Chromones, containing an oxepin ring, from

Dean, F. H.; Parton, Brian; Somvichien, Nongyow; Taylor, David A.

doi:10.1016/s0040-4039(01)89821-x

Cited by 34 publications

(24 citation statements)

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“…Pennington and Styles (1975) merged Cedrelopsis with Ptaeroxylon based on the similarity of the structure of their secondary xylems and pollen morphology. The fusion of Cedrelopsis and Ptaeroxylon are also supported by the presence of some phytochemical data [e.g., the presence of a wide variety of simple and prenylated 6,7-dioxygenated coumarins (e.g., Randrianarivelojosia et al, 2005) and 5,7-dioxygenated prenylated chromones (e.g., Dean et al, 1967;Dean and Robinson, 1971) and of some unusual limonoids (e.g., Mulholland et al, 1999Mulholland et al, , 2002Mulholland et al, , 2003Mulholland et al, , 2004]. On the other hand, the two genera can easily be distinguished from each other.…”

Section: And Phylogenetic Position Of the Malagasy Genus Cedrelopsismentioning

confidence: 76%

Implications of a molecular phylogenetic study of the Malagasy genus Cedrelopsis and its relatives (Ptaeroxylaceae)

Razafimandimbison

Appelhans

Rabarison

et al. 2010

Molecular Phylogenetics and Evolution

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Section: And Phylogenetic Position Of the Malagasy Genus Cedrelopsismentioning

confidence: 76%

Implications of a molecular phylogenetic study of the Malagasy genus Cedrelopsis and its relatives (Ptaeroxylaceae)

Razafimandimbison

Appelhans

Rabarison

et al. 2010

Molecular Phylogenetics and Evolution

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“…Several biosynthetic schemes have been advanced to account for the formation of these compounds, but little experimental evidence has suggested that the chromones were derived from shikimate, and the derivation of some coumarins and chromones from C,-substituted phloroglucinol has also been proposed (9). Egger (10) obtained incorporation of '"C-acetate into &hello1 in Eranthis hiemelis (Ranunculaceae) and showed by chemical degradation that both the benzene and pyrone rings were acetate-derived.…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Furanochromones

Harrison¹,

Bailey²,

Steck³

1971

Can. J. Biochem.

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of furanocbomones. Can. 9. Biochern. 49,[964][965][966][967][968][969][970].Radioactive khellin, visnagin, and visarnminol were recovered from Anarni oisnaga plants fed [I-14C]-acetate. A trapping experiment with 5,7-dihydroxy-2-methylchromone indicated that this compound was formed from acetate in the plant. It was then prepared labelled with I4C and 'H and administered to shoots, demonstrating its conversion to visarnrninol and furancdshomones. A biosynthetic pathway is proposed: acetate + 5,7-dihydroxy-2-methylchron10ne -+ peu~nin++visamminol++visnagin and khellin.The gas chromatography of some A. visnaga constituents is described. The furamocoumarins xanthotoxin and isopimpinellin were shown to be present in the plant.Administration of labelled 5,7-dihydsoxy-Zrnethylchromone to shoots of Angelica archangelica resulted in the elaboration of labelled furanochrsmones, suggesting that the furan moiety of furamochromones and fwamocoumarins may be formed via similar if not identical enzyme systems. HARRISON, P. G., BAILEY, B. K., et STECK, W. Biosynthesis of furanochromones. Can. J. Biochem. 49, 964-970 (1971).Apr6s ingestion de [I-14C] acktate par des plants d9Ammi visnaga, nous avons recouvrk de la radioactivitb dans la kheIline, la visnagine et Ie visamminol. Une experience de trappage dkmontre que dans 8 wtte plante, la $7-dihydroxy-2-mCthylc~omone est formke h partir de l'acbtate. Nous I'avons alors marquke avec le I4C et le 'H et nous l'avons administree ii des pousses pour demontrer sa conversion en visamminol et en furanochrsmones. Voici la route biosynthetique proposie: acbtate-+5,7-dihydroxy-2-m~thylchromone-+peucenine++visarnminol++visnagine et khelline.Nous decrivons la chromatographie en phase gazeuse de quelques constituants d'A. oisnaga. Ees furanocoumarines xanthotoxine et isopimpinelline, sont prtsentes dans la plamte. L'administration de 5,7-dihydroxy-2-m$thylchromone masquk a des pousses d9Angelisa archangelica entraine 1'elaboration de furanmhromones marquees. II semble done que la fraction furame des furanochromones et des furanocoumarines wit formde par des systkmes enzymatiques semblables sinon identiques.INRCC No. 11993. 2NRCC summer student 1970. Present address :

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“…The heartwood of Ptaeroxylon obliquum has yielded several chromonescontaining an oxepin ring, 3) and so have the plants Cneorumpulverulentum^and Cnidium monnieri.5) However, no bioactivities of these compoundshave been reported.…”

mentioning

confidence: 99%

Pterulinic Acid and Pterulone, Two Novel Inhibitors of NADH: Ubiquinone Oxidoreductase (Complex I) Produced by a Pterla Species. II. Physico-chemical Properties and Structure Elucidationt.

Engler¹,

Anke²,

Sterner

1997

J. Antibiot.

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The structures of two novel fungal antibiotics, isolated from a Pterula species, that interfere with the NADH :ubiquinone oxidoreductase and inhibit the respiration of eucaryotes, were determined by spectroscopic techniques. Both compounds, pterulinic acid (la) and pterulone (2), contain a 1-benzoxepin ring system and are chlorinated. Pterulinic acid (la), which was obtained as a 1 : 5 inseparable mixture of the two isomers (Z)-la and (E)-la, in addition contains a furan.Their structures were determined by mass spectrometry and NMR spectroscopy, and 2Dheteronuclear correlation experiments permitted the assignment of all NMRsignals.The fungal metabolites pterulinic acid (la) and pterulone (2) were isolated from fermentations of a Pterula species in the course of a screening of basidiomycetes for the production of new antifungal compounds.1} la and 2 exhibit strong antifungal and weak cytotoxic activities.Both antibiotics are inhibitors of eucaryotic respiration, interfering with NADH:ubiquinone oxidoreductase. 1}

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Chromones, containing an oxepin ring, from

Cited by 34 publications

References 0 publications

Implications of a molecular phylogenetic study of the Malagasy genus Cedrelopsis and its relatives (Ptaeroxylaceae)

Implications of a molecular phylogenetic study of the Malagasy genus Cedrelopsis and its relatives (Ptaeroxylaceae)

Biosynthesis of Furanochromones

Pterulinic Acid and Pterulone, Two Novel Inhibitors of NADH: Ubiquinone Oxidoreductase (Complex I) Produced by a Pterla Species. II. Physico-chemical Properties and Structure Elucidationt.

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