499-4500. Fabricius, K. and Alderslade, P. 2001. Soft Corals and Sea Fans : A comprehensive guide to the tropical shallow water genera of the central-west Pacific, the Indian Ocean and the Red Sea. Australian Institute of Marine Science. Fabricius, K. E., Benayahu, Y. and Genin, A. 1995. Herbivory in asymbiotic soft corals. Science. 268, 90-92. Goud, T. V., Reddy, N. S., Krishnaiah, P. and Venkateswarlu, Y. 2002. Spathulenol: a rare sesquiterpene from soft coral Sinularia kavarattiensis. Biochemical Systematics and Ecology. 30, 493-495. Haefner, B. 2003. Drugs from the Deep. Drug Discovery Today. 8, 536-544. Harvey, A. 2000. Strategies for discovering drugs from previously unexplored natural products. Drug Discovery Today. 5, 294-300. Hay, M. E. 1996. Marine chemical ecology: What's known and what's next? Journal of Experimental Marine Biology and Ecology. 200, 103-121. Hogg, R. W. and Gillan, F. T. 1984. Fatty acids, sterols and hydrocarbons in the leaves from eleven species of mangrove. Phytochemistry. 23: 1, 93-97. Iguchi, K., Nishimura, K., Yamazaki, K., Iwashima, M. and Yamada. Y. 1992. New cembranolide Diterpenes with a Dimethylamino Group from the Okinawan Soft Coral (Sinularia sp.). Chemistry Letters. 1, 127-130. Iwashima, M., Matsumoto, Y., Takenaka, Y., Iguchi, K., Yamori, T. 2002. New marine diterpenoids from Okinawan Soft Coral Clavularia koellikeri. Journal Natural Product. 65, 1441-1446. Iwagana, T., Nakamura,S., Masuda, T., Okamura, H., Nakatani, M. and Siro, M. 1995. Irregular cembranoids containing a 13-membered carbocyclic Skeleton Isolated from a Soft Coral, Sacrophyton species. Tetrahedron. 51:18, 5291-5298. Jha, R. K. and Xu, l. 2004. Biomedical Compounds from Marine Organisms. Marine Drugs. 2, 123-146. Khotimchenko, S. V. 1991. Fatty acid composition of seven Sargassum species. Phytochemistry. 30(8), 2639-2641. Li, X., Fan,X., Han, L. and lou, Q. 2002. Fatty acids of some algae from the Bohai Sea. Phytochemistry. 59, 157-161. Liu, l., Li, W. l., Peng, L., Li, Y. and Li, Y. 2000. First anantio selective total synthesis of (natural) (+ )-l1,12-epoxy-ll,12-dihydrocembrene-C and (-)- 7,8-epoxy-7,8-dihydrocembrene-C. Journal of Chemical Society, Perkin Trans. 1, 4250-4257. McCarthy, P. J. and Pomponi, A. A. 2004. A search for new Pharmaceutical Drugs from marine organisms. Marine Biomedical Research. 1-2. Mokbel, M. S. and Hashinaga. 2005. Antibacterial and antioxidant activities of banana (Musa, AAA 01. Cavendish) fruits peel. American Journal of Biochemistry and Biotechnology. 1:3, 126-132. NCCLS (National Committee for Clinical laboratory Standards). 2003. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standards. NCCLS Document M7-A6, Wayne. Pawlik, J. R. 1993. Marine invertebrate chemical defense. Chem. Review. 93, 1911- 1916. Radhika, P. Rao, P. V. S., Anjaneyulu, V., Asolkar, R.A. and Laatsch, H. 2002. Horiolide, a Novel Norditerpenoid from Indian Ocean Soft Coral of the Genus Sinularia. Journal of Natural Product. 65, 737-739. Shan, B., Cai, Y.Z., Brooks, J.D. and Corke, H. 2008. Antibacterial properties of Polygonum cuspidatum roots and their major bioactive constituents. Food Chemistry. 109, 530-537 Shen, Y. c., Cheng, Y. B., Lin, Y. c., Guh, J. H., Teng, C. M. and Koh, C. L. 2004. New prostanoids with cytotoxic activity from Taiwanese octocoral Clavularia viridis. Journal of Natural Product. 67, 542-546. Sheu, J. H., Ahmed, A. F., Shiue, R. T., Dai, C. F. and Kuo, Y. K. 2002. Scabrolides A-D, Four New Norditerpenoids Isolated from the Soft Coral Sinularia scabra. Journal of Natural Product. 65, 1904-1908. Sheu, J. H., Wang, G. H., Duh, C. Y. and Soong, K. 2003. Pacyclavulariolides M-R, Six Novel Diterpenoids from a Taiwanese Soft Coral Pacyc/avularia violacea. Journal of Natural Product. 66, 662-666. Sheu, J. H., Wang, G. H., Sung, P. J., Duh, C. Y. and Chiang, M. Y. 200l. Pachyclavulariolides G-L and secopachyclavulariaenone A, seven novel diterpenoids from the soft coral Pachyc/avularia violacea. Tetrahedron. 57, 7639-7648. Subrahmanyam, C., Rao, C. v., Anjaneyulu, V., Satyanarayana, P. and Rao, P. V. S. 1992. New diterpenes from a new species of Lobophytum soft coral of the south Andaman Coast. Tetrahedron. 48:15, 3111-3120. Suleimenova, A. M., Kuznetsova, T. A., Denisenko, V. A., Gorshkova, I. A. and Elyakov G. B. 1991. Cembrenolides of a Soft Coral Lobophytum sp .. Plenum Publishing Corporation. 647. Uchio, Y., Eguchi, S., Kuramoto, J., Nakayama, M. and Hase, T. 1985. Denticulatolide, an ichthyotoxic peroxide-containing cembranolide from soft coral Lobophytum denticulatum. Tetrahedron Letters. 26:3737,4487-4490. Uchio, Y., Toyota, J., Nozaki, H., Nakayama, M. 1981. Lobohedleolide and (7Z) Lobohedleolide, new cembranolides from the soft coral Lobophytum hedleyi Whitelegge. Tetrahedron Letters. 22, 4089-4092. Vairappan, C. S., Daitoh,M., Suzuki, M., Abe, T. and Masuda, M. 2001. Antibacterial halogenated metabolites from the Malaysian Laurencia species. Phytochemistry. 58, 291-297. Vairappan, C.S., Sangeetha, A.P., Matsunaga, S. 2009. Diet derived halogenated metabolite from Sea Hare Aplysia palVula. Malaysian Journal of Science. 28{3}, 269-274. Vairappan, C. S., Suzuki, M.,Kawamoto, T., Ishii, T., Abe, T. and Masuda, M. 2005. Halogenated metabolites from Japanese Laurencia spp. Phytochemistry. 66, 2787-2793. Vaskovsky, V. E., Khotimchenko, S. V., Xia, B. and Hefang, L. 1996. Polar lipids and fatty acids of some marine macrophytes from the Yellow Sea. Phytochemistry. 42:5, 1347-1356. Wang, G. H., Sheu, J. H., Duh, C. Y. and Chiang, M. Y. 2002. Pacyclavulariaenones D-G, New Diterpenoids from the Soft Coral Pachyc/avularia violacea. Journal of Natural Product. 65, 1475-1478. Watanabe, K., Sekine, M., Takahashi, H. and Iguchi, K. 2001. New Halogennated marine prostanoids with cytotoxic activity from the Okinawan soft coral Clavularia viridis. Journal of Natural Product 64, 1421-1425. Yamada, K., Ryu, K., Miyamoto, T., Higuchi, R. 1997. Bioactive terpenoids from Octocorallia. Three new cembrane type diterpenoids from soft coral Lobophytum schoedei. Journal Natural Product. 60, 798-801. Yamada, Y., Suzuki, S. and Iguchi, K. 1980. Studies on marine natural products IV the stereochemistry of 13-membered carbocyclic cembranolide diterpenes from the soft coral Lobophtyum pauciflorum (Ehrenberg). Tetrahedron Letters. 21, 3911-3914. Zhang, W. H., Williams, I. D. and Che, C. T. 2001. Chabrolols A, Band C, three new norditerpenes from soft coral Nepthea chabroli. Tetrahedron Letters. 42, 4681-4685. |