Isoepitaondiol, a diterpenoid of Stypopodium flabelliforme and the insecticidal activity of stypotriol, epitaondiol and derivatives

Rovirosa, Juana; Sepúlveda, M. S.; Quezada, Elías; San-Martı́n, Aurelio

doi:10.1016/0031-9422(92)83610-b

Cited by 44 publications

(46 citation statements)

References 8 publications

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“…Isolation and characterization procedures were previously reported by us [19–21]. Generally, fresh algae were repeatedly extracted with dichloromethane.…”

Section: Methodsmentioning

confidence: 99%

Anti-Proliferative Activity of Meroditerpenoids Isolated from the Brown Alga Stypopodium flabelliforme against Several Cancer Cell Lines

et al. 2011

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The sea constitutes one of the most promising sources of novel compounds with potential application in human therapeutics. In particular, algae have proved to be an interesting source of new bioactive compounds. In this work, six meroditerpenoids (epitaondiol, epitaondiol diacetate, epitaondiol monoacetate, stypotriol triacetate, 14-ketostypodiol diacetate and stypodiol) isolated from the brown alga Stypopodium flabelliforme were tested for their cell proliferation inhibitory activity in five cell lines. Cell lines tested included human colon adenocarcinoma (Caco-2), human neuroblastoma (SH-SY5Y), rat basophilic leukemia (RBL-2H3), murine macrophages (RAW.267) and Chinese hamster fibroblasts (V79). Antimicrobial activity of the compounds was also evaluated against Staphylococcus aureus, Salmonella typhimurium, Proteus mirabilis, Bacillus cereus, Enterococcus faecalis and Micrococcus luteus. Overall, the compounds showed good activity against all cell lines, with SH-SY5Y and RAW.267 being the most susceptible. Antimicrobial capacity was observed for epitaondiol monoacetate, stypotriol triacetate and stypodiol, with the first being the most active. The results suggest that these molecules deserve further studies in order to evaluate their potential as therapeutic agents.

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“…Isolation and characterization procedures were previously reported by us [19–21]. Generally, fresh algae were repeatedly extracted with dichloromethane.…”

Section: Methodsmentioning

confidence: 99%

Anti-Proliferative Activity of Meroditerpenoids Isolated from the Brown Alga Stypopodium flabelliforme against Several Cancer Cell Lines

et al. 2011

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“…In this way, errors arising from assignments of configuration based on single NOE correlations may be avoided. Other common single stereocenter misassignments occur at ring junctions, as in the cases of manzacidin B, 74, 75 agelasine C 76, 77 and its epimer, 78 peyssonol A, 79, 80 isoepitaondiol, 81, 82 suberoretisteroid B 83, 84 and the green algal lanostane-type triterpenoid 85, 86 (Table 7), and are caused primarily by NMR spectral overlap. Assignment is also difficult for an isolated substituent on a macrocycle or extended chain, perhaps too far from the point of derivatization in a flexible system.…”

Section: Sources Of Natural Product Structural Misassignmentsmentioning

confidence: 99%

Survey of marine natural product structure revisions: A synergy of spectroscopy and chemical synthesis

Suyama

Gerwick

McPhail

2011

Bioorganic & Medicinal Chemistry

166

175

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The structural assignment of new natural product molecules supports research in a multitude of disciplines that may lead to new therapeutic agents and or new understanding of disease biology. However, reports of numerous structural revisions, even of recently elucidated natural products, inspired the present survey of techniques used in structural misassignments and subsequent revisions in the context of constitutional or configurational errors. Given the comparatively recent development of marine natural products chemistry, coincident with the modern spectroscopy, it is of interest to consider the relative roles of spectroscopy and chemical synthesis in the structure elucidation and revision of those marine natural products which were initially misassigned. Thus, a tabulated review of all marine natural product structural revisions from 2005 to 2010 is organized according to structural motif revised. Misassignments of constitution are more frequent than perhaps anticipated by reliance on HMBC and other advanced NMR experiments, especially considering the full complement of all natural products. However, these techniques also feature prominently in structural revisions, specifically of marine natural products. Nevertheless, as is the case for revision of relative and absolute configuration, total synthesis is a proven partner for marine, as well as terrestrial, natural products structure elucidation. It also becomes apparent that considerable ‘detective work’ remains in structure elucidation, in spite of the spectacular advances in spectroscopic techniques.

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“…The known compounds taondiol (Gonzalez et al, 1971) isoepitaondiol (Rovirosa et al, 1992) stypodiol, (Gerwick and Fenical, 1981), stypoldione (Gerwick et al, 1979) and sargaol (Numata et al, 1992), isolated from brown alga Taonia atomaria exhibited free radical-scavenging activity (DPPH and chemiluminescence tests) (Nahas et al, 2007).…”

Section: Antiviral Activity a New Dollabelladiene Derivativementioning

confidence: 99%

Biological importance of marine algae

Gamal

2010

Saudi Pharmaceutical Journal

405

166

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Marine organisms are potentially prolific sources of highly bioactive secondary metabolites that might represent useful leads in the development of new pharmaceutical agents. Algae can be classified into two main groups; first one is the microalgae, which includes blue green algae, dinoflagellates, bacillariophyta (diatoms)… etc., and second one is macroalgae (seaweeds) which includes green, brown and red algae. The microalgae phyla have been recognized to provide chemical and pharmacological novelty and diversity. Moreover, microalgae are considered as the actual producers of some highly bioactive compounds found in marine resources. Red algae are considered as the most important source of many biologically active metabolites in comparison to other algal classes. Seaweeds are used for great number of application by man. The principal use of seaweeds as a source of human food and as a source of gums (phycocollides). Phycocolloides like agar agar, alginic acid and carrageenan are primarily constituents of brown and red algal cell walls and are widely used in industry.

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Isoepitaondiol, a diterpenoid of Stypopodium flabelliforme and the insecticidal activity of stypotriol, epitaondiol and derivatives

Cited by 44 publications

References 8 publications

Anti-Proliferative Activity of Meroditerpenoids Isolated from the Brown Alga Stypopodium flabelliforme against Several Cancer Cell Lines

Anti-Proliferative Activity of Meroditerpenoids Isolated from the Brown Alga Stypopodium flabelliforme against Several Cancer Cell Lines

Survey of marine natural product structure revisions: A synergy of spectroscopy and chemical synthesis

Biological importance of marine algae

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