Synthesis of macrocyclic trichothecene mycotoxins

Tamm, Christoph; Jeker, N.

doi:10.1016/s0040-4020(01)83438-4

Cited by 14 publications

(6 citation statements)

References 90 publications

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“…15 Compound 1 was also markedly cytotoxic, whereas the remaining compounds were moderately active. These results agree with generalized conclusions about the structure-cytotoxicity relationship of trichothecenes 26,27 and indicate that the C-3 R-hydroxy substituent in 1 and 6 is responsible for the increase of activity, compared to that of trichothecolone and trichothecin. A similar effect was observed in the brine shrimp assay, with LC 50 values of 2.2 and 0.52 µg/mL for 5 and 6, respectively.…”

Section: Resultssupporting

confidence: 90%

“…8-Dihydrotrichothecinol A (1): amorphous white solid (4 mg, 0.011% of extract); mp 119-120 °C, [R]D -25°(c 0. (8), 153 (27), 136 (100).…”

Section: Methodsmentioning

confidence: 99%

“…After evaporation of the solvent, the residue was filtered through a small column of Si gel. Elution with CH2Cl2-EtOAc (9:1) gave the corresponding monoacetate 2a (6 mg, 94%), [R]D +6.5°(c 0.18, CH2Cl2); UV (MeOH) λmax ( ) 223 (5390) nm; IR νmax (NaCl) 3435, 2924, 2853, 1740, 1682, 1454, 1369, 1240, and 1057 cm -1 ; 1 H and 13 C NMR data, see Table 1; EIMS(m/z, %) 322 [M] + (12), 249 (1), 221 (2), 207 (2), 201 (7), 191 (5), 175 (7), 165 (15), 149 (14), 137 (27), 121 (27) 13-Acetoxyloukacinol B (3a). Compound 3 (1.3 mg) was dissolved in a mixture of Ac2O (0.4 mL), pyridine (0.4 mL), 4; UV, IR, and EIMS data identical to those reported in the literature.…”

Section: Methodsmentioning

confidence: 99%

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New Trichothecenes Isolated from Holarrhena floribunda

et al. 1999

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Bioassay-guided fractionation of an extract of Holarrhena floribunda stem, has led to the isolation of the new trichothecenes, 8-dihydrotrichothecinol A (1), loukacinol A (2), and loukacinol B (3), and the known compounds, trichothecolone (4), trichothecin (5), trichothecinol A (6), rosenonolactone (7), 6beta-hydroxyrosenonolactone (8), and rosololactone (9). The structures were determined by spectral and chemical methods, and absolute configurations were established by a modified Horeau's method using HPLC. Compounds 1 and 6 exhibited significant cytotoxicity against several human tumor cell lines, whereas compound 8 showed moderate and weak antileishmanial activity toward extracellular and intracellular Leishmania donovani, respectively.

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Section: Resultssupporting

confidence: 90%

“…8-Dihydrotrichothecinol A (1): amorphous white solid (4 mg, 0.011% of extract); mp 119-120 °C, [R]D -25°(c 0. (8), 153 (27), 136 (100).…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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New Trichothecenes Isolated from Holarrhena floribunda

et al. 1999

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“…The synthesis of macrocyclic trichothecenes was reviewed in 1989 by Tamm and Jeker. 944 Examples of the most interesting macrocyclic trichothecenes are summarized in Figures 11-13. Although some trichothecenes like miophytocen A were isolated from shrubs, it is believed that they are primarily/generally produced by fungi.…”

Section: Macrocyclic Trichothecenesmentioning

confidence: 99%

Chemistry and Biology of Mycotoxins and Related Fungal Metabolites

et al. 2009

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Table 2. Mycotoxins Produced by Aspergillus sp. fungus mycotoxin produced Aspergillus aculeatus Secalonic acid D (10) Aspergillus albertensis Ochratoxin A (7), Ochratoxin B (155) Aspergillus alliaceus Ochratoxin A (7), Ochratoxin B (155) Aspergillus auricomus Ochratoxin A (7), Ochratoxin B (155) Aspergillus bombycis Aflatoxin B 1 (1), Aflatoxin G (13) Aspergillus breVipes Viriditoxin Aspergillus caespitosus Fumitremorgin A Aspergillus candidus Citrinin (2), Acetylisoneosolaniol Aspergillus carneus Citrinin (2) Aspergillus claVatus Patulin (3), Tryptoquivaline A (C), Cytochalasin E (443) Aspergillus flaVipes Citrinin (2) Aspergillus flaVus Aflatoxin B 1 (1), Aflatoxin B 2 (15), Aflatoxin M 1 (12), Cyclopiazonic acid, Aflatrem (indole alkaloid), 3-Nitropropionic acid, Sterigmatocystin (62), Versicolorin A (597), Aspertoxin Aspergillus fresenii Xanthomegnin (591) Aspergillus fumigatus Fumitremorgin A, Verruculogen (543), Gliotoxin (527), Fumagillin, Helvolic acid, Sphingofungins, Brevianamide A (545), Phthioic acid, Fumigaclavin C, Aurasperone C Aspergillus giganteus Patulin (3) Aspergillus melleus Ochratoxin A (7), Viomellein, Xanthomegnin (591) Aspergillus microcysticus Aspochalasin Aspergillus nidulans (Emericella nidulans) Sterigmatocystin (62), Dechloronidulin, Emestrin Aspergillus niger Malformin, Ochratoxin A (7), Fumonisin B 2 (5) Aspergillus nomius Aflatoxin B 1 (1), Aflatoxin B 2 (15), Aflatoxin G 1 (13), Aflatoxin G 2 (19) Aspergillus ochraceoroseus Aflatoxin B 1 (1), Sterigmatocystin (62) Aspergillus ochraceus Ochratoxin A (7), Ochratoxin B (155), Ochratoxin C (156), Viomellein, Penicillic acid (187) Aspergillus oryzae Cyclopiazonic acid, Maltoryzine, 3-Nitropropionic acid Aspergillus ostianus Ochratoxin A (7) Aspergillus parasiticus Aflatoxin B 1 (1), Aflatoxin B 2 (15), Aflatoxin G 1 (13), Aflatoxin G 2 (19), Aflatoxin M 1 (12), Versicolorin A (597) Aspergillus petrakii Ochratoxin A (7) Aspergillus pseudotamarii Cyclopiazonic acid, Aflatoxin B 1 (1) Aspergillus restrictus Restrictocin Aspergillus sclerotiorum Ochratoxin B (155) Aspergillus sulfureus Ochratoxin A (7), Ochratoxin B (155)

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“…The key structural feature of the trichothecene skeleton 27 is having a tricyclic structure, in which the stereochemistries of the three rings are all in the cis configuration (Figure ). One frequently found strategy for the synthesis of trichothecenes is A and C ring formation with stereoselective functionalization (e.g., 28 ), followed by ring closure to construct the B ring (Figure A) …”

Section: Resultsmentioning

confidence: 99%

Development of Diastereoselective Birch Reduction−Alkylation Reactions of Bi- and Tricyclic β-Alkoxy-α,β-unsaturated Ketones

et al. 2009

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Diastereoselective Birch reduction-alkylation reactions of bicyclic beta-alkoxy-alpha,beta-unsaturated carbonyl compounds and tricyclic analogues were investigated. Although the relative configuration of the product was altered according to the structure of the starting material, stereoselectivity of the reaction could be accounted for by similar reaction pathways. The product from the tricyclic beta-alkoxy-alpha,beta-unsaturated carbonyl compound corresponded to the trichothecene skeleton.

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Synthesis of macrocyclic trichothecene mycotoxins

Cited by 14 publications

References 90 publications

New Trichothecenes Isolated from Holarrhena floribunda

New Trichothecenes Isolated from Holarrhena floribunda

Chemistry and Biology of Mycotoxins and Related Fungal Metabolites

Development of Diastereoselective Birch Reduction−Alkylation Reactions of Bi- and Tricyclic β-Alkoxy-α,β-unsaturated Ketones

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