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Constituents of the flowers of Persea gratissima
Fitoterapia 71 Ž2000. 94]96
Phytochemical communication
Constituents of the flowers of Persea gratissima Anil Kumar Kruthiventi a,U , N.R. Krishnaswamy b a
Department of Chemistry, Sri Satya Sai Institute of Higher Learning, Prashantinilayam, A.P. 515 134, India b No: 12, 9th Main Road, Banashankari Second Stage, Bangalore, India Received 17 March 1999; accepted 30 June 1999
Abstract The flowers of Persea gratissima yielded an acylated flavonol 3-O-trans-pcoumaroylkaempferol (1), in addition to quercetin 3-O-rhamnoside (2) and isorhamnetin 3-O-glucoside (3). Q 2000 Elsevier Science B.V. All rights reserved. Keywords: Persea gratissima; Flavonoids
Plant. Persea gratissima Gaertn. ŽLauraceae ., fresh flowers were collected in August]September 1997 from the Lalbagh gardens at Bangalore and authenticated by the Biosciences Department of this Institute. Uses in traditional medicine. The aqueous extract of the leaves is said to have a fairly prolonged hypotensive action w1x. Extracts of the dried peel and the seeds showed antibiotic activity w2x. Previously isolated constituents. Flavonoids w3x. New-isolated constituents. 3-O-trans-p-Coumaroylkaempferol (1), quercetin 3-Orhamnoside (2), isorhamnetin 3-O-glucoside (3) Žyields: 0.005, 0.0225, 0.015%, respectively.. U
Corresponding author.
0367-326Xr00r$ - see front matter Q 2000 Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 9 9 . 0 0 1 2 5 - 2
A.K. Kruthi¨ enti, N.R. Krishnaswamy r Fitoterapia 71 (2000) 94]96
95
3-O-trans-p-Coumaroylkaempferol (1). M.p. 2308C; UV max ŽMeOH.: 315, 267, 354 Žsh.; NaOMe 371, 312 Žsh., 275; AlCl 3 397, 305 Žsh., 275; AlCl 3rHCl 396, 305 Žsh., 275; NaOAc 369, 312 Žsh., 275; NaOAcrH 3 BO 3 314, 268 and 353 Žsh.; IR bands Žnujol.: 3460, 3500]3000, 1700, 1650, 1600, 1500, 1420, 1360 and 1080 cmy1 ; MS m r z Ž%.; M q 1.q 433 Ž6.73., M .q 432 Ž22.75., 389 Ž10.26., 287 Ž15.65., 286 Ž100., 285 Ž29.76., 164 Ž12.26., 153 Ž4.09., 147 Ž19.99., 121 Ž16.08., 120 Ž18.82., 102 Ž2.45., 91 Ž42.56. and 43 Ž42.68.; 1 H-NMR Ž90 MHz, DMSO.: d 7.92 Ž d, J 8 Hz, 2H, 39, 59., 7.32 Ž d, J 16 Hz, 1H., 7.24 Ž d, J 7.2 Hz, 2H, 30, 50 ., 6.86 Ž d, J 8 Hz, 2H, 29, 69., 6.72 Ž d, J 7.2 Hz, 2H, 20, 60 ., 6.34 Ž d, J 2 Hz, 1H., 6.12 Ž d, J 2 Hz, 1H. and 6.02 Ž d, J 16 Hz, 1H.. Quercetin 3-O-rhamnoside (2). M.p. 1858C; UV max ŽMeOH.: 360, 258, 296 Žsh.; NaOMe 409, 341 Žsh., 300 Žsh., 274; AlCl 3 432, 341 Žsh., 300 Žsh., 274; AlCl 3rHCl
96
A.K. Kruthi¨ enti, N.R. Krishnaswamy r Fitoterapia 71 (2000) 94]96
382, 326 Žsh., 272; NaOAc 382, 326 Žsh., 272; NaOAcrH 3 BO 3 375, 263 and 295 Žsh.; IR bands Žnujol.: 3600]3000, 2900, 1650, 1600, 1500, 1440, 1360 and 1086 cmy1 ; MS m r z Ž%.; M-1.q 447 Ž1.85., 358 Ž1.45., 303 Ž17.73., 302 Ž100., 286 Ž8.09., 273 Ž8.77., 259 Ž91.37., 257 Ž3.53., 153 Ž5.34., 137 Ž8.94., 121 Ž3.14., 109 Ž5.36., 97 Ž9.61., 69 Ž24.81., 55 Ž27.23. and 44 Ž43.16.; 1 H-NMR Ž90 MHz, DMSO.: d 7.66 Ž1H, dd, J 9 Hz and 2.5 Hz., 7.60 Ž1H, d, J 2.5 Hz, 6.84 Ž1H, d, J 9 Hz., 6.40 Ž1H, d, J 2.5 Hz., 6.20 Ž1H, d, J 2.5 Hz., 5.32 Ž1H, d, J 8 Hz., 4.34 Ž1H, m. and 0.93 Ž3H, s .. Isorhamnetin 3-O-glucoside (3). M.p. 1798C; UV max ŽMeOH.: 358, 256; NaOMe 406, 326 Žsh., 272; AlCl 3 414, 345 Žsh., 300 Žsh., 273; AlCl 3rHCl 414, 362 Žsh., 300 Žsh., 270; NaOAc 409, 341 Žsh., 272; NaOAcrH 3 BO 3 360, 260 and 295 Žsh.; IR bands Žnujol.: 3600]3000, 2900, 1650, 1600, 1500, 1440, 1360 and 1080 cmy1 ; MS m r z Ž%. M-1.q 477 Ž0.05., 436 Ž1.30., 417 Ž0.02., 397 Ž0.02., 358 Ž0.25., 351 Ž0.03., 347 Ž0.03., 317 Ž0.21., 316 Ž1.99., 315 Ž0.33., 302 Ž1.58., 286 Ž0.53., 273 Ž0.27., 153 Ž0.93., 148 Ž0.03., 144 Ž0.96., 123 Ž0.54., 121 Ž1.06., 97 Ž2.69., 69 Ž7.69., 51 Ž14.35. and 44 Ž100.; 1 H-NMR Ž90 MHz, DMSO.: d 7.60 Ž 1 H, dd, J 8 Hz and 2.5 Hz., 7.56 Ž1H, d, J 2.5 Hz., 6.86 Ž1H, d, J 8 Hz., 6.34 Ž1H, d, J 2 Hz., 6.16 Ž1H, d, J 2 Hz., 3.92 Ž3H, s ..
Acknowledgements The authors are grateful to the Institute ŽSSSIHL, PN. for providing the necessary facilities.
References w1x Lambo A. In: Sofowara A, editor. The symposium on antihypertensive agents in conjunction with Ciba-Geigy ŽNig.. Ltd. 1975. w2x Thompson RS, Jacques D, Haslam E, Tanner RJN. JCS Perkin Transaction-I 1972:1378. w3x Krishnaswamy NR, Sudhakar Rao B. M.Sc. Dissertation. Sri Satya Sai Institute of Higher Learning. Prashantinilayam, India, 1987.
Phytochemical communication
Constituents of the flowers of Persea gratissima Anil Kumar Kruthiventi a,U , N.R. Krishnaswamy b a
Department of Chemistry, Sri Satya Sai Institute of Higher Learning, Prashantinilayam, A.P. 515 134, India b No: 12, 9th Main Road, Banashankari Second Stage, Bangalore, India Received 17 March 1999; accepted 30 June 1999
Abstract The flowers of Persea gratissima yielded an acylated flavonol 3-O-trans-pcoumaroylkaempferol (1), in addition to quercetin 3-O-rhamnoside (2) and isorhamnetin 3-O-glucoside (3). Q 2000 Elsevier Science B.V. All rights reserved. Keywords: Persea gratissima; Flavonoids
Plant. Persea gratissima Gaertn. ŽLauraceae ., fresh flowers were collected in August]September 1997 from the Lalbagh gardens at Bangalore and authenticated by the Biosciences Department of this Institute. Uses in traditional medicine. The aqueous extract of the leaves is said to have a fairly prolonged hypotensive action w1x. Extracts of the dried peel and the seeds showed antibiotic activity w2x. Previously isolated constituents. Flavonoids w3x. New-isolated constituents. 3-O-trans-p-Coumaroylkaempferol (1), quercetin 3-Orhamnoside (2), isorhamnetin 3-O-glucoside (3) Žyields: 0.005, 0.0225, 0.015%, respectively.. U
Corresponding author.
0367-326Xr00r$ - see front matter Q 2000 Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 9 9 . 0 0 1 2 5 - 2
A.K. Kruthi¨ enti, N.R. Krishnaswamy r Fitoterapia 71 (2000) 94]96
95
3-O-trans-p-Coumaroylkaempferol (1). M.p. 2308C; UV max ŽMeOH.: 315, 267, 354 Žsh.; NaOMe 371, 312 Žsh., 275; AlCl 3 397, 305 Žsh., 275; AlCl 3rHCl 396, 305 Žsh., 275; NaOAc 369, 312 Žsh., 275; NaOAcrH 3 BO 3 314, 268 and 353 Žsh.; IR bands Žnujol.: 3460, 3500]3000, 1700, 1650, 1600, 1500, 1420, 1360 and 1080 cmy1 ; MS m r z Ž%.; M q 1.q 433 Ž6.73., M .q 432 Ž22.75., 389 Ž10.26., 287 Ž15.65., 286 Ž100., 285 Ž29.76., 164 Ž12.26., 153 Ž4.09., 147 Ž19.99., 121 Ž16.08., 120 Ž18.82., 102 Ž2.45., 91 Ž42.56. and 43 Ž42.68.; 1 H-NMR Ž90 MHz, DMSO.: d 7.92 Ž d, J 8 Hz, 2H, 39, 59., 7.32 Ž d, J 16 Hz, 1H., 7.24 Ž d, J 7.2 Hz, 2H, 30, 50 ., 6.86 Ž d, J 8 Hz, 2H, 29, 69., 6.72 Ž d, J 7.2 Hz, 2H, 20, 60 ., 6.34 Ž d, J 2 Hz, 1H., 6.12 Ž d, J 2 Hz, 1H. and 6.02 Ž d, J 16 Hz, 1H.. Quercetin 3-O-rhamnoside (2). M.p. 1858C; UV max ŽMeOH.: 360, 258, 296 Žsh.; NaOMe 409, 341 Žsh., 300 Žsh., 274; AlCl 3 432, 341 Žsh., 300 Žsh., 274; AlCl 3rHCl
96
A.K. Kruthi¨ enti, N.R. Krishnaswamy r Fitoterapia 71 (2000) 94]96
382, 326 Žsh., 272; NaOAc 382, 326 Žsh., 272; NaOAcrH 3 BO 3 375, 263 and 295 Žsh.; IR bands Žnujol.: 3600]3000, 2900, 1650, 1600, 1500, 1440, 1360 and 1086 cmy1 ; MS m r z Ž%.; M-1.q 447 Ž1.85., 358 Ž1.45., 303 Ž17.73., 302 Ž100., 286 Ž8.09., 273 Ž8.77., 259 Ž91.37., 257 Ž3.53., 153 Ž5.34., 137 Ž8.94., 121 Ž3.14., 109 Ž5.36., 97 Ž9.61., 69 Ž24.81., 55 Ž27.23. and 44 Ž43.16.; 1 H-NMR Ž90 MHz, DMSO.: d 7.66 Ž1H, dd, J 9 Hz and 2.5 Hz., 7.60 Ž1H, d, J 2.5 Hz, 6.84 Ž1H, d, J 9 Hz., 6.40 Ž1H, d, J 2.5 Hz., 6.20 Ž1H, d, J 2.5 Hz., 5.32 Ž1H, d, J 8 Hz., 4.34 Ž1H, m. and 0.93 Ž3H, s .. Isorhamnetin 3-O-glucoside (3). M.p. 1798C; UV max ŽMeOH.: 358, 256; NaOMe 406, 326 Žsh., 272; AlCl 3 414, 345 Žsh., 300 Žsh., 273; AlCl 3rHCl 414, 362 Žsh., 300 Žsh., 270; NaOAc 409, 341 Žsh., 272; NaOAcrH 3 BO 3 360, 260 and 295 Žsh.; IR bands Žnujol.: 3600]3000, 2900, 1650, 1600, 1500, 1440, 1360 and 1080 cmy1 ; MS m r z Ž%. M-1.q 477 Ž0.05., 436 Ž1.30., 417 Ž0.02., 397 Ž0.02., 358 Ž0.25., 351 Ž0.03., 347 Ž0.03., 317 Ž0.21., 316 Ž1.99., 315 Ž0.33., 302 Ž1.58., 286 Ž0.53., 273 Ž0.27., 153 Ž0.93., 148 Ž0.03., 144 Ž0.96., 123 Ž0.54., 121 Ž1.06., 97 Ž2.69., 69 Ž7.69., 51 Ž14.35. and 44 Ž100.; 1 H-NMR Ž90 MHz, DMSO.: d 7.60 Ž 1 H, dd, J 8 Hz and 2.5 Hz., 7.56 Ž1H, d, J 2.5 Hz., 6.86 Ž1H, d, J 8 Hz., 6.34 Ž1H, d, J 2 Hz., 6.16 Ž1H, d, J 2 Hz., 3.92 Ž3H, s ..
Acknowledgements The authors are grateful to the Institute ŽSSSIHL, PN. for providing the necessary facilities.
References w1x Lambo A. In: Sofowara A, editor. The symposium on antihypertensive agents in conjunction with Ciba-Geigy ŽNig.. Ltd. 1975. w2x Thompson RS, Jacques D, Haslam E, Tanner RJN. JCS Perkin Transaction-I 1972:1378. w3x Krishnaswamy NR, Sudhakar Rao B. M.Sc. Dissertation. Sri Satya Sai Institute of Higher Learning. Prashantinilayam, India, 1987.