Cercosporin. A Pigment of Cercosporina Kikuchii Matsumoto et Tomoyasu. II. Physical and Chemical Properties of Cercosporin and its Derivatives

Kuyama, Shimpei; Tamura, Teiichi

doi:10.1021/ja01578a039

Cited by 41 publications

(26 citation statements)

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“…The extracts were dried over Na 2 S0 4 and concentrated to dryness, and the residue was fractionated by silica gel column chromatography, using CHCI 3 -MeOH (9: 1) as the eluent, into eight fractions (Fr. [1][2][3][4][5][6][7][8]. Fraction 1 showed two red spots at R f =0.34 and 0.68 on silica gel TLC with CHClrMeOH (95: 5), and showed a yellow spot at R r =0.45 and a blue spot at Rf=0.21 on silica gel TLC with benzene-ethyl acetate (8: 2) by p~anisaldehyde-acetic acid-conc.…”

Section: Methodsmentioning

confidence: 99%

“…2) The present paper reports the further isolation and structural elucidation of two new cercosporins, (+ )-isocercosporin (1)3) and ( + )-14-acetylisocercosporin (2), and the identification of three phenol compounds, 1-(2,4-dihydroxy-6-methylphenyl)ethanone (3), isosclerone (4), and trans-3,4-dihydro-3,4,8-trihydroxy-l (2H)-naphthalenone (5). Compound 3 was isolated for the first time as a natural products.…”

mentioning

confidence: 98%

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Phytotoxic Metabolites Isolated fromScolecotrichum graminisFuckel

Tabuchi

Tajimi

Ichihara

1994

Bioscience, Biotechnology, and Biochemistry

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 98%

Phytotoxic Metabolites Isolated fromScolecotrichum graminisFuckel

Tabuchi

Tajimi

Ichihara

1994

Bioscience, Biotechnology, and Biochemistry

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“…Cercosporin, 3 , was first isolated by Kuyama and Tamura from Cercospora kikuchii ,9 a fungus responsible for the “purple speck disease” of soy beans as well as damage to a host of plant species worldwide 10. The structures were elucidated through a series of chemical transformations and subsequent spectroscopic analysis 7,8,11,12.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Investigation of Protein Kinase C Inhibitors: Total Syntheses of (+)-Calphostin D, (+)-Phleichrome, Cercosporin, and New Photoactive Perylenequinones

et al. 2009

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The total syntheses of the PKC inhibitors (+)-calphostin D, (+)-phleichrome, cercosporin, and 10 novel perylenequinones are detailed. The highly convergent and flexible strategy developed employed an enantioselective oxidative biaryl coupling and a double cuprate epoxide opening, allowing the selective syntheses of all the possible stereoisomers in pure form. In addition, this strategy permitted rapid access to a broad range of analogs, including those not accessible from the natural products. These compounds provided a powerful means for evaluation of the perylenequinones structural features necessary to PKC activity. Simpler analogs were discovered with superior PKC inhibitory properties and superior photopotentiation in cancer cell lines relative to the more complex natural products.

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“…The pigments 1a–d and 2 are isolates of the Cladosporium fungi , specifically Cladosporium cladosporioides ( 1a–d ) and Cladosporium phlei (2). 2,3 The more architecturally complex perylenequinones, cercosporin ( 3 )4 and hypocrellin A ( 4 )5 have also been isolated from different fungi.…”

Section: Introductionmentioning

confidence: 99%

Perylenequinone Natural Products: Total Syntheses of the Diastereomers (+)-Phleichrome and (+)-Calphostin D by Assembly of Centrochiral and Axial Chiral Fragments

et al. 2009

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The first total synthesis of (+)-calphostin D and the total synthesis of (+)-phleichrome are outlined. The convergent syntheses utilize an enantiopure biaryl common intermediate, which is formed via an enantioselective catalytic biaryl coupling. The established axial chirality is transferred to the perylenequinone helical stereochemistry with good fidelity. Additionally, efforts focus on the installation of the stereogenic C7,C7′-2-hydroxypropyl groups. Three routes were evaluated to establish the C7,C7′-stereochemistry, in which the successful route involved a double epoxide alkylation with a complex axial chiral biscuprate. This strategy not only allowed the synthesis of the unnatural isomers of calphostin D and phleichrome for assessment in biological systems, but also provided valuable information for the syntheses of the more complex cercosporin and hypocrellin A.

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Cercosporin. A Pigment of Cercosporina Kikuchii Matsumoto et Tomoyasu. II. Physical and Chemical Properties of Cercosporin and its Derivatives

Cited by 41 publications

References 0 publications

Phytotoxic Metabolites Isolated fromScolecotrichum graminisFuckel

Phytotoxic Metabolites Isolated fromScolecotrichum graminisFuckel

Design, Synthesis, and Investigation of Protein Kinase C Inhibitors: Total Syntheses of (+)-Calphostin D, (+)-Phleichrome, Cercosporin, and New Photoactive Perylenequinones

Perylenequinone Natural Products: Total Syntheses of the Diastereomers (+)-Phleichrome and (+)-Calphostin D by Assembly of Centrochiral and Axial Chiral Fragments

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