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Flavonols from Cryptocarya Alba Only One Alkaloid, (-I-)-Reticuline, Was Reported Barbara N

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Flavonols from Cryptocarya Alba Only One Alkaloid, (-I-)-Reticuline, Was Reported Barbara N 898 Notes Flavonols from Cryptocarya alba Only one alkaloid, (-i-)-reticuline, was reported Barbara N. Timmermann3, Susanne Valcic3, from the bark and leaves of this species (Urzüa Yong-Long Liua and Gloria Montenegro 11 et al., 1975). In continuation of the phytochemical investigations of medicinal plants indigenous to a Department of Pharmacology and Toxicology, College of Pharmacy, The University of Arizona, South America, we now report for the first time Tucson, AZ 85721, U.S.A. the isolation and characterization of ten known b Pontificia Universidad Catölica de Chile, flavonols and chlorogenic acid from the leaves and Departamento de Ecologi'a. Casilla 114-D. stems of Cryptocarya alba. Santiago, Chile Z. Naturforsch. 50c, 898-899 (1995); received April 25/July 30, 1995 Materials and Methods Cryptocarya alba, Lauraceae, Flavonols, Plant material Flavonol Glycosides, Chlorogenic Acid The plant material was collected on October 11, Ten flavonoids and chlorogenic acid were isolated from the leaves and stems of Cryptocarya alba (L au­ 1991 in Chile. Cuesta La Dormida (33°02'15" S; raceae). The flavonoids were identified as isorhamnetin. 71°00'07" W) at 1,250 m above sea level. A kaempferol, quercetin and their glycosides isorham- voucher specimen (No. 91-0023) has been depos­ netin-3-O-rhamnoside, isorhamnetin-3-O-galactoside, isorhamnetin-3-O-glucoside, kaempferol-3-O-galacto- ited in the Herbarium at the Pontificia Universi­ side, quercetin-3-O-rhamnoside (quercitrin), quercetin- dad Catölica de Chile, Santiago, Chile. 3-O-galactoside (hyperoside), and quercetin-3-O-gluco- side (isoquercitrin). Extraction and isolation 2.5 kg of air-dried leaves and stems from C. alba Introduction were ground with a mill (Laboratory Construction Co., Kansas City, Missouri) to 5 mm particle and Cryptocarya alba (Mol.) Looser, a species of the macerated with 95% ethanol (ethanol 95% [190 family Lauraceae, is native to Chile and is distrib­ proof], Quantum Chemical Corporation, Cincin­ uted from Coquimbo to Valdivia, where it grows nati, Ohio). The crude alcoholic extract was dis­ as high as 20 m in the coastal mountain range as solved in water and the aqueous phase was ex­ well as in the Andes, up to 1,500 m above sea level haustively extracted with CH 2C12 followed by (Hoffmann. 1982). The evergreen trees, also EtOAc. C H 2C12 and EtOAc, both quality AR known as “peumo”, “pegu” or “peugo”, are widely (ACS) were purchased from Mallinckrodt Chemi­ used in popular medicine in Chile. Infusions of the cals, Paris, Kentucky. The EtOAc extract (20 g) bark are used for treating liver diseases and for was chromatographed on a 6x60 cm column stopping hemorrhages (Hoffmann, 1982; Wilhelm packed with 200 g of Polyclar AT (polyvinylpoly- de Mösbach, 1992), whereas infusions of the pyrrolidone, GAF Corporation, Linden, New Jer­ leaves, as well as bark, are recommended for the sey) using M e0H-H 20-gradient as eluent (Liu treatment of rheumatism and for wound healing et al., 1989). (Hoffm ann, 1982). An ointm ent is prepared from ground seeds to treat vaginal infections. Although Identification C. alba is very much used in popular medicine, its chemical composition is virtually unknown. Previ­ All compounds were identified by 'H NMR. ous investigations have reported tanins and resins Quercitrin. hyperoside, kaempferol-3-O-galacto- from its leaves, bark, and fruits (Gautier, 1956), side. isorhamnetin-3-O-rhamnoside, isorhamnetin- and the composition of essential oils was described 3-O-galactoside, and isorhamnetin-3-O-glucoside from its aromatic leaves (Montes et al., 1988). as well as chlorogenic acid were further elucidated by 13C NMR. In addition the structures of kaemp- ferol-3-O-galactoside, isorhamnetin-3-O-rhamno- Reprint requests to Prof. Dr. B. N. Timmermann. side and chlorogenic acid were confirmed by Telefax: (520) 626-4063. EIMS. Isorhamnetin-3-O-rhamnoside. isorham- 0939-5075/95/1100-0898 $ 06.00 © 1995 Verlag der Zeitschrift für Naturforschung. All rights reserved. D Notes 899 netin-3-O-galactoside, and isorhamnetin-3-O-glu- Results coside were also determined by FABMS. All com­ The ethanolic extract of leaves and stems from pounds were purified through a small column of C. alba was dissolved in water and further ex­ Sephadex LH 20 (Pharmacia LKB, Uppsala, Swe­ tracted with CH 2C12 followed by EtOAc. The den) before spectral analysis (Liu et al., 1989). The EtOAc fraction was subjected to Polyclar AT col­ NMR were run on a Varian-Unity 300 spectrome­ umn chromatography using water-methanol as ter (JH NMR and 13C NMR frequencies were 300 eluent. Eleven compounds were isolated and char­ MHz and 75 MHz, respectively). The solvent for acterized as isorhamnetin (22 mg); kaempferol the flavonols and their glycosides was DMSO-d6, (23 mg); quercetin (32 mg); isorhamnetin-3-O- the solvent for chlorogenic acid was CD OD. The 3 rhamnoside (36 mg); isorhamnetin-3-O-galacto- internal reference for all compounds was tetra- side (26 mg); isorhamnetin-3-O-glucoside (30 mg); methylsilane (TMS). EIMS were recorded on a kaempferol-3-O-galactoside (72 mg); quercetin- Finnigan MAT 90 (Bremen, Germany) with elec­ 3-O-rhamnoside (quercitrin) 204 mg; quercetin- tron ionization at 70 eV. FABMS were performed 3-O-galactoside (hyperoside) 121 mg; quercetin- using MS-1 of a custom-built four-sector instru­ 3-O-glucoside (isoquercitrin) 173 mg and chlo­ m ent of BEBE Geometry (AMD Intectra, Harp­ rogenic acid (128 mg). Although none of these stedt, Germany) equipped with two KWS MC phenolics is a rare natural product, this is the first 68000 computer systems for instrument control time, however, that their occurrence is reported in and data acquisition. The matrix was glycerol. leaves and stems of Cryptocarya alba. Comparison with authentic samples were done by thin layer chromatography on polyamide and on Acknowledgments silica gel as reported previously (Wollenweber et al., 1993; Tim m erm ann et al., 1994). All markers The authors thank Mr. Luis Gonzalez for plant were available in B.T.’s lab. The TLC plates (Poly­ collections. B.N.T. gratefully appreciates the par­ gram, Polyamid -6 U V 254 and SIL G/UV 254 ) were tial financial support by RIKEN, The Institute of purchased from Alltech Associates, Inc., Deer­ Physical and Chemical Research, Tokyo, Japan. field, Illinois, manufactures: Macherey-Nagel, G. M. acknowledges partial support to Fondecyt Düren, Germany. grant 1940655. Gautier E. (1956), Estado Actual de la Fitoquimica en Timmermann B. N, Wollenweber E., Dörr M., Armbru- Chile. Escuela de Quimica y Farmacfa, Santiago de ster S., Valant-Vetschera K. M. and Fuentes E. R. Chile, 1, p. 14 and p. 21. (1994), External flavonoids in two Grindelia species. Hoffmann A. (1982), Flora Silvestre de Chile, Zona Z. Naturforsch. 49c, 395-397. Austral. Ediciones Fundaciön Claudio Gay, Santiago Urzüa A., Torres R. and Cassels B. (1975), (+)-Reticu- de Chile, p. 64. lina en Cryptocarya alba. Rev. Latinoamer. Qufm. 6, Liu Y.-L., Neuman P., Timmermann B. N. and Mabry 102-103. T. J (1989), Techniques for Flavonoid Analysis. Rev. Wilhelm de Mösbach E. (1992), Botänica Indfgena de Latinoamer. Qui'm. Suppl. 1, 90-130. Chile (Andres Bello, ed.). Santiago, p. 140. Montes M., Valenzuela L., Wilkomirsky T., Sanguinetti Wollenweber E., Dörr M., Timmermann B. N, Strand J. A. and Von Baer D. (1988), Etude de la composition and Fuentes E. R. (1993), Exudate flavonoids from chimique de l'huile essentielle de Cryptocarya alba Grindelia tarapacana of Chile. Z. Naturforsch. 48c, (Mol.) Looser (Lauraceae) du Chili. Ann. Pharm. Fr. 533-534. 46, 41-47..
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