(+)-Agelasine D:  Improved Synthesis and Evaluation of Antibacterial and Cytotoxic Activities

Vik, Anders; Hedner, Erik; Charnock, Colin; Samuelsen, Ørjan; Larsson, Rolf; Gundersen, Lise‐Lotte; Bohlin, Lars

doi:10.1021/np050424c

Cited by 62 publications

(68 citation statements)

References 26 publications

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“…All assignments in the 1 H-NMR and 13 C-NMR were based on measurements of HSQC, HMBC and 1 H-1 H COSY. The final structure of compound 1 was confirmed by a comparison of spectroscopic values to those reported in the literature (Ribo et al, 1974;Conner and Rowe, 1976;Yasui et al, 1993;Su et al, 1994;He et al, 1997;Li and Kuo, 1998;Sepúlveda et al, 2005;Vik et al, 2006) (Fig. 3).…”

Section: Resultssupporting

confidence: 70%

Inhibition of nitric oxide production in RAW 264.7 macrophages by diterpenoids from Phellinus pini

Jang

Yang

2011

Arch. Pharm. Res.

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8,14-labdadien-13-ol (1) and dehydroabietic acid (2) were isolated from the fruit body of Phellinus pini. Elucidation of their structures was based on spectroscopic methods including IR, MS, and NMR (1D and 2D). Two compounds were screened for their ability to inhibit NO production in LPS-activated RAW 264.7 cells. Compounds 1 and 2 at 30 μM and 50 μM, respectively, inhibited NO production in activated macrophages.

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Section: Resultssupporting

confidence: 70%

Inhibition of nitric oxide production in RAW 264.7 macrophages by diterpenoids from Phellinus pini

Jang

Yang

2011

Arch. Pharm. Res.

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“…More than ten agelasines are currently known, of which agelasine A-F have the highest antibacterial activity [81][82][83][84][85][86]. Agelasimines are also purine derivatives carrying a diterpenoid side chain, but they are neutral 3,7-dialkylated purines.…”

Section: Antibacterial Activitymentioning

confidence: 99%

Marine Sponges: Potential Sources of New Antimicrobial Drugs

Laport¹,

Santos²,

Muricy³

2009

CPB

261

191

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Sponges (phylum Porifera) are sessile marine filter feeders that have developed efficient defense mechanisms against foreign attackers such as viruses, bacteria, or eukaryotic organisms. Marine sponges are among the richest sources of pharmacologically-active chemicals from marine organisms. It is suggested that (at least) some of the bioactive secondary metabolites isolated from sponges are produced by functional enzyme clusters, which originated from the sponges and their associated microorganisms. More than 5,300 different products are known from sponges and their associated microorganisms, and more than 200 new metabolites from sponges are reported each year. As infectious microorganisms evolve and develop resistance to existing pharmaceuticals, the marine sponge provides novel leads against bacterial, viral, fungal and parasitic diseases. Many marine natural products have successfully advanced to the late stages of clinical trials, as for example ara-A (vidarabine), an anti-viral drug used against the herpes simplex encephalitis virus. This substance is in clinical use for many years. Moreover, a growing number of candidates have been selected as promising leads for extended preclinical assessment, including manzamine A (activity against malaria, tuberculosis, HIV, and others), lasonolides (antifungal activity) and psammaplin A (antibacterial activity). In this review we have surveyed the discoveries of products derived from marine sponges and associated bacteria that have shown in vivo efficacy or potent in vitro activity against infectious and parasitic diseases, including bacterial, viral, fungal and protozoan infections. Our objective was to highlight the substances that have the greatest potential to lead to clinically useful treatments.

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“…The remaining analogs tested displayed either no effect, only a week effect, or were highly toxic to the cyprids. Since several of the compounds displayed a strong effect on larval mortality, a comparison of earlier results concerning cytotoxic effects of the compounds was made (Vik et al 2006(Vik et al , 2007 (Table 1). However, a lethal effect in the cyprid settlement assay did not necessarily correlate with a strong cytotoxic effect.…”

Section: Discussionmentioning

confidence: 99%

“…The agelasine and agelasimine analogs tested in the present study were synthesised as previously described (Bakkestuen et al 2005;Vik et al 2006Vik et al , 2007. Out of 24 agelasine and agelasimine analogs, 20 were evaluated for AF activity in the larval bioassay.…”

Section: Methodsmentioning

confidence: 99%

“…The known bioactivities of the agelasines are antimicrobial and cytotoxic effects (Bakkestuen et al 2005;Vik et al 2006;Proszenya´k et al 2007;Vik et al 2007) as well as contractive responses of smooth muscles and inhibition of Na, KATPase Wu et al 1984). To date, eleven 9-methyladeninium salts, agelasine A-I, epiagelasine C and ageline B, have been isolated from Agelas species.…”

Section: Introductionmentioning

confidence: 99%

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Antifouling activity of the sponge metabolite agelasine D and synthesised analogs onBalanus improvisus

et al. 2008

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This study reports a screening study for antifouling (AF) activity of the natural compound agelasine D isolated from marine sponges of the genus Agelas and 20 synthesised analogs of agelasines and agelasimines. Agelasine D, together with two of the analogs, ie AV1003A and AKB695, displayed a strong inhibitory effect on settlement of Balanus improvisus cypris larvae. Agelasine D had an EC50 value of 0.11 microM while the two analogs AV1033A and AKB695 had EC50 values of 0.23 and 0.3 microM, respectively. None of these three compounds affected larval mortality as was the case with several of the analogs tested. Moreover, the effect of AV1033A and AKB695 was reversible. When cyprids after 24 h exposure to the compounds were transferred to fresh seawater, the settlement frequency compared with the controls was completely recovered. The properties of the agelasine D analogs AV1003A and AKB695 make them highly attractive candidates as AF agents in future marine coatings.

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(+)-Agelasine D: Improved Synthesis and Evaluation of Antibacterial and Cytotoxic Activities

Cited by 62 publications

References 26 publications

Inhibition of nitric oxide production in RAW 264.7 macrophages by diterpenoids from Phellinus pini

Inhibition of nitric oxide production in RAW 264.7 macrophages by diterpenoids from Phellinus pini

Marine Sponges: Potential Sources of New Antimicrobial Drugs

Antifouling activity of the sponge metabolite agelasine D and synthesised analogs onBalanus improvisus

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