The unusual canangafruticosides A-E: Five monoterpene glucosides, two monoterpenes and a monoterpene glucoside diester of the aryldihydronaphthalene lignan dicarboxylic acid from leaves of Cananga odorata var. fruticosa

Phytochemistry

Volumn 71, Issue 13, 2010, Pages 1564-1572

  Nagashima, Jiro ^a   Matsunami, Katsuyoshi ^a   Otsuka, Hideaki ^a   Lhieochaiphant, Duangporn ^b   Lhieochaiphant, Sorasak ^b  

^a HIROSHIMA UNIVERSITY   (Japan)

^b CHIANG MAI UNIVERSITY   (Thailand)

Author keywords

Annonaceae; Aryldihydronaphthalene dicarboxylate; Cananga odorata var. fruticosa; Canangafruticoside; Shrubby cananga; Unusual monoterpene

Indexed keywords

ESTER; GLUCOSIDE; LIGNAN; TERPENE;

ARTICLE; CANANGA; CHEMISTRY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF;

CANANGA; ESTERS; GLUCOSIDES; LIGNANS; MAGNETIC RESONANCE SPECTROSCOPY; MONOTERPENES; PLANT LEAVES;

ANNONACEAE; CANANGA; CANANGA ODORATA; INSECTIVORA;

EID: 77955415314     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2010.06.009     Document Type: Article

References (16)

1. E. Caloprisco, J.-D. Fourneron, R. Faure, and F.-E. Demarne Unusual lactones from Cananga odorata (Annonaceae) J. Agric. Food Chem. 50 2002 78-80
2. E.M. Gaydou, R. Randriamiharisoa, and J.P. Bianchini Composition of the essential oil of ylang-ylang (Cananga odorata Hook. Fil. et Thomson forma genuina) from Madagascar J. Agric. Food Chem. 34 1986 481-487
3. T.-J. Hsieh, F.-R. Chang, Y.-C. Chia, C.-Yi. Chen, H.-F. Chiu, and Y.-C. Wu Cytotoxic constituents of the fruits of Cananga odorata J. Nat. Prod. 64 2001 616-619
4. IPNI, 2005. < http://www.ipni.org/ipni/plantnamesearchpage.do >.
5. D.B. Katague, and E.R. Kirch Analysis of the volatile components of ylang-ylang oil by gas chromatography J. Pharm. Sci. 52 1963 252-258
6. Koripelly, D., Saak, W., Christoffers, J., 2007. Synthesis of optically active (+)-canangone, its 6-epimer, and determination of absolute configuration. Eur. J. Org. Chem. 5840-5841.
7. M. Leboeuf, and A. Cavé Alkaloids of Annonaceae. XIV. Identification of canangine and eupolauridine, new alkaloids with a naphthyridine nucleus J. Nat. Prod. (Lloydia) 39 1976 459-460
8. M. Leboeuf, J. Streith, and A. Cavé Alkaloids of Annonaceae: alkaloids of the bark of Cananga odorata Hook. F. and Thomson Ann. Pharm. Fr. 33 1975 43-47
9. M. Nishizawa, M. Tuda, and K. Hayashi Two caffeic acid tetramers having enantiomeric phenyldihydronaphthalene moiety from Macrotomia euchroma Chem. Pharm. Bull. 29 1990 2645-2649
10. I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa High-field FT NMR application of Mosher′s method. The absolute configurations of marine terpenoids J. Am. Chem. Soc. 113 1991 4092-4096
11. J. Olivero, T. Gracia, P. Payares, R. Vivas, D. Díaz, E. Daza, and P. Geerlings Molecular structures and gas chromatographic retention behavior of the components of ylang-ylang oil J. Pharm. Sci. 86 1997 625
12. Porcher, M.H., 2004. 1995-2020, Sorting Cananga names. Multilingual Multiscript Plant Name Database - A Work in Progress. Institute for Land and Food Resources, The University of Melbourne. < http://gmr.landfood.unimelb. edu.au/Plantnames/Sorting/Cananga.html >.
13. J.U.M. Rao, G.S. Giri, T. Hanumaiah, and K.V.J. Rao Sampangine, a new alkaloid from Canaga odorata J. Nat. Prod. 49 1986 346 347
14. A.A. Shahat, N.S. Abdel-Azim, L. Pieters, and A.J. Vlietinck Isolation and NMR spectra of syringaresinol-β-d-glucoside from Cressa cretica Fitoterapia 75 2004 771 773
15. A.F. Thomas 1,4-Dimethylcyclohex-3-enyl methyl ketone, a monoterpenoid with a novel skeleton Helv. Chim. Acta 56 1973 1800 1802
16. M. Yoshikawa, H. Shimada, M. Saka, S. Yoshimizu, J. Yamahara, and H. Matsuda Medicinal foodstuffs. V. Moroheiya. (1): absolute stereostructures of corchoionosides A, B, and C, histamine release inhibitors from the leaves of Vietnamese Corchorus olitorius L. (Tiliaceae) Chem. Pharm. Bull. 45 1997 464 469