A Cytotoxic Xanthone Dimer from the Entomopathogenic Fungus <i>Aschersonia</i> sp. BCC 8401

Isaka, Masahiko; Palasarn, Somporn; Kocharin, Kanokarn; Saenboonrueng, Janya

doi:10.1021/np058028h

Cited by 45 publications

(47 citation statements)

References 10 publications

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“…Dimeric tetrahydroxanthones and their derivatives like xanthone−chromanone and chromanone dimers, with attractive antibacterial12, antifungal3 and antimalarial activities4, are a class of structurally interesting natural products produced by multiple fungal and lichenous species5. More than 70 members with 2,2′-, 4,4′- or 2,4′-axial linkages have been isolated and identified since 19585.…”

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confidence: 99%

“…Generally, a rotary energy barrier greater than 23.3 kcal/mol will prevent atropisomeric racemization and lead to stable axially chiral compounds1011. Due to the presence of axial chiralities and their complicated spatial structures, the absolute configuration determinations of these compounds were quite challenging and mostly unsettled141213. Electronic circular dichroism (ECD) calculation was the commonly used method.…”

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confidence: 99%

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Unusual dimeric tetrahydroxanthone derivatives from Aspergillus lentulus and the determination of their axial chiralities

Yang

Wang

et al. 2016

Sci Rep

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The research on secondary metabolites of Aspergillus lentulus afforded eight unusual heterodimeric tetrahydroxanthone derivatives, lentulins A−H (2−9), along with the known compound neosartorin (1). Compounds 1−6 exhibited potent antimicrobial activities especially against methicillin-resistant Staphylococci. Their absolute configurations, particularly the axial chiralities, were unambiguously demonstrated by a combination of electronic circular dichroism (ECD), Rh2(OCOCF3)4-induced ECD experiments, modified Mosher methods, and chemical conversions. Interestingly, compounds 1–4 were the first samples of atropisomers within the dimeric tetrahydroxanthone class. Further investigation of the relationships between their axial chiralities and ECD Cotton effects led to the proposal of a specific CD Exciton Chirality rule to determine the axial chiralities in dimeric tetrahydroxanthones and their derivatives.

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confidence: 99%

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confidence: 99%

Unusual dimeric tetrahydroxanthone derivatives from Aspergillus lentulus and the determination of their axial chiralities

Yang

Wang

et al. 2016

Sci Rep

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“…Xanthones are a class of secondary metabolites with a dibenzo-γ-pirone structure, occurring in a few higher plant families, such as the Gentianaceae and Gutiferae, and in some fungi and lichens (Hostettmann and Hostettmann 1989;Rezanka et al 2003;Isaka et al 2005). Such compounds occupy an important position in the chemistry of natural products.…”

Section: Secondary Metabolitesmentioning

confidence: 99%

Biotechnology and Phytochemistry of Gentianella Species from the Central Regions of the Balkan Peninsula

Krstić-Milošević

Vinterhalter

Janković

et al. 2015

The Gentianaceae - Volume 2: Biotechnology and Applications

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In the central regions of the Balkan Peninsula, the genus Gentianella is represented by six species. Five of them G. albanica, G. austriaca, G. bulgarica, G. ciliata, and G. crispata were subject of phytochemical and in vitro studies. Two species, G. austriaca and G. bulgarica, were established as shoot cultures and procedures developed for their in vitro propagation. Difficulties with seed germination and precocious flowering affected the final propagation stages. Phytochemical analyses were performed on five species from nature and on cultured shoots. Plant material was rich in secondary metabolites with xanthones, flavone-C-glucosides, and secoiridoids as the principal constituents. The xanthone aglycones, demethybellidifolin, bellidifolin, corymbiferin, and their corresponding glucosides were dominant components in all the species investigated. The predominant substitution pattern of xanthones found in the genus Gentianella was 1,3,5,8 and to a lesser extent, 1,3,7,8. Lanceoside and veratriloside were new compounds found in European Gentianella species. In vitro material generally contained less secondary metabolites than plants from nature; the content of secondary products was influenced by the concentration of benzyladenine (BAP) in the culture medium.

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“…Xanthones are a class of secondary metabolites with a dibenzo-γ-pirone structure, occurring in a few higher plant families, such as the Gentianaceae and Gutiferae, and in some fungi and lichens Rezanka et al 2003;Isaka et al 2005). Such compounds occupy an important position in the chemistry of natural products.…”

Section: Secondary Metabolitesmentioning

confidence: 99%

The Gentianaceae - Volume 2: Biotechnology and Applications

Rybczyński¹,

Davey²,

Mikuła³

2015

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A Cytotoxic Xanthone Dimer from the Entomopathogenic Fungus Aschersonia sp. BCC 8401

Cited by 45 publications

References 10 publications

Unusual dimeric tetrahydroxanthone derivatives from Aspergillus lentulus and the determination of their axial chiralities

Unusual dimeric tetrahydroxanthone derivatives from Aspergillus lentulus and the determination of their axial chiralities

Biotechnology and Phytochemistry of Gentianella Species from the Central Regions of the Balkan Peninsula

The Gentianaceae - Volume 2: Biotechnology and Applications

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