nach oben

Journal of Natural Medicines

Erschienen in:

01.04.2015 | Original Paper

Intestinal bacterial metabolism and anti-complement activities of three major components of the seeds of Entada phaseoloides

verfasst von: Shihua Xing, Mengyue Wang, Ying Peng, Yuqiong Dong, Xiaobo Li

Erschienen in: Journal of Natural Medicines | Ausgabe 2/2015

Einloggen, um Zugang zu erhalten

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.

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 82:1102–1105CrossRefPubMed

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):S9CrossRef

Zhang T, Chen DF (2008) Anticomplementary principles of a Chinese multiherb remedy for the treatment and prevention of SARS. J Ethnopharmacol 117:351–361CrossRefPubMed

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 344:1319–1324CrossRefPubMed

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 130:165–170CrossRef

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 33:5153–5154CrossRef

10.

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 28:881–882CrossRef

11.

Dai J, Kardono LBS, Tsauri S, Padmawinata K, Pezzuto JM, Kinghorn AD (1991) Phenylacetic acid derivatives and a thioamide glycoside from Entada phaseoloides. Phytochemistry 30:3749–3752CrossRef

12.

Xiong H, Xiao E, Zhao YH, Yang GZ, Mei ZN (2010) Sulfur-containing amides from Entada phaseoloides. Acta Pharm 45:624–626

13.

Barua AK, Chakrabarty M, Datta PK, Ray S (1988) Phaseoloidin, a homogentisic acid glucoside from Entada phaseoloides. Phytochemistry 27:3259–3261CrossRef

14.

Okada Y, Shibata S, Javellan MJA, Kamo O (1987) Entada saponin-III, a saponin isolated from the bark of Entada phaseoloides. Phytochemistry 26:2789–2796CrossRef

15.

Okada Y, Shibata S, Javellana MJA, Kamo O (1988) Entada saponins (ES) II and IV from the bark of Entada phaseoloides. Chem Pharm Bull 36:1264–1269CrossRef

16.

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 37:1932–1933CrossRefPubMed

17.

Liu WC, Kugelman M, Wilson RA, Rao KV (1972) A crystalline saponin with anti-tumor activity from Entada phaseoloides. Phytochemistry 11:171–173CrossRef

18.

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 46:135–137CrossRefPubMed

19.

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 21:17–23CrossRefPubMed

20.

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 17:211–216CrossRef

21.

Dong YQ, Shi HM, Wang MY, Li XB (2010) A validated LC method for simultaneous determination of three major components in Entada phaseoloides. Chromatographia 71:125–129CrossRef

22.

Lee JG, Baek SH, Lee YY, Park SY, Park JH (2011) Anti-complementary ginseosides isolated from processed ginseng. Biol Pharm Bull 34:898–900CrossRefPubMed

23.

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 63:215–220CrossRef

24.

Zuo F, Zhou ZM (2002) Metabolism of constituents in Huangqin-Tang, a prescription in traditional Chinese Medicine, by human intestinal flora. Biol Pharm Bull 25:558–563CrossRefPubMed

25.

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 47:407–416CrossRefPubMed

26.

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 363:1–25CrossRefPubMed

27.

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 134:2691–2697PubMed

28.

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 26:1042–1044CrossRefPubMed

29.

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 125:171–178CrossRef

30.

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 7:175–182CrossRefPubMed

31.

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 152:183–189CrossRefPubMed

32.

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 25:165–169CrossRefPubMed

Titel: Intestinal bacterial metabolism and anti-complement activities of three major components of the seeds of Entada phaseoloides
verfasst von: Shihua Xing
Mengyue Wang
Ying Peng
Yuqiong Dong
Xiaobo Li
Publikationsdatum: 01.04.2015
Verlag: Springer Japan
Erschienen in: Journal of Natural Medicines / Ausgabe 2/2015
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-014-0874-4

Live-Webinar: Aktuelle Leitlinien bei Herz-Kreislauf-Erkrankungen

Springer Medizin

Intestinal bacterial metabolism and anti-complement activities of three major components of the seeds of Entada phaseoloides

Abstract

Live-Webinar: Aktuelle Leitlinien bei Herz-Kreislauf-Erkrankungen

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Weitere Artikel der Ausgabe 2/2015

Pharmacokinetic interaction between Kaempferia parviflora extract and sildenafil in rats

The TLR2 agonist in polysaccharide-K is a structurally distinct lipid which acts synergistically with the protein-bound β-glucan

Antidepressant-like effect of essential oil isolated from Toona ciliata Roem. var. yunnanensis

Satureja khuzestanica prevents the development of morphine analgesic tolerance through suppression of spinal glial cell activation in rats

Antinociceptive and anti-inflammatory activity of the siaresinolic acid, a triterpene isolated from the leaves of Sabicea grisea Cham. & Schltdl. var. grisea

Dendrofalconerol A sensitizes anoikis and inhibits migration in lung cancer cells