References
- Parada , F. , Krajewski , D. , Schreier , P. and Duque , C. 1995 . Flav. Fragr. J. , in press
- Duque , C. , Wintoch , H. , Suärez , M. and Schreier , P. 1993 . Progress in Flavour Precursor Studies , Edited by: Schreier , P. and Winterhalter , P. 279 Carol Stream : Allured Publ. Corp. .
- Günata , Y. Z. , Bayonove , C. L. , Baumes , R. L. and Cordonnier , R. E. 1985 . J. Chromatogr. , 331 : 83
- RLCC: Eyela RLCC UP-60 (Tokyo Rikakikai Co.). Solvent system: CHCl3-MeOH-H2O (7:13:8); ascending mode; flow rate: 1.0 ml/min; rotation speed: 80 rpm; slope 30°
- MLCCC: ITO Multilayer Coil Separator-Extractor (P.C. Inc., Potomac) with a 160 m × 1.6 mm i. d. PTFE column. Solvent system: CHCl3-MeOH-H2O (7:13:8); flow rate: 1.0 ml/min; elution mode: tail to head; rotation speed: 800 rpm
- Wintoch , H. , Morales , A. , Duque , C. and Schreier , P. 1993 . J. Agric. Food Chem. , 41 : 1311
- Flash Chromatography. 400 × 10 mm glass column filled with silica gel (activity grade II, 0.032–0.063 mm; Merck); gradient elution, 200 ml pentane-CHCl3 (1:1), (1:2) and CHCl3
- HPLC: Preparative HPLC: Eurospher Si 100 column, 5 μm, 250 × 16 mm, Knauer, Berlin, flow rate 5 ml/min; UV detection 280 nm; eluent: tert.-butylmethylether. Analytical HPLC: Eurospher 100 C-18 column, 4 μm, 250 × 4 mm, Knauer, Berlin, flow rate 1 ml/min; UV detection 280 nm; eluent: H2O-MeOH (1:1)
- ESI-MS: Finnigan TSQ 7000 triple stage quadrupol mass spectrometer; solvent: MeOH-H2O-TFA (50:50:0.05); flow rate 200 μmin; loop injection 5 μl; potential of the capillary 4kV; capillary temperature 200°C; mass range: 150–500; scan duration 1s. MS/MS-experiments: collision pressure 1.89 mTorr argon; collision energies -15 eV for daughter ion and -20 eV for neutral loss experiments
- Spectral data of 1b: UV 228 nm (δmax), 282 nm. ESI-MS pseudomolecular ions m/z 485 [M+H]+, 502 [M+18]+, 507 [M+Na]+ and 523 [M+K]+. Most abundant MS/MS daugther ions [M+H]+: m/z 485, 245, 305, 169, 211, 331, 263. 1H-NMR (600 MHz, CDCl3, δ in ppm, Jin Hz): aglycone part: 3.84 (2 × 3H, s, 2 OMe), 6.53 (1H, dd, J=8.7, 2.7, H-6), 6.60 (1H, d, J=2.7, H-2), 6.76 (1H, d, J=8.7, H-5); sugar part: 2.03, 2.04, 2.07, 2.08 (4 × 3H, s, 4 CH3-COO), 3.81 (1H, m, H-5′), 4.17 (1H, dd, J=12.4, 2.3, H-6a′), 4.27 (1H, dd, J=12.4, 5.2, H-6b′), 5.00 (1H, d, J=7.7, H-1′), 5.16 (1H, t, J=9.5, H-4′), 5.23 (1H, dd, J=9.4, 7.7, H-2′), 5.28 (1H, t, 9.3, H-3′). 13C-NMR (150 MHz, CDCl3, δ in ppm, J in Hz): aglycone part: 56.0 (OCH3), 56.4 (OCH3), 103.3 (C-2), 107.8 (C-6), 111.5 (C-5), 145.5 (C-4), 149.7 (C-3), 151.2 (C-1); sugar part: 20.5–20.7 (CH3-COO), 62.0 (C-6′), 68.3 (C-4), 71.2 (C-2′), 72.0 (C-5′), 72.7(C-3′), 100.0 (C-1′), 169.3–170.1 (CH3-COO)
- 3,4-dimethoxyphenol (Aldrich): Ri (CBWAX) 2770; HRGC-MS (EI) m/z (rel.int.): 154(100), 139(99), 111(97), 55(55), 69(51), 93(46)
- Pabst , A. , Barron , D. , Adda , J. and Schreier , P. 1990 . Phytochemistry , 29 : 3853
- Taguchi , H. , Yosioka , I. , Yamasaki , K. and Kim , I. H. 1981 . Chem. Pharm. Bull. , 29 : 55
- Takeoka , G. R. , Flath , R. A. , Buttery , R. G. , Winterhalter , P. , Güntert , M. , Ramming , D. W. and Teranishi , R. 1992 . Flavor Precursors , ACS Symp. Series 490 Edited by: Teranishi , R. , Takeoka , G. R. and Güntert , M. 116 Washington : Amer. Chem. Soc .
- Itokawa , H. , Oshida , Y. , Ikuta , A. , Inatomi , H. and Adachi , T. 1982 . Phytochemistry , 21 : 1935
- Ushiyama , M. and Furuya , T. 1989 . Phytochemistry , 28 : 3009