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Relevant bibliographies by topics / Marine sponges; Alkaloids; Vasodilators

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Academic literature on the topic 'Marine sponges; Alkaloids; Vasodilators'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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Journal articles on the topic "Marine sponges; Alkaloids; Vasodilators"

1

Sfecci, Estelle, Thierry Lacour, Philippe Amade, and Mohamed Mehiri. "Polycyclic Guanidine Alkaloids from Poecilosclerida Marine Sponges." Marine Drugs 14, no. 4 (April 9, 2016): 77. http://dx.doi.org/10.3390/md14040077.

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Yasuda, Tetsuro, Atsushi Araki, Takaaki Kubota, Junji Ito, Yuzuru Mikami, Jane Fromont, and Jun’ichi Kobayashi. "Bromopyrrole Alkaloids from Marine Sponges of the GenusAgelas⊥." Journal of Natural Products 72, no. 3 (March 27, 2009): 488–91. http://dx.doi.org/10.1021/np800645q.

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Laville, Rémi, Olivier P. Thomas, Fabrice Berrué, Diana Marquez, Jean Vacelet, and Philippe Amade. "Bioactive Guanidine Alkaloids from Two Caribbean Marine Sponges." Journal of Natural Products 72, no. 9 (September 25, 2009): 1589–94. http://dx.doi.org/10.1021/np900244g.

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Elissawy, Ahmed M., Ebrahim Soleiman Dehkordi, Negin Mehdinezhad, Mohamed L. Ashour, and Pardis Mohammadi Pour. "Cytotoxic Alkaloids Derived from Marine Sponges: A Comprehensive Review." Biomolecules 11, no. 2 (February 10, 2021): 258. http://dx.doi.org/10.3390/biom11020258.

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Marine sponges (porifera) have proved to be a prolific source of unique bioactive secondary metabolites, among which the alkaloids occupy a special place in terms of unprecedented structures and outstanding biological activities. Identification of active cytotoxic alkaloids extracted from marine animals, particularly sponges, is an important strive, due to lack of knowledge on traditional experiential and ethnopharmacology investigations. In this report, a comprehensive survey of demospongian bioactive alkaloids in the range 1987–2020 had been performed with a special emphasis on the potent cytotoxic activity. Different resources and databases had been investigated, including Scifinder (database for the chemical literature) CAS (Chemical Abstract Service) search, web of science, Marin Lit (marine natural products research) database. More than 230 representatives of different classes of alkaloids had been reviewed and classified, different genera belonging to the phylum porifera had been shown to be a prolific source of alkaloidal molecules, including Agelas sp., Suberea sp., Mycale sp., Haliclona sp., Epipolasis sp., Monanchora sp., Crambe sp., Reniera sp., and Xestospongia sp., among others. The sufficient production of alkaloids derived from sponges is a prosperous approach that requires more attention in future studies to consider the constraints regarding the supply of drugs, attained from marine organisms.

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Tanaka, Naonobu, Rei Momose, Azusa Takahashi-Nakaguchi, Tohru Gonoi, Jane Fromont, and Jun'ichi Kobayashi. "Hyrtimomines, indole alkaloids from Okinawan marine sponges Hyrtios spp." Tetrahedron 70, no. 4 (January 2014): 832–37. http://dx.doi.org/10.1016/j.tet.2013.12.032.

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Tanaka, N., T. Kusama, Y. Kashiwada, and J. Kobayashi. "Agelamadins, bromopyrrole alkaloids from Okinawan marine sponges Agelas spp." Planta Medica 81, S 01 (December 14, 2016): S1—S381. http://dx.doi.org/10.1055/s-0036-1596645.

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Lee, Sanghoon, Naonobu Tanaka, Sakura Takahashi, Daisuke Tsuji, Sang-Yong Kim, Mareshige Kojoma, Kohji Itoh, Jun’ichi Kobayashi, and Yoshiki Kashiwada. "Agesasines A and B, Bromopyrrole Alkaloids from Marine Sponges Agelas spp." Marine Drugs 18, no. 9 (August 30, 2020): 455. http://dx.doi.org/10.3390/md18090455.

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Exploration for specialized metabolites of Okinawan marine sponges Agelas spp. resulted in the isolation of five new bromopyrrole alkaloids, agesasines A (1) and B (2), 9-hydroxydihydrodispacamide (3), 9-hydroxydihydrooroidin (4), and 9E-keramadine (5). Their structures were elucidated on the basis of spectroscopic analyses. Agesasines A (1) and B (2) were assigned as rare bromopyrrole alkaloids lacking an aminoimidazole moiety, while 3–5 were elucidated to be linear bromopyrrole alkaloids with either aminoimidazolone, aminoimidazole, or N-methylated aminoimidazole moieties.

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Li, Fengjie, Michelle Kelly, and Deniz Tasdemir. "Chemistry, Chemotaxonomy and Biological Activity of the Latrunculid Sponges (Order Poecilosclerida, Family Latrunculiidae)." Marine Drugs 19, no. 1 (January 9, 2021): 27. http://dx.doi.org/10.3390/md19010027.

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Marine sponges are exceptionally prolific sources of natural products for the discovery and development of new drugs. Until now, sponges have contributed around 30% of all natural metabolites isolated from the marine environment. Family Latrunculiidae Topsent, 1922 (class Demospongiae Sollas, 1885, order Poecilosclerida Topsent, 1928) is a small sponge family comprising seven genera. Latrunculid sponges are recognized as the major reservoirs of diverse types of pyrroloiminoquinone-type alkaloids, with a myriad of biological activities, in particular, cytotoxicity, fuelling their exploration for anticancer drug discovery. Almost 100 pyrroloiminoquinone alkaloids and their structurally related compounds have been reported from the family Latrunculiidae. The systematics of latrunculid sponges has had a complex history, however it is now well understood. The pyrroloiminoquinone alkaloids have provided important chemotaxonomic characters for this sponge family. Latrunculid sponges have been reported to contain other types of metabolites, such as peptides (callipeltins), norditerpenes and norsesterpenes (trunculins) and macrolides (latrunculins), however, the sponges containing latrunculins and trunculins have been transferred to other sponge families. This review highlights a comprehensive literature survey spanning from the first chemical investigation of a New Zealand Latrunculia sp. in 1986 until August 2020, focusing on the chemical diversity and biological activities of secondary metabolites reported from the family Latrunculiidae. The biosynthetic (microbial) origin and the taxonomic significance of pyrroloiminoquinone related alkaloids are also discussed.

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Li, Fengjie, Michelle Kelly, and Deniz Tasdemir. "Chemistry, Chemotaxonomy and Biological Activity of the Latrunculid Sponges (Order Poecilosclerida, Family Latrunculiidae)." Marine Drugs 19, no. 1 (January 9, 2021): 27. http://dx.doi.org/10.3390/md19010027.

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Marine sponges are exceptionally prolific sources of natural products for the discovery and development of new drugs. Until now, sponges have contributed around 30% of all natural metabolites isolated from the marine environment. Family Latrunculiidae Topsent, 1922 (class Demospongiae Sollas, 1885, order Poecilosclerida Topsent, 1928) is a small sponge family comprising seven genera. Latrunculid sponges are recognized as the major reservoirs of diverse types of pyrroloiminoquinone-type alkaloids, with a myriad of biological activities, in particular, cytotoxicity, fuelling their exploration for anticancer drug discovery. Almost 100 pyrroloiminoquinone alkaloids and their structurally related compounds have been reported from the family Latrunculiidae. The systematics of latrunculid sponges has had a complex history, however it is now well understood. The pyrroloiminoquinone alkaloids have provided important chemotaxonomic characters for this sponge family. Latrunculid sponges have been reported to contain other types of metabolites, such as peptides (callipeltins), norditerpenes and norsesterpenes (trunculins) and macrolides (latrunculins), however, the sponges containing latrunculins and trunculins have been transferred to other sponge families. This review highlights a comprehensive literature survey spanning from the first chemical investigation of a New Zealand Latrunculia sp. in 1986 until August 2020, focusing on the chemical diversity and biological activities of secondary metabolites reported from the family Latrunculiidae. The biosynthetic (microbial) origin and the taxonomic significance of pyrroloiminoquinone related alkaloids are also discussed.

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Bjoersvik, Hans-Rene, and Alexander H. Sandtorv. "ChemInform Abstract: Synthesis of Imidazole Alkaloids Originated in Marine Sponges." ChemInform 45, no. 42 (October 2, 2014): no. http://dx.doi.org/10.1002/chin.201442268.

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Dissertations / Theses on the topic "Marine sponges; Alkaloids; Vasodilators"

1

Firkin, Catherine R. "A biomimetic approach to the synthesis of xestospongin A." Thesis, University of Oxford, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.389208.

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Segraves, Nathaniel Lee. "Chemical investigation of biologically active alkaloids from marine sponges /." Diss., Digital Dissertations Database. Restricted to UC campuses, 2005. http://uclibs.org/PID/11984.

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Romeril, Stuart P. "Synthesis and structural elucidation of the Bis-3-alkylpyridine alkaloid pyrinodemin A and other monomeric alkaloids." Thesis, University of Oxford, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.288526.

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Spring, David R. "Studies on the biomimetic synthesis of the manzamine alkaloids." Thesis, University of Oxford, 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.268166.

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Lerata, Mookho Sylvia. "Discovery of cytotoxic natural products from South African marine sponges." University of the Western Cape, 2018. http://hdl.handle.net/11394/6447.

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Magister Pharmaceuticae - Mpharm
Cancer is a major health problem worldwide and killing millions of people each year. The use of natural products as chemotherapeutic agents is well established, however, many of the currently available drugs are associated with undesirable side effects and high toxicity. Furthermore, the development of drug resistant cancers makes the search for anticancer lead compounds a priority. In this study a library of prefractionated marine sponge extracts was established and used to prioritise samples for isolation of bioactive metabolites. From the generated library, two of the sponges of genera Ircinia sp. and Latrunculid sp. resulted in isolation of furanosesterterpenes (7E,12Z,20Z,18S-variabilin) and pyrroloiminoquinone (tsitsikammamine A and tsitsikammamine N-18 oxime) alkaloids respectively. The structures of these compounds were elucidated by analysis of 1D and 2D NMR data. These compounds displayed moderate to potent cytotoxicity against MCF-7, PC-3, U-87 and HEK-293 cells lines through apoptosis, with lack of selectivity for cancer cell lines.

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Veale, Clinton Gareth Lancaster. "Synthetic analogues of marine bisindole alkaloids as potent selective inhibitors of MRSA pyruvate kinase." Thesis, Rhodes University, 2014. http://hdl.handle.net/10962/d1020893.

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Globally, methicillin resistant Staphylococcus aureus (MRSA) has become increasingly difficult to manage in the clinic and new antibiotics are required. The structure activity relationship (SAR) study presented in this thesis forms part of an international collaborative effort to identify potent and selective inhibitors of an MRSA pyruvate kinase (PK) enzyme target. In earlier work the known marine natural product bromodeoxytopsentin (1.6), isolated from a South African marine sponge Topsentia pachastrelloides, exhibited selective and significant inhibition of MRSA PK (IC₅₀ 60 nM). Accordingly bromodeoxytopsentin provided the initial chemical scaffold around which our SAR study was developed. Following a comprehensive introduction, providing the necessary background to the research described in subsequent Chapters, this thesis has been divided into three major parts. Part one (Chapter 2) documents the synthesis of two natural imidazole containing topsentin analogues 1.40, 1.46, five new synthetic analogues 1.58—1.61, 2.104. In the process we developed a new method for the synthesis of topsentin derivatives via selenium dioxide mediated oxidation of N-Boc protected 3-acetylindoles to yield glyoxal intermediates which were subsequently cyclized and deprotected to yield the desired products. Interestingly we were able to demonstrate a delicate relationship between the relative equivalents of selenium dioxide and water used during the oxidation step, careful manipulation of which was required to prevent the uncontrolled formation of side products. Synthetic compounds 1.40, 1.46, 1.58—1.61 were found to be potent inhibitors of MRSA PK (IC₅₀ 238, 2.1, 23, 1.4, 6.3 and 3.2 nM respectively) with 1000-10000 fold selectivity for MRSA PK over four human orthologs. In the second part of this thesis (Chapter 3) we report the successful synthesis of a cohort of previously unknown thiazole containing bisindole topsentin analogues 1.62—1.68 via a Hantzsch thiazole synthesis. Bioassay results revealed that these compounds were only moderate inhibitors of MRSA PK (IC₅₀ 5.1—20 μM) which suggested that inhibitory activity was significantly reduced upon substitution of the central imidazole ring of topsentin type analogues with a thiazole type ring. In addition in Chapter 3 we describe unsuccessful attempts to regiospecifically synthesize oxazole and imidazole topsentin analogues through a similar Hantzsch method. As a consequence of our efforts in this regard we investigated three key reactions in depth, namely the synthesis of 2.2, 3.38, 3.40, 3.41 via α-bromination of 3-acetylindole and the synthesis of indolyl-3-carbonylnitriles 2.13, 3.45—3.47 and α-oxo-1H-indole-3-thioacetamides 3.48—3.51. The investigation of the latter led to the isolation and elucidation of two anomalous N,N-dimethyl-1H-indole-3-carboxamides 3.52 and 3.53. Finally the third part of this thesis (Chapter 4) deals with in silico assessment of the binding of both the imidazole and thiazole containing bisindole alkaloids to the MRSA PK protein which initially guided our SAR studies. In this chapter we reveal that there appears to be no correlation between in silico binding predictions and in vitro MRSA PK inhibitory bioassay data. Superficially it seems that binding energy as determined by the docking program used for these studies correlated with the size of the indole substituents and did not reflect IC₅₀ MRSA PK inhibitory data. Although this led us to computationally explore possible alternative binding sites no clear alternative has been identified.

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Bastos, de lemos e. silva Siguara. "Chimie et biosynthèse de substances naturelles hautement complexes de la biodiversité méditerranéenne." Thesis, Université Paris-Saclay (ComUE), 2017. http://www.theses.fr/2017SACLS214.

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Le but de ce travail de doctorat est l’étude chimique et biosynthétique de familles d’alcaloïdes guanidiniques d’origine marine provenant d’éponges de Méditerranée.Le travail est divisé en trois parties successives : 1) l’isolement d’alcaloïdes produits par des éponges marines de l’ordre des Poeciloscerida; 2) l’élucidation de la biosynthèse de la crambescine C1 par des études in vivo d’incorporation de précurseurs marqués au 14C; 3) la synthèse biomimétique de la crambescine A2 448 et de dérivés proches.La famille des alcaloïdes guanidiniques cycliques des crambescines est au coeur de la thèse, ces substances naturelles sont produites par l’éponge incrustante Crambe crambe. Ces alcaloïdes ont été découverts dans les années 1990 et ont suscité beaucoup d’intérêt pour leurs propriétés biologiques et écologiques et leurs synthèses totales. Par contre, leur biosynthèse était encore inconnue à ce jour. La seule synthèse biomimétique disponible était basée sur une hypothèse d’origine polyacétique. Les hypothèses récentes de nos groupes ont permis de mettre en avant une origine mixte: la partie cyclique guanidinique proviendrait d’un pyrrolidinium issu de l’arginine et d’un précurseur “céto-acide” proche des acides gras. Sur la base de cette hypothèse, nous avons mis au point une expérience d’incorporation qui a ensuite inspirée une voie de synthèse biomimétique pour l’accès aux crambescines et dérivés. Les premières conclusions quant à l’origine biosynthétique de ces molécules sont les faits les plus marquants de ce travail. Nous apportons une meilleure compréhension de la biochimie des alcaloïdes guanidiniques marins de structures complexes
This thesis aims at the study of the chemical and biogenetic origin of specialized guanidine-alkaloid metabolites produced by sponges from the Mediterranean Sea.The work is divided into three main parts: 1) isolation of alkaloids produced by sponges of the Poeciloscerida order; 2) biosynthesis of crambescin C1 by in-vivo 14C-feeding experiments with Crambe crambe sponge; 3) biomimetic synthesis of crambescin A2 448 and derivatives. The main focus of the thesis will be the family of cyclic-guanidine alkaloids "crambescins", produced by the red incrusting sponge Crambe crambe.These alkaloids were discovered in the early 90s and despite the large interest on their biological activities, ecological roles, and synthesis, their biosynthesis is still unknown.The only available biomimetic synthesis of crambescins was based on a fully polyketide origin hypothesis. Recently our groups suggested an alternative biosynthetic hypothesis in which the guanidine-core would be originated from a condensation between a guanidinated pyrrolidinium derived from arginine and a beta-keto fatty acid. Based on this hypothesis, we designed a biosynthesis experiment that inspired a biomimetic synthesis route to access the crambescins and derivatives. The insights from these studies are the first experimental conclusions about the biosynthesis of crambescins. Finally, this work leads to a better comprehension of the biochemistry involved in guanidine marine alkaloids of complex structures

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Ballette, Roberto. "Total synthesis of (+)-Madangamine D." Doctoral thesis, Universitat de Barcelona, 2014. http://hdl.handle.net/10803/145559.

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Madangamines are a small group of marine alkaloids isolated from sponges of the order Haplosclerida collected by hand using scuba on reefs off Madang, Papua New Guinea. Madangamine A show significant in vitro cytotoxicity against murine leukemia (P388), human lung (A549), brain (U373) and breast (MCF-7). However, no bioactivity data have been reported for madangamines B-E, and further pharmacological research on this alkaloid group has been prevented by the minute amount of alkaloid samples. We present herein the enantioselective synthesis of (+)-madangamine D, which represents the first total synthesis of an alkaloid of the madangamine group. Using a phenylglycinol-derived bicyclic lactam as the starting enantiomeric scaffold we were able to control the stereochemistry of all three contiguous stereogenic centers on the BC ring system, while A ring was formed through a stereocontrolled cascade aminohydroxylation reaction, in which an “in situ generated” amine attacks an epoxide ring. This strategy provides a direct route to the diazatricyclic ABC core common to all madangamines, with the appropriate functionalization to allow the subsequent building of the macrocyclic D and E rings of these alkaloids. The saturated 14-membered D ring of madangamine D, leading to the tetracyclic ABCD system was efficiently constructed using a ring-closing metathesis reaction followed by a catalytic hydrogenation of the resulting double bond. The (Z,Z)-unsaturated 11-membered E ring, required to complete the synthesis of madangamine D was successfully assembled in a straightforward manner using a Z-stereoselective Wittig reaction followed by an intramolecular macrolactamization. Madangamine D showed significant in vitro cytotoxic activity against human colon HT29 (GI50 4.4 µg/mL) and pancreas PSN1 (GI50 7.4 µg/mL) cancer cell lines, but was inactive against lung NSCLC A549 and breast MDA-MB-231 cancer cell lines at the highest assayed concentration (10 µg/mL).
Las esponjas del orden Haplosclerida representan una importante fuente de alcaloides estructuralmente diversos pero biogenéticamente relacionados, siendo las madangaminas uno de los menos estudiados desde el punto de vista sintético. En 1994 fue aislada el primer alcaloide de este grupo, la Madangamina A de la esponja marina Xestospongia ingens1 y unos años más tarde se aislaron cuatro nuevos alcaloides, las madangaminas BE.2 Estructuralmente, las madangamines son alcaloides pentacíclicos y se caracterizan por presentar un núcleo diazatricíclico (anillos ABC) y dos puentes de carbonados. El anillo macrocíclico D es diferente en cada madangamina en tamaño, así como en el grado y la posición de insaturación, mientras que el anillo E es idéntico en todas ellas. En la presente Tesis Doctoral presentamos la síntesis enantioselectiva de ()-madangamine D,3 que ofrece por primera vez una muestra pura de este producto natural y constituye la primera síntesis total de un alcaloide de la grupo de las madangamines. Usando de una lactama bicíclica derivada del fenilglicinol como el scafold enantiomérico de partida, nuestro enfoque consiste en la construcción inicial del núcleo diazatricíclico ABC y la posterior construcción de los anillos macrocíclicos D y E. La lactama de partida 2 es fácilmente accesible por ciclocondensación de oxoester 1 con el (R)-fenilglicinol, en un proceso en donde se instala el primer estereocentro. El intermedio diazatríclico se prepara a partir de una lactama insaturada derivada de 2. En este proceso son claves una reacción de adición conjugada estereoselectiva, el cierre del anillo carbocíclico mediante metátesis, una alquilación estereoselectiva y finalmente cierre del anillo A por aminohidroxilación. La anulación de los anillos macrocíclicos se lleva a cabo mediante una reacción de cierre del anillo por metátesis (anillo D) y una olefinación de Wittig seguida de macrolactamización (anillo E). Los datos de RMN de 1H y 13C de nuestra madangamina sintética fueron coincidentes con los reportados para el producto natural. La madangamina D sintética muestra citotoxicidad in vitro contra las líneas celulares de cáncer HT29 de colon humano y PSN1 páncreas.

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Yager, Kraig M. "Synthetic studies on marine natural products : Part 1. Synthesis of the sesquiterpenoid dihydropallescensin D via manganese(III)- mediated carbocyclization. Part 2. Approaches toward the synthesis of prianosin and discorhabdin alkaloids." Thesis, 1993. http://hdl.handle.net/1957/35875.

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Putz, Annika [Verfasser]. "Secondary metabolites from marine sponges, with focus on the chemical ecology and biochemical characterisation of the stress induced biotransformation of Aplysina alkaloids = Sekundärmetabolite mariner Schwämme, mit Schwerpunkt auf der chemischen Ökologie und biochemischen Charakterisierung der stressinduzierten Biotransformation von Aplysina-Alkaloiden / vorgelegt von Annika Putz." 2009. http://d-nb.info/994615175/34.

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Books on the topic "Marine sponges; Alkaloids; Vasodilators"

1

Yager, Kraig M. Synthetic studies on marine natural products: Part 1. Synthesis of the sesquiterpenoid dihydropallescensin D via manganese(III)- mediated carbocyclization. Part 2. Approaches toward the synthesis of prianosin and discorhabdin alkaloids. 1993.

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Book chapters on the topic "Marine sponges; Alkaloids; Vasodilators"

1

Singh, Keisham S., and Mahesh S. Majik. "Bioactive Alkaloids from Marine Sponges." In Marine Sponges: Chemicobiological and Biomedical Applications, 257–86. New Delhi: Springer India, 2016. http://dx.doi.org/10.1007/978-81-322-2794-6_12.

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Berlinck, Roberto G. S. "Polycyclic Diamine Alkaloids from Marine Sponges." In Topics in Heterocyclic Chemistry, 211–38. Berlin, Heidelberg: Springer Berlin Heidelberg, 2007. http://dx.doi.org/10.1007/7081_2007_083.

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Bjørsvik, Hans-René, and Alexander H. Sandtorv. "Synthesis of Imidazole Alkaloids Originated in Marine Sponges." In Studies in Natural Products Chemistry, 33–57. Elsevier, 2014. http://dx.doi.org/10.1016/b978-0-444-63281-4.00002-1.

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Andersen, Raymond J., Rob W. M. Van Soest, and Fangming Kong. "Chapter Three 3-Alkylpiperidine alkaloids isolated from marine sponges in the order haplosclerida." In Alkaloids: Chemical and Biological Perspectives, 301–55. Elsevier, 1996. http://dx.doi.org/10.1016/s0735-8210(96)80027-6.

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Singh, Keisham S., and Mahesh S. Majik. "Pyrrole-Derived Alkaloids of Marine Sponges and Their Biological Properties." In Studies in Natural Products Chemistry, 377–409. Elsevier, 2019. http://dx.doi.org/10.1016/b978-0-444-64185-4.00010-1.

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