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Externally Accumulated Flavonoids in Three Mediterranean Ononis Species Eckhard Wollenwebera*, Marion Dörra, Diego Riverab, and James N

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Externally Accumulated Flavonoids in Three Mediterranean Ononis Species Eckhard Wollenwebera*, Marion Dörra, Diego Riverab, and James N Externally Accumulated Flavonoids in Three Mediterranean Ononis Species Eckhard Wollenwebera*, Marion Dörra, Diego Riverab, and James N. Roitmanc a Institut für Botanik der Technischen Universität Darmstadt, Schnittspahnstrasse 3, D-64287 Darmstadt, Germany. Fax: 0049-6151/163602. E-mail: [email protected] b Departamento Biologia Vegetal, Facultad Biologia, Universidad de Murcia, Murcia, Spain. E-mail: [email protected] c USDA Western Regional Research Center, Albany, CA 94710, USA * Author for correspondence and reprint requests Z. Naturforsch. 58c, 771Ð775 (2003); received July 21/August 15, 2003 The Mediterranean Ononis species, O. fruticosa, O. natrix subsp. ramosissima and O. triden- tata, have been analyzed for their exudate flavonoids. More than 20 flavonoid aglycones were identified, some of which are rather rare natural compounds. One of them, namely hypolae- tin-8,3Ј,4Ј-trimethyl ether, had been found only once before. The results are presented in a table along with literature data, and the chemotaxonomic impact of the flavonoid patterns is discussed. Key words: Ononis, Epicuticular Flavonoids, Chemosystematics Introduction Extraction and isolation Ononis is a Fabaceae genus (tribe Trifolieae) Fresh material was briefly rinsed with acetone that comprises some 75 species, occurring in the to dissolve the lipophilic material accumulated on Canaries, the Mediterranean region, Europe to the plant surfaces and the solutions were evapo- Central Asia (Willis,1973). Many species bear rated to dryness. Amounts of air-dried plant glandular trichomes that produce a more or less material and resinous exudates were as follows: O. viscid excretion, which in several cases has been tridentata 97 g/0.85 g, O. fruticosa 54 g/1.33 g, O. reported to contain flavonoids. In the scope of our natrix a) 57 g/3.26 g, and b) 170 g/12.3 g. The resin- ongoing studies on the occurrence and distribution ous residues were dissolved in a small volume of of externally accumulated flavonoid aglycones in hot methanol, cooled to Ð 10 ∞C, and the precipi- higher plants we now studied three species: O. tating material was eliminated by centrifugation. fruticosa, O. natrix subsp. ramosissima and O. tri- The thus defatted solutions were passed over dentata. Sephadex LH-20 (Pharmacia), eluted with MeOH, to separate the flavonoids from the overwhelming Material and Methods terpenoids. In the cases of O. fruticosa and O. tri- Plant material dentata, the flavonoid aglycones were then iden- Ononis tridentata L. was field collected in July, tified directly by TLC comparisons with authentic 2000 at Los Castan˜ os (Sorbas, Almeria, Spain) by samples. The flavonoid fractions of the two dif- D. Rivera Nun˜ ez (DRN) and C. Obo´ n. Ononis ferent collections of O. natrix subsp. ramosissima fruticosa L. was collected in May, 1990 near Salida were essentially identical and were therefore com- de Tibi direccion a Jijona (Alicante, Spain). Ono- bined. They were further chromatographed over nis natrix ssp. ramosissima Desf. comes from a) acetylated polyamide (Macherey-Nagel), eluted Molino Rio Aguas (DRN, 04/1990) and b) Los with toluene and increasing quantities of methyl- Castan˜ os (Sorbas, Almeria; DRN and C. Obo´ n, ethyl ketone and methanol. 07/2000). Voucher specimens are deposited at the Fractions were monitored and comparisons with Herbarium of Murcia University. markers were done by TLC on polyamide (DC 11, Macherey-Nagel) with the solvents i) PE100Ð140/ toluene/MeCOEt/MeOH (12:6:1:1 v/v/v/v), ii) to- 0939Ð5075/2003/1100Ð0771 $ 06.00 ” 2003 Verlag der Zeitschrift für Naturforschung, Tübingen · http://www.znaturforsch.com · D 772 E. Wollenweber et al. · Epicuticular Flavonoids in Ononis luene/PE100Ð140/MeCOEt/MeOH (12:6:2:1 v/v/v/ (C-7), 132.6 (C-8), 145.1*, (C-9),106.1 (C-10), v), and iii) toluene/MeCOEt/MeOH (12:5:3 v/v/v), 121.0 (C-1Ј), 128.4 (C-2Ј and C-6Ј), 116.1 (C-3Ј and and on silica gel with solvent iv) toluene/MeCOEt C-5Ј), 161.4 (C-4Ј), 60.5, (6-OMe), 61.8 (7-OMe), 1 δ (9:1 v/v). Chromatograms were viewed under UV 61.4 (8-OMe). Ð H NMR: H = 6.88 (s, H-3), 7.95 light (366 nm) before and after spraying with “Na- (d, J = 8.8 Hz, H-2Ј and H-6Ј), 6.97 (d, J = 8.8 Hz, turstoffreagenz A” (1% of diphenyl-boric acid H-3Ј and H-5Ј), 12.77 (s, 5-OH), 10.41 (s, 4Ј-OH), ethanolamine complex in MeOH). Authentic sam- 3.82 (s, OMe), 3.92 (s, OMe), 4.02 (s, OMe). 13 δ ples of flavonoids were available in E. W.’s lab. Agecorynin D: C NMR: C = 161.9 (C-2), 104.3 Some flavonoids were isolated (purified) after a (C-3), 182.4 (C-4), 148.4 (C-5), 135.5 (C-6), 152.2 further passage over Sephadex LH-20, eluted with (C-7), 132.4 (C-8), 145 (C-9), 106.6 (C-10), 105.9 Ј Ј Ј Ј CHCl3/MeOH (99:1 v/v), followed by CTLC on the (C-1 ), 153.3 (C-2 ), 106.5 (C-3 ), 151.9 (C-4 ), Chromatotron with benzene/2-propanol (95:5). 141.6 (C-5Ј), 110.6 (C-6Ј), 60.4 (6-OMe), 61.6 (7-OMe), 61.4 (8-OMe), 55.9 (5Ј-OMe). Ð 1H NMR: δ = 6.58 (s, H-3), 7.12 (s, H-3Ј), 7.41 (s, NMR and MS H H-6Ј), 12.85 (s, 5-OH), 10.50 (s, 2Ј-OH)*, 10.08 (s, Carbon and proton NMR spectra were recorded 4Ј-OH)*, 3.80 (s, 5Ј-OMe), 3.82 (s, OMe), 3.93 (s, in DMSO-d6 on a Bruker AMX 400 spectrometer OMe), 4.02 (s, OMe). at 100 MHz and 400 MHz, respectively. Electron 5,4Ј-Dihydroxy-6,7,8,3Ј-tetramethoxyflavone: 13C δ impact mass spectra were obtained on a Varian NMR: C = 164.0 (C-2), 102.9 (C-3), 182.5 (C-4), MAT 212 Spectrometer at 70 eV. The mass and 148.4 (C-5), 135.8 (C-6), 152.4 (C-7), 132.5 (C-8), NMR spectra confirmed the structures of the 145.1 (C-9), 106.1 (C-10), 121.3 (C-1Ј), 110.0 following flavones: acerosin, agecorynin D, (C-2Ј), 148.0 (C-3Ј), 151.0 (C-4Ј), 115.9 (C-5Ј), desmethylsudachitin, hymenoxin, nevadensin, 120.3 (C6Ј), 60.5 (6-OMe), 61.8 (7-OMe), 61.4 Ј 1 δ pectolinarigenin, sideritiflavone, xanthomicrol and (8-OMe), 55.8 (3 -OMe). Ð H NMR: H = 7.00 5,7-dihydroxy-8,3Ј,4Ј-trimethoxyflavone. In the (s, H-3), 6.98 (d, J = 8.8 Hz, H-5Ј), 7.59 (m, H-2Ј following we report the NMR data of the less com- and H-6Ј), 12.76 (s, 5-OH), 10.02 (s, 4Ј-OH), 3.82 δ mon compounds [DMSO-d6, (ppm) downfield (s, OMe), 3.90 (s, OMe), 3.93 (s, OMe), 4.02 (s, from tetramethylsilane]. OMe). 13 δ Sideritiflavone: C NMR: C = 164.3 (C-2), 102.5 (C-3), 182.3 (C-4), 148.4 (C-5), 135.7 (C-6), Results and Discussion 152.3 (C-7), 132.6 (C-8), 145.1 (C-9), 106.1 (C-10), Structure elucidation 121.3 (C-1Ј), 113.3 (C-2Ј), 145.7 (C-3Ј), 150.0 (C-4Ј), 116.1 (C-5Ј), 119.1 (C-6Ј) 60.5 (6-OMe), A good number of flavonoid aglycones were 1 δ 61.9 (7-OMe), 61.4 (8-OMe). Ð H NMR: H = found in the lipophilic material accumulated on 6.77 (s, H-3), 7.47 (d, J = 2.4 Hz, H-2Ј), 6.92 (d, J = aerial parts of Ononis fruticosa, O. natrix, and O. 8 Hz, H-5Ј), 7.46 (dd, J = 8, 2.4 Hz, H-6Ј), 12.79 (s, tridentata. The following compounds from O. nat- 5-OH), 3.82 (s, OMe), 3.93 (s, OMe), 4.02 (s, rix were identified by their MS, NMR, and UV OMe). spectra: scutellarein-6,4Ј-di-O-methyl ether (pec- 13 δ Ј Acerosin: C NMR: C = 163.3 (C-2), 102.9 tolinarigenin), 5,7,4 -trihydroxy-6,8-dimethoxy fla- (C-3), 182.1 (C-4), 148.3 (C-5), 131.5 (C-6), 150.8 vone (desmethylsudachitin), 5,4Ј-dihydroxy-6,7,8- (C-7), 127.9 (C-8), 145.3 (C-9), 102.9 (C-10), 123.1 trimethoxy flavone (xanthomicrol), 5,7-dihydroxy- (C-1Ј), 112.8* (C-2Ј), 146.8 (C-3Ј), 151.2 (C-4Ј), 6,8,4Ј-trimethoxy flavone (nevadensin), 5-hy- 112.3* (C-5Ј), 118.5 (C-6Ј), 60.1 (6-OMe), 61.2 droxy-6,7,8,4Ј-tetramethoxy flavone (gardenin B), Ј 1 δ Ј Ј (8-OMe), 55.7 (4 -OMe). Ð H NMR: H = 6.77 5,7-dihydroxy-8,3 ,4 -trimethoxy flavone (hypo- (s, H-3), 7.12 (d, J = 8.4 Hz, H-5Ј), 7.55 (dd, J = laetin-8,3Ј,4Ј-tri-O-methyl ether), 5,3Ј,4Ј-trihy- 2.4, 8.4 Hz, H-6Ј), 12.77 (s, 5-OH), 9.52 (s, 7-OH), droxy-6,7,8-trimethoxy flavone (sideritiflavone), 10.37 (s, 3Ј-OH), 3.79 (s, OMe), 3.87 (s, OMe), 3.89 5,7,3Ј-trihydroxy-6,8,4Ј-trimethoxy flavone (acero- (s, OMe). sin), 5,4Ј-dihydroxy-6,7,8,3Ј-tetramethoxy flavone, 13 δ Ј Ј Xanthomicrol: C NMR: C = 164.1 (C-2), 102.6 5,7-dihydroxy-6,8,3 ,4 -tetramethoxy flavone (hy- (C-3), 182.5 (C-4), 145.5* (C-5), 135.8 (C-6), 152.4 menoxin) and 5,2Ј,4Ј-trihxdroxy-6,7,8,5Ј-tetrame- E.
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