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Flavichalasines A – M, cytochalasan alkaloids from Aspergillus flavipes

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ABSTRACT

12356131421215614614: Two new tetracyclic cytochalasans, flavichalasines A and B ( and ), three new pentacyclic cytochalasans, flavichalasines C–E (–), and eight new tricyclic cytochalasans, flavichalasines F–M (–), together with eight known analogues (–), were isolated from the solid culture of Aspergillus flavipes. Structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses including 1D, 2D NMR and HRESIMS data. Their absolute configurations were determined by comparison of their experimental ECD with either computed ECD or experimental ECD spectrum of known compound. The structure and absolute configuration of were further determined by X-ray crystallographic diffraction. Flavichalasine A () represents the first example of cytochalasan with a terminal double bond at the macrocyclic ring and flavichalasine E () is the only cytochalasan with an α-oriented oxygen-bridge in D ring. These new compounds were evaluated for their cytotoxic activities against seven human cancer cell lines, of which, and displayed moderate inhibitory activities against tested cell lines. In addition, compounds and induced apoptosis of HL60 cells by activation of caspase-3 and degradation of PARP.

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Structures of isolated compounds.
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f1: Structures of isolated compounds.

Mentions: As part of our ongoing search for novel bioactive secondary metabolites from fungi, dozens of cytochalasans with distinctive cytotoxic or anti-HIV activities have been isolated from the arthropod-derived fungus Chaetomium globosum2223. In order to find more structure intriguing and bioactive cytochalasans, secondary metabolites of the fungus Aspergillus flavipes have been systemically investigated. In the previous researches on A. flavipes, a series of cytochalasan dimmers were isolated, with asperchalasine A24 and epicochalasines A and B25 as their representatives, in addition to monomeric aspochalasin derivatives5. Further investigation on this fungus led to the isolation of thirteen new (1–13) and eight known (14–21) cytochalasans belonging to the aspochalasin group from the EtOH extract of A. flavipes (Fig. 1), including two new tetracyclic (1 and 2) and three new pentacyclic cytochalasans (3–5).


Flavichalasines A – M, cytochalasan alkaloids from Aspergillus flavipes
Structures of isolated compounds.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5304325&req=5

f1: Structures of isolated compounds.
Mentions: As part of our ongoing search for novel bioactive secondary metabolites from fungi, dozens of cytochalasans with distinctive cytotoxic or anti-HIV activities have been isolated from the arthropod-derived fungus Chaetomium globosum2223. In order to find more structure intriguing and bioactive cytochalasans, secondary metabolites of the fungus Aspergillus flavipes have been systemically investigated. In the previous researches on A. flavipes, a series of cytochalasan dimmers were isolated, with asperchalasine A24 and epicochalasines A and B25 as their representatives, in addition to monomeric aspochalasin derivatives5. Further investigation on this fungus led to the isolation of thirteen new (1–13) and eight known (14–21) cytochalasans belonging to the aspochalasin group from the EtOH extract of A. flavipes (Fig. 1), including two new tetracyclic (1 and 2) and three new pentacyclic cytochalasans (3–5).

View Article: PubMed Central - PubMed

ABSTRACT

12356131421215614614: Two new tetracyclic cytochalasans, flavichalasines A and B ( and ), three new pentacyclic cytochalasans, flavichalasines C–E (–), and eight new tricyclic cytochalasans, flavichalasines F–M (–), together with eight known analogues (–), were isolated from the solid culture of Aspergillus flavipes. Structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses including 1D, 2D NMR and HRESIMS data. Their absolute configurations were determined by comparison of their experimental ECD with either computed ECD or experimental ECD spectrum of known compound. The structure and absolute configuration of were further determined by X-ray crystallographic diffraction. Flavichalasine A () represents the first example of cytochalasan with a terminal double bond at the macrocyclic ring and flavichalasine E () is the only cytochalasan with an α-oriented oxygen-bridge in D ring. These new compounds were evaluated for their cytotoxic activities against seven human cancer cell lines, of which, and displayed moderate inhibitory activities against tested cell lines. In addition, compounds and induced apoptosis of HL60 cells by activation of caspase-3 and degradation of PARP.

No MeSH data available.