• Journal of Microbiology and Biotechnology
• /
• v.16 no.1
• /
• pp.46-51
• /
• 2006

The inhibitory effects of flavanone derivatives on Helicobacter pylori (HP) growth, infection and VacA toxininduced vacuolation were investigated. Among flavanones tested, ponciretin potently inhibited the growth of HP with a MIC value of 0.01 mg/ml and VacA toxin-induced vacuolation in HeLa cells with $IC_{50}$ value of 0.078 mM. However, other flavanones inhibited neither HP growth nor VacA toxininduced vacuolation. All flavanones tested did not inhibit HP infection to KATO III cells. Ponciretin also inhibited activation of procaspase-3 to caspase-3 in HeLa cell induced by HP VacA toxin, but did not affect Bax and Bcl-2 protein levels. These findings indicate that ponciretin inhibits growth as well as vacuolation by HP VacA toxin, which induces cell death via proteolytic activation of a cascade of caspases.

• YAKHAK HOEJI
• /
• v.38 no.3
• /
• pp.286-292
• /
• 1994

Poncirin and naringin which are the flavanone rhamnoglucoside showed anti-inflammatory activity as the major component of fruit of Poncirus trifoliata. Poncirin was metabolized by intestinal bacteria of human and rats. Among the human intestinal bacteria, Bacteroides JY-6 converted a poncirin to naringin, ponciretin-${\beta}$-D-glucopyranoside, naringenin-${\beta}$-D-glucopyranoside, naringenin and ponciretin and did a naringin to poncirin, ponciretin-${\beta}$-D-glucopyranoside, naringenin-${\beta}$-D-glucopyranoside, naringenin and ponciretin.

• YAKHAK HOEJI
• /
• v.37 no.3
• /
• pp.262-269
• /
• 1993

Poncirin which is one of the flavanone rhamnoglucosides showed anti-inflammatory activity as the major component of fruit of Poncirus trifoliata. Poncirin did not show antiinflammatory effect when it was intraperitoneally administered, but it was very effective when orally administered. Poncirin was not metabolized by blood and liver enzymes but by intestinal bacteria of human and rats. Among the human intestinal bacteria, Streptococcus Y-25 converted poncirin to ponciretin through the poncirenin and Staphylococcus Y-88 converted to ponciretin directly.

• Archives of Pharmacal Research
• /
• v.21 no.1
• /
• pp.17-23
• /
• 1998

Flavonoid glycosides were metabolized to phenolic acids via aglycones by human intestinal microflora producing ${\alpha}$-rhamnosidase, exo-${\beta}$-glucosidase, endo- ${\beta}$-glucosidase and/or ${\beta}$-glucuronidase. Rutin, hesperidin, naringin and poncirin were transformed to their aglycones by the bacteria producing ${\alpha}$-rhamnosidase and ${\beta}$-glucosidase or endo- ${\beta}$-glucosidase, and baicatin, puerarin and daidzin were transformed to their aglycones by the bacteria producing ${\beta}$glucuronidase, C-glycosidase and ${\beta}$-glycosidase, respectively. Anti-platelet activity and cytotoxicity of the metabolites of flavonoid glycosides by human intestinal bacteria were more effective than those of the parental compounds. 3,4-Dihydroxyphenylacetic acid and 4-hydroxyl-phenylacetic acid were more effective than rutin and quercetin on anti-platelet aggregation activity. 2,4,6-Trihydroxybenzaidehyde, quercetin and ponciretin were more effective than rutin and ponciretin on the cytotoxicity for tumor cell lines. We insist that these flavonoid glycosides should be natural prodrugs.

• Journal of Microbiology and Biotechnology
• /
• v.18 no.6
• /
• pp.1109-1114
• /
• 2008

To understand the role of intestinal microflora in the biological effect of functional herbs, which have been used in Korea, Japan, and China as traditional medicines, and suggest new bioactive compounds transformed from herbal constituents, the metabolic activities of the functional herb components (ginsenoside Rb1, crocin, amygdalin, geniposide, puerarin, ginsenoside Re, poncirin, hesperidin, glycyrrhizin, and baicalin) toward their bioactive compounds (compound K, crocetin, benzaldehyde, genipin, daidzein, ginsenoside Rh1, ponciretin, hesperetin, 18b-glycyrrhetic acid, and baicalein) were measured in fecal specimens. The metabolic activities of these components were $882.7{\pm}814.5$, $3,938.1{\pm}2,700.8$, $2,375.5{\pm}913.7$, $1,179.4{\pm}795.7$, $24.6{\pm}10.5$, $11.4{\pm}10.8$, $578.8{\pm}206.1$, $1,150.0{\pm}266.1$, $47.3{\pm}58.6$, and $12,253.0{\pm}6,527.6\;{\mu}mol/h/g$, respectively. No differences were found in the metabolic activities of the tested components between males and females, although these metabolic activities between individuals are extensively different. The metabolites of functional herb components showed more potent cytotoxicity against tumor cells than nonmetabolites. These findings suggest that intestinal microflora may activate the pharmacological effect of herbal food and medicines and must be the biocatalytic converter for the transformation of herbal components to bioactive compounds.

• Korean Journal of Pharmacognosy
• /
• v.51 no.2
• /
• pp.93-99
• /
• 2020

This study was performed to find anti-inflammatory or antitumor compounds from the polar fraction obtained from the extract of Clinopodium chinense var. shibetchense (H. Lev) Koidz (Labiatae). Chromatography of the BuOH fraction yielded two flavonoid glycosides (compounds 1 and 2) and two saponins (compounds 3 and 4). On the basis of spectroscopic data, compounds 1 and 2 were identified to be ponciretin 7-O-α-L-rhamnopyranosyl-(1→6)-α-D-glucopyranoside (neoponcirin) and naringenin 7-O-α-L-rhamnopyranosyl-(1→6)-α-D-glucopyranoside (isonaringin). Compounds 3 and 4 were identified to be 3-O-{β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-fucopyranosyl}-saikogenin F (buddlejasaponin IV) and 3-O-{β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-fucopyranosyl}-21β-hydroxysaikogenin F (clinoposaponin XV). In addition, ursolic acid (5) was isolated and identified from the CHCl₃ fraction. Inducible nitric oxide synthase (iNOS) assay and sulforhodamine B (SRB) assay were performed to lead a potential anti-inflammatory or anti-tumor compounds from C. chinense var. shibetchense. Of the four compounds (1 - 4), compound 3 considerably inhibited cancer cell growth and NO production (IC₅₀s, 5.59 μM in iNOS assay and 6.62 - 14.88 μM in SRB assay).

• Korean Journal of Pharmacognosy
• /
• v.40 no.4
• /
• pp.370-375
• /
• 2009

Overproduction of peroxynitrite ($ONOO^-$) causes a variety of disease such as atherosclerosis, hypercholesterolemia, diabetes mellitus or obesity. Peroxynitrite scavenging activities and HPLC analysis on the five Oriental medicinal drugs belonging to the genus Citrus, Aurantium or Poncirus (Rutaceae family) and HPLC analysis were taken to evaluate flavanone glycosides with peroxynitrite scavenging activity. The $IC_{50}s$ of the five crude drugs were shown as follows: Aurantii nobilis Pericarpium (Jinpi, 18.3 ${\mu}g$/ml), Citrii unshiu Pericarpium (Chungpi, 7.50${\mu}g$/ml), Citrii unshiu Semen (Gyulhaek, >50.0${\mu}g$/ml), Aurantii Fructus (Jigak, 18.3${\mu}g$/ml), and Poncirii Fructus (Jisil, >50.0${\mu}g$/ml) where Korean crude drug's names are noted in the parenthesis. Peroxynitrite scavenging effect of flavanones or their glycosides usually contained in Citrus species were observed as follows: hesperetin (1.89 ${\mu}g$/ml), naringenin (7.77 ${\mu}g$/ml), hesperidin (8.44 ${\mu}g$/ml), poncirin (>50.0 ${\mu}g$/ml)and ponciretin(>50.0 ${\mu}g$/ml). The activities of naringin and poncirin with ${\alpha}$-L-rhamnopyranosyl($1{\rightarrow}2$)-${\beta}$-D-glucopyranosyl moiety were weak. HPLC analytical data revealed that Jinpi (the peels of mature fruits of Citrus unshiu) and Chungpi (the peels of immature fruits of C. unshiu) had high quantities of hesperidin as the value of 142.1${\pm}$0.21 and 104.51${\pm}$1.10 mg/g dried weight, respectively. Poncirin was clearly detected in only Jisil and naringenin and naringin were not observed on the HPLC chromatogram of the five crude drugs.