Gonzalo R Malca-Garcia1, Daniel Zagal1, James Graham2, Dejan Nikolić1, J Brent Friesen3, David C Lankin4, Shao-Nong Chen4, Guido F Pauli5. 1. UIC/NIH Center for Botanical Dietary Supplements Research, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., Chicago, IL, 60612, USA. 2. Center for Natural Product Technologies (CENAPT), Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., Chicago, IL, 60612, USA. 3. Center for Natural Product Technologies (CENAPT), Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., Chicago, IL, 60612, USA; Physical Sciences Department, Rosary College of Arts and Sciences, Dominican University, River Forest, IL, 60305, USA. 4. UIC/NIH Center for Botanical Dietary Supplements Research, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., Chicago, IL, 60612, USA; Center for Natural Product Technologies (CENAPT), Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., Chicago, IL, 60612, USA. 5. UIC/NIH Center for Botanical Dietary Supplements Research, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., Chicago, IL, 60612, USA; Center for Natural Product Technologies (CENAPT), Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., Chicago, IL, 60612, USA. Electronic address: gfp@uic.edu.
Abstract
ETHNOPHARMACOLOGICAL RELEVANCE: The flowering tops of Trifolium pratense L., popularly known as red clover, are used in ethnic Western and Traditional Chinese medicine, in a variety of preparations, including infusions, decoctions and tinctures. Red clover has been reported to be helpful for treatment of menopausal symptoms, premenstrual syndrome, mastalgia, high cholesterol, and other conditions. AIMS OF THE STUDY: The aims were to compare the chemical dynamics between traditional preparations of infusions, decoctions, and tinctures, as well as to identify the chemical variability over time in a traditional red clover tincture. For this purpose, eight isoflavone aglycones as well as two glucosides, ononin and sissotrin, were used as marker compounds. MATERIALS AND METHODS: Quantitative NMR (qHNMR), LC-MS-MS, and UHPLC-UV methods were used to identify and quantitate the major phenolic compounds found within each extract. RESULTS: Infusions, decoctions and tinctures were shown to produce different chemical profiles. Biochanin A and formononetin were identified and quantified in infusion, decoction, and tinctures of red clover. Both infusion and decoction showed higher concentrations of isoflavonoid glucosides, such as ononin and sissotrin, than 45% ethanolic tinctures. Dynamic chemical variability ("dynamic residual complexity") of the red clover tincture was observed over time (one-month), with biochanin A and formononetin reaching peak concentrations at around six days. CONCLUSIONS: Insight was gained into why different formulation methods (infusions, decoctions, and tinctures) are traditionally used to treat different health conditions. Moreover, the outcomes show that tinctures, taken over a period of time, are dynamic medicinal formulations that allow for time-controlled release of bioactive compounds.
ETHNOPHARMACOLOGICAL RELEVANCE: The flowering tops of Trifolium pratense L., popularly known as red clover, are used in ethnic Western and Traditional Chinese medicine, in a variety of preparations, including infusions, decoctions and tinctures. Red clover has been reported to be helpful for treatment of menopausal symptoms, premenstrual syndrome, mastalgia, high cholesterol, and other conditions. AIMS OF THE STUDY: The aims were to compare the chemical dynamics between traditional preparations of infusions, decoctions, and tinctures, as well as to identify the chemical variability over time in a traditional red clovertincture. For this purpose, eight isoflavone aglycones as well as two glucosides, ononin and sissotrin, were used as marker compounds. MATERIALS AND METHODS: Quantitative NMR (qHNMR), LC-MS-MS, and UHPLC-UV methods were used to identify and quantitate the major phenolic compounds found within each extract. RESULTS: Infusions, decoctions and tinctures were shown to produce different chemical profiles. Biochanin A and formononetin were identified and quantified in infusion, decoction, and tinctures of red clover. Both infusion and decoction showed higher concentrations of isoflavonoid glucosides, such as ononin and sissotrin, than 45% ethanolic tinctures. Dynamic chemical variability ("dynamic residual complexity") of the red clovertincture was observed over time (one-month), with biochanin A and formononetin reaching peak concentrations at around six days. CONCLUSIONS: Insight was gained into why different formulation methods (infusions, decoctions, and tinctures) are traditionally used to treat different health conditions. Moreover, the outcomes show that tinctures, taken over a period of time, are dynamic medicinal formulations that allow for time-controlled release of bioactive compounds.
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