Isolation And Structure Elucidation Of Bioactive Secondary Metabolites From Indonesian Marine Sponges

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A total of 35 compounds comprising diverse structural groups of compounds including both alkaloids and terpenes were isolated; fourteen of which are new derivatives. The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, 1H-detected direct and long range 13C-1H correlations) and mass spectrometric (EI, and ESI) data. The identities of the known compounds were established by comparison with published data. Sponge samples originated from several collection sites in Indonesia. A combination of a chemically-and biologically driven approach for drug discovery was employed. Extracts were screened for antibacterial, antifungal, and cytotoxic activities as well as protein kinase inhibition parallel to the usage of TLC, and HPLC coupled to UV and MS in the isolation of the chemically most interesting substances. Enumerated below are the compounds which have been isolated and structurally elucidated and whose bioactivities have been further characterized. 1. Agelas n.sp. secondary metabolites Extract of the unidentified Agelas sponge from Peniki East Island (Seribu Islands), Jakarta, yielded sixteen structurally related brominated pyrroles, including eleven new congeners. Diverse structures of the brominated pyrroles are elucidated wherein several new functionalities are shown to be introduced in the molecule such as in agelanin A (2), agelanin B (3), and agelanesins (4 to 7). Pronounced cytotoxicity against mouse lymphoma cell (L5178Y) was shown by all agelanesins. The tyramine moiety must be responsible for the cytotoxic activity since other congeners without the tyramine unit displayed no cell-growth inhibition. Less degree of bromination on the pyrrole ring may also play a role in its cytotoxicity, considering that the monobrominated pyrrole-agelanesins, agelanesin A (4) and B (5) display lower IC50 in comparison to their dibrominated congeners, agelanesin C (6) and D (7). The iodine substituent presumably is not important for the cytotoxicity. 2. Agelas nakamurai secondary metabolites Extract of the sponge Agelas nakamurai collected in Menjangan Island, yielded five monobrominated pyrrole derivatives, one of which is found to be a new congener, longamide C (20). A hypotaurocyamine diterpenoid, (+)-agelasidine C (19) was isolated together along with adenine related compounds, adenosine and 9-methyladenine as well as the new diterpenoids derivatves, (-)-agelasine-D (18) and its congener (-)-ageloxime-D (17). (-)-Agelasine D, (-)-ageloxime D and (+)-agelasidine-C exhibit prominent cytotoxicity towards the mouse lymphoma cell line L5178Y. Biofilm inhibition assay done on (-)-agelasine D, (-)-ageloxime D, (+)-agelasidine C as well as on (-)-agelasine I suggests that the diterpene part is important for the activity together with the adeninium part. Between the (-)-agelasine D and (-)-ageloxime D, the amine unit on C-6’ is important for the antibacterial activity. A replacement of the amine unit with an oxime group as in the ageloxime D will displace the antibacterial activity but on the other hand will inhibit biofilm-formation of S. epidermidis. Both (-)-agelasine-D and (-)-ageloxime D were toxic to the cyprids larva of Balanus improvisus Darwin, where (-)-ageloxime D was approximately 10 times more toxic than (-)-agelasine D. 3. Pseudoceratina purpurea secondary metabolites Extract of the sponge Pseudoceratina purpurea collected in Watudodol, Banyuwangi, yielded five brominated tyrosine derivatives. The presence of the antifouling substance, aplysamine-2 (27) as well as isofistularin-3-bioconversion products, (+)-aeroplysinin-1 (28), bisoxazolidinone derivatives (29), together with the dienone ketal congeners 30 and 31 were identified. 4. Axynissa sp. secondary metabolites Search on bioactive compounds as protein kinase inhibitors has lead to the isolation of two bisabolene phenol derivatives, (+)-curcuphenol (33) and (+)-curcudiol (34) in the active fractions of Axynissa sp. collected from Ambon, Maluku. 5. Mycale phyllophyla secondary metabolites Study on the sponge extract Mycale phyllophyla collected from Menjangan Island, Bali, revealed the presence of 5-pentadecyl-1H-pyrrole-2-carbaldehyde derivatives (32a) together with (E)-5-pentadec-6-enyl-1H-pyrrole-2-carbaldehyde (32b) in a cytotoxic active fraction. 6. Rhabdastrella rowi secondary metabolite The quinolin-4-ol (35) was obtained from the Balinese marine sponge Rhabdastrella rowi extract in minute quantity. Up to now this compound has only been obtained synthetically and has never been reported from natural sources.

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Genre : Medical
Author : Triana Hertiani
Publisher : Cuvillier Verlag
Release : 2007-08-14
File : 344 Pages
ISBN-13 : 9783736923270


Secondary Metabolites From Marine Sponges

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A comprehensive review of literature published during the last five years, covering the chemistry, biosysthesis, synthetic studies and the diverse physiological properties of marine sponge metabolites in general, and detailed studies on the potential cytotoxic and anti-HIV properties of avarol and avarone from the sponge genus Dysidea.

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Genre : Biological products
Author : Aluru S. Sarma
Publisher :
Release : 1993
File : 182 Pages
ISBN-13 : UCSD:31822016271157


Marine Sponges Chemicobiological And Biomedical Applications

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The main focus of this book entitled is to provide an up-to-date coverage of marine sponges and their significance in the current era. This book is an attempt to compile an outline of marine sponge research to date, with specific detail on these bioactive compounds, and their pharmacological and biomedical applications. The book encompasses twenty chapters covering various topics related to Marine Sponges. Initial couple of chapters deal about the worldwide status of marine sponge research, the recent findings regarding dynamics of sponges, and several interesting research areas, that are believed to be deserving of increased attention. Variety of sponges, their toxicology, metagenomics, pharmaceutical significance and their possible applications in biomedicine has been discussed in detail. The second half of this part includes chapters on chemical ecology of marine sponges followed by the discussion on importance of bioeroding sponges in aquaculture systems. The following four chapters of the book deal majorly with the chemical molecules of marine sponges. In the fifth chapter, marine sponge-associated actinobacteria and their pysicochemical properties have been discussed followed by their bioactive potential. The biological application of marine sponges has been presented in later chapters with the classification of biologically active compounds being explored in detail. The second half of the book presents the vast repertoire of secondary metabolites from marine sponges, which include terpenoids, heterocycles, acetylenic compounds, steroids and nucleosides. Further, the bioactive potential of these compounds has also been discussed. One of the constituent chapter elaborates the bioactive alkaloids from marine sponges namely, pyridoacridine, indole, isoquinolene, piperidene, quinolizidine, steroidal and bromotyrosine alkaloids isolated from them. In the next couple of chapters, important sponge polymers and the anticancer effects of marine sponge compounds have been presented. The most interesting aspect of sponge biology is their use in biomedical arena. An effort has been made in this book, to cover the major constituents of sponges and their biomedical potentials. The major portion of sponge body is composed of collagen and silica and used in tissue engineering as scaffold material. This part of the book compiles chapters delineating the isolation of sponge biomaterials including collagen and their use in medical diagnostics. Overall, this book would be an important read for novice and experts in the field of sponge biology.

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Genre : Science
Author : Ramjee Pallela
Publisher : Springer
Release : 2016-11-17
File : 383 Pages
ISBN-13 : 9788132227946


New Metabolites From Marine Sponges

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Genre : Biology
Author : D. J. Faulkner
Publisher :
Release : 1993
File : Pages
ISBN-13 : OCLC:1313682089


Chemistry Under The Sea

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Genre :
Author : Christopher John Wegerski
Publisher :
Release : 2007
File : 502 Pages
ISBN-13 : UCAL:X77841


Novel Secondary Metabolites From Marine Sponges And Sponge Associated Fungi

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Genre : Fungi
Author : Samuel Sperry
Publisher :
Release : 1998
File : 552 Pages
ISBN-13 : UCAL:X63534


Isolation And Structure Elucidation Of Bioactive Secondary Metabolites From Marine Sponges And Sponge Derived Fungi

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Genre : Metabolites
Author : Raquel C. Jadulco
Publisher : Cuvillier Verlag
Release : 2002
File : 174 Pages
ISBN-13 : 3898735605


Chemical Ecological Insights Into Metabolites Of The New Zealand Marine Sponge Cliona Celata

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Genre : Chemical ecology
Author : Nicola G. Webb
Publisher :
Release : 2015
File : 90 Pages
ISBN-13 : OCLC:982030147


Secondary Metabolites From The New Zealand Marine Sponge Mycale Hentscheli

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Genre : Marine metabolites
Author : Ameet Jonathan Singh
Publisher :
Release : 2007
File : 254 Pages
ISBN-13 : OCLC:174108184


The Isolation Of Secondary Metabolites From New Zealand Marine Sponges

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Genre : Bioactive compounds
Author : Lyndon Michael West
Publisher :
Release : 2001
File : 500 Pages
ISBN-13 : OCLC:155448528