Studies towards Trichodimerol: Novel Cascade Reactions and Polycyclic Frameworks

Nicolaou, K. C.; Jautelat, Rolf; Vassilikogiannakis, Georgios; Baran, Phil S.; Simonsen, Klaus B.

doi:10.1002/(sici)1521-3765(19991203)5:12<3651::aid-chem3651>3.0.co;2-y

Cited by 44 publications

(20 citation statements)

References 23 publications

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“…with different origins (Maskey et al 2005). Many studies have been carried out on their isolation and chemical characterization (Trifonov et al 1983(Trifonov et al , 1986Gao et al 1995;Andrade et al 1997;Shirota et al 1997;Abe et al 1998Abe et al , 1999Sperry et al 1998;Maskey et al 2005), their biosynthesis (Sperry et al 1998;Abe et al 2002), as well as their synthesis and biomimetic synthesis (Nicolaou et al 1999(Nicolaou et al , 2000Pitsinos et al 2008). In particular, bislongiquinolide (3) was previously isolated, together with an epoxysorbicillinoid, a new vertinoid pigment, from a T. longibrachiatum strain isolated from the marine sponge…”

Section: Discussionmentioning

confidence: 99%

Bisorbicillinoids Produced by the Fungus Trichoderma citrinoviride Affect Feeding Preference of the Aphid Schizaphis graminum

et al. 2009

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We report the effects of some bisorbicillinoids isolated from biomass of the fungus Trichoderma citrinoviride on settling and feeding preference of the aphid Schizaphis graminum. Purification of the fungal metabolites was carried out by a combination of column chromatography and thin-layer chromatography using direct and reverse phases. Chemical identification was performed by spectroscopic methods including nuclear magnetic resonance and mass spectrometry. The identified bisorbicillinoids appeared to be bislongiquinolide, its 16,17-dihydro derivative, trichodimerol, and dihydrotrichodimerol. A feeding preference test with alate morphs of S. graminum was used to identify the active fractions. Among the four bisorbicillinoids, dihydrotrichodimerol and bislongiquinolide influenced aphid feeding preference, restraining specimens from settling on leaves treated with metabolites. Taste neurons sensitive to these compounds, particularly to bislongiquinolide, were located on tarsi of the S. graminum alate morphs.

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Section: Discussionmentioning

confidence: 99%

Bisorbicillinoids Produced by the Fungus Trichoderma citrinoviride Affect Feeding Preference of the Aphid Schizaphis graminum

et al. 2009

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“…Further studies led to the isolation of another two new bisorbicillinoids [3] possessing an unusual open-ended cage structure [4], dihydrotrichodimerol (1) and tetrahydrotrichodimerol (2). This kind of compounds is rare in nature.…”

Section: Introductionmentioning

confidence: 99%

Dihydrotrichodimerol and Tetrahydrotrichodimerol, Two New Bisorbicillinoids, from a Marine-derived Penicillium terrestre

Liu

Zhu

et al. 2005

J Antibiot

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“…In the course of our screening program for free radical scavengers by detecting the radical scavenging activity of the DPPH radical, 5) we have isolated twelve sorbicillinoids and bisorbicillinoids, [6][7][8][9][10][11][12] including eight novel radical scavengers, from the fermentation broth of Trichoderma sp. USF-2690 strain.…”

mentioning

confidence: 99%

Novel DPPH Radical Scavengers, Demethylbisorbibutenolide and Trichopyrone, from a Fungus

Washida¹,

Abe²,

Sugiyama³

et al. 2007

Bioscience, Biotechnology, and Biochemistry

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In our screening program for antioxidants with 1,1-diphenyl-2-picrylhydrazyl (DPPH)-radical scavenging activity, two novel compounds, demethylbisorbibutenolide (1) and trichopyrone (2), were isolated from the fermentation broth of the fungus of USF-4860 strain isolated from a soil sample. The structures of these compounds were determined from spectroscopic evidence. The biosynthetic origin of the carbon atoms of 2 was unambiguously determined by feeding experiments using (13)C-labeled precursors and elucidation of the (13)C-NMR spectrum of (13)C-labeled 2. These studies showed that 2 was derived from five acetates and a methyl group of methionine. In the DPPH-radical scavenging assay, 1 and 2 gave ED(50) values of 149 and 167 muM after standing for 2.0 hr. Compound 2 reacted with the DPPH radical to form reaction product 3 which was determined to be 1-[4-(3,4-dihydro-3-methyl-6-{1,3-pentadienyl}-2,4-dioxo-2H-pyran-3-yl)-phenyl]-1-phenyl-2-picrylhydrazine from spectroscopic evidence.

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Studies towards Trichodimerol: Novel Cascade Reactions and Polycyclic Frameworks

Cited by 44 publications

References 23 publications

Bisorbicillinoids Produced by the Fungus Trichoderma citrinoviride Affect Feeding Preference of the Aphid Schizaphis graminum

Bisorbicillinoids Produced by the Fungus Trichoderma citrinoviride Affect Feeding Preference of the Aphid Schizaphis graminum

Dihydrotrichodimerol and Tetrahydrotrichodimerol, Two New Bisorbicillinoids, from a Marine-derived Penicillium terrestre

Novel DPPH Radical Scavengers, Demethylbisorbibutenolide and Trichopyrone, from a Fungus

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