• Natural Product Sciences
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• 제9권4호
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• pp.235-240
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• 2003

Tectorigenin has an apoptosis-inducing ability and immunosuppressive activity. We investigated the effect of tectorigenin on Phase I and II enzyme activities to elucidate the pharmacological action of the immunosuppressive tectorigenin in the diabetic rat. This compound was obtained from the hydrolysis of tetoridin isolated from the flower of Pueraria thumbergiana (Leguminosae). This crude drug (Puerariae Flos) has been used as a therapeutic for diabetes mellitus in traditional Korean medicine. Tecotrigenin inhibited the formation of malondialdehyde (MDA) and hydroxy radicals in serum and liver but promoted superoxide dismutase (SOD) activity. Low MDA contents and low xanthine oxidase and aldehyde oxidase activities were observed in the tectorigenin-treated rats, suggesting that such Phase I enzyme activities are the major source of lipid peroxidation. However, tectorigenin increased Phase II enzyme activities such as SOD, glutathione peroxidase and catalase, suggesting the activation of free radical-scavenging enzymes. The activities of tectorigenin were comparable to those of glibenclamide, which was employed as a positive control. These results suggest that tectorigenin may share some biological properties with glibenclamide in insulin-dependent-diabetes mellitus (IDDM).

• 대한화장품학회지
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• 제45권1호
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• pp.49-56
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• 2019

분갈(Pueraria thomsonii Benth)은 전통적으로 중국 의학에서 발열, 급성 이질, 설사, 당뇨병 및 심혈관 질환 치료를 위한 약재로 사용되어 왔다. 이러한 분갈의 꽃인 분갈화의 피부 효능은 아직까지 밝혀진 바 없어, 본 연구에서는 멜라닌세포인 B16F1 세포주와 섬유아세포인 HS68 세포주를 이용하여 분갈화의 피부효능을 검증하고자 하였다. 분갈화의 에탄올 추출물이 멜라닌세포의 멜라닌 합성을 농도 의존적으로 감소시킴을 확인하고, 분갈화 추출물의 효능 성분을 추적하고자 high performance liquid chromatography (HPLC)를 이용하여 분석하였다. 그 결과, 분갈화에 함유된 이소플라본류 화합물인 tectorigenin, tectoridin, tectorigenin 7-O-xylosylglucoside 3종 성분을 확인하였다. 3종 성분 모두 독성을 보이지 않는 농도에서 멜라닌세포의 멜라닌 생합성을 농도 의존적으로 감소시켰으며, 이러한 멜라닌 생합성 감소는 tyrosinase와 microphthalmia-associated transcription factor (MITF) 유전자 발현을 감소시키는 것에 기인함을 확인하였다. 멜라닌 합성저해의 또 다른 기전을 확인하기 위하여, 섬유아세포에서 유래되는 멜라닌 합성억제 인자인 DKK-1의 발현에 대한 영향을 측정한 결과, 분갈화 추출물, tectoridin, tectorigenin 7-O-xylosylglucoside는 DKK-1의 발현을 농도 의존적으로 감소시킨 반면, tectorigenin은 DKK-1의 발현을 농도 의존적으로 증가시키는 것을 확인하였다. 이상의 연구 결과를 바탕으로, 분갈화 성분 중 tectorigenin은 멜라닌세포에서의 멜라닌 합성 억제와 섬유아세포에서의 멜라닌 생성 억제 인자 분비를 촉진하는 효과적인 미백 개선제로 활용할 수 있을 것으로 판단된다.

• Archives of Pharmacal Research
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• 제27권10호
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• pp.1023-1028
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• 2004

A new 12a-dehydrorotenoid 1, 11-dihydroxy-9, 10-methylenedioxy-12a-dehydrorotenoid (1), together with a new isoflavonoid glycoside tectorigenin-7-O-${\beta}$-glucosyl-4'-O-${\beta}$-glucoside (3), were isolated and identified from the rhizomes of I. spuria (Zeal). In addition, 4 known compounds, tectorigenin (2) tectorigenin-7-O-${\beta}$-glucosyl $(1{\leftrightarrow}6)$ glucoside (4), tectoridin (a tectorigenin- 7-O-${\beta}$-glucoside) (5) and tectorigenin-4'-O-${\beta}$-glucoside (6) were isolated and identified for the first time from this plant. The structures of the isolated compounds were determined by spectroscopic methods (UV, IR, $^1H,\;^{13}C$NMR, DEPT, HMQC, NOESY, and HMBC experiments and MS spectrometry) and by comparison with literature data of known compounds. Compounds 2, 4, 5, and 6 are reported for the first time from this plant through the present study.

• Archives of Pharmacal Research
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• 제23권5호
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• pp.461-466
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• 2000

Tectorigenin and kaikasaponin III from the flowers of Pueraria thunbergiana showed potent hypoglycemic and hypolipidemic effects in the streptozotocin-induced diabetic rats. Intraperitoneal administration of these two compounds with 5 and 10 mg/kg, respectively, for seven days to streptozotocin-induced rats significantly reduced the blood glucose, total cholesterol, LDL- and VLDI-cholesterol and triglyceride levels when compared with those of control group. Glycitein in which 5-OH is unlinked and tectoridin (7-O-glycoside of tectorigenin) isolated from the flowers of P. thunbergiana did not improve hyperglycemia and hyperlipidemia. In addition, tectorigenin showed in vitro antioxidant effects on 1,1-diphenyl-B-pirylhydrazyl (DPPH) radical, xanthine-xanthine oxidase superoxide anion radical, and lipid peroxidation in rat microsomes induced by enzymatic and non-enzymatic methods. We further found that tectorigenin and kaikasaponin III protected the Vero cell line(normal monkey kidney) from injury by hydrogen peroxide. From these findings, it seems likely that the antioxidant action of tectorigenin and kaikasaponin III may alleviate the streptozotocin-induced toxicity and contribute to hypoglycemic and hypolipidemic effects.

• 약학회지
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• 제43권6호
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• pp.736-742
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• 1999

Antioxidative and cytoprotective effects of tectorigenin and glycitein isolated from the pueraria thunbergiana and its derivative, genistein, were determined. Among these three compounds, tectorigenin and glycitein bearing 6-methoxyl groups in both isoflavones showed significant free radical scavenging activities on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and xanthine/xanthine oxidase (XOD) generating superoxide anion radical. Tectorigenin only showed a slight inhibitory effect on XOD. We further studied the inhibitory effects of these isoflavones on the lipid peroxidation in rat liver microsomes induced by enzymatic and non-enzymatic methods. Each of them exhibited inhibitory effect on both ascorbic $acid/Fe^{2+}-{\;}and{\;}ADP/NADPH/Fe^{+3}-induced$ lipid peroxidation. Moreover, tectorigenin exhibited the highest protection of hydrogen peroxide damage on HepG2 and Vero cells among the three isoflavones, in the cytoprotective assay. It was suggested that the pattern of antioxidative and cytoprotective effect of isoflavones could be crucially by the aromatic substitution of oxygen-containing groups.

• Archives of Pharmacal Research
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• 제25권3호
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• pp.320-324
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• 2002

The MeOH extract of Pueraria thunbergiana (Leguminosae) flowers and its fractions were subjected to Ames test to test the antimutagenicity. EtOAc fraction (1 mg/plate) decreased the number of revertants of Salmonella typhymurium TA100 by 95% against aflatoxin $B_1{\;}(AFB_1)$. Phytochemical isolation of the EtOAc fraction afforded four isoflavonoids (tectorigenin, glycitein, tectoridin and glycitin) and one saponin (kaikasaponin III). Though the three isoflavonoids other than tectoridin showed significant antimutagenicity, the activity of kaikasaponin III was the most potent. Kaikasaponin III (1 mg/plate) decreased the number of revertants of S. typhymurium TA 100 by 99% against $AFB_1$ but by 75% against N-methyl-N'-nitro-N-nitrosoguanidine (MNNG). Tectorigenin (1 mg/plate) inhibited the $AFB_1$-induced mutagenicity by 90% and MNNG-induced one by 76%. Glycitein and glycitin were less active than tectorigenin and kaikasaponin III. This result suggested that kaikasponin III prevents the metabolic activation of $AFB_1$ and scavenge electrophilic intermediate capable of mutation. The two components with potent activities, tectorigenin and kaikasaonin III, significantly prevented the malondialdehyde formation caused by bromobenzene in the rat.

• Archives of Pharmacal Research
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• 제25권3호
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• pp.306-312
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• 2002

Aldose reductase, the key enzyme of the polyol pathway, is known to play important roles in the diabetic complication. The inhibitors of aldose reductase, therefore, would be potential agents for the prevention of diabetic complications. To evaluate active principles for the inhibition of aldose reductase from the rhizomes of Belamcanda chinensis, twelve phenolic compounds were isolated and tested for their effects on rat lens aldose reductase. As a result, isoflavones such as tectorigenin, irigenin and their glucosides were found to show a strong aldose reductase inhibition. Tectoridin and tectorigenin, exhibited the highest aldose reductase inhibitory potency, their $IC_{50}$ values, being $1.08{\times}10^{-6}{\;}M{\;}and{\;}1.12{\times}10^{-6}{\;}M$, respectively, for DL-glyceraldehyde as a substrate. Both compounds, when administered orally at 100 mg/kg for 10 consecutive days to streptozotocin-induced diabetic rats, caused a significant inhibition of sorbitol accumulation in the tissues such as lens, sciatic nerves and red blood cells. Tectorigenin showed a stronger inhibitory activity than tectoridin. From these results, it is suggested that tectorigenin is attributed to be a promising compound for the prevention and/or treatment of diabetic complications.

• 한국식품영양과학회지
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• 제29권5호
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• pp.935-942
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• 2000

갈화(flower of Pueraria lobata) 분획 및 활성 성분의 급여가 아급성 알코올 중독된 흰쥐에서의 해독에 미치는 영향을 연구할 목적으로, 25% alcohol을 6주간 투여하여 아급성 알코올 중독상태를 유발한 흰쥐를 3주 더 사육하면서 혈액중 지질 함량의 변동, 알코올 대사계 효소의 활성을 비교 검퇀 결과는 다음과 같다. 알코올 단독 급여군은 대조군에 비하여 체중이 감소되었으며, 알코올-갈화 tectorigenin 급여군의 체중증가량은 대조군 수준에는 미치지 못하였으나, 알코올 단독 급여군보다는 유의적인 회복을 나타냈다. 알코올 단독 급여군의 총지방, 중성 지방, 인지질 함량이 대조군에 비하여 중가하엿고, 알코올-갈화 tcctorigcnin 급여군과 알코올-갈화 kaikasapomin III 급여군의 총지방, 주성지방 함량은 대조군 수준에는 미치지 못하였으나, 알코올 단독 급여군에 비하여 유의적으로 회복되었다. 알코올 단독 급여군의 total cholesterol, LDL-cholesterol, VLDL-cholesterol 함량, AI는 대조군에 비하여 증가하였고, 알코올-갈화 tectorigcnin, kaikasaponin III 급여군은 대조군 수준에는 미치지 못했으나, 알코올 단독 급여군에 버해 유의적으로 회복되았다. 알코올 단독 급여군의 HDL-cholcsterol의 함량은 대조군에 비하여 감소하던 것이 알코올-갈화 tectorigenin 급여군과 알코올-갈화 kaikasaponin III 급여군에서는 대조군 수준에서는 미치지 못하나, 알코올 단독 급여군에 비하여 증가하였다. 알코올 급여 시 cytochrome P 450, AH와 AD활성은 대조군에 비하여 증가했으나, 알코올-갈화 tectorigenin 급여군과 알코올-갈화 kaikasaponin III 급여군의 경우 알코올 단독 급여군보다 낮게 나타났다. 알코올 급여시 ADH활성이 증가하였으며 알코올-갈화 tectorigenin 급여군과 알코올-갈화 kaikasponin III 급여군은 알코올 단독 급여군보다 높게 나타났다. MEOS의 활성은 알코올 급여 시 대조군에 비하여 중가를 보였고, 알코올-갈화 tectorigenin 급여군에서는 알코올 단독 급여군보다 유의적인 증가를 나타냈다. Catalase의 활성은 각 군간의 유의적인 차이를 볼 수 없었다. ALDH의 활성은 알코올 단독 급여군은 대조군의 활성에 비하여 감소되었으나, 알코올-갈화 tectorigenin 급여군과 알코올-갈화 kaikasaponin III 급여군에서 알코올 단독 급여군보다 유의적인 활성증가를 보였다. 이상의 결과를 종합해 볼 때 갈화로부터 분리된 tectorigenin과 kaikasaponin III는 아급성 알코올 중독된 흰쥐 간의 free radical 생성계 효소를 억제시켜 알코올로 인한 간손상을 회복시키고, 알코올 대사 효소계에 관여하여 해독작용에 영향을 미침으로써 알코올 해독에 도움을 줄 수 있을 것으로 사료된다.

• Archives of Pharmacal Research
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• 제27권2호
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• pp.184-188
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• 2004

The present study was carried out to clarify whether tectorigenin and tectoridin isolated from the rhizomes of Belamcanda chinensis (Iridaceae) inhibit hepatic damage induced by carbon tetrachloride ($CCl_4$)-intoxication in rats by the experimental methods in vitro and in vivo. Tectorigenin and tectoridin exhibited a significant decrease in serum transaminase activities elevated by hepatic damage induced by $CCl_4$-intoxication in rats, as well as in a lipid peroxidation causing a significant decrease in malondialdehyde (MDA) production by thiobarbituric acid (TBA)-reactant assay. Both compounds also showed strong increase in the antioxidant enzymes such as hepatic cytosolic superoxide dismutase (SOD), catalase and glutathione peroxidase (GSH-px) activities in $CCl_4$-intoxicated rats. These results suggested that tectorigenin and tectoridin isolated from the rhizomes of B. chinensis possess not only the antioxidative, but also the hepatoprotective activities in $CCl_4$ -intoxicated rats.

• Archives of Pharmacal Research
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• 제22권1호
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• pp.18-24
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• 1999

Various flavonoid derivatives were previously reported to possess the inhibitory activity on cyclooxygenase/lipoxygenase. And these properties of flavonoids might contribute to their anti-inflammatory activity in vivo. In this study, several polyhydroxylated/methoxylated flavonoid derivatives such as oroxylin A. wogonin, skullcapflavone II, tectorigenin and iristectorigenin A were isolated from the medicinal plants. these compounds were evaluated fro their inhibitory effects on cyclooxygenase/lipoxygenase from the homogenate of human platelets in vitro. It was found that isoflavones including daidzein and tectorigenin possessed the inhibitory activity on cycloooxygenase, although the potency of inhibition was far less than that of indomethacin. In addition, oroxylin A, baicalein and wogonin inhibited 12-lipoxygenase activity without affecting cyclooxygenase, which suggested that 5,6,7- or 5,7,8-trisubstitutions of A-ring of flavone gave favorable results. The IC50 values of oroxylin A and NDGA against 12-lipoxygenase were found to be 100 and 1.5 uM, respectively.