Phenolic glucosides from Flacourtia indica

S. Madan, S.T. Pannakal, S. Ganapaty, G.N. Singh, Y. Kumar

Research output: Contribution to journalArticle

110 Citations (Scopus)

Abstract

A new phenolic glucoside, (rel)-2-(4′,6′-dibenzoyl-β- glucopyranosyloxy)-7-(1́-hydroxy-2́-ethoxy-6́-acetyloxy-3- oxocyclohex-4-enoyl)-benzyl alcohol (Flacourticin) (1) and the known, 2-(4′,6′-dibenzoyl-β-glucopyranosyl)-5-hydroxy benzyl alcohol (4′-benzoylpoliothrysoside) (2) together with the new, (2E)-heptyl-3-(3,4-dihydroxyphenyl) acrylate (3), (+)-catechin (4) and sitosterol-β-D-glucoside were isolated from Flacourtia indica. Their structures were assigned on the basis of 1D, 2D-NMR and as well by analysis of the LC-ESIMS data. The isolated compounds (1-4) were evaluated for α,α-diphenyl-β-picrylhydrazyl (DPPH) radical scavenging activity, and 3 was found to be two-fold less potent, with an IC50 =12.01 μg/mL, compared to the positive control, Rutin, (IC50 = 5.83 μg/mL).
Original languageEnglish
Pages (from-to)381-384
Number of pages4
JournalNatural Product Communications
Volume4
Issue number3
DOIs
Publication statusPublished - 2009

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Flacourtiaceae
Benzyl Alcohol
benzyl alcohol
Glucosides
Inhibitory Concentration 50
glucosides
inhibitory concentration 50
Rutin
sitosterols
Catechin
rutin
catechin
biphenyl
Flacourtia indica

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Madan, S., Pannakal, S. T., Ganapaty, S., Singh, G. N., & Kumar, Y. (2009). Phenolic glucosides from Flacourtia indica. Natural Product Communications, 4(3), 381-384. https://doi.org/10.1021/jf010678d
Madan, S. ; Pannakal, S.T. ; Ganapaty, S. ; Singh, G.N. ; Kumar, Y. / Phenolic glucosides from Flacourtia indica. In: Natural Product Communications. 2009 ; Vol. 4, No. 3. pp. 381-384.
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title = "Phenolic glucosides from Flacourtia indica",
abstract = "A new phenolic glucoside, (rel)-2-(4′,6′-dibenzoyl-β- glucopyranosyloxy)-7-(1́-hydroxy-2́-ethoxy-6́-acetyloxy-3- oxocyclohex-4-enoyl)-benzyl alcohol (Flacourticin) (1) and the known, 2-(4′,6′-dibenzoyl-β-glucopyranosyl)-5-hydroxy benzyl alcohol (4′-benzoylpoliothrysoside) (2) together with the new, (2E)-heptyl-3-(3,4-dihydroxyphenyl) acrylate (3), (+)-catechin (4) and sitosterol-β-D-glucoside were isolated from Flacourtia indica. Their structures were assigned on the basis of 1D, 2D-NMR and as well by analysis of the LC-ESIMS data. The isolated compounds (1-4) were evaluated for α,α-diphenyl-β-picrylhydrazyl (DPPH) radical scavenging activity, and 3 was found to be two-fold less potent, with an IC50 =12.01 μg/mL, compared to the positive control, Rutin, (IC50 = 5.83 μg/mL).",
author = "S. Madan and S.T. Pannakal and S. Ganapaty and G.N. Singh and Y. Kumar",
note = "Cited By :7 Export Date: 10 November 2017 Correspondence Address: Pannakal, S. T.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Madhav Nagar, Manipal University, Manipal-576 104, Karnataka, India; email: stevethomas.p@manipal.edu Chemicals/CAS: rutoside, 153-18-4, 22519-99-9; 1,1 diphenyl 2 picrylhydrazyl, 1898-66-4; glucoside, 50986-29-3; picric acid, 14798-26-6, 88-89-1; 2,2-diphenyl-1-picrylhydrazyl, 1898-66-4; Biphenyl Compounds; Glucosides; Phenols; Picrates References: Duthie, J.S., (1994) Flora of the Upper Gangetic Plain, 1, pp. 215-220. , Bishen singh Mahendra pal singh New Connaught place, Dehra doon; Raw materials (1956) The Wealth of India, 4, p. 43. , Council of Scientific and Industrial Research; New Delhi; Amarasinghe, N.R., Jayasinghe, L., Hara, N., Fujimoto, Y., Flacourside, a new 4-oxo-2-cyclopentenylmethyl glucoside from the fruit juice of Flacourtia indica (2007) Food Chemistry, 102, pp. 95-97; Ndhlala, A.R., Kasiyamhuru, A., Mupure, C., Chitindigu, K., Benhura, M.A., Muchuweti, Phenolic composition of Flacourtia indica, Opuntia megacantha and Sclerocarya birrea (2007) Food Chemistry, 103, pp. 82-87; Gibbons, S., Grey, A.I., Waterman, P.G., Benzoylated derivatives of 2-glucopyranosyloxy-2,5- dihydroxybenzyl alcohol from Xylosma flexuosum: Structure and relative configuration of Xylosmin (1995) Journal of Natural Products, 58, pp. 554-559; Mosaddik, M.A., Forster, P.I., Booth, R., Waterman, P.G., Phenolic glycosides from some Australian species of Flacourtiaceae (Salicaceae Sensu lato) (2007) Biochemical Systematics and Ecology, 35, pp. 166-168; Shaari, K., Waterman, P.G., Scoloposides A-E, a series of 2-glucopyranosyloxy-5-hydroxybenzyl alcohol derivatives from Scolopia spinosa (1994) Phytochemistry, 36 (4), pp. 1021-1026. , DOI 10.1016/S0031-9422(00)90483-7; Shaari, K., Waterman, P.G., Glucosides of 2,5-dihydroxybenzyl alcohol from Homalium longifolium (1995) Phytochemistry, 39, pp. 1415-1421; Batterham, T.J., Highet, R.J., Nuclear magnetic resonance spectra of flavonoids (1963) Australian Journal of Chemistry, 17, pp. 428-439; Ohnishi, M., Morishita, H., Iwahashi, H., Toda, S., Shirataki, Y., Kimura, M., Kido, R., Inhibitory effects of chlorogenic acids on linoleic acid peroxidation and haemolysis (1994) Phytochemistry, 36 (3), pp. 579-583. , DOI 10.1016/S0031-9422(00)89778-2; Okawa, M., Kinjo, J., Nohara, T., Ono, M., DPPH (1,1-diphenyl-2-Picrylhydrazyl) radical scavenging activity of flavonoids obtained from some medicinal plants (2001) Biological and Pharmaceutical Bulletin, 24 (10), pp. 1202-1205. , DOI 10.1248/bpb.24.1202; Silva, M.M., Santos, M.R., Caroco, G., Rocha, R., Justino, G., Mira, L., Structure-antioxidant activity relationships of flavonoids: A re-examination (2002) Free Radical Research, 36 (11), pp. 1219-1227; Chase, M.W., Zmartzty, S., Lledo, M.D., Wurdack, K.J., Swenson, S.M., Fay, M.F., When in doubt, put it in Flacourtiaceae: A molecular phylogenetic analysis based on plastid rbcL DNA sequences (2002) Kew Bulletin, 57, pp. 141-181; Ogawa, Y., Oku, H., Iwaoka, E., Iinuma, M., Ishiguro, K., Allergy-preventive phenolic glycosides from Populus sieboldii (2006) Journal of Natural Products, 69 (8), pp. 1215-1217. , DOI 10.1021/np0505216; Germano, M.P., De Pasquale, R., D'Angelo, V., Catania, S., Silvari, V., Costa, C., Evaluation of extracts and isolated fraction from Capparis spinosa L. buds as an antioxidant source (2002) Journal of Agricultural and Food Chemistry, 50 (5), pp. 1168-1171. , DOI 10.1021/jf010678d",
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Madan, S, Pannakal, ST, Ganapaty, S, Singh, GN & Kumar, Y 2009, 'Phenolic glucosides from Flacourtia indica', Natural Product Communications, vol. 4, no. 3, pp. 381-384. https://doi.org/10.1021/jf010678d

Phenolic glucosides from Flacourtia indica. / Madan, S.; Pannakal, S.T.; Ganapaty, S.; Singh, G.N.; Kumar, Y.

In: Natural Product Communications, Vol. 4, No. 3, 2009, p. 381-384.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Phenolic glucosides from Flacourtia indica

AU - Madan, S.

AU - Pannakal, S.T.

AU - Ganapaty, S.

AU - Singh, G.N.

AU - Kumar, Y.

N1 - Cited By :7 Export Date: 10 November 2017 Correspondence Address: Pannakal, S. T.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Madhav Nagar, Manipal University, Manipal-576 104, Karnataka, India; email: stevethomas.p@manipal.edu Chemicals/CAS: rutoside, 153-18-4, 22519-99-9; 1,1 diphenyl 2 picrylhydrazyl, 1898-66-4; glucoside, 50986-29-3; picric acid, 14798-26-6, 88-89-1; 2,2-diphenyl-1-picrylhydrazyl, 1898-66-4; Biphenyl Compounds; Glucosides; Phenols; Picrates References: Duthie, J.S., (1994) Flora of the Upper Gangetic Plain, 1, pp. 215-220. , Bishen singh Mahendra pal singh New Connaught place, Dehra doon; Raw materials (1956) The Wealth of India, 4, p. 43. , Council of Scientific and Industrial Research; New Delhi; Amarasinghe, N.R., Jayasinghe, L., Hara, N., Fujimoto, Y., Flacourside, a new 4-oxo-2-cyclopentenylmethyl glucoside from the fruit juice of Flacourtia indica (2007) Food Chemistry, 102, pp. 95-97; Ndhlala, A.R., Kasiyamhuru, A., Mupure, C., Chitindigu, K., Benhura, M.A., Muchuweti, Phenolic composition of Flacourtia indica, Opuntia megacantha and Sclerocarya birrea (2007) Food Chemistry, 103, pp. 82-87; Gibbons, S., Grey, A.I., Waterman, P.G., Benzoylated derivatives of 2-glucopyranosyloxy-2,5- dihydroxybenzyl alcohol from Xylosma flexuosum: Structure and relative configuration of Xylosmin (1995) Journal of Natural Products, 58, pp. 554-559; Mosaddik, M.A., Forster, P.I., Booth, R., Waterman, P.G., Phenolic glycosides from some Australian species of Flacourtiaceae (Salicaceae Sensu lato) (2007) Biochemical Systematics and Ecology, 35, pp. 166-168; Shaari, K., Waterman, P.G., Scoloposides A-E, a series of 2-glucopyranosyloxy-5-hydroxybenzyl alcohol derivatives from Scolopia spinosa (1994) Phytochemistry, 36 (4), pp. 1021-1026. , DOI 10.1016/S0031-9422(00)90483-7; Shaari, K., Waterman, P.G., Glucosides of 2,5-dihydroxybenzyl alcohol from Homalium longifolium (1995) Phytochemistry, 39, pp. 1415-1421; Batterham, T.J., Highet, R.J., Nuclear magnetic resonance spectra of flavonoids (1963) Australian Journal of Chemistry, 17, pp. 428-439; Ohnishi, M., Morishita, H., Iwahashi, H., Toda, S., Shirataki, Y., Kimura, M., Kido, R., Inhibitory effects of chlorogenic acids on linoleic acid peroxidation and haemolysis (1994) Phytochemistry, 36 (3), pp. 579-583. , DOI 10.1016/S0031-9422(00)89778-2; Okawa, M., Kinjo, J., Nohara, T., Ono, M., DPPH (1,1-diphenyl-2-Picrylhydrazyl) radical scavenging activity of flavonoids obtained from some medicinal plants (2001) Biological and Pharmaceutical Bulletin, 24 (10), pp. 1202-1205. , DOI 10.1248/bpb.24.1202; Silva, M.M., Santos, M.R., Caroco, G., Rocha, R., Justino, G., Mira, L., Structure-antioxidant activity relationships of flavonoids: A re-examination (2002) Free Radical Research, 36 (11), pp. 1219-1227; Chase, M.W., Zmartzty, S., Lledo, M.D., Wurdack, K.J., Swenson, S.M., Fay, M.F., When in doubt, put it in Flacourtiaceae: A molecular phylogenetic analysis based on plastid rbcL DNA sequences (2002) Kew Bulletin, 57, pp. 141-181; Ogawa, Y., Oku, H., Iwaoka, E., Iinuma, M., Ishiguro, K., Allergy-preventive phenolic glycosides from Populus sieboldii (2006) Journal of Natural Products, 69 (8), pp. 1215-1217. , DOI 10.1021/np0505216; Germano, M.P., De Pasquale, R., D'Angelo, V., Catania, S., Silvari, V., Costa, C., Evaluation of extracts and isolated fraction from Capparis spinosa L. buds as an antioxidant source (2002) Journal of Agricultural and Food Chemistry, 50 (5), pp. 1168-1171. , DOI 10.1021/jf010678d

PY - 2009

Y1 - 2009

N2 - A new phenolic glucoside, (rel)-2-(4′,6′-dibenzoyl-β- glucopyranosyloxy)-7-(1́-hydroxy-2́-ethoxy-6́-acetyloxy-3- oxocyclohex-4-enoyl)-benzyl alcohol (Flacourticin) (1) and the known, 2-(4′,6′-dibenzoyl-β-glucopyranosyl)-5-hydroxy benzyl alcohol (4′-benzoylpoliothrysoside) (2) together with the new, (2E)-heptyl-3-(3,4-dihydroxyphenyl) acrylate (3), (+)-catechin (4) and sitosterol-β-D-glucoside were isolated from Flacourtia indica. Their structures were assigned on the basis of 1D, 2D-NMR and as well by analysis of the LC-ESIMS data. The isolated compounds (1-4) were evaluated for α,α-diphenyl-β-picrylhydrazyl (DPPH) radical scavenging activity, and 3 was found to be two-fold less potent, with an IC50 =12.01 μg/mL, compared to the positive control, Rutin, (IC50 = 5.83 μg/mL).

AB - A new phenolic glucoside, (rel)-2-(4′,6′-dibenzoyl-β- glucopyranosyloxy)-7-(1́-hydroxy-2́-ethoxy-6́-acetyloxy-3- oxocyclohex-4-enoyl)-benzyl alcohol (Flacourticin) (1) and the known, 2-(4′,6′-dibenzoyl-β-glucopyranosyl)-5-hydroxy benzyl alcohol (4′-benzoylpoliothrysoside) (2) together with the new, (2E)-heptyl-3-(3,4-dihydroxyphenyl) acrylate (3), (+)-catechin (4) and sitosterol-β-D-glucoside were isolated from Flacourtia indica. Their structures were assigned on the basis of 1D, 2D-NMR and as well by analysis of the LC-ESIMS data. The isolated compounds (1-4) were evaluated for α,α-diphenyl-β-picrylhydrazyl (DPPH) radical scavenging activity, and 3 was found to be two-fold less potent, with an IC50 =12.01 μg/mL, compared to the positive control, Rutin, (IC50 = 5.83 μg/mL).

U2 - 10.1021/jf010678d

DO - 10.1021/jf010678d

M3 - Article

VL - 4

SP - 381

EP - 384

JO - Natural Product Communications

JF - Natural Product Communications

SN - 1934-578X

IS - 3

ER -

Madan S, Pannakal ST, Ganapaty S, Singh GN, Kumar Y. Phenolic glucosides from Flacourtia indica. Natural Product Communications. 2009;4(3):381-384. https://doi.org/10.1021/jf010678d