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Phytochemical study of Mentha longifolia of Morocco
Fitoterapia 72 Ž2001. 596᎐598
Phytochemical communication
Phytochemical study of Mentha longifolia of Morocco Saıd ¨ Ghoulami, Abdelkader Il IdrissiU , Souad Fkih-Tetouani Laboratoire de Chimie des Plantes et de Synthese de ` Organique et Bioorganique, Departement ´ Chimie, Faculte´ des Sciences, B.P 1014, Rabat RP 10000, Morocco
Received 6 December 2000; accepted in revised form 7 February 2001
Abstract A phytochemical study of Moroccan Mentha longifolia was carried out. The essential oil showed unusual relevant amounts of piperitenone oxide and piperitone oxide, which constitute a new chemotype. From the non-volatile extract, five flavonoids were isolated, among which 5,7,4⬘-trihydroxy-6,2⬘,3⬘-trimethoxyflavone Ž1. is reported for the first time. 䊚 2001 Elsevier Science B.V. All rights reserved. Keywords: Mentha longifolia; Essential oil; Flavonoids
Plant. Mentha longifolia ŽL.. Hudson ŽLamiaceae. aerial parts were harvested at the end of the vegetative cycle in the valley of Ifrane in the Middle Atlas ŽMorocco.. Morphologically, the harvested species did not present any hybrid character and corresponded to the botanical description by Quezel and Santa w1x. Uses in traditional medicine. As antibacterial and against gastric problems w2,3x. Previously isolated classes of constituents. Terpenoids w4᎐8x and flavonoids w9,10x. U
Corresponding author. E-mail address: [email protected] ŽA. Il Idrissi.. 0367-326Xr01r$ - see front matter 䊚 2001 Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 0 1 . 0 0 2 7 9 - 9
S. Ghoulami et al. r Fitoterapia 72 (2001) 596᎐598
597
New-isolated constituents. 5,6-Dihydroxy-7,8,3⬘,4⬘-tetramethoxyflavone w11x Žyield: 0.015% on dried wt.., 5,7,4⬘-trihydroxy-6,2⬘,3⬘-trimethoxyflavone (1) Ž0.01., along with the previously isolated luteolin, luteolin 7-O-glucoside and hesperidin, Žq.piperitenone oxide w12x Ž25% in the oil. and Žy.-trans-piperitone oxide w13x Ž24% in the oil..
5,7,4⬘-Trihydroxy-6,2⬘,3⬘-trimethoxyfla¨ one (1). Mp 228᎐229⬚C; UV max ŽMeOH.: 343, 287; ŽNaOMe. 398, 324, 265; ŽNaOAc. 403, 288; ŽAlCl 3 . 379, 304; ŽAlCl 3rHCl. 372, 300 nm; IR bands ŽKBr.: 3495, 1654, 1625 cmy1 ; 1 H-NMR Ž200 MHz, acetone.: ␦ 3.80 Ž3H, s, C 6-OMe., 3.85 Ž3H, s, C 2 ⬘-OMe., 3.90 Ž3H, s, C 3⬘-OMe., 6.55 Ž1H, s, H-3., 7.40 Ž1H, s, H-8., 6.80 Ž1H, d, J 9 Hz, H-5⬘., 7.50 Ž1H, d, J 9 Hz, H-6⬘.; MS mrz Žrel. int..: 360 Ž10. wMxq ŽC 18 H 14 O 8 ., 182 Ž15., 178 Ž15., 43 Ž100.. Conclusion. Due to the high contents in piperitenone and piperitone oxides, the studied Moroccan Mentha longifolia constitutes a new chemotype, only traces of piperitenone oxide having been previously reported in the essential oil w5x.
References w1x Quezel P, Santa S. Nouvelle flore de l’Algerie desertiques meridionales, II. Ed. du ´ et des regions ´ ´ ´ C.N.R.S, 1963. w2x Sticher O, Fluck H. Pharm Acta Helv 1968;43:411. w3x Banthorpe DV, Duprey RJH, Hassan M, Janes JF, Modawi BM. Egypt J Chem 1980;23:63. w4x Hefendhel FW. Herba Hungarica 1977;16:39. w5x Hefendhel FW, Nagell A. Parfum und Kosm 1975;7:189. w6x Vanos FHL, Hendriks H. Acta Pot Neerl 1975;24:129. w7x Sinha GK, Gupta R. Flavour Ind 1971;2:310. w8x Nagell A, Hefendhel FW, Hoyer JZ. Naturforsch 1974;29:294.
598
S. Ghoulami et al. r Fitoterapia 72 (2001) 596᎐598
w9x w10x w11x w12x w13x
Bourweig D, Pohl R. Planta med 1973;24:304. Al Hazimi H. Orient J Chem 1988;4:281. Jullien F, Voirin B, Bernillon J. Phytochemistry 1984;23:2972. Almeida RN, Hiruma CA, Barbosa-Filho JM. Fitoterapia 1996;67:334. Shibata H, Shiulzu S, Agr Biol Chem 1973;37:2675.
Phytochemical communication
Phytochemical study of Mentha longifolia of Morocco Saıd ¨ Ghoulami, Abdelkader Il IdrissiU , Souad Fkih-Tetouani Laboratoire de Chimie des Plantes et de Synthese de ` Organique et Bioorganique, Departement ´ Chimie, Faculte´ des Sciences, B.P 1014, Rabat RP 10000, Morocco
Received 6 December 2000; accepted in revised form 7 February 2001
Abstract A phytochemical study of Moroccan Mentha longifolia was carried out. The essential oil showed unusual relevant amounts of piperitenone oxide and piperitone oxide, which constitute a new chemotype. From the non-volatile extract, five flavonoids were isolated, among which 5,7,4⬘-trihydroxy-6,2⬘,3⬘-trimethoxyflavone Ž1. is reported for the first time. 䊚 2001 Elsevier Science B.V. All rights reserved. Keywords: Mentha longifolia; Essential oil; Flavonoids
Plant. Mentha longifolia ŽL.. Hudson ŽLamiaceae. aerial parts were harvested at the end of the vegetative cycle in the valley of Ifrane in the Middle Atlas ŽMorocco.. Morphologically, the harvested species did not present any hybrid character and corresponded to the botanical description by Quezel and Santa w1x. Uses in traditional medicine. As antibacterial and against gastric problems w2,3x. Previously isolated classes of constituents. Terpenoids w4᎐8x and flavonoids w9,10x. U
Corresponding author. E-mail address: [email protected] ŽA. Il Idrissi.. 0367-326Xr01r$ - see front matter 䊚 2001 Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 0 1 . 0 0 2 7 9 - 9
S. Ghoulami et al. r Fitoterapia 72 (2001) 596᎐598
597
New-isolated constituents. 5,6-Dihydroxy-7,8,3⬘,4⬘-tetramethoxyflavone w11x Žyield: 0.015% on dried wt.., 5,7,4⬘-trihydroxy-6,2⬘,3⬘-trimethoxyflavone (1) Ž0.01., along with the previously isolated luteolin, luteolin 7-O-glucoside and hesperidin, Žq.piperitenone oxide w12x Ž25% in the oil. and Žy.-trans-piperitone oxide w13x Ž24% in the oil..
5,7,4⬘-Trihydroxy-6,2⬘,3⬘-trimethoxyfla¨ one (1). Mp 228᎐229⬚C; UV max ŽMeOH.: 343, 287; ŽNaOMe. 398, 324, 265; ŽNaOAc. 403, 288; ŽAlCl 3 . 379, 304; ŽAlCl 3rHCl. 372, 300 nm; IR bands ŽKBr.: 3495, 1654, 1625 cmy1 ; 1 H-NMR Ž200 MHz, acetone.: ␦ 3.80 Ž3H, s, C 6-OMe., 3.85 Ž3H, s, C 2 ⬘-OMe., 3.90 Ž3H, s, C 3⬘-OMe., 6.55 Ž1H, s, H-3., 7.40 Ž1H, s, H-8., 6.80 Ž1H, d, J 9 Hz, H-5⬘., 7.50 Ž1H, d, J 9 Hz, H-6⬘.; MS mrz Žrel. int..: 360 Ž10. wMxq ŽC 18 H 14 O 8 ., 182 Ž15., 178 Ž15., 43 Ž100.. Conclusion. Due to the high contents in piperitenone and piperitone oxides, the studied Moroccan Mentha longifolia constitutes a new chemotype, only traces of piperitenone oxide having been previously reported in the essential oil w5x.
References w1x Quezel P, Santa S. Nouvelle flore de l’Algerie desertiques meridionales, II. Ed. du ´ et des regions ´ ´ ´ C.N.R.S, 1963. w2x Sticher O, Fluck H. Pharm Acta Helv 1968;43:411. w3x Banthorpe DV, Duprey RJH, Hassan M, Janes JF, Modawi BM. Egypt J Chem 1980;23:63. w4x Hefendhel FW. Herba Hungarica 1977;16:39. w5x Hefendhel FW, Nagell A. Parfum und Kosm 1975;7:189. w6x Vanos FHL, Hendriks H. Acta Pot Neerl 1975;24:129. w7x Sinha GK, Gupta R. Flavour Ind 1971;2:310. w8x Nagell A, Hefendhel FW, Hoyer JZ. Naturforsch 1974;29:294.
598
S. Ghoulami et al. r Fitoterapia 72 (2001) 596᎐598
w9x w10x w11x w12x w13x
Bourweig D, Pohl R. Planta med 1973;24:304. Al Hazimi H. Orient J Chem 1988;4:281. Jullien F, Voirin B, Bernillon J. Phytochemistry 1984;23:2972. Almeida RN, Hiruma CA, Barbosa-Filho JM. Fitoterapia 1996;67:334. Shibata H, Shiulzu S, Agr Biol Chem 1973;37:2675.