인삼의 항산화 활성성분에 관한 연구 ( Ⅴ ) Maltol 과 Phenolic acid 류의 항산화 활성의 메카니즘

한병훈,박명환,한용남 ( Byung Hoon Han,Myung Hwan Park,Yong Nam Han ) 생화학분자생물학회 1985 BMB Reports Vol.18 No.4

The effects of maltol and phenolic acids on lipid peroxidation of liver homogenate were studied. Gallic acid and protocatechuic acid showed more potent inhibitory effect on lipid peroxidation on in vitro system than maltol and other phenolic acids tested. However, when they were administered orally maltol was more effective than gallic acid. Acceleration of the lipid peroxidation by ferric ion was completely suppressed when the liver homogenate was treated by ferric ion in the presence of two moles of maltol. The molar ratio of maltol to ferric ion in the chelate was determined as being two to one by the dilution and continuous variation method. Based on the results, we are proposing one plausible mechainism for the antioxidant activity of maltol that maltol will deprive ferric ion by forming chelate from the initiating complex of microsomal NADPH dependent peroxide generating system.

Stimulating Effect of Panax Saponins on the $C^{14}$-Leucine Incorporation

한병훈,김종현,한용남,Han, Byung-Hoon,Kim, Chong-Hyun,Han, Yong-Nam 생화학분자생물학회 1973 한국생화학회지 Vol.6 No.2

인삼에서 분리한 Panax Saponin A (protopanaxatriol 계)가 지효성 및 지속성의 anti-inflammatory activity를 나타내는 것은 이마 보고한 바 있다. 이 성분은 mouse의 간 및 혈청에서$C^{14}$-leucine의 동화를 촉진하였고 이 효과를 경시적으로 추구한 결 과 anti-inflammatory activity에 대한 경시적인 실험결과와 동일한 경향을 나타내었다. Maximum incorporation을 일으키는 시점 (투여후 4시간)에서 PSA (1~2 mg/mouse)는 $C^{14}$-leucine의 incorporation을 41 또는 61% 촉진하였고 이 효과는 부신피질 호르몬의 개입이 없이 일어난 것으로 밝혀졌다. Delayed and long-lasting characteristics of stimulating effect of Panax Saponin A, one of protopanaxatriol diglucoside of Korean ginseng, on the incorporation of labeled amino acid into liver and serum protein of mouse appear to be correlated with characteristics of anti-inflammatory activity of the substance. Intraperitoneal administration of PSA (1~2 mg/mouse) enhanced the incorporation rate of labeled amino acid into protein by 41~61% over that of control. At the time of maximum incorporation, The stimulating effect was proved not to be correlated with the intervention of corticak hormone.

韓國人蔘의 抗酸化 活性 成分에 관한 硏究(IV) 抗酸化 活性 成分의 抗疲勞 效果

한병훈,박명환,한용남,신상철,Han, Byung-Hoon,Park, Myung-Hwan,Han, Yong-Nam,Shin, Sang-Chul 대한약학회 1984 약학회지 Vol.28 No.4

Active principles for the anti-fatigue activity of Panax ginseng were studied in mice using the swimming performance method. Ginseng water extract maximized the prolongation of swimming time 18 hours after administration. The potencies of anti-fatigue activities were found as in the order of ether soluble fraction and butanol soluble fraction as those of antioxidant activities previously determined. The anti-oxidant components, maltol, salicylic acid and vanillic acid isolated from the ether soluble fraction of Panax ginseng strongly exhibited the antifatigue activities, where as highly purified crystalline ginsenoside $4Rb_1$, Re and $4Rg_1$ did not.

인삼성분 Panax Saponin A 가 흰쥐의 단백합성에 미치는 촉진효과

한병훈,한용남,김종현 ( Byung Hoon Han,Chong Hyun Kim,Yong Nam Han ) 생화학분자생물학회 1973 BMB Reports Vol.6 No.2

Delayed and long-lasting characteristics of stimulating effect of Panax Saponin A, one of protopanaxatriol diglucoside of Korean ginseng, on the incorporation of labeled amino acid into liver and serum protein of mouse appear to be correlated with characteristics of anti-inflammatory activity of the substance. Intraperitoneal administration of PSA (1∼2 ㎎/mouse) enhanced the incorporation rate of labeled amino acid into protein by 41∼61 % over that of control. At the time of maximum incorporation, The stimulating effect was proved not to be correlated with the intervention of cortical hormone.

인삼의 채취 시기에 따른 함유 성분의 함량 변화

한병훈,우린근,우원식 ( Byung Hoon Han,Lin Keun Woo,Won Sick Woo ) 생화학분자생물학회 1975 BMB Reports Vol.8 No.2

The seasonal variations in the contents of ginseng components were analyzed with the samples harvested from April to October. The contents of soluble components such as sugars, amino acids, terpenoid and total methanol extract, increased gradually from April to July and remained almost constant from July to October. Therefore the quality of ginseng harvested at July will not be expected to be significantly different with that of October.

트리테르페노이드의 코르티코이드 유사활성물질에 관한 연구(II) 11-옥소올레아놀산 및 유도체의 합성과 그 항염증 활성

한병훈,조명선,한용남,박명환,Han, Byung-Hoon,KimCho, Myung-Sun,Han, Yong-Nam,Park, Myung-Hwan 생화학분자생물학회 1984 한국생화학회지 Vol.17 No.1

11-oxo-olenolic acid [I] 및 유도체를 합성하고 이 화합물들의 corticoid-$5{\beta}$-reductase 저해활성과 항염증 활성을 연구하였다. [I]을 $CH_2N_2$로 메칠화하여 11-oxo-oleanolic acid methylester [II] $C_{31}H_{48}O_4$, mp $196{\sim}198^{\circ}$를 얻었고, oleanolic acid를 $CrO_3$-pyridine으로 산화하여 3-oxo-oleanolic acid [III] $C_{30}H_{46}O_3$, $198{\sim}202^{\circ}$를 얻고 [III]을 다시 $CrO_3$-초산으로 산화하여 3, 11-dioxo-olenolic acid [IV] $C_{30}H_{44}O_4$, mp $268{\sim}270^{\circ}$, UV (${\lambda}max$) 252nm와 부산물로 3, 11-dioxo-oleanolic acid lactone [V] $C_{30}H_{44}O_4$, mp $265{\sim}267^{\circ}$를 얻었다. [IV]는 [I]에 비하여 corticoid-$5{\beta}$-reductase를 강력히 저해하며 $K_i$값은 [IV]가 $4.2{\times}10^{-4}M$, [I]이 $4.6{\times}10^{-4}M$로 측정되었다. 이 화합물의 항염증 작용을 흰쥐의 카라게닌 유발부종시험법으로 측정한 결과 30mg/kg.s.c. 용량에서 hydrocortisone이 66% 부종을 억제한데 비하여 [I]은 63%, [II]는 78% [IV]는 70%, [V]는 66% 억제하였다. 이상의 연구결과로부터 구조와 활성의 관계를 고찰할 때 올레아놀산의 탄소 11 및 12 위치의 $\alpha,\beta$-unsaturated ketone 구조가 코르티코이드 유사활성에 필수적이며 탄소3위치의 수산기 보다 케톤기가 더 큰활성을 나타나게 하고 C 및 D 환의 락톤 형성에 의한 구조변화는 이 활성증가를 감소시키고 있다. 가장 강한 활성을 나타낸 [II]의 경우는 소수성의 증가에 기인된 것으로 추정된다. The effect of 11-oxo-oleanlic acid [I] and its derivatives on carrageenin-induced edema in rat kind paw was investigated. The following derivatives were synthesized ; 11-oxo-oleanolic acid methylester [II] $C_{31}H_{48}O_4$ mp $196-198^{\circ}$ was derived from [I] by methylation with $CH_2N_2$. 3-Oxo-oleanolic acid [III] $C_{30}H_{46}O_3$, mP $198-202^{\circ}$ was obtained from oleanolic acid by $CrO_3$-pyridine oxidation. Oxidation of [III] by $CrO_3$-HAc produced 3, 11-dioxooleanolic acid [IV] $C_{30}H_{44}O_4$, mp $268-270^{\circ}$ VU ($\lambda$ max) 252 nm and 3, 11-dioxo-oleanolic acid lactone [V] $C_{30}H_{44}O_4$, mp $265-267^{\circ}$ as a by-product. [IV] showed strong competitive inhibition against corticoid-$5{\beta}$-reductase, $K_i=4.2{\times}10^{-4}M$, compared to $4.6{\times}10^{-4}M$ of [I]. The anti-inflammatory activities of 11-oxo-oleanolic acid derivatives were evaluated by rat kind paw carrageenin edema test after s.c, injection with 30mg/kg doses. [I], [II], [IV] and [V] suppressed significantly the edema volumes by 63, 78, 70 and 66%, respectively, compared to 66% of hydrocortisone. The above results suggest that the replacement of OH group in $C_3$ position by ketone group increased the corticomimetic activity, but that the change on the steric structure in C and D rings by lactone formation reduced the activity increase. [II] showed the most powerful activities probably due to increased lipophilicity.

생약의 물 추출물에 대한 혈소판 활성화인자 수용체 결합 저해활성 검색

한병훈,양현옥,김용철,한용남,Han, Byung-Hoon,Yang, Hyun-Ok,Kim, Yong-Chul,Han, Yong-Nam 대한약학회 1994 약학회지 Vol.38 No.4

Hot aqueous extracts of 130 herbal medicines were screened for platelet activating factor (PAE) receptor binding antagonistic activity using rabbit platelet. The results suggested that 4 medicinal plants including Biota orientalis are potential sources of PAF antagonists.

Studies on the Antioxidant Components of Korean Ginseng [I]

한병훈,박명환,우린근,우원식,한용남,Han, Byung-Hoon,Park, Myung-Hwan,Woo, Lin-Keun,Woo, Won-Sick,Han, Yong-Nam 생화학분자생물학회 1979 한국생화학회지 Vol.12 No.1

한국인삼의 노화방지 효과를 입증하는 의도에서 인삼의 항산화활성을 다루었다. 인삼 또는 그 유효성분을 추출하여 마우스에 투여하면 알코홀 투여로 인하여 상승되는 지질 과산화물의 함량을 감소시켜주었으며 그 유효성분의 화학구조를 결정한 결과 3-hydroxy-2-methyl-$\gamma$-Pyrone (maltol)임을 밝혔다. This paper is concerned with the studies on the effective components possessing antioxidant activity, with a view to demonstrate the anti-aging activity of Korean ginseng. Feeding the extract of Korean ginseng or its effective component to mice inhibited strongly the lipid peroxidation induced by ethanol intoxication. From the extract of Korean red ginseng, one effective component, Compound A, mp. $143^{\circ}$, $C_6H_6O_3$, was isolated by chromatographic purification and its chemical structure was determined as 3-hydroxy-2-methyl-$\gamma$-pyrone (maltol).

인삼의 항산화활성 성분에 관한 연구 ( 1 )

한병훈,박명환,우린근,우원식,한용남 ( Byung Hoon Han,Myung Hwan Park,Lin Keun Woo,Won Sick Woo,Yong Nam Han ) 생화학분자생물학회 1979 BMB Reports Vol.12 No.1

This paper is concerned with the studies on the effective components possessing antioxidant activity, with a view to demonstrate the anti-aging activity of Korean ginseng. Feeding the extract of Korean ginseng or its effective component to mice inhibited strongly the lipid peroxidaiion induced by ethanol intoxication. From the; extract of Korean red ginseng, one effective component, Compound A, mp. 143^0 C_6H_6O₃, was isolated by chromatographic purification and its chemical structure was determine! as 3-hydroxy-2-methyl-γ-pyrone (maltol).

Studies on the Metabolic Fates of Ginsenosides

한병훈,박명한,김두화,홍순근,Han, Byung-Hoon,Park, Myung-Hwan,Kim, Doo-Hwa,Hong, Soon-Keun 생화학분자생물학회 1986 한국생화학회지 Vol.19 No.3

$^3H$-ginsenosides-$Rb_1$, Re. $Rg_1$을 이용하여 이들 물질의 위장관내 흡수 장기내분포, 배설, 단백질 결합 및 세포내분포 등에 대하여 조사하였다. 그 결과를 요약하연 다음과 같다. 1. Ginsenoside들의 생쥐 위장관내 흡수는 개체에 따라서 10-50%의 범위에서 변동된다. 약용량 상응량 이상으로 투여하면 흡수률을 감소시키는 것 같다. 2. Ginsenoside들을 경구투여하면 위장관 내에서 현저하게 분해가 되는데 뇨에는 주로 미분해물질이 배설되었다. 26시간 동안 뇨중배설의 총량은 투여량의 1-2%에 불과하였다. 3. 위장관내 흡수율은 투여량에 의하여 현저한 영향을 받지만 조직중에 잔류하는 양은 거의 변동이 없는데 폐의 경우 ginsenoside Rx로 환산하여 $2.2{\times}10^{-6}\;mol$ 농도에 해당된다. 4. $^3H$-ginsenosides는 주로 폐, 간, 신장 등 배설과 관련된 기관에 많이 분포되지만 범세포적인 분포를 하고 있으며 뇌에도 소량은 분포되었다. 5. 세포내분포 실험에서 mitochondria 분획에는 분포되지 않은 것으로 나타났다. 6. $^3H$-ginsenosides-$Rb_1$은 혈청 또는 조직 Homogenate의 고분자 막성분과 강한 결합력을 나타내고 있으며 $Rg_1$은 약한 결합력을 나타내고 Re는 전혀 결합을 하지 않았다. Using $^3H$-ginsenosides $Rb_1$, Re, and $Rg_1$, gastrointestinal absorption, organ distribution, excretion, protein binding, and subcellular distribution of them were studied. The results are summarized as following; 1) The absorptions of $^3H$-ginsenosides in the gastro-intestinal ract of mice showed individual variation between 10-50%. Higher dosage of $^3H$-ginsenosides above the pharmacological dosage seems to reduce the absorption rate. 2) After oral administration, all $^3H$-ginsenosides were markedly decomposed in GI tract, but major component excreted through urine was found to be the intact ginsenosides. The total amount of excreted radioactivity during 26 h was only 1-2% of the administered dose. 3) Although the absorption rates are markedly affected by the change in the dosage, the retention in tissue seems to give roughly a constant value around $2.2{\times}10^{-6}$ molar concentration as the ginsenosides Rx bases in lung. 4) $^3H$-ginsenosides were distributed mainly in lung, kidney, and liver but only a trace amount in brain. 5) In subcellular distribution experiments, $^3H$-ginsenosides $Rb_1$ was not found in the mitochondrial fraction. 6) On the equilibrium dialysis experiments, $^3H$-ginsenosides $Rb_1$ showed a strong binding affinity with the high molecular membrane fractions of organ homogenates and with serum proteins, but $^3H$-ginsenosides Re and $Rg_1$ showed very weak binding to the same fractions.