• Natural Product Sciences
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• v.22 no.2
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• pp.107-110
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• 2016

A new stereoisomeric monoterpene glycoside and five already-known compounds were isolated from the n-BuOH soluble fraction of Clematis heracleifolia leaves. On the basis of spectral data, the structures of the isolated compounds were identified as protocatechuic acid (1), ferulic acid (2), caffeic acid (3), aesculin (4), (6Z)-9-hydroxylinaloyl glucoside (5), and 9-hydroxylinaloyl glucoside (6) and these were isolated for the first time from this plant. Among these compounds, (6Z)-9-hydroxylinaloyl glucoside (5) is a newly isolated from plant source.

• Archives of Pharmacal Research
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• v.29 no.10
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• pp.815-820
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• 2006

Antibacterial activity-guided fractionation of the $CHCl_3-MeOH$ (1:1) extract of Paeonia suffruticosa root bark furnished three monoterpene glycosides, 6-O-vanillyoxypaeoniflorin (1), mudanpioside-H (2), and galloyl-oxypaeoniflorin (3). Of the isolated compounds, compound 1 is a new compound. All isolated compounds showed broad, but moderate, antibacterial activity with minimum inhibitory concentration (MIC) values in the range of 100 to $500\;{\mu}g/mL$ against eighteen pathogenic microorganisms of concern for public health or zoonosis.

• Korean Journal of Pharmacognosy
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• v.47 no.4
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• pp.301-306
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• 2016

Four phenylpropanoid glycosides and a monoterpene glycoside were isolated from the flower of Clerodendrum trichotomum. Structures of the isolated compounds were identified as acteoside (1), martynoside (2), leucosceptoside A (3), isoacteoside (4) and neohancoside A (5) by spectroscopic analysis. Compounds 1-4 were isolated from the flower of C. trichotomum for the first time. Compound 5 was first obtained from genus Clerodendrum as well as family Verbenaceae. The antioxidant activity of compounds 1-5 were evaluated by the DPPH free radical scavenging assay. Compounds 1-4 exhibited strong antioxidant activity.

• Archives of Pharmacal Research
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• v.24 no.2
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• pp.105-108
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• 2001

$\alpha$-Benzoyloxypaeoniflorin (1), a new antioxidant monoterpene $\alpha$-glycoside anomer was isolated from Paeonia suffruticosa along with known compounds, $\beta$-benzoyloxypaeoniflorin (2), paeonolide, paeoniflorin and mudanpioside H. The structure of 1 has been determined by comparing spectral data with those of $\beta$-Benzoyloxypaeoniflorin(2). Compound 1 exhibited moderately potent radical scavenging activity on DPPH radical.

• Proceedings of the KAIS Fall Conference
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• 2003.06a
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• pp.320-321
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• 2003

최근 천연물을 중심으로 한 학문이 발전하면서 천연물이 가지는 생리활성 물질에 대한 관심이 중대되고 있다. 또한 인공합성품의 일부가 안정성의 문제가 제기되면서 천연물의 이용분야는 더욱 확대되고 있다. 급속한 경제발전과 생활수준의 향상으로 식생활을 포함한 생활방식의 다양화로 인하여 과거 감염 위주의 질병이 감소하고 선진국형의 만성퇴행성 질환이 증가하는 추세이다. 혈소판은 혈전증(thrombosis)과 지혈증(haemstasis)에서 중요한 역할을 담당하고 있는 인자로서 현관 내 병적 이상으로 인한 과도한 혈전의 생성은 뇌 -심혈관계 질환의 중요한 유발인자로 작용하므로 뇌ㆍ심혈관계 질환이나 항고지혈증을 연구하는데 유용하게 이용되고 있다. 본 연구에서는 토끼 혈액에서 분리한 세정 혈소판 부유액을 이용하여 작약 MeOH 추출물에서 분리한 천연생리활성물질들을 대상으로 혈소판 응집억제활성에 대하여 연구하였다. 작약 MeOH 추출물의 혈소판 응집억제활성 측정에서 강한 혈소판 응집억제활성 작용을 보였다. 따라서 작약 MeOH 추출물을 크로마토그라피법을 이용하여 분리하였고, NMR을 이용한 분광학적 방법으로 지금까지의 분리한 자료와 비교ㆍ분석하였다. Monoterpene glycoside 계열의 성분들인 15개의 compound와 다수의 fraction들을 HPLC를 이용하여 분리하였으며, collagen으로 유도된 혈소판 응집억제활성측정 방법에서 뛰어난 응집억제활성을 보였다. 표준물질을 이용한 HPLC 분석과 ¹H-NMR 관련 자료의 검색을 통하여 최종적으로 compound 1b가 benzoyloxy-paeoniflorin(2.6％). compound 1d가 paeond(1.3％), compound 2c가 albiflorin(3.2％), compound 2e가 paeoniflorin(33.6％)임을 확인할 수 있었다. Compound 3a의 분석결과 benzoyloxypaeoniflorin과 구조적 유사성은 있으나 동일한 구조식으로 확인할 수 없었다. 그러나 collagen에서 응집억제활성이 90％ 이상으로 뛰어난 활성을 나타내므로 benzoyloxypaeoniflorin과 유사한 구조에서 benzoyl group이 다른 작용기로 치환되었거나 R₁ group이 다른 작용기로 치환된 형태로 추측하였다. Benzoyloxypaeoniflorin은 collagen＞thrombin＞U46616＞A.A(arachidonic acid)＞PAF의 순으로 활성을 보였다. 이는 paeoniflorin의 glycoside 5-carbon위치에 위치한 OH기 대신에 benzoyl기로 치환된 benzoyl 기가 혈소판 억제 산물로 작용한 것으로 추측했다. Paeoniflorin.은 U46619＞thrombin＞collagen＞A.A＞PAF순으로 억제를 보였다. Paeoniflorin이 collagen보다 thrombin에서 강한 억제를 보이는 것으로 Ca/sup 2＋/ chelate를 형성함으로 인해 calciu 대사를 저해하는 것으로 추축했다. Compound 3a는 U46619＞collagen＞A.A＞thrombin＞PAF순으로 억제율을 보이므로 이 화합물은 paeoniflorin의 benzoyl기에 OH기가 다른 치환기로 바뀌거나 paeoniflorin의 glycoside 5-carbon 위치의 OH기 대신에 다른 작용기로 치환된 것으로 추정하였다. 이러한 결과로 작약의 주성분인 paeoniflorin과 유사한 구조를 가진 다른 monoterpene glycoside 계열의 화합물들과 비교 분석하고 구조를 화인하고 이들 성분이 어떻게 혈소판 응집억제활성에 작용하는지를 연구하였다.

• Natural Product Sciences
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• v.16 no.2
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• pp.68-74
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• 2010

Phytochemical investigation on the ethyl acetate and n-butanol fractions of Moutan Cortex resulted in the isolation and characterization of a new monoterpene glycoside (3) and twenty known monoterpene glycosides (1, 2, 4-21). The structure of 3 was determined by spectroscopic data interpretation and physico-chemical properties. Compounds 1 and 8 presented a remarkable inhibitory activity against lipoxygenase-1 (LOX-1) with $IC_{50}$ values of 45.2 and $37.5\;{\mu}M$, respectively. Compounds 9, 10, 13, 18, 19, and 21 showed significant 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging effect with $IC_{50}$ values of 9.8, 25.5, 6.4, 15.2, 18.7, and $23.7\;{\mu}M$, respectively. Benzoylpaeoniflorin (8), which exhibited the highest inhibitory effect with an $IC_{50}$ value of $37.5{\pm}0.7{\mu}M$, was further analyzed the inhibition kinetics by Lineweaver-Burk plots. Results indicated that 8 is a non-competitive inhibitor, and the kinetic parameter values were estimated to be ($31.04\;{\mu}M$, Ki), ($0.29\;{\mu}M/min$, $V_m$), and ($48.50\;{\mu}M$, $K_m$).

• Korean Journal of Food Science and Technology
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• v.22 no.5
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• pp.543-548
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• 1990

Volatile components of fresh apricot (Prunus armeniaca var. ansu Max.) were isolated by simultaneous distillation-extraction at two different pH values of 3.1 and 7.0 and by headspace trapping method. The volatiles were analyzed by GC and GC-MS. A total of 80 components were identified in the three aroma concentrates, including 9 naphthalene derivatives that were not previously reported in apricot. Of components identified in native pH (3.1) sample, the major components were aliphatic $C_6$ aldehydes and alcohols, monoterpene alcohols, benzyl alcohol, ${\beta}-phenylethyl$ alcohol and naphthalene derivatives, while those in neutral pH(7.0) sample and headspace volatiles were aliphatic $C_6$ aldehydes and alcohols. Simultaneous distillation-extraction at pH 3.1 was significantly increased the concentration of n-hexanal, trans-2-hexenal, cis-3-hexen-1-ol, linalool oxide, linalool, ${\alpha}-terpineol$, nerol, geraniol, benzyl alcohol, ${\beta}-phenylethyl$ alcohol and naphthalene derivatives. These results demonstrate that above the components are present in glycosidically bound forms in apricot.

• Korean Journal of Pharmacognosy
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• v.40 no.2
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• pp.123-127
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• 2009

In an ongoing investigation into anti-oxidative compounds from natural products, the EtOAc soluble fraction of Aster tataricus L. (Compositae) showed significant anti-oxidative activity on the NBT superoxide scavenging assay. By means of an activity-guided purification, three flavonoids, kaempferol (1), quercetin (2), astragalin (3) and one monoterpene glycoside, shionoside A (4) were isolated. Their structures were determined spectral analyses. Compounds 2 and 3 showed potent antioxidative activity, while, compounds 1 and 4 were inactive $IC_{50}$>120${\mu}g/mL$. In addition, these compounds were examined for the effect of interleukin-6 (IL-6) production in TNF-${\alpha}$ stimulated MG-63 cell. Compounds 1-3 showed negligible inhibitory activity against IL-6 production in $TNF-{\alpha}$ stimulated $MG-6{\beta}$ cell, and compound 4 was inactive.

• Korean Journal of Pharmacognosy
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• v.47 no.3
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• pp.237-245
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• 2016

In present study, we conducted quantification analysis of phenolic compound (paeonol), monoterpene glycoside (paeoniflorin), and tannin ((+)-catechin in the 70% ethanol extracts of non-processed Moutan Radicis Cortex (MRC) and processed MRC by roasting using a high-performance liquid chromatography coupled with photodiode array detector. Three marker components were separated on Gemini $C_{18}$ analytical column and the column was maintained at $40^{\circ}C$ using two mobile phase system consisting of 1.0% (v/v) aqueous acetic acid and 1.0% (v/v) acetic acid in acetonitrile. The flow rate and injection volume were 1.0 mL/min and 10 mL. In non-processed MRC sample, the concentrations of three marker compounds, (+)-catechin, paeoniflorin, and paeonol were 0.20, 1.18, and 2.12%, respectively. On the other hand, the concentrations of the three compounds in processed MRC samples were 0.03-0.24, not detected-1.08, and 0.76-1.82%, respectively.

• Bulletin of the Korean Chemical Society
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• v.25 no.10
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• pp.1555-1558
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• 2004

Prunioside A is a unique, highly oxidized monoterpene glycoside isolated from the methanol extract of Spiraea prunifolia var. Simpliciflora's root. The ester derivatives were synthesized from the hydrolyzed compounds of prunioside A by ${\beta}$-glucosidase. The derivatives showed suppressive effects on the generation of nitric oxide in murine machrophage-like RAW 264.7 cells stimulated by lipopolysaccharide and interferon- ${\gamma}$.