Polyoxygenated cyclohexane derivatives and other constituents from Kaempferia rotunda L.

Phytochemistry

Volumn 68, Issue 11, 2007, Pages 1579-1586

  Stevenson, Philip C ^a   Veitch, Nigel C ^a   Simmonds, Monique S J ^a  

^a JODRELL LABORATORY   (United Kingdom)

Author keywords

Cyclohexane epoxides; Diels Alder adduct; Kaempferia rotunda; Salicin; Zeylenol; Zingiberaceae

Indexed keywords

BENZYL ALCOHOL DERIVATIVE; CYCLOHEXANE DERIVATIVE; PLANT EXTRACT; SALICIN;

ANIMAL; ARMYWORM; ARTICLE; CHEMISTRY; DRUG EFFECT; FEEDING BEHAVIOR; ISOLATION AND PURIFICATION; LARVA; PHYSIOLOGY; RHIZOME; ZINGIBERACEAE;

ANIMALS; BENZYL ALCOHOLS; CYCLOHEXANES; FEEDING BEHAVIOR; LARVA; PLANT EXTRACTS; RHIZOME; SPODOPTERA; ZINGIBERACEAE;

ALNUS; KAEMPFERIA ROTUNDA; SPODOPTERA LITTORALIS; ZINGIBERACEAE;

EID: 34248645686     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.03.015     Document Type: Article

References (25)

1. Atsumi S., Umezawa K., Iinuma H., Nagagawa H., Nakamura H., Iitaka Y., and Takeuchi T. Production isolation and structure determination of a novel β-glucosidase inhibitor, cyclophellitol from Phellinus sp. J. Antibiot. 43 (1990) 49-53
2. bin Jantan I., Yassin M.S.M., Chin C.B., Chen L.L., and Sim N.L. Antifungal activity of the essential oils of nine Zingiberaceae species. Pharm. Biol. 41 (2003) 392-397
3. Boll P.M., Prasad A.K., Tyagi O.D., Wengel J., Olsen C.E., Kumar N., Bisht K.S., and Parmar V.S. Neolignans, cyclohexanes and alkaloids from Piper wightii. Recl. Trav. Chim. Pays-Bas 115 (1996) 9-12
4. Chane-Ming J., Vera R., Chalchat J.C., and Cabassu P. Chemical composition of essential oils from rhizomes, leaves and flowers of Curcuma longa L. from Reunion Island. J. Essent. Oil Res. 14 (2002) 249-251
5. Duus J.Ø., Gotfredsen C.H., and Bock K. Carbohydrate structural determination by NMR spectroscopy: modern methods and limitations. Chem. Rev. 100 (2000) 4589-4614
6. Grossel M.C. Alicyclic Chemistry (1997), Oxford University Press, Oxford pp. 28-29
7. Hegnauer R. Chemotaxonomie der Pflanzen, Bd 6 (1972), Birkhauser Verlag, Basel
8. Hegnauer R. Chemotaxonomie der Pflanzen, Bd 9 (1990), Birkhauser Verlag, Basel
9. Hiroya K., and Ogasawara K. The first enantiocontrolled synthesis of naturally occurring polyoxygenated cyclohexenylmethanol dibenzoates (-)-zeylenol, (-)-uvarigranol G, (-)-tonkinenin A and (+)-pipoxide. Chem. Commun. (1999) 2197-2198
10. Jolad S.D., Hoffman J.J., Schram K.H., and Cole J.R. Structures of zeylenol and zeylena, constituents of Uvaria zeylanica (Annonaceae). J. Org. Chem. 46 (1981) 4267-4272
11. Marco-Contelles J. Cyclohexane epoxides - Chemistry and biochemistry of (+)-cyclophellitol. Eur. J. Org. Chem. 9 (2001) 1607-1618
12. Marco-Contelles J., Molina M.T., and Anjum S. Naturally occurring cyclohexane epoxides: Sources, biological activities and synthesis. Chem. Rev. 104 (2004) 2857-2899
13. Masuda Y., Kikuzaki H., Hisamoto M., and Nakatani N. Antioxidant properties of gingerol related compounds from ginger. Biofactors 21 (2004) 293-296
14. Naik J.P., Rao L.J.M., Kumar T.M.M., and Sampathu S.R. Chemical composition of the volatile oil from the pericarp (husk) of large cardamom (Amomum subulatum Roxb.). Flavour Frag. J. 19 (2004) 441-444
15. Naumov V.A., and Bezzubov V.M. Electron diffraction study of the structure of cyclohexene and cyclohexene oxide molecules. J. Struct. Chem. 8 (1967) 530-531 Engl. Trans. 466-7
16. Pai B.R., Rao N.N., and Wariyar N.S. Occurrence of crotepoxide in Kaempferia rotunda L. Ind. J. Chem. 8 (1970) 468
17. Pancharoen O., Tuntiwachwuttikul P., and Taylor W.C. Cyclohexane diepoxides from Kaempferia rotunda. Phytochemistry 43 (1996) 305-308
18. Pino J.A., Marbot R., Rosado A., and Batista A. Chemical composition of the essential oil of Zingiber officinale Roscoe L. from Cuba. J. Essent. Oil Res. 16 (2004) 186-188
19. Schulte G.R., Kopinid M., Thebtaranonth C., and Thebtaranonth Y. Studies on highly oxidized cyclohexanes. Constitution of a new key metabolic intermediate. Tetrahedron Lett. 23 (1982) 4303-4304
20. Simmonds M.S.J., Blaney W.M., and Fellows L.E. Behavioural and electrophysiological study of antifeedant mechanisms associated with polyhydroxyalkaloids. J. Chem. Ecol. 16 (1990) 3167-3196
21. Sirat H.M., Jamil S., and Siew L.W. The rhizome oil of Kaempferia rotunda Val. J. Essent. Oil Res. 17 (2005) 306-307
22. Tatsuta K., Niwata Y., Umezawa K., Toshima K., and Masay N. Enantiospecific synthesis and biological evaluation of 1,6-epi-cyclophellitol. J. Antibiot. 44 (1991) 456-458
23. Wilson B., Abraham G., Manju V.S., Mathew M., Vimala B., Sundaresan S., and Nambisan B. Antimicrobial activity of Curcuma zedoaria and Curcuma malabarica tubers. J. Ethnopharmacol. 99 (2005) 147-151
24. Woerdenbag H.J., Windono T., Bos R., Riswan S., and Quax W.J. Composition of the essential oils of Kaempferia rotunda L. and Kaempferia angustifolia Roscoe rhizomes from Indonesia. Flavour Frag. J. 19 (2004) 145-148
25. Zhou G.X., Chen R.Y., and Yu D.Q. New polyoxygenated cyclohexenes from Uvaria calamistrata. J. Asian Nat. Prod. Res. 1 (1999) 227-238