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Alkaloids from Leaves and Stems of Vallesia Glabra

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Alkaloids from Leaves and Stems of Vallesia Glabra Letters Planta Med. 61 ('1995) -89 mutually coupled, high-field multiplets were also present (6 References = 1.49-2.05), accounting for a sequence of two methyl- enes. Selective decoupling and 'H-'H COSY experiments * De Mösbach, E. W. (1992) Botanica Indigena de Chile, p. 93, showed the coupling of these methylenes with the previous Fundaciòn Andes, Santiago de Chile. Soukoup, J. (1970) Vocabulario de los Nombres Vulgares de la Flora oxymethine, therefore assigning a gluc-O-CH(CH,)-CH2- Peruana, p. 211, Colegio Salesiano, Lima. CH2-sequence. Correu, D. S., Johnston, M.C. (1970) Manual of the Vascular Plants of Texas, pp. 1083-1087, Texas Research Foundation, Renner. The presence in the 13C-NMR spectrum of El-Naggar, L. J., Beal, J. L. (1980) J. Nat. Prod. 43,649- 707. the resonances corresponding to the saturated aliphatic car- Boros, C.A., Stermitz, F. R. (1990) J. Nat. Prod. 53, 1055-1147. bonyl and the carboxyl functions, at 201.1 and 171.1 ppm, Boros, C.A., Stermitz, F. R. (1991) J. Nat. Prod. 54,1173-1247. Crombie, L., King, R. W., Whiting, D. A. (1975) J. Chem. Soc., Perlcin respectively, together with the signal of a quaternary Trans. 1,913. carbon atom at 43.9ppm, allowed us to assign to 1 the Vogeli, U., Van Philipsborn, W. (1975) Org. Magn. Res. 7,617. structure of 9-O-P-D-glucopyranoside of the 9-hydroxy- 2,2,4-trimethyl-cleca-3-en-6-~n-l-oicacid. Finally, a Z- configuration was assigned to the three-substituted double bond on the basis of the chemical shift value of the methyl group at C-4, which did not show the shielding effect ex- pected for an E-configuration (7, 8). In the NOESY experi- ment, evident correlations between the two methyl singlets and the protons of the methylene at 6 = 2.14 and 2.65 were also in accordance with these assignments. Concerning the biosynthetic origin of the aglucone, it could be considered as derived from the junc- + Alkaloids from Leaves and Stems Of tion of three isoprenoid units and the subsequent loss of two terminal carbons. Vallesia glabru Materials and Methods M. Zèches'~~,K. Mesbah', B. Richard', C. Moretti'.', Plant material J. M. Nusillard', and L. Le Men-Oliuier ' ' Faculté de Pharmacie, URA au CNRS n" 492,51 rue Cognacq-Jay, Mentzelia incisa Urban et Gilg. was collected in F-51096 Reims Cedex, France the Monterrey district (N.L. Mexico) and identifed by Prof. H. z ORSTOM (UR 451,213 rue Lafayette, F-75480 Paris Cedex Sanchez at ITESM in Monterrey (voucher specimen SH-346). France Address for correspondence Isolation Received: March 21,1994; Accepted: May 21,1994 The aerial parts (350g) were exhaustively ex- tracted with MeOH at room temuerature and the extract evauo- rated to an aqueous suspension. After a further addition of water (0.511, the resulting solution was extracted with EtOAc and n- BuOH (0.5 1, each) in the sequence. The CC separation of the n- BuOH extract was performed on SiO? (ca. 100g) in CH,C1, : MeOH, 85 : 15, 1ml/min; elution vol. of 1700- 750ml. Eleven known indole alkaloids: vallesine, 'H- and I3C-NMR spectra were recorded on a aspidospermine, 11-methoxydichotine, apparicine, tu- Bruker AM-500 spectrometer. The assignments were confirmed botaïwine, vincadifformine, condylocarpine, (-)-rha- by COSY and NOESY experiments. zinilam, aspidospermatine, haplocidine, and 18-oxo- Compound 1 haplocidine, have been isolated from leaves and stems of Vallesia glabra (Cav.) Link. (Apocynaceae) from Bo- Amorphous powder; [a]:': -26.5 (c = 1.0, livia. Analysis of 2 D NMR spectra complete previous 'H MeOH). IR (KBr) v,, cm-': 3400, 1710, 1670, 1210. 'H-NMR and I3C data for vallesine, aspidospermine, and 11- i (CD30D, TMS): S= 1.01 (3H, s, H3-ll), 1.08 (3H, s, H3-12), 1.23 methoxydichotine. I (3H, d, J= 5.0Hz, &-lo), 1.49 (lH, m, H-Sb), 1.74-1.87 (ZH, m, ! ri-Sa and H-7bl2.03 (3H, d, J= 1.3 Hz, H3-13), 2.05 (lH, m, H-7a), 2.14 (lH, dd, J'= 18.0 and 1.3Hz, H-5b), 2.65 (lH, d,J= 18.0Hz, H-5a). 3.13 (lH, dd, J= 8.0 and 8.5Hz. H-2'). 3.26-3.33 (3H, m, The genus I/allesia includes 12 mecies. 8 H-4', H-5' andH-3'),3.67 (1H, dd, J= 12.0and5.8 HZ, H-6'b), 3.80 of which are spreaded out from Fiorida 'to (1H,m,H-9),3.84(1H,dd,J=12.0and3.0Hz,H-6'a),4.31(1H,d, heGCan, &gentina' To the best Of Only J = 8.0Hz, H-l'), 5.52 (IH, m, H-3). 13C-NMR (CD30D, TMS): 6 = 22.2 (C-10 or c-13h22.3 (C-13 or C-IO), 24.3 (c-il or c-12),24.7 were chemically studied: Vallesia dichotoma Ruiz. and (c-12 or C-li), 33.2 (C-8), 34.9 (C-7), 43.1 (c-2), 51.2 (c-5), 62.8 PaV. (from Peru) (1, 2). Vallesia antillana (from Cuba) (3, (c-60, 71.8 (c-4'1, 75.2 (C-2'). 77.8 (C-5' or c-37, 78.0 (c-91, 78.3 41, and Vallesiaglabra (Cav.)Link. (5) from which only two IC-3' or C-5'1, 104.2 (C-1'1, 127.1 (C-31, 133.7 (C-41, 171.7 (C-l), alkaloids, vallesine and aspidospermine, were isolated. 201.0 (C-61. Plantabled. GI (1995) 89-91 Q Georg Thieme Verlag Stuttgart. New 'íurk -90 Planta Med. 61 (1995) Letters According to some botanical authorities V.glabra and V. dichotoma are synonyms but they may represent differ- ent varieties of the same species (6). We report here on the alkaloidal contents of leaves and stems of Vallesia glabra from Bolivia. Val- lesia glabra is a small shrub common in the arid valleys of Bolivia and Paraguay. Plant materials were collected in the Bolivian Province of Misque, in September 1991 during an ÒCH3 ethnobotanical field work (ORSTOM - U.M.S.S. project: 1 R = CHO, vallesine Medicinal plants of Bolivian tropical region). Voucher 2 R = COCH3, aspidospermine 3 Il-methoxydichotine specimens (Morem No 1510) are deposited in the National Herbarium of Bolivia, La Paz. Botanical identification was Vallesine (1) confirmed by L. borge (Museum National d'Histoire Na- turelle de Paris). [alD: -91" (c 1, CHCI,). 'H-NMR (300MHz, CDCl,, TMS, Gvalues inppm): 9.3 (s, CHO), 7.0 (t, J= 7.5 Hz, H-lo), The extraction of the alkaloid mixtures (A. 6.85 (d,J= 7.5Hz, H-9), 6.8 (d, J= 7.5Hz, H-ll), 4.53 (dd, J= 11, M.) was carried out according to the usual acid-base pro- 6.1 Hz, H-2),3.87 (s, OCH,), 3.1 (td, J= 9,3.3 Hz, H-5),3 (br. d, J= 11 Hz, H-3), 2.25 (s, N-CO-CH3 and H-21). 2.23 (m,H-57, 2.15 (m, cess (7), and the following yields were obtained: 2.4 % H-16), 2.08 (m, H-17), 2.03 (dd,J= 12,3.3Hz, H-6), 1.93 (dd,J= (stems), 2.9% (leaves). The purification of A.M. was per- 11, 2.8Hz, H-3'). 1.75 (qt, J= 13, 4Hz, H-141, 1.63 (br. d, J= formed by column chromatography (silica gel, CH2C12- 13HZ, H-15), 1.5 (dd, J= 12, 3HZ, H-6'), 1.45 (dd, J= 13, ~Hz, MeOH with increasing amounts of MeOH), and the isolation H-14'), 1.4 (dq, J= 14,7.3Hz, H-19), 1.27 (m, H-16'). 1.1 (dd, J= of pure alkaloids was realized by preparative TLC, CC (with 13.4, 4.4Hz, H-17'). 1.05 (dd, J= 13,4.3Hz, H-15'). 0.85 (dq,J= the same solvents), or by crystallization. Eleven known al- 14, 7.3Hz, H-19'1, 0.63 (t, J= 7.3Hz, CH3-18).'3C-NMR 6: 161.2 kaloids were obtained (Table l)and their structures were (CHO), 148.1 (C-12). 140.8 (C-13), 127 (C-8), 124.4 (C-10). 115.6 elucidated by comparing their spectra with literature data, (C-9),110.1 (C-ll), 70.7 (C-21), 63.9 (C-2). 55.2 (OCH3), 53.5 (C-3), 52.3 (C-5 and C-71, 39.6 (C-61, 35.3 (C-201, 34.1 (C-151, 29.8 (C- or with those of reference samples available in our labora- 19),24.2 (C-16), 22.5 (C-17),21.4 (C-14),6.6 (C-18). tory. Aspidospermine (2) [alo: -99" 0.5, CHC1,). 'H-NMR (300MHz, Table 1 Alkaloids from Vailesia giabra. (C CDCl,, TMS, 6 values in ppm): 7.07 (t, J= 8.7 Hz, H-101, 6.83 (d, J Alkaloids I Leaves r',Stems%' , Isolation I Spectral analysis,Ref. =8.7Hz,H-9),6.8(d.J= 8.7Hz,H-ll),3.87(s,0CH3),3.11(td,J= I I 9, 3.2Hz, H-5), 3 (br. d, J= 10.7Hz, H-3), 2.25 (m, H-5'1, 2.23 (s, Vallesine (1) I 31.91 I TLC I a+b+c (5) H-21). 2.2 (s, N-CO-CH,), 2.05 (m, H-6), 2 (m, H-17), 1.95 (m, H-161, Aspidospermine (2) 5.52 7.42 TLC aibic (5) 1.9(m,H-3'),1;73(qt,J=13,4Hz,H-14),1.6(m,H-15),1.55(m, Il-methoxydichotine(3) 0.13 crystallization a + b + c (9) H-6').
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