Cytotoxic cytochalasans from a Penicillium species separated from a marine alga

Iwamoto, Chika; Yamada, Takeshi; Ito, Yoshinori; Minoura, Katsuhiko; Numata, Atsushi

doi:10.1016/s0040-4020(01)00153-3

Cited by 86 publications

(59 citation statements)

References 13 publications

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“…A close inspection of the 1 H-and 13 C-NMR spectra of 2 (Table 3) by DEPT and HMQC experiments revealed the presence of three secondary methyls (C-17, C-18 and C-19), one sp 3 -hybridized methylene (C-2), five oxygen-bearing sp 3 methines (C-3, C-8, C-9, C-14 and C-15), two 1,2-disubstituted double bonds (C-6, C-7, C-12 and C-13) and three ester carbonyl groups. The Table 3).…”

Section: Resultsmentioning

confidence: 97%

Cell-adhesion Inhibitors Produced by a Sea Hare-derived Periconia sp.

et al. 2007

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Peribysin J and macrosphelide M have been isolated from a strain of Periconia byssoides originally isolated from the sea hare Aplysia kurodai. Their absolute stereostructures have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and some chemical transformations including the modified Mosher's method. These fungal metabolites inhibited the adhesion of human-leukemia HL-60 cells to humanumbilical-vein endothelial cells (HUVEC).Keywords fungus, cell-adhesion inhibitor, peribysin, macrosphelide, Periconia sp. IntroductionBased on the fact that some of the bioactive materials isolated from marine animals have been produced by bacteria, we have turned our attention to new antitumour materials from microorganisms inhabiting the marine environment [1ϳ3]. As part of this study, we have previously isolated the cell-adhesion inhibitors, macrosphelides EϳI, L [4, 5] and peribysins AϳI [6ϳ8], from a strain of Periconia byssoides OUPS-N133 originally isolated from the sea hare Aplysia kurodai. All of these compounds, except for macrosphelide I, inhibited the adhesion of human-leukemia HL-60 cells to human-umbilical-vein endothelial cells (HUVEC) more potently than herbimycin A [9,10]. Further investigation of the metabolites from this fungal strain has now led to the isolation of new antiadhesion compounds designated peribysin J (1) and macrosphelide M (2) (Fig. 1). We describe herein the absolute stereostructures of 1 and 2 (Fig. 1) in addition to their inhibition of cell adhesion. Results and DiscussionThe fungal strain was cultured at 27°C for 4 weeks in a medium containing malt extract 1.0%, glucose 1.0% and peptone 0.05% in artificial seawater adjusted to pH 7.5, as reported previously [4ϳ8]. The AcOEt extract of the culture filtrate was purified by chromatography on Sephadex LH-20 and silica gel by reversed phase HPLC to afford 1 and 2. The physico-chemical properties of these compounds are summarized in Table 1.1 had the molecular formula C 15 H 26 O 5 established by the [M] ϩ peak of 1 in high-resolution electron-impact mass spectrometry (HREI-MS). Its IR spectrum exhibited bands at 3384 and 1653 cm

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Section: Resultsmentioning

confidence: 97%

Cell-adhesion Inhibitors Produced by a Sea Hare-derived Periconia sp.

et al. 2007

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“…The general features of the 1 H-and 13 C-NMR spectra ( 1 H COSY and HMBC correlations (from 9-H to C-3, from 4-H to C-9 and C-5, from 1-H to C-3, C-4a, C-8 and C-8a, from 8-H to C-4a, C-6, C-7, 7-CH 3 , C-1Ј and C-2Ј, from 5Ј-H to C-1Ј and C-3Ј, and from the methoxyl group to C-3Ј) led to the planar structure for 5. In NOESY experiments, NOE correlations (8-H/5Ј-H, 7-CH 3 /4Ј-CH 3 , 8-H/4Ј-CH 3 and 6Ј-H/3Ј-OCH 3 ) suggested that the relative configulation of 5 was the same as that of 4.…”

Section: Resultsmentioning

confidence: 99%

Chaetomugilins, New Selectively Cytotoxic Metabolites, Produced by a Marine Fish-derived Chaetomium Species

et al. 2008

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Chaetomugilins AϳF have been isolated from a strain of Chaetomium globosum originally isolated from the marine fish Mugil cephalus, and their absolute stereostructures have been elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR techniques, some chemical transformations and an X-ray analysis. These compounds exhibited significant growth inhibition against cultured P388 cells and HL-60 cells. In addition, chaetomugilins A, C and F showed selective cytotoxic activities against 39 human cancer cell lines.

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“…Penicillium sp. isolated from the alga U. intestinalis were observed to produce cytotoxic metabolites including communesins (Numata et al, 1993), penochalasius A-C (Numata et al, 1995), penostatins A-I (Takahashi et al, 1996, Iwamoto et al, 1998 and penochalasius D-H (Iwamoto et al, 2001). The antibacterial and cytotoxic compounds di(2-ethyl hexayl) phthalate and fungisterol were isolated from P. brevicompactum, which was isolated from the associated marine alga Pterocladia sp.…”

Section: Biological Activitiesmentioning

confidence: 99%

Diversity and bioprospecting of fungal communities associated with endemic and cold-adapted macroalgae in Antarctica

et al. 2013

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We surveyed the distribution and diversity of fungi associated with eight macroalgae from Antarctica and their capability to produce bioactive compounds. The collections yielded 148 fungal isolates, which were identified using molecular methods as belonging to 21 genera and 50 taxa. The most frequent taxa were Geomyces species (sp.), Penicillium sp. and Metschnikowia australis. Seven fungal isolates associated with the endemic Antarctic macroalgae Monostroma hariotii (Chlorophyte) displayed high internal transcribed spacer sequences similarities with the psychrophilic pathogenic fungus Geomyces destructans. Thirty-three fungal singletons (66%) were identified, representing rare components of the fungal communities. The fungal communities displayed high diversity, richness and dominance indices; however, rarefaction curves indicated that not all of the fungal diversity present was recovered. Penicillium sp. UFMGCB 6034 and Penicillium sp. UFMGCB 6120, recovered from the endemic species Palmaria decipiens (Rhodophyte) and M. hariotii, respectively, yielded extracts with high and selective antifungal and/or trypanocidal activities, in which a preliminary spectral analysis using proton nuclear magnetic resonance spectroscopy indicated the presence of highly functionalised aromatic compounds. These results suggest that the endemic and cold-adapted macroalgae of Antarctica shelter a rich, diversity and complex fungal communities consisting of a few dominant indigenous or mesophilic cold-adapted species, and a large number of rare and/or endemic taxa, which may provide an interesting model of algal-fungal interactions under extreme conditions as well as a potential source of bioactive compounds.

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Cytotoxic cytochalasans from a Penicillium species separated from a marine alga

Cited by 86 publications

References 13 publications

Cell-adhesion Inhibitors Produced by a Sea Hare-derived Periconia sp.

Cell-adhesion Inhibitors Produced by a Sea Hare-derived Periconia sp.

Chaetomugilins, New Selectively Cytotoxic Metabolites, Produced by a Marine Fish-derived Chaetomium Species

Diversity and bioprospecting of fungal communities associated with endemic and cold-adapted macroalgae in Antarctica

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