Synthesis and biological activities of the marine bryozoan alkaloids convolutamines A, C and F, and lutamides A and C

Hashima, Hirofumi; Hayashi, Masahiko; Kamano, Yoshiaki; Sato, Nobuhiro

doi:10.1016/s0968-0896(00)00110-3

Cited by 16 publications

(21 citation statements)

References 18 publications

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“…In addition, Sherwood et al [95] analyzed 34 epizoic species that colonize A. wilsoni and only one, the sea spider Stylopallene longicauda, which was present at high average densities, contained amathamides in concentrated amounts, thus, amathamides may also function as chemical defenses for S. longicauda. Another family of compounds from the genus Amathia are the convolutamines A-J (7a-7j, Figure 8) [96][97][98][99][100]. In particular, convolutamine F was shown to inhibit the cell division of fertilized sea urchin eggs [97].…”

Section: Chemoecologymentioning

confidence: 99%

The Phylum Bryozoa: From Biology to Biomedical Potential

et al. 2020

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Less than one percent of marine natural products characterized since 1963 have been obtained from the phylum Bryozoa which, therefore, still represents a huge reservoir for the discovery of bioactive metabolites with its ~6000 described species. The current review is designed to highlight how bryozoans use sophisticated chemical defenses against their numerous predators and competitors, and which can be harbored for medicinal uses. This review collates all currently available chemoecological data about bryozoans and lists potential applications/benefits for human health. The core of the current review relates to the potential of bryozoan metabolites in human diseases with particular attention to viral, brain, and parasitic diseases. It additionally weighs the pros and cons of total syntheses of some bryozoan metabolites versus the synthesis of non-natural analogues, and explores the hopes put into the development of biotechnological approaches to provide sustainable amounts of bryozoan metabolites without harming the natural environment.

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Section: Chemoecologymentioning

confidence: 99%

The Phylum Bryozoa: From Biology to Biomedical Potential

et al. 2020

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Section: Cytotoxic Compounds From Marine Bryozoans With Activity Amentioning

confidence: 99%

“…Convolutamines A–G (brominated β-phenylethylamine alkaloids) and lutamides A and C (2,4,6-tribromo-3-methoxyphenethylamine alkaloids) were also isolated from the Floridian A. convoluta [54]. Convolutamines A, C, and F exhibited inhibition against adriamycin (ADM)-resistant P-388/ADM (IC 50 values 7.0, 3.0, and 9.5 μg/mL, respectively) and vincristine (VCR)-resistant P-388/VCR (IC 50 values 3.0, 1.4, and 8.0 μg/mL, respectively) [54]. Convolutamines B and D also exhibited cell growth inhibitory activity against P-388 with IC 50 values of 4.8 and 8.6 μg/mL, respectively [55] and convolutamine F ( 4 ) against its vincristine-resistant KB/VJ-300 cells with an IC 50 value of 9.6 μg/mL [56].…”

Section: Cytotoxic Compounds From Marine Bryozoans With Activity Amentioning

confidence: 99%

The Phylum Bryozoa as a Promising Source of Anticancer Drugs

Figuerola

Ávila

2019

Marine Drugs

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Recent advances in sampling and novel techniques in drug synthesis and isolation have promoted the discovery of anticancer agents from marine organisms to combat this major threat to public health worldwide. Bryozoans, which are filter-feeding, aquatic invertebrates often characterized by a calcified skeleton, are an excellent source of pharmacologically interesting compounds including well-known chemical classes such as alkaloids and polyketides. This review covers the literature for secondary metabolites isolated from marine cheilostome and ctenostome bryozoans that have shown potential as cancer drugs. Moreover, we highlight examples such as bryostatins, the most known class of marine-derived compounds from this animal phylum, which are advancing through anticancer clinical trials due to their low toxicity and antineoplastic activity. The bryozoan antitumor compounds discovered until now show a wide range of chemical diversity and biological activities. Therefore, more research focusing on the isolation of secondary metabolites with potential anticancer properties from bryozoans and other overlooked taxa covering wider geographic areas is needed for an efficient bioprospecting of natural products.

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“…Convolutamines A, C and F showed inhibition of cell growth of both drug-sensitive and -resistant P388 cell lines and U937. Convolutamine C only displayed weak growth inhibition against IL-6dependent MH-60 cells [44]. Convolutamines B and D also exhibited cell growth inhibitory activity against P388 with IC50 values of 4.8 and 8.6 µg/ml, respectively [45] and convolutamine F against human epidermoid carcinoma KB cells and its vincristine-resistant KB/VJ-300 cells [46].…”

Section: Convolutamides Convolutamydines and Convolutaminesmentioning

confidence: 99%

“…Convolutamines I-J, isolated from the Southern Ocean bryozoan A. tortuosa Tenison-Woods, 1880, were recently validated as potential ATP competitive inhibitors [47]. Lutamides A and C exhibited inhibition against adriamycin (ADM)-resistant P388/ADM, vincristine (VCR)-resistant P388/VCR and KB/VJ300 cells in the presence of ADM or VCR whose concentration did not affect growth of the cells examined [44].…”

Section: Convolutamides Convolutamydines and Convolutaminesmentioning

confidence: 99%

The Understudied Phylum Bryozoa as a Promising Source of Anticancer Drugs

Figuerola¹,

Ávila²

2019

Preprint

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Recent advances in sampling and novel techniques in drug synthesis and isolation have promoted the discovery of anticancer agents from marine organisms to combat this major threat to public health worldwide. Bryozoans, filter-feeding, sessile aquatic invertebrates often characterized by a calcified skeleton, are an excellent source of pharmacologically interesting compounds including well-known chemical classes such as alkaloids and polyketides. This review covers the literature for secondary metabolites isolated from marine cheilostome and ctenostome bryozoans that have shown potential as cancer drugs. Moreover, we highlight examples such as bryostatins, the most known class of marine-derived compounds from this animal phylum, which is advancing through anticancer clinical trials due to their low toxicity and antineoplastic activity. The bryozoan antitumour compounds discovered until now show a wide range of chemical diversity and biological activities. Therefore, more research focusing on the isolation of secondary metabolites with potential anticancer properties from bryozoans and other overlooked taxa covering wider geographic areas is needed for an efficient bioprospecting of natural products.

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Synthesis and biological activities of the marine bryozoan alkaloids convolutamines A, C and F, and lutamides A and C

Cited by 16 publications

References 18 publications

The Phylum Bryozoa: From Biology to Biomedical Potential

The Phylum Bryozoa: From Biology to Biomedical Potential

The Phylum Bryozoa as a Promising Source of Anticancer Drugs

The Understudied Phylum Bryozoa as a Promising Source of Anticancer Drugs

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