- Email: [email protected]
A new isoflavone from the roots of Abrus precatorius
Fitoterapia 70 Ž1999. 328]329
Phytochemical communication
A new isoflavone from the roots of Abrus precatorius V.K. SaxenaU , D.N. Sharma Natural Products Laboratory, Department of Chemistry, Dr. Harisingh Gour Uni¨ ersity, Sagar 470 003 (M.P.), India Received 26 October 1998; accepted 19 December 1998
Abstract The isolation and spectral data of the new 7,5-dihydroxy-6,49-dimethoxy isoflavone 7-O-b-Dgalactopyranoside Ž1. from the roots of Abrus precatorius are reported. Q 1999 Published by Elsevier Science B.V. All rights reserved. Keywords: Abrus precatorius; Isoflavone
Plant. Abrus precatorius L. ŽFabaceae. w1]4x, dried roots, collected around Sagar, in November 1996 and identified by staff of the Botany Department, Dr. H.S. Gour University, Sagar ŽM.P... Voucher specimen No. XXXIV A is deposited at the Department of Chemistry, Dr. H.S. Gour University, Sagar. Uses in traditional medicine. Leucoderma, itching, wounds w5x. Previously isolated constituents. Triterpenoid sapogenin from roots w6x. New-isolated constituents. 7,5-Dihydroxy-6,49dimethoxyisoflavone-7-O-b -D galactopyranoside Ž1., 1.35 g from 2.5 kg of air-dried powdered roots. U
Corresponding author.
0367-326-Xr99r$ - see front matter Q 1999 Published by Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 9 9 . 0 0 0 3 6 - 2
V.K. Saxena, D.N. Sharma r Fitoterapia 70 (1999) 328]329
329
7,5-Dihydroxy-6,49-dimethoxy-isofla¨ one-7-O- b - D -galactopyranoside ( 1 ) . M.p. 204]2058C; UV max ŽMeOH.: 256, 306; ŽNaOMe. 254, 330; ŽAlCl 3 . 260, 342; ŽAlCl 3 q HCl. 261, 340; ŽNaOAc. 256, 326 nm; IR bands ŽKBr.: 3350, 2860, 1600, 1580, 1125, 826 cmy1 ; 13 C-NMR Ž400 MHz DMSO-d6 .: d 152.22 ŽC-2., 124.5 ŽC-3., 172.4 ŽC-4., 160.21 ŽC-5., 150.22 ŽC-6., 188.4 ŽC-7., 110.2 ŽC-8., 152.4 ŽC-9., 104.6 ŽC-10., 111.6 ŽC-19., 108.6 ŽC-29., 142.4 ŽC-39., 145.5 ŽC-49., 95.4 ŽC-59., 150.2 ŽC-69., 98.5 ŽC-10 ., 71.05 ŽC-20 ., 75.4 ŽC-30 ., 67.5 ŽC-40 ., 75.4 ŽC-50 ., 66.1 ŽC-60 ., 54.8, 54.9 ŽOMe.; MS m r z: 314, 299, 183, 155, 137, 135, 138. Pentaacetate: m.p. 1828C. H-NMR Ž400 MHz, Me 2 CO-d6 .: d 7.89 Ž1H, s, H-2., d 4.01 Ž3 H, s, OAc-5., d 7.34 Ž2H, d, J 8.5 Hz, H-29, 69., d 6.62 Ž2H, d, J 8.5 Hz H-39,59., d 5.48 Ž1H, J 9 Hz 1H-gal., d 2.06]2.16 Ž12 H, m, 4 x OAc..
Acknowledgements The authors are thankful to the Head, RSIC CDRI, Lucknow ŽIndia. for spectral analysis and the Head of the Department of Chemistry, Dr. H.S. Gour University, Sagar ŽM.P.. for providing necessary laboratory facilities.
References w1x Chopra RN, Nayar SL, Chopra IC. Glossary of Indian medicinal plants. New Delhi: CSIR Publication, 1956:1. w2x Chopra RN, Chopra IC, Verma BS. Supplement to glossary of Indian medicinal plants. New Delhi: CSIR Publication, 1968:63. w3x Singh RS. Vanosadhi Nirdasica, Ayurvedic Pharmacopoeia. Lucknow: Uttar Pradesh Hindi Sansthan, 1983:129-130. w4x Wealth of India } A directory of raw material and industrial products. vol. 1. New Delhi: CSIR Publication, 1948:2]3. w5x Kirtikar KR, Basu BD. Indian medicinal plants. vol. I. Allahabad: Lalit Mohan Basu and Co, 1935:764]766. w6x Chang HM, Chaing TC. J Chem Soc Chem England, 1982:1197.
Phytochemical communication
A new isoflavone from the roots of Abrus precatorius V.K. SaxenaU , D.N. Sharma Natural Products Laboratory, Department of Chemistry, Dr. Harisingh Gour Uni¨ ersity, Sagar 470 003 (M.P.), India Received 26 October 1998; accepted 19 December 1998
Abstract The isolation and spectral data of the new 7,5-dihydroxy-6,49-dimethoxy isoflavone 7-O-b-Dgalactopyranoside Ž1. from the roots of Abrus precatorius are reported. Q 1999 Published by Elsevier Science B.V. All rights reserved. Keywords: Abrus precatorius; Isoflavone
Plant. Abrus precatorius L. ŽFabaceae. w1]4x, dried roots, collected around Sagar, in November 1996 and identified by staff of the Botany Department, Dr. H.S. Gour University, Sagar ŽM.P... Voucher specimen No. XXXIV A is deposited at the Department of Chemistry, Dr. H.S. Gour University, Sagar. Uses in traditional medicine. Leucoderma, itching, wounds w5x. Previously isolated constituents. Triterpenoid sapogenin from roots w6x. New-isolated constituents. 7,5-Dihydroxy-6,49dimethoxyisoflavone-7-O-b -D galactopyranoside Ž1., 1.35 g from 2.5 kg of air-dried powdered roots. U
Corresponding author.
0367-326-Xr99r$ - see front matter Q 1999 Published by Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 9 9 . 0 0 0 3 6 - 2
V.K. Saxena, D.N. Sharma r Fitoterapia 70 (1999) 328]329
329
7,5-Dihydroxy-6,49-dimethoxy-isofla¨ one-7-O- b - D -galactopyranoside ( 1 ) . M.p. 204]2058C; UV max ŽMeOH.: 256, 306; ŽNaOMe. 254, 330; ŽAlCl 3 . 260, 342; ŽAlCl 3 q HCl. 261, 340; ŽNaOAc. 256, 326 nm; IR bands ŽKBr.: 3350, 2860, 1600, 1580, 1125, 826 cmy1 ; 13 C-NMR Ž400 MHz DMSO-d6 .: d 152.22 ŽC-2., 124.5 ŽC-3., 172.4 ŽC-4., 160.21 ŽC-5., 150.22 ŽC-6., 188.4 ŽC-7., 110.2 ŽC-8., 152.4 ŽC-9., 104.6 ŽC-10., 111.6 ŽC-19., 108.6 ŽC-29., 142.4 ŽC-39., 145.5 ŽC-49., 95.4 ŽC-59., 150.2 ŽC-69., 98.5 ŽC-10 ., 71.05 ŽC-20 ., 75.4 ŽC-30 ., 67.5 ŽC-40 ., 75.4 ŽC-50 ., 66.1 ŽC-60 ., 54.8, 54.9 ŽOMe.; MS m r z: 314, 299, 183, 155, 137, 135, 138. Pentaacetate: m.p. 1828C. H-NMR Ž400 MHz, Me 2 CO-d6 .: d 7.89 Ž1H, s, H-2., d 4.01 Ž3 H, s, OAc-5., d 7.34 Ž2H, d, J 8.5 Hz, H-29, 69., d 6.62 Ž2H, d, J 8.5 Hz H-39,59., d 5.48 Ž1H, J 9 Hz 1H-gal., d 2.06]2.16 Ž12 H, m, 4 x OAc..
Acknowledgements The authors are thankful to the Head, RSIC CDRI, Lucknow ŽIndia. for spectral analysis and the Head of the Department of Chemistry, Dr. H.S. Gour University, Sagar ŽM.P.. for providing necessary laboratory facilities.
References w1x Chopra RN, Nayar SL, Chopra IC. Glossary of Indian medicinal plants. New Delhi: CSIR Publication, 1956:1. w2x Chopra RN, Chopra IC, Verma BS. Supplement to glossary of Indian medicinal plants. New Delhi: CSIR Publication, 1968:63. w3x Singh RS. Vanosadhi Nirdasica, Ayurvedic Pharmacopoeia. Lucknow: Uttar Pradesh Hindi Sansthan, 1983:129-130. w4x Wealth of India } A directory of raw material and industrial products. vol. 1. New Delhi: CSIR Publication, 1948:2]3. w5x Kirtikar KR, Basu BD. Indian medicinal plants. vol. I. Allahabad: Lalit Mohan Basu and Co, 1935:764]766. w6x Chang HM, Chaing TC. J Chem Soc Chem England, 1982:1197.