Cytotoxic coumarins from the root of<Emphasis Type="Italic">Angelica dahurica</Emphasis>

Ten coumarins were isolated from the root of Angelica dahurica by repeated silica gel column chromatography. Their chemical structures were elucidated on the basic of physicochemical and spectroscopic data. Among them, oxypeucedanin hydrate acetonide (7) was isolated for the first time from this plant. Cytotoxicity of coumarins isolated were determined in vitro against L1210, HL-60, K562, and B16F10 tumor cell lines by MTT method. Pangelin (5) and oxypeucedanin hydrate acetonide (7) showed a potent cytotoxic activity with the IC50 values of 8.6 to 14.6 microg/mL against four kinds of tumor cell lines. Other compounds showed the moderate cytotoxic activity or no activity against the tumor cell lines.     

Acetylcholinesterase inhibitors from the roots of Angelica dahurica

In the course of finding Korean natural products for acetylcholinesterase (AChE) inhibitory activity, we found that a methanolic extract of the roots of Angelica dahurica showed significant inhibitory effects on AChE. Bioassay-guided fractionation of the methanolic extract resulted in the isolation of three furanocoumarins, isoimperatorin (1), imperatorin (2) and oxypeucedanin (3), as active principles. These compounds inhibited AChE activity in a dose-dependent manner, and the IC50 values of compounds 1-3 were 74.6, 63.7 and 89.1 microM, respectively.     

Platelet anti-aggregatory effects of coumarins from the roots of<Emphasis Type="Italic">Angelica genuflexa</Emphasis> and<Emphasis Type="Italic">A. gigas</Emphasis>

Five coumarins, isoimperatorin (1), pabulenol (2), isooxypeucedanin (3), oxypeucedanin hydrate (4) and osthol (5) were isolated from the MeOH extract of Angelica genuflexa in the course of searching for anti-platelet and anti-coagulant components from plants. Pabulenol (2) was isolated from A. genuflexa for the first time. The five compounds isolated from A. genuflexa, together with decursinol angelate (6), decursin (7) and nodakenin (8) from A. gigas were evaluated for their effects on platelet aggregation and blood coagulation. Compounds 2, 5, 6 and 7 were observed to be either equally effective or 2-4 times more inhibitory than ASA in both arachidonic acid and U46619 (TXA2 mimetic) induced platelet aggregations.     

High-performance liquid chromatographic method for the determination and pharmacokinetic study of oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma

A high-performance liquid chromatographic method was developed and validated for the determination and pharmacokinetic study of oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma. The coumarin components and the internal standard isopsoralen were extracted from plasma samples with the mixture of tert-butyl methyl ether and n-hexane (4:1, v/v). Chromatographic separation was performed on a C(18) column (200 mm x 4.6mm, 5 microm) with the mobile phase acetonitrile-methanol-water-acetic acid (20:15:65:2, v/v/v/v) at a flow-rate of 1.0 ml/min. Only the peak of oxypeucedanin hydrate and byak-angelicin could be detected in dog plasma after oral administration of ethanol extracts of A. dahurica mainly containing xanthotoxol, osthenol, imperatorin, oxypeucedanin hydrate and byak-angelicin. The calibration curves of oxypeucedanin hydrate and byak-angelicin were linear over a range of 22.08-8830.00 and 6.08-2430.00 ng/ml in dog plasma, respectively. The quantification limit of oxypeucedanin hydrate and byak-angelicin in dog plasma was 22.08 and 6.08 ng/ml, respectively. The intra- and inter-day precision was less than 7.6% and 8.5% and the accuracy was from 91.9% to 106.1%. The lowest absolute recoveries of oxypeucedanin hydrate and byak-angelicin were 85.7% and 87.0%, respectively. The method was successfully applied to the pharmacokinetic studies of oxypeucedanin hydrate and byak-angelicin in dog plasma after oral administration of ethanol extracts from A. dahurica.     

N2-芳基三嗪青霉素和N2-苯基-N4-烷基(芳基)三嗪青霉素的合成及其抗菌活性

设计合成了十个N²-芳基三嗪青霉素和六个N²-苯基-N⁴-烷基(芳基)三嗪青霉素,这十六个化合物均为未见文献报道的新化合物,元素分析数据和光谱数据证实了它们的结构。初步体外抑菌试验表明,十六个化合物对G(+)菌和G(-)菌均有一定的活性,其中的五个化合物具有一定程度的广谱特征。     

氧前胡素的降压作用

氧菌胡素Oxypencedanin0.6g/kg胃肠道给药能明显降低麻醉和清醒大鼠以及清醒肾型高血压大鼠的血压,其降压作用与直接扩张血管有关。     

亮叶杨桐的三萜皂苷类成分

为研究亮叶杨桐(Adinandra nitida Merr. ex Li)叶的化学成分，亮叶杨桐叶的乙醇提取物经大孔树脂、硅胶、Sephadex LH-20以及ODS柱色谱分离得到6个化合物，通过波谱(¹H NMR、 ¹³C NMR、 HR-ESI-MS)和化学方法进行结构鉴定，6个化合物分别被鉴定为2α,3α,19α-trihydroxy-olean-12-en-28-oic acid-28-O-β-D-glucopyranoside (1)、 arjunetin (2)、 sericoside (3)、 glucosyl tormentate (4)、 nigaichigoside F1 (5)和arjunglucoside I (6)。化合物1为新化合物，化合物2～6均为首次从该植物中分离得到。     

Coumarins and triterpenoid glycosides from the roots ofPatrinia scabiosaefolia

From the roots ofPatrinia scabiosaefolia (Valerianaceae), scopoletin (1), esculetin (2), oleanonic acid (3), 3-O-α-l-rhamnopyranosyl(1→2)-α-l-arabinopyranosyl oleanolic acid (4) and 3-O-α-l-rhamnopyranosyl (1→2)-α-l-arabinopyranosyl hederagenin (5) were isolated and characterized by spectral data.     

山慈菇的化学成分

为研究山慈菇药材——杜鹃兰(Cremastra appendiculata (D.Don) Makino)干燥假鳞茎的化学成分,采用硅胶、葡聚糖凝胶和反相硅胶柱色谱法分离纯化,运用现代波谱技术进行结构鉴定。本文分离得到7个化合物,分别鉴定为5-甲氧基联苄-3,3′-二-O-β-D-吡喃葡糖苷(1)、 militarine (2)、 loroglossin (3)、 原儿茶酸(4)、 丁二酸(5)、 天麻苷(6)和胡萝卜苷(7)。化合物1为新化合物,化合物2～6均为首次从杜鹃兰中分得。     

In vitro antioxidant activity of some selected Prunus species in Korea

In the course of the investigations of natural antioxidants, we examined the antioxidant activities of the methanol (MeOH) extracts of some selected Prunus species, including P buergeriana, P davidiana, P padus, P pendula for. ascendens, P. sargentii, P. serrulata var. spontanea and P. yedoensis by three methods as represented by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, total ROS (reactive oxygen species) and the peroxynitrite (ONOO-) scavenging activity tests. We also evaluated the activities of the organic solvent-soluble fractions, including the dichloromethane (CH2Cl2), ethyl acetate (EtOAc), n-butanol (n-BuOH) fractions and the water (H2O) layer of P serrulata var. spontanea leaves. By means of bioassay-directed fractionation, we isolated eleven known flavonoids (1-11) from the EtOAc soluble fraction of the MeOH extract of the Prunus serrulata var. spontanea leaves, exhibiting strong antioxidant activity and characterized as prunetin (1), genistein (2), quercetin (3), prunetin 4'-O-beta-glucopyranoside (4), kaempferol 3-O-alpha-arabinofuranoside (5), prunetin 5-O-beta-glucopyranoside (6), kaempferol 3-O-beta-xylopyranoside (7), genistin (8), kaempferol 3-O-beta-glucopyranoside (9), quercetin 3-O-beta-glucopyranoside (10) and kaempferol 3-O-beta-xylopyranosyl-(1-->2)-beta-glucopyranoside (11). Compounds 3 and 10 showed good activities in all tested model systems. Compounds 2 and 8 showed scavenging activities in the DPPH and ONOO- tests, while compounds 5, 7, 9 and 11 were active in the ONOO- and ROS tests. On the other hand, compounds 1, 4 and 6 did not show any activities in the tested model systems.     

通光散藤茎的C21甾体成分

为了研究通光散藤茎中的C₂₁甾体类成分，采用不同的色谱方法对通光散藤茎乙醇提取物进行分离纯化，并用波谱学的方法鉴定化合物的结构。从氯仿部位共分离得到8个C₂₁甾体类化合物，其结构分别被鉴定为11α-O-tigloyl-17β-tenacigenin B (1)、 17β-tenacigenin B (2)、 tenacigenoside A (3)、 11α-O-2-methylbutyryl-12β-O-acetyl tenacigenin B (4)、 tenacissoside H (5)、 marsdenoside A (6)、 tenacissoside G (7)和tenacissoside I (8)。其中化合物1为新化合物。     

卷柏中化学成分的分离与结构鉴定

目的研究中药卷柏(Selaginella tamariscina (Beauv.) Spring)水提物中的化学成分。方法用Sephadex LH-20及硅胶等色谱技术进行分离纯化,根据理化性质、光谱数据进行结构鉴定。结果得到9个化合物,分别鉴定为(2r,3s)-二氢-2-(3′,5′-二甲氧基-4′-羟基苯基)-3-羟甲基-7-甲氧基-5-乙酰基苯骈呋喃(1),3-羟基-苯丙酸-(2′-甲氧基-4′-羧基苯酚)酯(卷柏酯A,2),丁香脂素(3),1-(4′-羟基-3′-甲氧基苯基)丙三醇(4),阿魏酸(5),咖啡酸(6),香荚兰酸(7),丁香酸(8),7-羟基香豆素(9)。结论化合物1,2为新化合物,其余化合物均为首次从卷柏属植物中分离得到。     

大叶藤黄中三个新酮类成分

为了研究大叶藤黄树皮中酮类成分，运用正相和反相硅胶柱色谱法对大叶藤黄树皮乙酸乙酯萃取物进行分离纯化，并用波谱技术鉴定化合物结构。共分离得到3个新酮类化合物，其结构分别鉴定为1,2,5-三羟基-6-甲氧基酮(1)，1,4,6-三羟基-5-甲氧基酮(2)，1,2,7-三羟基-4-(1,1-二甲基烯丙基)酮(3)。     

Terpene and phenolic constituents of <Emphasis Type="Italic">Lactuca indica</Emphasis> L.

We isolated seven terpenes and five phenolic constituents from the aerial parts of Lactuca indica L. using column chromatographic separation of its MeOH extract. Their structures were determined by spectroscopic methods to be trans-phytol (1), 3beta-hydroxyglutin-5-ene (2), 5,6-epoxy-3-hydroxy-7-megastigmen-9-one (3), 11beta-13-dihydrolactucin (4), 2-phenylethyl beta-D-glucopyranoside (5), cichorioside B (6), 1-hydroxylinaloyl-6-O-beta-D-glucopyranoside (7), (6S,9S)-roseoside (8), benzyl-beta-D-glucopyranoside (9), 2-(3'-O-beta-D-glucopyranosyl-4'-hydroxyphenyl)-ethanol (10), 3-(beta-D-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-dihydrobenzofuran (11), and (+)-taraxafolin-B (12). Compounds 1-3, 5, and 7-12 were isolated for the first time from this plant source. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay.     

A benzenoid from the stem of<Emphasis Type="Italic">Acanthopanax senticosus</Emphasis>

Seven compounds were isolated from the stem of Acanthopanax senticosus by repeated column chromatography. Their structures were elucidated as isovanillin (1), (-)-sesamin (2), isofraxidin (3), (+)-syringaresinol (4), 5-hydroxymethylfurfural (5), eleutheroside B (6), and eleutheroside E (7) by spectral analysis. Among them, isovanillin (1) was isolated for the first time from the family Araliaceae.     

Bioactive Flavonoids from the Black Locust Tree,Robinia Pseudoacacia

Five flavonoids, acacetin ( 1 ), secundiflorol I ( 2 ), mucronulatol ( 3 ), isomucronulatol ( 4 ), and isovestitol ( 5 ) were isolated, with the fractionation being guided by the brine shrimp lethality test (BST), from the ethanolic extract of the whole plant of Robinia pseudoacacia (Fabaceae). The structures of 1 – 5 were identified by spectral analyses. Compounds 2 – 5 are, for the first time, reported from this species. Corrections have been made for the previous literature assignments of the 13 C NMR resonances of compounds 1 – 3 . Bioactivities in BST and cytotoxicities against a panel of six solid human tumor cell lines were determined, and 1 was significantly cytotoxic in the prostate cell line (PC-3).     

岗松中的一个新黄酮醇苷类化合物

为了研究岗松的化学成分，采用硅胶、聚酰胺柱层析色谱和重结晶的方法对化合物进行分离纯化，通过理化性质和波谱技术鉴定化合物结构。分离并鉴定了8个化合物：6，8-二甲基山柰酚-3-O-α-L-鼠李糖苷(1)、槲皮素(2)、槲皮素-3-O-α-L-鼠李糖苷(3)、杨梅素(4)、杨梅素-3-O-α-L-鼠李糖苷(5)、没食子酸(6)、熊果酸(7)和1,3-二羟基-2-(2′-甲基丙酰基)-5-甲氧基-6-甲基苯(8)。其中，化合物1为新黄酮醇苷类化合物，化合物2～7为首次从该植物中分离得到，化合物8为首次从植物中分离得到。     

Isolation of limonoids and alkaloids from<Emphasis Type="Italic">Phellodendron amurense</Emphasis> and their multidrug resistance (MDR) reversal activity

Three limonoids and five alkaloids were isolated from the chloroform layer of the MeOH extract of the bark of Phellodendron amurense (Rutaceae). The structures of the compounds isolated were determined to be obacunone (1), limonin (2), 12alpha-hydroxylimonin (3), gamma-fagarine (4), oxyberberine (5), canthin-6-one (6), 4-methoxy-N-methyl-2-quinolone (7) and oxypalmatine (8) based on the physicochemical and spectroscopic data. Compounds 3, 5, 7, and 8 were first isolated from the Phellodendron amurense. The isolated compounds were then tested for their cytotoxicity against five human tumor cell lines in vitro using the SRB method. Compound 5 showed significant cytotoxicity against the five tumor cell lines with ED50 values ranging from 0.30 to 3.0 microg/mL. The marginal or noncytotoxic compounds (1, 2, 3, 4, and 7) were examined for their P-gp related MDR reversal activities. Compound 1 showed significant P-gp MDR inhibition activity in MES-SA/DX5 and HCT15 cells with an ED50 value of 0.028 microg/mL and 0.0011 microg/mL, respectively.     

黄花倒水莲的一个新酮

Aim To study the chemical constituents of Polygala aureocauda Dunn.. Methods Chemical compounds were isolated by column chromatography and their structures were determined mainly by spectroscopic means (UV, IR, MS, ^1HNMR, ^13CNMR, HMQC, HMBC). Results Three compounds were isolated and identified as 3-hydroxy-1,4-dimethoxyxanthone (Ⅰ), 1,7-dihydroxy-2,3-methylendioxyxanthone ( Ⅱ ), 7-hydroxy-1-methoxy-2, 3-methylendioxyxanthone ( Ⅲ ). Conclusion Compounds Ⅰ -Ⅲ were isolated from Polygala aureocauda Dunn. for the first time, whereas compound Ⅰ is a new xanthone.     

黄丝郁金中的生物碱和倍半萜类成分

姜科植物姜黄(Curcuma longa)的块根称为黄丝郁金，是常用中药郁金的来源之一。为了研究黄丝郁金的利胆活性成分，采用柱色谱法对姜黄干燥块根的化学成分进行了研究。本文主要报道从中分离得到的1个喹啉类生物碱2-(2′-methyl-1′-propenyl)-4,6-dimethyl-7-hydroxyquinoline (1)，7个没药烷型倍半萜2,5-dihydroxybisabola-3,10-diene (2), 4,5-dihydroxybisabola-2,10-diene (3), turmeronol A (4), bisacurone (5), bisacurone A (6), bisacurone B (7)和bisacurone C (8)，以及dehydrozingerone (9)和zingerone (10)的分离和鉴定。化合物1为一个新的生物碱类化合物，化合物6～8为首次从姜黄中分得，化合物9～10为首次从姜黄属植物中分离得到。