New Diketopiperazines from the Sponge<i>Dysidea chlorea</i>

Fu, X.; Ferreira, Maria Lurdes; Schmitz, Francis J.; Kelly‐Borges, Michelle

doi:10.1021/np980123l

Cited by 50 publications

(23 citation statements)

References 19 publications

(70 reference statements)

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“…Diketopiperazines (DKPs), the smallest cyclic peptides, have been isolated from marine microorganisms (bacteria, fungi, and actinomycete) [14–17] or the microorganisms associated with sponge [18–20]. As cyclic peptide derivatives, DKPs have been considered as cell-cell signalling compounds.…”

Section: Discussionmentioning

confidence: 99%

A Preliminary Study of the Microbial Resources and Their Biological Activities of the East China Sea

Lü

Liu

et al. 2011

Evidence-Based Complementary and Alternative Medicine

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East China Sea is one of the four sea areas in China, which possesses peculiar ecological environment and many kinds of living creatures, especially the microorganisms. We established the East China Sea microorganism library (during 2006–2010) for the first time, which stored about 30000 strains that covered most kinds of the species. In this paper, 395 pure strains of East China Sea microorganism library which belong to 33 different genera were mainly introduced. Sulfitobacter, Halomonas, Bacillus, Pseudoalteromonas, and Idiomarina were the most dominant species. On the large-scale biological activity screening of the 395 strains, 100 strains possess different biological activities based on different screening models, of which 11.4% strains have antibacterial activities, 15.9% have cytotoxicity activities, and 6.1% have antioxidation activities. Besides, the secondary metabolites of 6 strains with strong biological activities were studied systematically; diketopiperazines and macrocyclic lactones are the active secondary metabolites. The species and the biological activity of microorganisms diversity, the abundant structure type of the secondary metabolites, and their bioactivities all indicate that East China Sea is a potent marine microorganisms-derived developing resource for drug discovery.

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Section: Discussionmentioning

confidence: 99%

A Preliminary Study of the Microbial Resources and Their Biological Activities of the East China Sea

Lü

Liu

et al. 2011

Evidence-Based Complementary and Alternative Medicine

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“…Twelve polychlorinated DKPs, dysamides I -T (100 -111, resp. ), were obtained from D. chlorea from Yap, Micronesia [82]. Of greater interest is the unusual S-containing diketopiperazine 112 from the marine sponge Tedania ignis [83].…”

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confidence: 99%

Diketopiperazines from Marine Organisms

Huang

Zhou

Tian

et al. 2010

Chemistry & Biodiversity

145

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Diketopiperazines (DKPs), which are cyclic dipeptides, have been detected in a variety of natural resources. Recently, the interest in these compounds increased significantly because of their remarkable bioactivity. This review deals with the chemical structures, biosynthetic pathways, and biological activities of DKPs from marine microorganisms, sponges, sea stars, tunicates (ascidians), and red algae. The literature has been covered up to December 2008, and a total 124 DKPs from 104 publications have been discussed and reviewed. Some of these compounds have been found to possess various bioactivities including cytotoxicity, and antibacterial, antifungal, antifouling, plant-growth regulatory, and other activities.

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“…Por otro lado, la biosíntesis a través de la conexión de cada grupo amino con el C-2 del otro precursor, presumiblemente vía oxidación benzílica y formación de imina, conduce a anillos de piperazina 2,5-disustituidas. En el esquema 1 se presentan algunos ejemplos representativos (Fahy et al, 1991;Fu et al, 1998) de metabolitos marinos derivados a través de estas dos rutas. Ninguna de las dos rutas mencionadas proporciona una explicación satisfactoria a la novedosa estructura de la botryllazina B [6].…”

Section: Discussionunclassified

“…Ninguna de las dos rutas mencionadas proporciona una explicación satisfactoria a la novedosa estructura de la botryllazina B [6]. Sin embargo, parece biosinteticamente factible la condensación de tirosina con tiramina para dar una amida seguida de ciclización vía Garrido et al, 2001 Acetates 14a/18a Synthesis 5 5 10 10 Garrido et al, 2001(Fahy et al, 1991Fu et al, 1998) of marine metabolites derived through these two biosynthetic routes are given in scheme 1. Neither of these routes provides a satisfactory explanation to the novel structure of botryllazine B [6].…”

Section: Discussionunclassified

Antitumor potential of natural products from marine ascidians of the Gibraltar Strait: A survey

2003

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The chemical study of a selection of marine ascidians from the Gibraltar Strait has led to the characterization of a collection of natural products of diverse biosynthetic origin. The structures were elucidated by spectroscopic methods and, in certain instances, the absolute stereochemistry was determined using chiral auxiliaries following the Mosher method. In particular, the new compounds isolated from the ascidians Phallusia fumigata (Grübe, 1864), Botryllus leachi (Savigny, 1816), Stolonica socialis (Hartmayer, 1903), and Pseudodistoma obscurum (Pères, 1959) are presented and key aspects of the structural elucidation are discussed. In order to anticipate a possible antitumor application, the cytotoxicity of the new compounds was evaluated against cell lines P-388 (suspension culture of a lymphoid neoplasm from a DBA/2 mouse), A-549 (monolayer culture of a human lung carcinoma), HT-29 (monolayer culture of a human colon carcinoma), and MEL-28 (monolayer culture of a human melanoma). ResumenEl estudio químico de una serie de ascidias seleccionadas procedentes del Estrecho de Gibraltar ha llevado a la caracterización de una colección de productos naturales de muy diverso origen biosintético. Las estructuras se establecieron mediante métodos espectroscópicos y, en algunos casos, la estereoquímica absoluta se determinó usando auxiliares quirales siguiendo el método de Mosher. En concreto, se presentan los nuevos compuestos aislados a partir de las ascidias Phallusia fumigata (Grübe, 1864), Botryllus leachi (Savigny, 1816), Stolonica socialis (Hartmayer, 1903) y Pseudodistoma obscurum (Pères, 1959) y se discuten aspectos clave acerca de la elucidación estructural. Para poder anticipar una posible aplicación antitumoral, se ha realizado una evaluación de citotoxicidad de los nuevos compuestos frente a las líneas celulares P-388 (cultivo en suspensión de un neoplasma linfoide de ratón DBA/2), A-549 (cultivo en monocapa de un carcinoma de pulmón humano), HT-29 (cultivo en monocapa de un carcinoma de colon humano) y MEL-28 (cultivo en monocapa de un melanoma humano).Palabras clave: productos naturales, ascidias, elucidación estructural, citotoxicidad.

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New Diketopiperazines from the SpongeDysidea chlorea

Cited by 50 publications

References 19 publications

A Preliminary Study of the Microbial Resources and Their Biological Activities of the East China Sea

A Preliminary Study of the Microbial Resources and Their Biological Activities of the East China Sea

Diketopiperazines from Marine Organisms

Antitumor potential of natural products from marine ascidians of the Gibraltar Strait: A survey

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