Abstract
The present study aimed to investigate the metabolism of Entadae Semen by human fecal bacteria to clarify the relationship between its pharmacological activities and intestinal metabolism. Three major components (phaseoloidin, entadamide A-β-d-glucopyranoside and entadamide A) were isolated and identified from Entadae Semen and then incubated with human fecal microflora in vitro to investigate the metabolic processes. The metabolites were analyzed with high-performance liquid chromatography (HPLC). The anti-complement activities of the three components and their metabolites produced by human fecal microflora were evaluated in vitro using a hemolysis assay. Phaseoloidin and entadamide A-β-d-glucopyranoside were metabolized into their respective aglycones during the incubation process, which enhanced their anti-complement effects. These results indicated that the presence of intestinal bacteria likely plays an important role and that the pharmacological effects of Entadae Semen may be dependent on intestinal bacterial metabolism.



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References
Editorial Board of Flora of China of Chinese Academy of Sciences (1988) Flora Republicae Popularis Sinicae. Science Press, Beijing, 40, p 150
Nanjing University of Traditional Chinese Medicine (2006) Dictionary of Chinese Materia Medica. Shanghai Science and Technology Publishing House, Shanghai, p 3563
Zhao ZX, Jin J, Lin CZ, Zhu CC, Liu YM, Lin AH, Liu YX, Zhang L, Luo HF (2011) Two new chalcone glycosides from the stems of Entada phaseoloides. Fitoterapia 82:1102–1105
Makridea SC (1998) Therapeutic inhibition of the complement system. Pharmacol Rev 50:59–87
Chen DF (2011) Isolation and characterization of anti-complementary agents from medicinal plants. Planta Med 77(5):S9
Zhang T, Chen DF (2008) Anticomplementary principles of a Chinese multiherb remedy for the treatment and prevention of SARS. J Ethnopharmacol 117:351–361
Zhu HW, Di HY, Zhang YY, Zhang JW, Chen DF (2009) A protein-bound polysaccharide from the stem bark of Eucommia ulmoides and its anti-complementary effect. Carbohydr Res 344:1319–1324
Xi ZX, Chen WS, Wu ZJ, Wang Y, Zeng PY, Zhao GJ, Li X, Sun LN (2012) Anti-complementary activity of flavonoids from Gnaphalium affine D Don. Food Chem 130:165–170
Ikegami F, Shibasaki I, Ohmiya S, Ruangrungsi N, Murakoshi I (1985) Entadamide A, a new sulphur-containing amide from Entada phaseoloides seeds. Chem Pharm Bull 33:5153–5154
Ikegami F, Sekine T, Duangteraprecha S, Matsushita N, Matsuda N, Ruangrungsi N, Murakoshi I (1989) Entadamide C, a sulphur-containing amide from Entada phaseoloides. Phytochemistry 28:881–882
Dai J, Kardono LBS, Tsauri S, Padmawinata K, Pezzuto JM, Kinghorn AD (1991) Phenylacetic acid derivatives and a thioamide glycoside from Entada phaseoloides. Phytochemistry 30:3749–3752
Xiong H, Xiao E, Zhao YH, Yang GZ, Mei ZN (2010) Sulfur-containing amides from Entada phaseoloides. Acta Pharm 45:624–626
Barua AK, Chakrabarty M, Datta PK, Ray S (1988) Phaseoloidin, a homogentisic acid glucoside from Entada phaseoloides. Phytochemistry 27:3259–3261
Okada Y, Shibata S, Javellan MJA, Kamo O (1987) Entada saponin-III, a saponin isolated from the bark of Entada phaseoloides. Phytochemistry 26:2789–2796
Okada Y, Shibata S, Javellana MJA, Kamo O (1988) Entada saponins (ES) II and IV from the bark of Entada phaseoloides. Chem Pharm Bull 36:1264–1269
Ikegami F, Sekine T, Aburada M, Fujii Y, Komatsu Y, Murakoshi I (1989) Synthesis of entadamide A and entadamide B isolated from Entada phaseoloides and their inhibitory effects on 5-lipoxygenase. Chem Pharm Bull 37:1932–1933
Liu WC, Kugelman M, Wilson RA, Rao KV (1972) A crystalline saponin with anti-tumor activity from Entada phaseoloides. Phytochemistry 11:171–173
Akao T, Hayashi T, Kobashi K (1994) Intestinal bacterial hydrolysis is indispensable to absorption of 18 beta-glycyrrhetic acid after oral administration of glycyrrhizin in rats. J Pharm Pharmacol 46:135–137
Kim DH, Jung EA, Sohng IS, Han JA, Kim TH, Han MJ (1998) Intestinal bacterial metabolism of flavonoids and its relation to some biological activities. Arch Pharm Res 21:17–23
Trinh HT, Jang SY, Han MJ, Kawk HY, Beak NI, Kim DH (2009) Metabolism of wogonoside by human fecal microflora and its anti-pruritic effect. Biomol Ther 17:211–216
Dong YQ, Shi HM, Wang MY, Li XB (2010) A validated LC method for simultaneous determination of three major components in Entada phaseoloides. Chromatographia 71:125–129
Lee JG, Baek SH, Lee YY, Park SY, Park JH (2011) Anti-complementary ginseosides isolated from processed ginseng. Biol Pharm Bull 34:898–900
Klerx JP, Beukelman CJ, Van DH, Willers JM (1983) Microassay for colorimetric estimation of complement activity in guinea pig, human and mouse serum. J Immunol Method 63:215–220
Zuo F, Zhou ZM (2002) Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese Medicine, by human intestinal flora. Biol Pharm Bull 25:558–563
Mcbain AJ, Macfarlane GT (1998) Ecological and physiological studies on large intestinal bacteria in relation to production of hydrolytic and reductive enzymes involved in formation of genotoxic metabolites. J Med Microbiol 47:407–416
Sousa T, Paterson R, Moore V, Carlsson A, Abrahamsson B, Basit AW (2008) The gastrointestinal microbiota as a site for the biotransformation of drugs. Int J Pharm 363:1–25
Johnsen NF, Hausner H, Olsen A, Tetens I, Christensen J, Knudsen KE, Overvad K, Tjønneland A (2004) Intake of whole grains and vegetables determines the plasma enterolactone concentration of Danish women. J Nutr 134:2691–2697
Min BS, Lee SY, Kim JH, Lee JK, Kim TJ, Kim DH, Kim YH, Joung H, Lee HK, Nakamura N, Miyashiro H, Hattori M (2003) Anti-complement activity of constituents from the stem-bark of Juglans mandshurica. Biol Pharm Bull 26:1042–1044
Gyurkovska V, Alipieva K, Maciuk A, Dimitrova P, Ivanovska N, Haas C, Bley T, Georgiev M (2011) Anti-inflammatory activity of Devil’s claw in vitro systems and their active constituents. Food Chem 125:171–178
Xu H, Zhang YY, Zhang JW, Chen DF (2007) Isolation and characterization of an anti-complementary polysaccharide D3-S1 from the roots of Bupleurum smithii. Int Immunopharmacol 7:175–182
Xing SH, Wang MY, Peng Y, Chen DF, Li XB (2014) Simulated gastrointestinal tract metabolism and pharmacological activities of water extract of Scutellaria baicalensis roots. J Ethnopharmacol 152:183–189
Lee DS, Kim YS, Ko CN, Cho KH, Bae HS, Lee KS, Kim JJ, Park EK, Kim DH (2002) Fecal metabolic activities of herbal components to bioactive compounds. Arch Pharm Res 25:165–169
Acknowledgments
This work was financially supported by the National Project in Significant Creation of New Drugs (2012ZX09103201-038) and the National Natural Science Foundation of China (No. 81173551 and No. 81274062).
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Xing, S., Wang, M., Peng, Y. et al. Intestinal bacterial metabolism and anti-complement activities of three major components of the seeds of Entada phaseoloides . J Nat Med 69, 171–177 (2015). https://doi.org/10.1007/s11418-014-0874-4
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DOI: https://doi.org/10.1007/s11418-014-0874-4


