Evaluation of silymarin extraction from Silybum marianum (L.) Gaertn seeds by water

Subject Areas : Genetic

طاهره  Hasanloo ¹ (Department of Plant Physiology, Agricultural Biotechnology Research Institute of Iran, Mahdasht Road,)
روشنک  Sepehrifar ² (Department of Plant Physiology, Agricultural Biotechnology Research Institute of Iran, Mahdasht Road,)

Received: 2006-07-15 Accepted : 2007-12-15 Published : 2008-02-20

Keywords: Solvent, silymarin, Silybum marianum (L.) Gaertn,

Abstract :

  The seeds extract of Silybum marianum (L.) Gaertn is named silymarin and used in treatment of liver diseases, diabetes (II) and hypercholesterolemia. There are different solvents (methanol, ethanol, acetonitrile and acetone) for extraction of this compound. Water is an inetersting alternative because of its low operating and disposal costs. This study was undertaken to evaluate the efficiency of different methods on silymarin production and followed by HPLC analysis of extracted flavonolignans. The highest content of taxifolin, silychristin and silydianin were 0.63, 0.9 and 2.35 mg g-1 DW, respectively in a soxhlet extraction with water for 12 h after a pre-treatment step involving defatting with petroleum ether. The highest content of silybin and isosilybin were extracted 0.24 and 0.15 mg g-1 DW in a soxhlet extraction with water without defatting process. Although the ratio of the extracted componds with water were less than methanolic extraction, for increasing the quality of the products, the water extraction steps should be well studied both in terms of time and methods.

References:

حسنلو، ط.، خاوری نژاد، ر.ع.، مجیدی، ا. و ضیایی س. ع. (1383) مطالعه و تعیین فلاونولیگنان ها در میوه‌های گیاه خارمریم جمع آوری شده از نقاط مختلف ایران به روش‌های اسپکتروفتومتری TLC و HPLC. فصلنامه گیاهان دارویی، ویژه نامه خارمریم، سال چهارم، صفحات 25-32.

ضیایی، س. ع.، حسینی، ح. ف.، رجبیان، ط.، پور حسینی، ل.، نقدی بادی، ح. و رضازاده، ش. (1383) بررسی اثر حلال­های مختلف در  استخراج  سیلی­مارین از بذر گیاه خارمریم. فصلنامه گیاهان دارویی، ویژه نامه خارمریم، سال چهارم، صفحات 7-12.

ولاگ، ژ. و استودولا، ژ.، ترجمه ساعد زمان، س.(1376) گیاهان دارویی، انتشارات دانشگاه تهران، صفحه 309.

 

 

Alikaridis, F., D. Papadakis, K. Pantelia and T. Kephalas (2000) Flavonolignan  production from Silybum marianum transformed and untransformed root culture. Fitotrapia, 71: 379-384.

Alvarezbarreto, J., S. N. Wallace, D. J. Carrier and E. C. Clausene (2003) Extraction of nutraceuticals from milk thistle. I. Hot water extraction. Applied Biochemistry and Biotechnology, 105: 881-889.

Basile, A., M. Jimenez-Carmona and A. Clifford (1998) Extraction of rosemary by superheated water. Journal of Agricultural and Food Chemistry, 46: 5205-5209.

Benthin B., H. Danz and M. Hamburger (1999) Pressurized liquid extraction of medicinal plants. Journal of Chromatography A, 837: 211-219.

Bosisio, E., C. Benelli and O. Pirola (1992) Effect of the flavonolignans of Silybum marianum L. Gaertn on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes. Pharmacology Research, 25: 147-154.

Bourgand, F., A. Gravot, S. Milesi and E. Gontier (2001) Production of plant secondary metabolites: a historical perspective. Plant Science, 161: 839-851.

Brenda, W.S. (2000) Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiology, 126: 485-493.

Briskin, D.P. (2000) Medicinal plants and phytomedicines. linking plant biochemistry and physiology to human health. Plant Physiology, 124: 507-514.

Cacho, M., M. Moran, P. Corchete and J. Fernandez-Tarrago (1999) Influence of medium composition on the accumulation of flavonolignans in cultured cells of Silybum marianum (L.)Gaertn. Plant Science, 144: 63-68.

 

 

 

Ding, T.M., S.J. Tian Z.X. Zhang, D.Z. Gu, Y.F. Chen, Y.H. Shi and Z.P. Sun (2001) Determination of active component in silymarin by RP-LC and LC/MS. Journal of Phamaceutical and Biochemical Analysis, 26: 155-161.

Duan, L., D. J. Carrier and E. C. Clausen (2004) Silymarin extraction from milk thistle using hot water. Applied Biochemistry and Biotechnology, 114: 559-568.

Hasanloo, T., R. A. Khavari-Nejad, E. Majidi and M. R. Shams- Ardakani (2005) Analysis of flavonolignans in dried fruits of Silybum marianum (L.) Gaertn from Iran. Pakistan Journal of Biological Science, 8: 1778-1782.

Kahol, A., K. Singh, S. Tandon and S. Kumar (2001) Process for isolation of hepaprotective agent silymarin from the seeds of the plant silybum marianum. Indian Patent Number: 06309678.

Katiyar, S. K. (2002) Treatment of silymarin, a plant flavonoid, prevents ultraviolet light- induced immune suppression and oxidative stress in mouse skin. International Journal of Oncology, 21: 1213-1222.

Kren, V., J. Ulrichova, P. Kosina, D. Stevenson, P. Sedmera, V. Prikrylova, P. Halada and V. Simanek (2000) Chemoenzymatic preparation of silybin β- glucoronides and their biological evaluation. Drag Metobolism and Disposition, 28: 1513-1517.

Kubatova A., D. Miller and S. Hawthorne (2001) Selective extraction of oxygenated natural products with subcritical water. 10^th International symposium and exhibit on supercritical fluid chromatography, extraction and processing. August 19-22, 2001. Myrtle Beach, SC, USA. E-05.

Li, W., K. Koike, Y. Asada, T. Yoshikawa and T. Nikaido (2005) Rosmarinic acid production by coleus forskohlii hairy root cultures. Plant Cell, Tissue and Organ Cultur, 80: 151-155.

Minakhmetov, R. A., L. A. Onuchak, V. A. Kurkin, E. V. Avdeeva and A. V. Volotsueva (2001) Analysis of flavonoids in silybum marianum fruit by HPLC. Chemistry of Natural Compounds, 3: 318-321.

Narayana, K.R., R. Sripal, M. R. Chaluvadi and D. R. Krishan, D.R. (2001) Bioflavonoids classification, pharmacological, biochemical effects and therapeutic potential. Indian Journal of Pharmacology, 33:2-6.

Quaglia, M.G., E. Bossu, E. Donati, G. Mazzanti and A. Brandt (1999) Determination of silymarin in the extract from the dried Silybum marianum fruits by high performance liquid chromatography and capillary electrophoresis. Journal of Pharmaceutical and Biomedical Analysis, 19: 435-442.

Samuelsson, G. (1999) Drugs of natural origin. 4th revised edition. Swedish pharmaceutical press, Stockholm, Sweden. 226-233.

Sánchez-Sampedro, A., H.K. Kim, H.Y. Choi, R. Verpoorte and P. Corchete (2007) Metabolomic alterations in elicitor treated Silybum marianum suspension cultures monitored by nuclear magnetic resonance spectroscopy. J Biotechnol., 130: 133-142.

Schnfeld, J.V., B. Weisbrod and M. K. Muller (1997) Silibinin, a plant extract with antioxidant and membrane stabilizing properties protects exocrine pancreas from cyclosporine A toxicity. Cellular and Molecular Life Sciences, 53:917-920.

Sonnenbichler, J., F. Scaleram, I. Sonnenbichler and R. Weyhenmeyer (1999) Stimulatory effects of silibinin and silichristin form the Milk thistle silybum marianum on kidney cells. The Journal of Pharmacology and Experimental Therapeutics, 290: 1375-1383.

Titel, G. and H. Wagner (1977) High-performance liquid chromatographic seperation of silymarins and their determination in a raw extract of silybum marianum. Journal of Chromatography, 135: 499-501.

Venkataramanan, R. (2000) Milke thistle, a herbal supplement, decreases the activity of CYP3A4 and uridine diphosphoglucuronosyl transferase in human hepatocyte cultures. Drug Metabolism and Dispositions, 28: 1270-1273.

Wagner, H., P. Diesel and M. Seites (1974) The chemistry and analysis of silymarin from Silybum marianum. Arzheimittle Forschung, 24: 466-71.

Wagner, H., L. Horhammer and M. Seitz (1968) Chemical evaluation of a silymarin-contaning   flavonoid concentrate from Silybum marianum. Arzheimittel Forschung, 18: 696-8.

Wallace, S. N., D. J. Carrier and E. C. Clausen (2003) Extraction of nutraceuticals from milk thistle: part II. Extraction with organic solvents. Applied Biochemistry Biotechnology, 105: 891-903.

Wallace, S. N., D. J. Carrier and E. C. Clausen (2005) Batch solvent extraction of flavanolignans from milk thistle (Silybum marianum L. Gaertn). Phytochemical Analysis, 16: 7-16

حسنلو، ط.، خاوری نژاد، ر.ع.، مجیدی، ا. و ضیایی س. ع. (1383) مطالعه و تعیین فلاونولیگنان ها در میوه‌های گیاه خارمریم جمع آوری شده از نقاط مختلف ایران به روش‌های اسپکتروفتومتری TLC و HPLC. فصلنامه گیاهان دارویی، ویژه نامه خارمریم، سال چهارم، صفحات 25-32.

ضیایی، س. ع.، حسینی، ح. ف.، رجبیان، ط.، پور حسینی، ل.، نقدی بادی، ح. و رضازاده، ش. (1383) بررسی اثر حلال­های مختلف در  استخراج  سیلی­مارین از بذر گیاه خارمریم. فصلنامه گیاهان دارویی، ویژه نامه خارمریم، سال چهارم، صفحات 7-12.

ولاگ، ژ. و استودولا، ژ.، ترجمه ساعد زمان، س.(1376) گیاهان دارویی، انتشارات دانشگاه تهران، صفحه 309.

 

 

Alikaridis, F., D. Papadakis, K. Pantelia and T. Kephalas (2000) Flavonolignan  production from Silybum marianum transformed and untransformed root culture. Fitotrapia, 71: 379-384.

Alvarezbarreto, J., S. N. Wallace, D. J. Carrier and E. C. Clausene (2003) Extraction of nutraceuticals from milk thistle. I. Hot water extraction. Applied Biochemistry and Biotechnology, 105: 881-889.

Basile, A., M. Jimenez-Carmona and A. Clifford (1998) Extraction of rosemary by superheated water. Journal of Agricultural and Food Chemistry, 46: 5205-5209.

Benthin B., H. Danz and M. Hamburger (1999) Pressurized liquid extraction of medicinal plants. Journal of Chromatography A, 837: 211-219.

Bosisio, E., C. Benelli and O. Pirola (1992) Effect of the flavonolignans of Silybum marianum L. Gaertn on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes. Pharmacology Research, 25: 147-154.

Bourgand, F., A. Gravot, S. Milesi and E. Gontier (2001) Production of plant secondary metabolites: a historical perspective. Plant Science, 161: 839-851.

Brenda, W.S. (2000) Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiology, 126: 485-493.

Briskin, D.P. (2000) Medicinal plants and phytomedicines. linking plant biochemistry and physiology to human health. Plant Physiology, 124: 507-514.

Cacho, M., M. Moran, P. Corchete and J. Fernandez-Tarrago (1999) Influence of medium composition on the accumulation of flavonolignans in cultured cells of Silybum marianum (L.)Gaertn. Plant Science, 144: 63-68.

 

 

 

Ding, T.M., S.J. Tian Z.X. Zhang, D.Z. Gu, Y.F. Chen, Y.H. Shi and Z.P. Sun (2001) Determination of active component in silymarin by RP-LC and LC/MS. Journal of Phamaceutical and Biochemical Analysis, 26: 155-161.

Duan, L., D. J. Carrier and E. C. Clausen (2004) Silymarin extraction from milk thistle using hot water. Applied Biochemistry and Biotechnology, 114: 559-568.

Hasanloo, T., R. A. Khavari-Nejad, E. Majidi and M. R. Shams- Ardakani (2005) Analysis of flavonolignans in dried fruits of Silybum marianum (L.) Gaertn from Iran. Pakistan Journal of Biological Science, 8: 1778-1782.

Kahol, A., K. Singh, S. Tandon and S. Kumar (2001) Process for isolation of hepaprotective agent silymarin from the seeds of the plant silybum marianum. Indian Patent Number: 06309678.

Katiyar, S. K. (2002) Treatment of silymarin, a plant flavonoid, prevents ultraviolet light- induced immune suppression and oxidative stress in mouse skin. International Journal of Oncology, 21: 1213-1222.

Kren, V., J. Ulrichova, P. Kosina, D. Stevenson, P. Sedmera, V. Prikrylova, P. Halada and V. Simanek (2000) Chemoenzymatic preparation of silybin β- glucoronides and their biological evaluation. Drag Metobolism and Disposition, 28: 1513-1517.

Kubatova A., D. Miller and S. Hawthorne (2001) Selective extraction of oxygenated natural products with subcritical water. 10^th International symposium and exhibit on supercritical fluid chromatography, extraction and processing. August 19-22, 2001. Myrtle Beach, SC, USA. E-05.

Li, W., K. Koike, Y. Asada, T. Yoshikawa and T. Nikaido (2005) Rosmarinic acid production by coleus forskohlii hairy root cultures. Plant Cell, Tissue and Organ Cultur, 80: 151-155.

Minakhmetov, R. A., L. A. Onuchak, V. A. Kurkin, E. V. Avdeeva and A. V. Volotsueva (2001) Analysis of flavonoids in silybum marianum fruit by HPLC. Chemistry of Natural Compounds, 3: 318-321.

Narayana, K.R., R. Sripal, M. R. Chaluvadi and D. R. Krishan, D.R. (2001) Bioflavonoids classification, pharmacological, biochemical effects and therapeutic potential. Indian Journal of Pharmacology, 33:2-6.

Quaglia, M.G., E. Bossu, E. Donati, G. Mazzanti and A. Brandt (1999) Determination of silymarin in the extract from the dried Silybum marianum fruits by high performance liquid chromatography and capillary electrophoresis. Journal of Pharmaceutical and Biomedical Analysis, 19: 435-442.

Samuelsson, G. (1999) Drugs of natural origin. 4th revised edition. Swedish pharmaceutical press, Stockholm, Sweden. 226-233.

Sánchez-Sampedro, A., H.K. Kim, H.Y. Choi, R. Verpoorte and P. Corchete (2007) Metabolomic alterations in elicitor treated Silybum marianum suspension cultures monitored by nuclear magnetic resonance spectroscopy. J Biotechnol., 130: 133-142.

Schnfeld, J.V., B. Weisbrod and M. K. Muller (1997) Silibinin, a plant extract with antioxidant and membrane stabilizing properties protects exocrine pancreas from cyclosporine A toxicity. Cellular and Molecular Life Sciences, 53:917-920.

Sonnenbichler, J., F. Scaleram, I. Sonnenbichler and R. Weyhenmeyer (1999) Stimulatory effects of silibinin and silichristin form the Milk thistle silybum marianum on kidney cells. The Journal of Pharmacology and Experimental Therapeutics, 290: 1375-1383.

Titel, G. and H. Wagner (1977) High-performance liquid chromatographic seperation of silymarins and their determination in a raw extract of silybum marianum. Journal of Chromatography, 135: 499-501.

Venkataramanan, R. (2000) Milke thistle, a herbal supplement, decreases the activity of CYP3A4 and uridine diphosphoglucuronosyl transferase in human hepatocyte cultures. Drug Metabolism and Dispositions, 28: 1270-1273.

Wagner, H., P. Diesel and M. Seites (1974) The chemistry and analysis of silymarin from Silybum marianum. Arzheimittle Forschung, 24: 466-71.

Wagner, H., L. Horhammer and M. Seitz (1968) Chemical evaluation of a silymarin-contaning   flavonoid concentrate from Silybum marianum. Arzheimittel Forschung, 18: 696-8.

Wallace, S. N., D. J. Carrier and E. C. Clausen (2003) Extraction of nutraceuticals from milk thistle: part II. Extraction with organic solvents. Applied Biochemistry Biotechnology, 105: 891-903.

Wallace, S. N., D. J. Carrier and E. C. Clausen (2005) Batch solvent extraction of flavanolignans from milk thistle (Silybum marianum L. Gaertn). Phytochemical Analysis, 16: 7-16

 

حسنلو، ط.، خاوری نژاد، ر.ع.، مجیدی، ا. و ضیایی س. ع. (1383) مطالعه و تعیین فلاونولیگنان ها در میوه‌های گیاه خارمریم جمع آوری شده از نقاط مختلف ایران به روش‌های اسپکتروفتومتری TLC و HPLC. فصلنامه گیاهان دارویی، ویژه نامه خارمریم، سال چهارم، صفحات 25-32.

ضیایی، س. ع.، حسینی، ح. ف.، رجبیان، ط.، پور حسینی، ل.، نقدی بادی، ح. و رضازاده، ش. (1383) بررسی اثر حلال­های مختلف در  استخراج  سیلی­مارین از بذر گیاه خارمریم. فصلنامه گیاهان دارویی، ویژه نامه خارمریم، سال چهارم، صفحات 7-12.

ولاگ، ژ. و استودولا، ژ.، ترجمه ساعد زمان، س.(1376) گیاهان دارویی، انتشارات دانشگاه تهران، صفحه 309.

 

 

Alikaridis, F., D. Papadakis, K. Pantelia and T. Kephalas (2000) Flavonolignan  production from Silybum marianum transformed and untransformed root culture. Fitotrapia, 71: 379-384.

Alvarezbarreto, J., S. N. Wallace, D. J. Carrier and E. C. Clausene (2003) Extraction of nutraceuticals from milk thistle. I. Hot water extraction. Applied Biochemistry and Biotechnology, 105: 881-889.

Basile, A., M. Jimenez-Carmona and A. Clifford (1998) Extraction of rosemary by superheated water. Journal of Agricultural and Food Chemistry, 46: 5205-5209.

Benthin B., H. Danz and M. Hamburger (1999) Pressurized liquid extraction of medicinal plants. Journal of Chromatography A, 837: 211-219.

Bosisio, E., C. Benelli and O. Pirola (1992) Effect of the flavonolignans of Silybum marianum L. Gaertn on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes. Pharmacology Research, 25: 147-154.

Bourgand, F., A. Gravot, S. Milesi and E. Gontier (2001) Production of plant secondary metabolites: a historical perspective. Plant Science, 161: 839-851.

Brenda, W.S. (2000) Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiology, 126: 485-493.

Briskin, D.P. (2000) Medicinal plants and phytomedicines. linking plant biochemistry and physiology to human health. Plant Physiology, 124: 507-514.

Cacho, M., M. Moran, P. Corchete and J. Fernandez-Tarrago (1999) Influence of medium composition on the accumulation of flavonolignans in cultured cells of Silybum marianum (L.)Gaertn. Plant Science, 144: 63-68.

 

 

 

Ding, T.M., S.J. Tian Z.X. Zhang, D.Z. Gu, Y.F. Chen, Y.H. Shi and Z.P. Sun (2001) Determination of active component in silymarin by RP-LC and LC/MS. Journal of Phamaceutical and Biochemical Analysis, 26: 155-161.

Duan, L., D. J. Carrier and E. C. Clausen (2004) Silymarin extraction from milk thistle using hot water. Applied Biochemistry and Biotechnology, 114: 559-568.

Hasanloo, T., R. A. Khavari-Nejad, E. Majidi and M. R. Shams- Ardakani (2005) Analysis of flavonolignans in dried fruits of Silybum marianum (L.) Gaertn from Iran. Pakistan Journal of Biological Science, 8: 1778-1782.

Kahol, A., K. Singh, S. Tandon and S. Kumar (2001) Process for isolation of hepaprotective agent silymarin from the seeds of the plant silybum marianum. Indian Patent Number: 06309678.

Katiyar, S. K. (2002) Treatment of silymarin, a plant flavonoid, prevents ultraviolet light- induced immune suppression and oxidative stress in mouse skin. International Journal of Oncology, 21: 1213-1222.

Kren, V., J. Ulrichova, P. Kosina, D. Stevenson, P. Sedmera, V. Prikrylova, P. Halada and V. Simanek (2000) Chemoenzymatic preparation of silybin β- glucoronides and their biological evaluation. Drag Metobolism and Disposition, 28: 1513-1517.

Kubatova A., D. Miller and S. Hawthorne (2001) Selective extraction of oxygenated natural products with subcritical water. 10^th International symposium and exhibit on supercritical fluid chromatography, extraction and processing. August 19-22, 2001. Myrtle Beach, SC, USA. E-05.

Li, W., K. Koike, Y. Asada, T. Yoshikawa and T. Nikaido (2005) Rosmarinic acid production by coleus forskohlii hairy root cultures. Plant Cell, Tissue and Organ Cultur, 80: 151-155.

Minakhmetov, R. A., L. A. Onuchak, V. A. Kurkin, E. V. Avdeeva and A. V. Volotsueva (2001) Analysis of flavonoids in silybum marianum fruit by HPLC. Chemistry of Natural Compounds, 3: 318-321.

Narayana, K.R., R. Sripal, M. R. Chaluvadi and D. R. Krishan, D.R. (2001) Bioflavonoids classification, pharmacological, biochemical effects and therapeutic potential. Indian Journal of Pharmacology, 33:2-6.

Quaglia, M.G., E. Bossu, E. Donati, G. Mazzanti and A. Brandt (1999) Determination of silymarin in the extract from the dried Silybum marianum fruits by high performance liquid chromatography and capillary electrophoresis. Journal of Pharmaceutical and Biomedical Analysis, 19: 435-442.

Samuelsson, G. (1999) Drugs of natural origin. 4th revised edition. Swedish pharmaceutical press, Stockholm, Sweden. 226-233.

Sánchez-Sampedro, A., H.K. Kim, H.Y. Choi, R. Verpoorte and P. Corchete (2007) Metabolomic alterations in elicitor treated Silybum marianum suspension cultures monitored by nuclear magnetic resonance spectroscopy. J Biotechnol., 130: 133-142.

Schnfeld, J.V., B. Weisbrod and M. K. Muller (1997) Silibinin, a plant extract with antioxidant and membrane stabilizing properties protects exocrine pancreas from cyclosporine A toxicity. Cellular and Molecular Life Sciences, 53:917-920.

Sonnenbichler, J., F. Scaleram, I. Sonnenbichler and R. Weyhenmeyer (1999) Stimulatory effects of silibinin and silichristin form the Milk thistle silybum marianum on kidney cells. The Journal of Pharmacology and Experimental Therapeutics, 290: 1375-1383.

Titel, G. and H. Wagner (1977) High-performance liquid chromatographic seperation of silymarins and their determination in a raw extract of silybum marianum. Journal of Chromatography, 135: 499-501.

Venkataramanan, R. (2000) Milke thistle, a herbal supplement, decreases the activity of CYP3A4 and uridine diphosphoglucuronosyl transferase in human hepatocyte cultures. Drug Metabolism and Dispositions, 28: 1270-1273.

Wagner, H., P. Diesel and M. Seites (1974) The chemistry and analysis of silymarin from Silybum marianum. Arzheimittle Forschung, 24: 466-71.

Wagner, H., L. Horhammer and M. Seitz (1968) Chemical evaluation of a silymarin-contaning   flavonoid concentrate from Silybum marianum. Arzheimittel Forschung, 18: 696-8.

Wallace, S. N., D. J. Carrier and E. C. Clausen (2003) Extraction of nutraceuticals from milk thistle: part II. Extraction with organic solvents. Applied Biochemistry Biotechnology, 105: 891-903.

Wallace, S. N., D. J. Carrier and E. C. Clausen (2005) Batch solvent extraction of flavanolignans from milk thistle (Silybum marianum L. Gaertn). Phytochemical Analysis, 16: 7-16