Novel alkaloids from the red ascidian botryllus leachi

Durán, Rosario; Zubı́a, Eva; Ortega, Marı́a J.; Naranjo, Santiago; Salvá, Javier

doi:10.1016/s0040-4020(99)00803-0

Cited by 57 publications

(30 citation statements)

References 13 publications

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“…Botryllazine A [5] represents the first example of a marine alkaloid containing a pyrazine nucleus derived from three tyrosine precursors. Two of the new alkaloids exhibited a mild cytotoxicity against the tumor cell lines assayed (Durán et al, 1999).…”

Section: Resultsmentioning

confidence: 97%

“…de un alcaloide marino que contiene un núcleo de pirazina derivado de tres precursores tirosínicos. Dos de los nuevos alcaloides exhibieron una citotoxicidad moderada frente al panel de células tumorales ensayado (Durán et al, 1999).…”

Section: Resultsunclassified

“…The structure of botryllazine A [5] is unprecedented since three tyrosine derived units are involved in the formation of the pyrazine nucleus. However, the way in which these units condense with each other is not apparent (Durán et al, 1999). Although the crude extract of B. leachi had shown significant cytotoxicity against the tumor cell lines P-388, A-549, HT-29 and MEL-28, botryllazine A [5] was inactive with IC 50 values over 10 µg/mL in all cases.…”

Section: Discussionmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 97%

Section: Resultsunclassified

Section: Discussionmentioning

confidence: 99%

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

2003

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“…For example, topsentin ( Figure 1) is a bis-indole alkaloid isolated from the Mediterranean sponge Topsentia genitrix. 3 Topsentin derivatives have been detected to have antitumor and antiviral activities. According to the literature, the product of 1a had two isomeric 2-aryloylimidazoles 2a and 2a'.…”

Section: Introductionmentioning

confidence: 99%

“…The results were shown in Table 2. Aromatic methyl ketones 1a-i bearing electron-neutral, electron-withdrawing or electrondonating substitutions at the benzene ring proceeded well to give good yields ( Table 1, entries [1][2][3][4][5][6][7][8][9]. The position of the substitution at benzene ring had little effect on the yield.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-aroyl-(4 or 5)-aryl-1H-imidazoles and 2-hydroxy-3,6-diarylpyrazines via a cascade process

Liu¹,

Dai²,

Yao³

et al. 2014

Arkivoc

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Eight-Membered Cyclic 1,2,3-Trithiocane Derivatives from Perophora viridis, an Atlantic Tunicate

Řezanka¹,

Dembitsky

2002

Eur. J. Org. Chem.

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Two novel sulfur derivatives, one of which is a glycoside, containing substituted 1,2,3‐trithiocane cycles were isolated from Perophora viridis which was collected off the Atlantic coast of North Carolina. They were characterized by spectroscopic methods, mainly 1H NMR, 13C NMR, IR and UV spectroscopy and mass spectrometry. The compounds gave positive results in the brine shrimp toxicity assay and the sea urchin test. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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Novel alkaloids from the red ascidian botryllus leachi

Cited by 57 publications

References 13 publications

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

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

Synthesis of 2-aroyl-(4 or 5)-aryl-1H-imidazoles and 2-hydroxy-3,6-diarylpyrazines via a cascade process

Eight-Membered Cyclic 1,2,3-Trithiocane Derivatives from Perophora viridis, an Atlantic Tunicate

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