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Planta Med 2010; 76(16): 1859-1863
DOI: 10.1055/s-0030-1250053
Pharmacology
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Metabolites of Protoberberine Alkaloids in Human Urine following Oral Administration of Coptidis Rhizoma Decoction

Yihui Yang1 , 3 , Ning Kang2 , Hongjun Xia1 , Jun Li1 , Lixia Chen1 , Feng Qiu1
  • 1Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical , University, Shenyang, People's Republic of China
  • 2Department of Biochemistry and Molecular Biology, Shenyang Pharmaceutical University, Shenyang, People's Republic of China
  • 3Department of Medicinal and Natural Medicinal Chemistry, Harbin Medical University, Harbin, People's Republic of China
Further Information

Publication History

received Nov. 21, 2009 revised April 22, 2010

accepted May 23, 2010

Publication Date:
14 June 2010 (online)

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Abstract

Coptidis Rhizoma has been used as a traditional Chinese herbal medicine to treat typhoid, pharyngolaryngitis, diabetes mellitus, gastroenteritis and secretory diarrhea for more than a thousand years in China. However, there is little information on the in vivo chemical constituents of Coptidis Rhizoma following oral administration. In this paper, the alkaloid constituents in urine were studied in humans following oral administration of Coptidis Rhizoma decoction. Using macroporous adsorption resin chromatography, open ODS column chromatography, and preparative high-performance liquid chromatography, twelve protoberberine alkaloid constituents were isolated. Their structures were elucidated by chemical evidence, enzymatic deconjugation and analyses of mass, 1H‐NMR and NOESY spectra. The identified alkaloid constituents include berberine (P1), groenlandicine 3-O-β-D-glucuronide (M1), dehydrocheilanthifoline 2-O-β-D-glucuronide (M2), thalifendine 10-O-β-D-glucuronide (M3), jatrorrhizine 3-O-β-D-glucuronide (M4), columbamine 2-O-β-D-glucuronide (M5), berberrubine 9-O-β-D-glucuronide (M6), jatrorrhizine 3-O-sulfate (M7), demethyleneberberine 2-O-sulfate (M8), dehydrocorydalmine 10-O-sulfate (M9), 3,10-demethylpalmatine 10-O-sulfate (M10) and 2,3,10-trihydroxyberberine 2-O-sulfate (M11). No other parent protoberberine alkaloids from Coptidis Rhizoma except for a trace of berberine were found in the urine. These findings suggested that the protoberberine alkaloids, which were absorbed in vivo following oral administration of Coptidis Rhizoma decoction, were mainly conjugated with glucuronic acid or sulfuric acid to form phase II metabolites directly or after biotransformation to phase I metabolites, and finally excreted in urine.

Key words

Coptidis Rhizoma - protoberberine alkaloids - metabolites - urine - humans

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Feng Qiu

Department of Natural Products Chemistry
School of Traditional Chinese Materia Medica
Shenyang Pharmaceutical University Mail Box 81

No. 103 Road WenHua

110016 Shenyang

People's Republic of China

Phone: + 86 24 23 98 64 63

Fax: + 86 24 23 99 39 94

Email: fengqiu2000@tom.com