Oxidative biosynthesis of phenylbenzoisochromenones from phenylphenalenones

Phytochemistry

Volumn 62, Issue 3, 2003, Pages 307-312

  Opitz, Stefan ^a   Schneider, Bernd ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

13C NMR; Biosynthesis; Haemodoraceae; Oxidative rearrangement; Phenylbenzoisochromenones; Phenylphenalenones; Wachendorfia thyrsiflora

Indexed keywords

CHROMENE DERIVATIVE; PHENYLBENZOISOCHROMENONE; PHENYLPHENALENONE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DATA ANALYSIS; DECARBOXYLATION; DRUG ISOLATION; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; SYNTHESIS;

CARBON ISOTOPES; CYCLIZATION; DECARBOXYLATION; HETEROCYCLIC COMPOUNDS; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OXIDATION-REDUCTION; OXYGENASES; PHENALENES; PHENYLALANINE; POLYCYCLIC COMPOUNDS; POLYCYCLIC HYDROCARBONS, AROMATIC; ZINGIBERALES;

HAEMODORACEAE; WACHENDORFIA THYRSIFLORA;

EID: 0037308163     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(02)00546-0     Document Type: Article

References (23)

1. Abd El-Mawla, A.M.A., Beerhues, L., 2002. Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum. Planta 214, 727-733.
2. Bazan, A.C., Edwards, J.M., 1976. Phenalenone pigments of the flowers of Lachanthes tinctoria 15, 1413-1415.
3. Cooke, R.G., 1970. Phenylnaphthalene pigments of Lachnanthes tinctoria. Phytochemistry 9, 1103-1106.
4. Cooke, R.G., Dagley, I.J., 1979. Colouring matters of Australian plants. XXI. Naphthoxanthenones in the Haemodoraceae. Australian Journal of Chemistry 32, 1841-1847.
5. Cooke, R.G., Edwards, J.M., 1981. Naturally occurring phenalenones and related compounds. Progress in the Chemistry of Organic Natural Products 40, 153-190.
6. Cooke, R.G., Thomas, R.L., 1975. Colouring matters of Australian plants. XVIII. Constituents of Anigozanthos rufus. Australian Journal of Chemistry 28, 1053-1057.
7. Edwards, J.M., 1974. Phenylphenalenones from Wachendorfia species. Phytochemistry 13, 290-291.
8. Edwards, J.M., Weiss, U., 1970. Perinaphthenone pigments from the fruit capsules of Lachnanthes tinctoria. Phytochemistry 9, 1653- 1657.
9. Edwards, J.M., Weiss, U., 1972. Quinone methides derived from 5-oxa and 5-aza-9-phenyl-1-phenalenone in the flowers of Lachnanthes tinctoria (Haemodoraceae). Tetrahedron Letters 17, 1631-1634.
10. Edwards, J.M., Weiss, U., 1974. Phenalenone pigments of the root system of Lachnanthes tinctoria. Phytochemistry 13, 1597-1602.
11. 13C-phenylalanine. Tetrahedron Letters 51, 4471-4474.
12. Hölscher, D., Schneider, B., 1995a. The biosynthetic origin of the central one-carbon unit of phenylphenalenones in Anigozanthos preissii. Natural Product Letters 7, 177-182.
13. Hölscher, D., Schneider, B., 1995b. A diarylheptanoid intermediate in the biosynthesis of phenylphenalenones in Anigozanthos preissii. Journal of the Chemical Society, Chemical Communications, 525-526.
14. Hölscher, D., Schneider, B., 1997. Phenylphenalenones from root cultures of Anigozanthos preissii. Phytochemistry 45, 87-91.
15. Jefford, C.W., Cadby, P.A., 1981. Molecular mechanism of enzyme-catalyzed dioxygenation. Progress in the Chemistry of Organic Natural Products 40, 191-265.
16. Kamo, T., Kato, N., Hirai, N., Tsuda, M., Fujioka, D., Ohigashi, H., 1998. Phenylphenalenone-type phytoalexins from unripe Bufigulan banana fruit. Bioscience, Biotechnology and Biochemistry 62, 95- 101.
17. Kamo, T., Hirai, N., Tsuda, M., Fujioka, D., Ohigashi, H., 2000. Changes in the content and biosynthesis of phytoalexins in banana fruit. Bioscience, Biotechnology and Biochemistry 64, 2089-2098.
18. Murashige, T., Skoog, F., 1962. A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiologia Plantarum 15, 473-497.
19. Luis, J.G., Fletcher, W.Q., Echeverri, F., Grillo, T.A., Perales, A., Gonzalez, A., 1995. Intermediates with biosynthetic implications in de novo production of phenyl-phenalenone-type phytoalexins by Musa acuminata. Revised structure of emenolone. Tetrahedron 51, 4117-4130.
20. Opitz, S., Otálvaro, F., Echeverri, F., Quiñones, W., Schneider, B., 2002a. Isomeric oxabenzochrysenones from Musa acuminata and Wachendorfia thyrsiflora. Natural Product Letters 16, 335-338.
21. Opitz, S., Hölscher, D., Oldham, N.J., Bartram, S., Schneider, B., 2002b. Phenylphenalenone-related compounds - chemotaxonomic markers of the Haemodoraceae from Xiphidium caeruleum. Journal of Natural Products 65, 1122-1130.
22. Schmitt, B., Schneider, B., 1999. Dihydrophenylpropanoids are involved in the biosynthesis of phenylphenalenones in Anigozanthos preissii. Phytochemistry 52, 45-53.
23. Schmitt, B., Schneider, B., 2001. Phenylpropanoid interconversion in Anigozanthos preissii observed by high-performance liquid chromatography-nuclear magnetic resonance spectroscopy. Phytochemical Analysis 12, 43-47.