Versixanthones A–F, Cytotoxic Xanthone–Chromanone Dimers from the Marine-Derived Fungus<i>Aspergillus versicolor</i>HDN1009

Wu, Guangwei; Yu, Ge; Kurtán, Tibor; Mándi, Attila; Peng, Jixing; Mo, Xiaomei; Liu, Ming; Li, Hui; Sun, Xinhua; Li, Jing; Zhu, Tianjiao; Gu, Qianqun; Li, Dehai

doi:10.1021/acs.jnatprod.5b00636

Cited by 73 publications

(92 citation statements)

References 32 publications

(51 reference statements)

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“…9), also suggesting the domination of chromophore interactions in ECD CEs. For further verification, different dimeric tetrahydroxanthone analogues were checked, which accurately revealed the same result as determined by X-ray analysis, chemical conversions or ECD calculations (Supporting Information Table S3)15172829.…”

Section: Resultsmentioning

confidence: 62%

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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Section: Resultsmentioning

confidence: 62%

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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“…From T. stipitatus DgCr2 2.1b, the new compound 1 was identified, in addition to the polyketides: secalonic acid A (2), 16 blennolide G (3), versixanthone A (4), 18 penicillixanthone A (5), 16 and paecillin B (6). 19 Talaromyces sp. VrTrb2 1.1 yielded a novel substance (7) and the known compounds ergosterol (9), 20 ergosterol peroxide (10), 21 ergosta-4,6,8(14),22-tetraen-3-one (11), 22 and citric acid (12).…”

Section: Isolated Compoundsmentioning

confidence: 99%

“…Thus, compound 1 was assigned as a new chromanone homodimer, and to avoid any misunderstanding was named as being paecilin D, in respect to the previously isolated dimeric xanthones bearing two chromanone monomers. 19 28 The presence of a heptet-like signal at d 2.21 (hept, J 6.8 Hz, H-7) was an indicative of a methinic hydrogen in a 3-ethylpentane system. Four double doublets at d 2.45 (dd, J 6.8, 13.9 Hz, H-6a), 2.59 (dd, J 6.8, 13.9 Hz, H-6β), 2.37 (dd, J 6.8, 13.9 Hz, H-8a), and 2.56 (dd, J 6.8, 13.9 Hz, H-8β) constituted two ABC-like spin systems.…”

Section: Isolated Compoundsmentioning

confidence: 99%

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Antifungal Polyketides and Other Compounds from Amazonian Endophytic Talaromyces Fungi

Silva

Souza

Bianco

et al. 2017

J. Braz. Chem. Soc.

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The continuous search for biologically active compound candidates pushes the pursuit of new substances produced by diverse organisms. Endophytic fungi are known as a promising source of metabolites with several biological activities. Based on the rich Amazonian biodiversity and the chemical potential of microbial sources, three Talaromyces strains, all major endophytes from their respective host plants, were studied aiming at the isolation of biologically active secondary metabolites. Through classical chromatographic approaches, 13 compounds were isolated from the antimicrobial extracts of the studied strains. From these, polyketides, steroids, anhydrides, and phenolic compounds were identified. Among them, two previously undescribed compounds were elucidated based on spectroscopic and spectrometric methods, a homodimer chromanone and a maleic anhydride methyl ester. The antimicrobial activity against a panel of pathogenic microorganisms from extracts, fractions, and isolated compounds was evaluated.

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“…The formation of ring opened variants ( 11 ), such as versixanthone F 18 ( 7 ) and bipolarinone ( 8 ), plausibly result from methanolysis during isolation. Notably, the ring‐opened lactone form (e.g., 7 ) can possess more potent cytotoxicity than the corresponding ring closed forms . Finally, the results of recently published studies conducted by Kikuchi and co‐workers aided in our dimeric chromenone library development .…”

Section: Resultsmentioning

confidence: 94%

Synthesis and Anticancer Activity of Structure Simplified Naturally Inspired Dimeric Chromenone Derivatives

et al. 2019

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Select dimeric chromenones exhibit low micromolar cytotoxicity toward lymphoma and leukemia cell lines, L5178Y and HL60, respectively. The bioactive dimeric chromenones were identified from a focused library of structurally simplified derivatives of naturally occurring dimeric chromenones and tetrahydroxanthones that was prepared as part of this study. The simple dimeric chromenone scaffolds contain no stereogenic centers, are easily synthesized, and may be utilized as lead compounds in cancer research and drug discovery.

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Versixanthones A–F, Cytotoxic Xanthone–Chromanone Dimers from the Marine-Derived FungusAspergillus versicolorHDN1009

Cited by 73 publications

References 32 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

Antifungal Polyketides and Other Compounds from Amazonian Endophytic Talaromyces Fungi

Synthesis and Anticancer Activity of Structure Simplified Naturally Inspired Dimeric Chromenone Derivatives

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