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Croweacin from Piper marginatum
BiochemicalSystematicsand Ecology, Vol. 25, No. 5, pp. 471-472,1997 © 1997 ElsevierScience Ltd All rights reserved.Printed in Great Britain 0305-1978/97 $17.00+0.00
Pergamon PII: S0305-1978(97)00037-9
Croweacin from
Piper marginatum*
B/kRBARA VIVIANA DE OLIVEIRA SANTOS,t EMIDIO V. L. DA-CUNHA,t MARIA CI~LIA DE OLIVEIRA CHAVESt and ALEXANDER I. GRAYt§ tLaboratbrio de Tecnologia Farmac6utica, Universidade Federal da Paraiba, Cx. Postal 5009, 58051-970 Jo~o Pessoa, PB, Brazil; $Phytochemistry Research Laboratories, Department of Pharmaceutical Sciences, University of Strathclyde, 204 George Street, Glasgow G1 I XW, U.K.
Key W o r d Index--Piper marginatum; Piperaceae; croweacin; 1-allyl-2-methoxy-3,4-methylenedioxybenzene; phenylpropanoids.
Subject and Source Piper marginatum Jacq. is a plant used in Paraiba, Brazil, as a food flavouring agent (seeds) and also as an antidote for snake bites (root). In this area of Brazil, it is known by the vernacular name "'malvaisco" (PioCorr6a, 1984). The root was collected in September 1993 near the city of Jo&o Pessoa, Paraiba. A voucher specimen (Agra 1500--JPB) is deposited at the Herbarium Lauro Pires Xavier--JPB of the Universidade Federal da Paraiba.
Previous Work Previous publications on P. marginatum describe only the analysis of essential oil from the leaves and stems (Ramos et aL, 1986) and the presence of prenylated 4-hydroxybenzoic acid derivatives from the aerial parts (Maxwell and Rampersad, 1988). Other species of Piper are well known for the production of amides (AraujoJunior et aL, 1997; Dictionary of Natural Products in CD-ROM, 1996), alkaloids, terpenes, flavonoids and phenylpropanoids (Maxwell and Rampersad, 1988; Dictionary of Natural Products in CD-ROM, 1996).
Present Study The dried ground root was moistened with a solution of 40% conc. NH4OH in H20 and extracted with EtOH at room temperature. The resultant extract was then acidified with 2% HCI and extracted with CHCI3. The CHCI3 extract was subjected to two successive columns (silica gel) and finally PTLC (silica gel: 1 mm). Croweacin is a pale yellow oil. UV (MeOH) ~,rnax 277 nm. I R (film) Vma. 2923, 1635, 1465, 1257, 1072cm -1 . MS m/z (rel. int.) 192 (M +, 100% 011H1203), 161 (28), 147 (28), 133 (32), 119 (29), 91 (26). 1H NMR (CDCl3, 400 MHz) & 6.601H b d J = 7 . 9 Hz (H-6); 6.49 1H d J = 7 . 9 Hz (H-5); 5.96 1H m (H-2'); 5.92 2H s (O-CH 2O); 4.9-5.1 2H m (H-3');3.98 3H s (2-OMe);3.31 2H m (H-1').13C NMR (CDCI3, 1 0 0 M H z ) 6:148.0 (C-4); 142.0 (C-2); 137.8 (C-2'); 137.0 (C-3); 126.0 (C-1); 122.4 (C-6); 115.3 (C-3'); 102.8 (C-5); 101.0 (OCH2-O), 59.9 (OMe); 34.3 (C-1 '). The spectroscopic data above is unambiguous. The NMR results are based on 1 D and 2D experiments and is being published here for the first time.
Chemotaxonomic Significance Although phenylpropanoids are common in the Piperaceae (Maxwell and Rampersad, 1988), it is the first time that croweacin has been reported from a member of this family. The only occurrence of this compound registered in the literature was as the main constituent of the essential oil of the Australian shrub Eriosternon crowei F. Muell. (syn =Crowea saligna= C. exaltata)~,"Rutaceae, and the structure was determined by degradation studies and synthesis (Penfold et aL, 1938; Baker et aL, 1939).
*This paper is based on the M.Sc. project of B.V.de O.S., LTF/UFPB, Brazil and on the Ph.D. research of E.V.L. da-C., University of Strathclyde. §Corresponding author. (Received 17 January 1997; accepted 7 April 1997) 471
472
B. V, DE OLIVEIRA SANTOS ETAL
References A r a u j o - J u n i o r , J. X., d a - C u n h a , E. V. L., Chaves, M. C. O. and Gray, A. I. (1997) Phytochemistry44, 559; Baker, W., P e n f o l d , A. R. and S i m o n s e n , J. L. (1939) J. Chem. Soc. 439; Dictionary of NaturalProducts in CD-ROM (1996) Version 5.1. Chapman & Hall, London; M a x w e l l , A. and R a m p e r s a d , D. (1988) J. Nat. Prod. 51,370; P e n f o l d , A. R., Ramage, G. R. and S i m o n s e n , J. L. (1938) J. Chem. Soc. 756; PioCorr&a, M. (1984) Dicion#rio das plantas E/teis do Brasil e das ex6ticas cultivadas, Vol. 1, p. 350. Minist~rio da Agricultura, Rio de Janeiro, GB, Brazil; Ramos, L. S., da Silva, M. L., Luz, A. I. R., Z o g h b i , M. G. B. and M a i a , J. G. S. (1986) J. Nat. Prod. 49, 712.
Pergamon PII: S0305-1978(97)00037-9
Croweacin from
Piper marginatum*
B/kRBARA VIVIANA DE OLIVEIRA SANTOS,t EMIDIO V. L. DA-CUNHA,t MARIA CI~LIA DE OLIVEIRA CHAVESt and ALEXANDER I. GRAYt§ tLaboratbrio de Tecnologia Farmac6utica, Universidade Federal da Paraiba, Cx. Postal 5009, 58051-970 Jo~o Pessoa, PB, Brazil; $Phytochemistry Research Laboratories, Department of Pharmaceutical Sciences, University of Strathclyde, 204 George Street, Glasgow G1 I XW, U.K.
Key W o r d Index--Piper marginatum; Piperaceae; croweacin; 1-allyl-2-methoxy-3,4-methylenedioxybenzene; phenylpropanoids.
Subject and Source Piper marginatum Jacq. is a plant used in Paraiba, Brazil, as a food flavouring agent (seeds) and also as an antidote for snake bites (root). In this area of Brazil, it is known by the vernacular name "'malvaisco" (PioCorr6a, 1984). The root was collected in September 1993 near the city of Jo&o Pessoa, Paraiba. A voucher specimen (Agra 1500--JPB) is deposited at the Herbarium Lauro Pires Xavier--JPB of the Universidade Federal da Paraiba.
Previous Work Previous publications on P. marginatum describe only the analysis of essential oil from the leaves and stems (Ramos et aL, 1986) and the presence of prenylated 4-hydroxybenzoic acid derivatives from the aerial parts (Maxwell and Rampersad, 1988). Other species of Piper are well known for the production of amides (AraujoJunior et aL, 1997; Dictionary of Natural Products in CD-ROM, 1996), alkaloids, terpenes, flavonoids and phenylpropanoids (Maxwell and Rampersad, 1988; Dictionary of Natural Products in CD-ROM, 1996).
Present Study The dried ground root was moistened with a solution of 40% conc. NH4OH in H20 and extracted with EtOH at room temperature. The resultant extract was then acidified with 2% HCI and extracted with CHCI3. The CHCI3 extract was subjected to two successive columns (silica gel) and finally PTLC (silica gel: 1 mm). Croweacin is a pale yellow oil. UV (MeOH) ~,rnax 277 nm. I R (film) Vma. 2923, 1635, 1465, 1257, 1072cm -1 . MS m/z (rel. int.) 192 (M +, 100% 011H1203), 161 (28), 147 (28), 133 (32), 119 (29), 91 (26). 1H NMR (CDCl3, 400 MHz) & 6.601H b d J = 7 . 9 Hz (H-6); 6.49 1H d J = 7 . 9 Hz (H-5); 5.96 1H m (H-2'); 5.92 2H s (O-CH 2O); 4.9-5.1 2H m (H-3');3.98 3H s (2-OMe);3.31 2H m (H-1').13C NMR (CDCI3, 1 0 0 M H z ) 6:148.0 (C-4); 142.0 (C-2); 137.8 (C-2'); 137.0 (C-3); 126.0 (C-1); 122.4 (C-6); 115.3 (C-3'); 102.8 (C-5); 101.0 (OCH2-O), 59.9 (OMe); 34.3 (C-1 '). The spectroscopic data above is unambiguous. The NMR results are based on 1 D and 2D experiments and is being published here for the first time.
Chemotaxonomic Significance Although phenylpropanoids are common in the Piperaceae (Maxwell and Rampersad, 1988), it is the first time that croweacin has been reported from a member of this family. The only occurrence of this compound registered in the literature was as the main constituent of the essential oil of the Australian shrub Eriosternon crowei F. Muell. (syn =Crowea saligna= C. exaltata)~,"Rutaceae, and the structure was determined by degradation studies and synthesis (Penfold et aL, 1938; Baker et aL, 1939).
*This paper is based on the M.Sc. project of B.V.de O.S., LTF/UFPB, Brazil and on the Ph.D. research of E.V.L. da-C., University of Strathclyde. §Corresponding author. (Received 17 January 1997; accepted 7 April 1997) 471
472
B. V, DE OLIVEIRA SANTOS ETAL
References A r a u j o - J u n i o r , J. X., d a - C u n h a , E. V. L., Chaves, M. C. O. and Gray, A. I. (1997) Phytochemistry44, 559; Baker, W., P e n f o l d , A. R. and S i m o n s e n , J. L. (1939) J. Chem. Soc. 439; Dictionary of NaturalProducts in CD-ROM (1996) Version 5.1. Chapman & Hall, London; M a x w e l l , A. and R a m p e r s a d , D. (1988) J. Nat. Prod. 51,370; P e n f o l d , A. R., Ramage, G. R. and S i m o n s e n , J. L. (1938) J. Chem. Soc. 756; PioCorr&a, M. (1984) Dicion#rio das plantas E/teis do Brasil e das ex6ticas cultivadas, Vol. 1, p. 350. Minist~rio da Agricultura, Rio de Janeiro, GB, Brazil; Ramos, L. S., da Silva, M. L., Luz, A. I. R., Z o g h b i , M. G. B. and M a i a , J. G. S. (1986) J. Nat. Prod. 49, 712.