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Exudate Flavonoids in Some Gnaphalieae and Inuleae (Asteraceae) Eckhard Wollenwebera,*, Matthias Christa, R

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Exudate Flavonoids in Some Gnaphalieae and Inuleae (Asteraceae) Eckhard Wollenwebera,*, Matthias Christa, R Exudate Flavonoids in Some Gnaphalieae and Inuleae (Asteraceae) Eckhard Wollenwebera,*, Matthias Christa, R. Hugh Dunstanb, James N. Roitmanc, and Jan F. Stevensd a Institut für Botanik der TU Darmstadt, Schnittspahnstrasse 4, D-64287 Darmstadt, Germany. Fax: 0049-6151/164630. E-mail: [email protected] b School of Environmental and Life Sciences, The University of Newcastle, Callaghan, NSW 2308, Australia c Western Regional Research Center, USDA-ARS, 800 Buchanan Street, Albany, CA 94710, U.S.A. d Department of Pharmaceutical Sciences, 203 Pharmacy Building, Oregon State University, Corvallis, OR 97331, U.S.A. * Author for correspondance and reprint requests Z. Naturforsch. 60c, 671Ð678 (2005); received May 19, 2005 Three members of the tribe Gnaphalieae and six members of the tribe Inuleae (Astera- ceae) were analyzed for their exudate flavonoids. Whereas some species exhibit rather trivial flavonoids, others produce rare compounds. Spectral data of rare flavonoids are reported and their structural identification is discussed. 6-Oxygenation of flavonols is a common feature of two Inula species and Pulicaria sicula. By contrast, flavonoids with 8-oxygenation, but lacking 6-oxygenation, are common in two out of three Gnaphalieae species examined. In addition, B-ring deoxyflavonoids are abundantly present in the leaf exudates of Helichrysum italicum (Gnaphalieae). These distinctive features of the two Asteraceae tribes are in agreement with previous flavonoid surveys of these and related taxa. Key words: Gnaphalieae, Inuleae, Flavonoids Introduction in the flowering stage between October 1997 and Plants belonging to the sunflower family are August 2004. Inula britannica L. was collected in well-known to produce a wealth of flavonoid agly- August 2000 on the bank of the river Elbe near cones (Bohm and Stuessy, 2001). These are nor- Arneburg (Sachsen-Anhalt) by H. Groh. Vou- mally dissolved in a terpenoid resin that is chers were deposited in the herbarium of the Bo- excreted by glandular structures on their aerial tanic Garden of the TU Darmstadt. parts. In the course of ongoing studies on the oc- currence of exudate flavonoids in Asteraceae (see Extraction and isolation e.g. Wollenweber et al., 1997a, b; Valant-Vetschera et al., 2003), we have now analyzed three members Aerial parts of freshly collected flowering plants of the tribe Gnaphalieae and six members of the were briefly rinsed with acetone to dissolve the tribe Inuleae (Bremer, 1994). The exudate flavo- exudate material. The solutions were evaporated noid patterns of these plants are presented as fol- to dryness, re-dissolved in a small volume of hot lows. MeOH, cooled to Ð 10 ∞C, and any precipitated material was separated by centrifugation. The so- Materials and Methods lutions were then passed over Sephadex LH-20 (Pharmacia), and eluted with MeOH, to separate Plant material the flavonoids from the predominant terpenoids. Asteriscus aquaticus (L.) Less. [syn.: Nauplius At this point, many flavonoids were readily and aquaticus (L.) Cass.], Helichrysum italicum (Roth) unambiguously identified by direct comparison Don., Helichrysum stoechas (L.) Moench, Helip- with markers. In several cases, however, further terum strictum (Lindl.) Benth., Inula conyzae workup of flavonoid fractions was required, as (Griess.) Meikle, Inula spiraeifolia L., Pulicaria si- well as further purification to isolate individual cula (L.) Moris, and Telekia speciosa (Schreb.) compounds. Relevant fractions were chromato- Baumg. were cultivated in the Botanic Garden of graphed over silica gel, polyamide SC-6 or ace- the Technical University Darmstadt and collected tylated polyamide (Macherey-Nagel), eluted with 0939Ð5075/2005/0900Ð0671 $ 06.00 ” 2005 Verlag der Zeitschrift für Naturforschung, Tübingen · http://www.znaturforsch.com · D 672 E. Wollenweber et al. · Exudate Flavonoids in Gnaphalieae and Inuleae toluene and increasing quantities of methylethyl MS/MS spectra were recorded on a PE Sciex API ketone and methanol. Fractions were monitored III Plus triple quadrupole instrument as described and comparisons with markers were achieved by in Stevens et al. (1999). TLC on polyamide (DC 11, Macherey-Nagel) with In the following we report spectral data for the solvents i) PE100Ð140/toluene/MeCOEt/MeOH those flavonoids that could not be readily iden- 12:6:1:1 v/v/v/v, ii) toluene/PE100Ð140/MeCOEt/ tified by co-TLC with authentic markers. MeOH 12:6:2:1 v/v/v/v, iii) toluene/dioxane/MeOH 5,7-Dihydroxy-3,8-dimethoxyflavone (1): APCI- 8:1:1 v/v/v, and iv) toluene/MeCOEt/MeOH 12:5:3 MS/MS (30 eV collision energy): m/z = 315 [MH]+, + + + v/v/v, and on silica gel with solvents v) toluene/ 300 [MH-CH3] , 285 [MH-2CH3] , 257 [285-CO] , MeCOEt 9:1 v/v and vi) toluene/dioxane/HOAc 105 [O ϵC-Ph]+. Ð 1H NMR: Table I. Ð The sub- 18:5:1 v/v/v. Chromatograms were viewed under stitution pattern of the A-ring was established by UV light (366 nm) before and after spraying with 1HÐ13C HMBC correlation as follows: The 5-OH δ “Naturstoffreagenz A” (1% of diphenyl-boric acid resonance at H 12.3 showed cross peaks with car- δ 2-aminoethyl ester in MeOH). In some cases, bon signals at C 155.0, 104.3 and 99.0, which were crude flavonoid materials were further purified to readily assigned to C-5, C-10 and C-6, respectively. homogeneity by semi-preparative HPLC as de- H-6 interacted with C-6 (1J coupling), C-10, C-8, scribed in Stevens et al. (1999). Authentic samples C-9, C-5 and the remaining A-ring carbon atom, δ of flavonoids were available in E.W.’s laboratory. C-7 ( C 156.0). The two methoxy groups showed δ Isolated flavonoids were characterized by UV- interactions with C-8 and C 138.8 (not C-7). The VIS, MS and NMR spectra. GC-MS was applied latter resonance could only be assigned to C-3, and to analyze mixtures of exudate flavonoids from confirms a C-3 methoxyl group. Thus, the two me- Pulicaria sicula. thoxy groups were placed at C-8 and C-3 and the two free hydroxyl groups assigned to C-5 and C-7. NMR and MS The compound was found to be 8-hydroxygalan- gin-3,8-di-O-methyl ether (gnaphalin), identical 1 13 Some H and C NMR spectra were recorded in with an authentic sample from Nothofagus (Wol- DMSO-d6 on a Bruker DRX 600 spectrometer at lenweber et al., 2003). 600 MHz and 150 MHz, respectively. 1HÐ13C he- 6-Hydroxykaempferol-3,7,4Ј-tri-O-methyl ether λ teronuclear multiple bond connectivity (HMBC) (2): UV: max (MeOH) = 336, 282; (+ AlCl3)= spectra were recorded on this instrument using 362, 298; (+ AlCl3/HCl) = 366, 298; (+ NaOH) = standard pulse sequences. 1H and 13C NMR 296 nm. Ð MS: m/z = 344 (100, M+), 329 (3, + + spectra of a flavonoid from Inula conyzae were M -CH3), 325 (17), 314 (M -2CH3), 301 (23), 295 1 recorded in DMSO-d6 on a Bruker AMX 400 (24), 283 (6), 258 (10), 158, (8), 135 (14). Ð H spectrometer at 100 MHz and 400 MHz, respec- NMR: Table I. Ð 13C NMR: Table II. Ð The iden- tively. Electron impact mass spectra were obtained tity of this product was confirmed by direct com- on a Varian MAT 212 Spectrometer at 70 eV. At- parison with a synthetic sample of 5,6-dihydroxy- mospheric Pressure Chemical Ionization (APCI) 3,7,4Ј-trimethoxyflavone (Horie et al., 1989). 1 Table I. H NMR spectroscopic data for compounds 1Ð4, recorded in DMSO-d6 at 400 MHz (compound 2)or 600 MHz (compounds 1, 3, 4). H Compound 1 Compound 2 Compound 3 Compound 4 5-OH 12.3, s 12.27, s 12.1, s 12.3, s 3-OH 9.9, s 3-OH and 4Ј-OH 10.2, s and 9.6, s 6 6.31, s 8 6.89, s 2Ј and 6Ј 8.03,dd, J = 7.9, 8.06, d, J = 9.2 Hz 8.18, d, J = 7.7 Hz 8.08, d, J = 8.9 Hz 1.6 Hz 3Ј and 5Ј 7.14, d, J = 9.2 Hz 6.97, d, J = 8.9 Hz 3Ј,4Ј and 5Ј 7.63Ð7.58, m 7.60Ð7.51, m 3 ¥ OMe 3.91, s, 3.87, s, 4.03, s, 3.91, s, 4.02, s, 3.90, s, 3.81, s 3.83, s 3.83, s 2 ¥ OMe 3.81, s E. Wollenweber et al. · Exudate Flavonoids in Gnaphalieae and Inuleae 673 Table II. 13C NMR spectroscopic data for flavonols 5,7- ble only in boiling acetic acid, was subjected to dihydroxy-3,8-dimethoxyflavone (1) and 6-hydroxy- GC-MS analysis. kaempferol-3,7,4Ј-tri-O-methyl ether (2), recorded in An aliquot of the flavone extract sample was DMSO-d6 at 100 MHz (compound 2) or 150 MHz (com- pound 1). transferred to a glass derivatisation tube, dried, and derivatized by first adding 100 mL 2% (w/v) C 12of methoxyamine hydrochloride in pyridine 2 157.3 155.2 (MOX) followed by heating at 60 ∞C for 30 min. 3 138.8 137.8 Bis(trimethylsilyl)trifluoro-acetamide (BSTFA, 4 178.3 178.1 150 µL) was then added and the sample was 5 155.0 145.7 heated at 100 ∞C for additional 60 min to form the 6 99.0 129.6 7 156.0 154.5 trimethylsilyl ether derivative (TMS) (Dunstan 8 127.6 90.9 et al., 1990). Samples were then transferred into 9 148.8 148.8 injection vials fitted with 100 µL inserts for analy- 10 104.3 105.6 sis by GC-MS. 1Ј 131.1 122.3 2Ј 128.0 129.9 Derivatized sample components were separated 3Ј 128.9 114.2 using a Hewlett Packard 6890 series gas chromato- 4Ј 130.2 161.3 graph and detected using a Hewlett Packard series Ј 5 128.9 114.2 5973 mass selective detector (MSD).
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