UCS1025A and B, New Antitumor Antibiotics from the Fungus <i>Acremonium</i> Species

Agatsuma, Tsutomu; Akama, Tsutomu; Nara, Shinji; Matsumiya, S.; Nakai, Ryuichiro; Ogawa, Harumi; Otaki, Shizuo; Ikeda, Shun‐ichi; Saitoh, Yutaka; Kanda, Yutaka

doi:10.1021/ol026923b

Cited by 86 publications

(48 citation statements)

References 14 publications

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“…Some secondary metabolites that contain the deoxy-tetramic acid ring system have been reported, such as oteromycin, [6] ZG-1494a, USC1025A and B, [8,9] pyrrocidines A and B, [10] ascosalipyrrolidinones A and B, [11] and talaroconvolutins A-D. [12] Although the biogenetic pathways of 1-5 and the deoxy-tetramic acid related compounds mentioned above remain unclear, a plausible pathway can be proposed. This pathway is based on the biosynthetic route of the tetramic acid analogue, trichosetin, and involves a polyketide reacting with one amino acid.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Polyketides Containing Tetramic Acid Moieties Isolated from the Fungus Myceliophthora Thermophila: Elucidation of the Relationship between Cytotoxicity and Stereoconfiguration

Yang

Chen

et al. 2007

Chemistry A European J

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Five new polyketides that contain tetramic acids, myceliothermophins A-E, were isolated from the thermophilic fungus Myceliophthora thermophila. Two sets of 5-alkyl-5-hydroxyl (or 5-methoxyl)-1H-pyrrol-2(5H)-one diastereomers, myceliothermophins A/B and C/D, were separated as pure compounds by using silica-gel column chromatography and recycling reverse-phase high-performance liquid chromatography (RP-HPLC). The relative configurations of the chiral centers in 5-alkyl-5-hydroxyl (or 5-methoxyl)-1H-pyrrol-2(5H)-one moieties were deduced from NOESY correlations. In the cytotoxic assay, the 5-(2-methylpropyldiene)-1H-pyrrol-2(5H)-one analogue (myceliothermophin E) exhibited inhibition against four cancer cell lines. In addition, the significant inhibitory effect of myceliothermophins A and C and the inactivity of myceliothermophins B and D revealed the importance of the relative configurations of 5-alkyl-5-hydroxyl (or 5-methoxyl)-1H-pyrrol-2(5H)-one moieties on their cytotoxicity potency against cancer cells.

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Section: Resultsmentioning

confidence: 99%

Cytotoxic Polyketides Containing Tetramic Acid Moieties Isolated from the Fungus Myceliophthora Thermophila: Elucidation of the Relationship between Cytotoxicity and Stereoconfiguration

Yang

Chen

et al. 2007

Chemistry A European J

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“…[1][2][3][4][5][6] Besides being abundant throughout nature,i zidine alkaloids are also of considerable importance owing to their potent and diverse biological activities. [11] Furthermore,the high and subtype-selective affinity for the nicotinic acetylcholine receptor, [7a,9,12] as well as the positive modulation of voltage-dependent sodium channels, [13] renders them potential candidates for the treatment of various important CNS disorders, [14] or as cardiotonic drugs, [13] respectively. Many of these compounds have been shown to exhibit potent antitumor properties and/or antimicrobial activities.…”

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confidence: 99%

Photooxygenation of Furylalkylamines: Easy Access to Pyrrolizidine and Indolizidine Scaffolds

et al. 2016

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Ahighly adaptable method targeting the ubiquitous and very important pyrrolizidine and indolizidine scaffolds is presented. The general synthetic utility of the method is underscored by its application to the rapid and easy synthesis of five natural products starting from readily accessible alkylfuran precursors.T hese unprotected primary furylalkylamines are subjected to photooxygenation conditions,w hich initiate ac omplex cascade reaction sequence concluding with the production of high value motifs.T his sequence can be tailored to need by varying the choice of both photosensitizer and base additive.

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“…KY4917 by Yamashita et al in 2000, [1] was shown to inhibit telomerase and have antimicrobial activity. [2] This remarkable biological activity coupled with its highly complex structure makes 1 an attractive target for total synthesis; several synthetic studies on this family of compounds have been published. [3] Three total syntheses have been reported to date: these were by the groups of Danishefsky, [4] Hoye, [5] and Christmann.…”

mentioning

confidence: 99%