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Flavonoids from Pseudotsuga Menziesii

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Flavonoids from Pseudotsuga Menziesii Flavonoids from Pseudotsuga menziesii Mirosława Krauze-Baranowskaa,*, Paweł Sowińskib, Anna Kawiakc,d, and Barbara Sparzakd a Department of Pharmacognosy, Medical University of Gdańsk, Gen. J. Hallera 107 str., 80-416 Gdańsk, Poland. Fax: +48583493160. E-mail: [email protected] b NMR Laboratory, Faculty of Chemistry, Technical University, Majakowskiego 11/12 str., Gdańsk, Poland c Department of Biotechnology, Intercollegiate Faculty of Biotechnology, University of Gdańsk and Medical University of Gdańsk, Kładki 24 str., 80-822 Gdańsk, Poland d Laboratory of Human Physiology, Faculty of Health Sciences with Subfaculty of Nursing, Medical University of Gdańsk, Tuwima 15 str., 80-210 Gdańsk, Poland * Author for correspondence and reprint requests Z. Naturforsch. 68 c, 87 – 96 (2013); received February 14, 2012/February 1, 2013 Four O-acylated fl avonol glycosides, new in the plant kingdom, were isolated from the needles of Pseudotsuga menziesii. Their structures were established by 1D and 2D NMR and MS data as: daglesioside I [kaempferol 3-O-[2’’,5’’-O-(4’’’,4IV-dihydroxy)-β- truxinoyl]-α-L-arabinofuranoside] (1), daglesioside II [kaempferol 3-O-[2’’,5’’-O-(4’’’- hydroxy)-β-truxinoyl]-α-L-arabinofuranoside] (2), daglesioside III [kaempferol 3-O-[2’’,5’’- di-O-(E)-p-coumaroyl]-α-L-arabinofuranoside] (3), and daglesioside IV [kaempferol 3-O-[3’’,6’’-di-O-(E)-cinnamoyl]-β-D-glucopyranoside] (4). In addition, the known fl avonoids (E)-tiliroside, (E)-ditiliroside, astragalin (kaempferol 3-O-β-D-glucopyranoside), isorhamne- tin, kaempferol, and quercetin were identifi ed. The cytotoxic activity of compounds 1 and 3 was evaluated towards the HL-60, HeLa, and MDA-MB468 cell lines. Key words: Pseudotsuga menziesii, O-Acylated Flavonol Glycosides, β-Truxinic Acid Deriva- tives Introduction the wood industry, as a source of medicinal and industrial compounds (Foo et al., 1992; Foo and Various species of the genus Pseudotsuga Karchesy, 1989a, b). (Pinaceae), including P. menziesii (Douglas fi r), Chromatographic analyses (TLC, HPLC) of are used in traditional medicine as antirheumatic, the chemical composition of P. menziesii leaves analgesic, diaphoretic, and diuretic agents (John- have also been performed (Krauze-Baranowska son, 1999). Previous phytochemical investigations et al., 2002, 2004). of the leaves, bark, and heartwood of P. menziesii In the present study, the isolation and structure focused on natural compounds belonging to the elucidation of four new O-acylated fl avonol gly- groups of fl avonoids (Dellus et al., 1997; Foo et al., cosides, namely daglesiosides I – IV (compounds 1992; Foo and Karchesy, 1989a; Niemann, 1988; 1 – 4), along with known compounds: acylated Stafford et al., 1989, 1986; Zou and Cates, 1995, fl avonol O-glycosides (tiliroside, ditiliroside), fl a- 1997), phenolic acids (Zou and Cates, 1997; Kuit- vonol O-glycoside (kaempferol 3-O-β-D-glu co- ers and Sarink, 1986), catechins (Stafford et al., pyranoside), and fl avonol aglycones (isorhamne- 1986; Foo and Karchesy, 1989b), fl avonolignans tin, kaempferol, quercetin) from the needles of P. (Foo and Karchesy, 1989b), lignans (Dellus et al., menziesii, growing in Poland, is described. 1997), and essential oils (Buchbauer et al., 1994; Montes et al., 1993; Tanaka et al, 1993). Exten- Experimental sive research on the chemical composition of P. menziesii was mainly undertaken in the USA or General Canada. These studies were aimed at using vari- Thin-layer chromatography (TLC) was per- ous parts of the plant, which are by-products in formed on glass plates covered with cellulose © 2013 Verlag der Zeitschrift für Naturforschung, Tübingen · http://znaturforsch.com 88 M. Krauze-Baranowska et al. · Flavonoids from Pseudotsuga menziesii (20 cm x 20 cm) (Merck, Darmstadt, Germany) amide column (50 g, 23 cm x 3 cm) eluted with and polyamide (20 cm x 20 cm) (Merck) using the MeOH/H2O (70:30) and MeOH. Fractions 9 – 18 following mobile phases: BuOH/H2O/CH3COOH were separated by chromatography over a Se- (4:1:5, v/v/v) (I), CHCl3/MeCOEt/MeOH (4:2:3) phadex G-10 column, eluted with MeOH, to give (II) (Krauze-Baranowska et al., 2002). Total hy- kaempferol 3-O-β-D-glucopyranoside (3 mg). drolysis was done by heating 1 mg of compounds Fractions 24 – 29 and 32 – 36 were subjected to 1 – 4 with 1 M HCl (100 °C, 30 min). Sugar analysis column chromatography over a polyamide col- was carried out on aluminium sheets precoated umn eluted with BuOH/MeOH/H2O (3:1:1) and with silica gel 60 F254 (0.2 mm thick; Merck) us- a Sephadex G-10 column eluted with MeOH to ing the mobile phase AcCN/H2O (15:85) (III). afford kaempferol 3-O-[6’’-O-(E)-p-coumaroyl]- The chromatograms were visualized by spray- β-D-glucopyranoside (tiliroside) (6 mg) and iso- ing with aniline phthalate, followed by heating rhamnetin (10 mg). Fractions 37 – 41 and 46 – 51 at 105 °C. For alkaline hydrolysis, 1 mg of com- were subjected to column chromatography over a pounds 1 – 4 was suspended in 4% aqueous KOH Sephadex G-10 column eluted with MeOH/H2O (4 h, room temperature). Analysis of phenolic ac- (70:30) to afford kaempferol (8 mg) and querce- ids was performed on aluminium sheets, precoat- tin (8 mg). Fractions 67 – 92, 93 – 99, and 100 – 107 ed with cellulose DC (20 cm x 20 cm) ( Merck) were separately subjected to column chromato- with HCOONa/85% HCOOH/H2O (10:1:200) graphy over a Sephadex LH-20 column eluted (IV); the following spray reagents were used for with MeOH to afford kaempferol 3-O-[3’’,6’’- visualization of the spots: NH3, 1% (w/v) FeCl3, di-O-(E)-p-coumaroyl]-β-D-glucopyranoside 0.5% diazotized sulfanilic acid solution, and 10% (ditiliroside) (30 mg) and two further fractions: Na2CO3. subfractions 12 – 19 and 16 – 28. The subfractions NMR spectra were recorded on a Bruker MSL 12 – 19 were separated over a polyamide col- 300 instrument (Coventry, UK) at 300 MHz (for 1 13 umn eluted with CHCl3/MeOH/Me2CO (4:2:1) H) and 75.5 MHz (for C) in DMSO-d6 using to afford compound 3 (10 mg). The subfractions tetramethylsilane (TMS) as an internal standard. 16 – 28 were rechromatographed over a Sephad- ESI mass spectra were recorded on a Finnigan ex LH-20 column to afford compound 1 (10 mg). MAT (+) TSQ 700 spectrometer (Bremen, Ger- The concentrated chloroform extract was subject- many) and FAB-MS on a Trio-3 VG instrument ed to column chromatography over a polyamide (Masslab, Manchester, UK). column (60 g, 30 cm x 2.5 cm) eluted with CHCl3 (300 mL) and CHCl /MeOEt (4:3) (200 mL). Fla- Plant material 3 vonoids were eluted with MeOH (7 x 300 mL). The needles of Pseudotsuga menziesii (Mirb.) The methanol fractions were concentrated and Franco (Pinaceae) were collected from the Me- subjected to column chromatography over a dicinal Plants Garden of the Medical University Sephadex LH-20 column (25 g, 50 cm x 1.5 cm) of Gdańsk (Gdańsk, Poland) in August 1997; a eluted with MeOH. From the obtained fractions voucher specimen (No. 99-001) has been depos- 6 – 12 compound 2 (10 mg) was separated using ited in the herbarium of the Medicinal Plants preparative TLC on silica gel RP-18 with MeOH/ Garden. H2O/HCOOH (75:25:6) and rechromatography over a Sephadex LH-20 column (5 g, 8 cm x 1 cm) Extraction and isolation with MeOH. From the second obtained fractions Dried and pulverized leaves of P. menziesii 14 – 16, compound 4 (15 mg) was separated em- (3 kg) were extracted initially with petroleum ploying column chromatography over polyamide ether in a Soxhlet apparatus. Next, the purifi ed with CHCl3/MeOEt/MeOH (4:0.5:3). material was extracted with chloroform, in a Sox- Daglesioside I [kaempferol 3-O-[2’’,5’’-O-(4’’’,4IV- hlet apparatus, and after drying, with methanol dihydroxy)-β-truxinoyl]-α-L-arabinofuranoside or (3 x 8 L) at 60 °C. The methanol extract was con- 3-O-(2’’,5’’-O-[7’’’-(4’’’-hydroxy)-phenyl,7IV-(4IV- IV IV centrated, suspended in H2O/MeOH (1:1), and hy droxy)-phenyl-(7’’’α,7 α,8’’’β,8 β)]-cyclo buta- IV successively extracted with EtOAc (6 x 300 mL). ne- 9’’’,9 -dioyl)-α-L-arabinofuranoside-3,5,7,4’- The extracts obtained were combined and con- tetrahydroxyfl avone, 1]: White powder. – TLC centrated, and next fractionated over a poly- (polyamide): Rf (II) = 0.40. – UV: λmax (MeOH) = M. Krauze-Baranowska et al. · Flavonoids from Pseudotsuga menziesii 89 267, 295sh, 348; (+AlCl3) 276, 316sh, 349, 399; NMR (DMSO-d6): see Table I. – Acid hydrolysis (+AlCl3/HCl) 277, 315sh, 349, 403; (+CH3ONa) gave the aglycone kaempferol, arabinose, and a 274, 335sh, 403; (+CH3COONa) 274, 317sh, 376, compound with Rf (IV) = 0.08. Alkaline hydroly- 403sh; (+CH3COONa/H3BO3) 267, 295sh, 353 nm. sis gave the secondary glycoside [Rf (I) = 0.82] 2+ – Positive FAB-MS: m/z = 712 [M+2H] (25), 425 and a compound with Rf (IV) = 0.08. 2+ 1 [M+2H–287] (100). – H NMR (DMSO-d6): δ = Daglesioside III [kaempferol 3-O-[2’’,5’’-di- 6.21 (1H, d, J = 2.1 Hz, H-6), 6.42 (2H, d, J = 8.8 Hz, O-(E)-p-coumaroyl]-α-L-arabinofuranoside or IV IV H-3 ,5 ), 6.45 (2H, d, J = 8.3 Hz, H-3’’’,5’’’), 6.48 3-O-[2’’,5’’-di-O-(E)-p-coumaroyl]-α-L-arabino- (1H, d, J = 2.1 Hz, H-8), 6.77 (2H, d, J = 8.8 Hz, furanoside-3,5,7,4’-tetrahydroxyfl avone, 3]: Yel- H-2IV,6IV), 6.81 (2H, d, J = 8.3 Hz, H-2’’’,6’’’), 6.89 lowish powder.
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