Chemical constituents from the aerial parts of Tirpitzia ovoidea

In the present study, we isolated 18 known compounds from Tirpitzia ovoidea (Linaceae), including seven terpenoids (1-7), three simple phenylproponoids (8-10), three coumarins (11-13) and five other compounds (14-18). The structures of these compounds were identified by spectroscopic methods and compared with those reported in the literature. Compounds 1-16 were isolated from this plant as well as the Linaceae family for the first time.     

Antibacterial and anticoagulant activities of coumarins isolated from the flowers of Magydaris tomentosa

The phytochemical investigation of the acetone and methanol extracts of the flowers of Magydaris tomentosa (Desf.) DC afforded six known coumarins as well as (+)-meranzin hydrate (7), not previously reported as a natural product. The antibacterial activity of umbelliprenin (1), osthol (2), imperatorin (3), citropten (4) and (+)-meranzin hydrate (7) was tested against Gram-positive and Gram-negative bacteria. All coumarins (1-7) isolated in this study inhibited growth of all bacterial strains tested (MIC between 16 and 256 microg/mL), the most active being imperatorin (3) (MICs between 32 and 128 microg/mL) and citropten (4) (MICs between 16 and 256 microg/mL). The anticoagulant activity of compounds 1-4 and 7 was also evaluated.     

Chemical constituents from Portulaca oleracea and their bioactivities

In the present study, we aimed to intensively study the chemical constituents, especially organic acids from a medicinal plant Portulaca oleracea L., and screen their anti-inflammatory and quinone reductase (QR, a phase II detoxyfication enzyme) inductive activity. A total of 20 compounds were isolated and identified based on spectroscopic methods, as succinic acid (1), mono-methyl succinate (2), L-malic acid (3), L-1-methyl malate (4), L-4-methyl malate (5), L-dimethyl malate (6), L-6-ethyl citrate (7), L-1-methyl citrate (8), L-1,5-dimethyl citrate (9), 4-hydroxy-5-methylfuran-3-carboxylic acid (10), 5-hydroxymethyl-furoic acid (11), stearic acid (12), L-pyroglutamic acid (13), cyclo-(tyrosine-leucine) (14), L-isoleucine (15), (–)-dehydrovomifoliol (16), (–)-epiloliolide (17), 3,4-dihydroxyphenylethanol (18), succinimide (19), and uracil (20). Among them, 14 compounds (2, 4–8, 10, 11, 13–18) were isolated from P. oleracea for the first time. Compound 18 (12.5 μM) exhibited potent anti-inflammatory effect in lipopolysaccharide (LPS)-induced macrophage cells (RAW264.7) by reducing NO production, and it also increased QR activity in Hepa lclc7 cells. Compound 16 (50 μM) showed weak QR inductive activity. None of other compounds showed anti-inflammatory or QR inductive activities.     

Chemical constituents from the leaves of Cistus parviflorus

A phytochemical investigation on the leaves of Cistus parviflorus led to the isolation of 18 compounds. The structures of the isolated compounds were elucidated as kaempferol 3-O-(3′′,6′′-di-O-E-p-coumaroyl)-β-D-glucopyranoside (1), scopoletin (2),kaempferol 3-O-(3′′-O-E-p-coumaroyl)-β-D-glucopyranoside (3), kaempferol 3-O-(6′′-O-E-p-coumaroyl)-β-D-glucopyranoside (4), kaempferol 3-O-β-D-glucopyranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-(6′′-O-E-p-coumaroyl)-β-D-glucopyranoside (6), methyl flavogallonate(7), quercetin 3-O-β-D-glucopyranoside (8), quercetin 3-O-β-D-galactopyranoside (9), hydroquinone (10), arbutin (11), methyl β-glucopyranoside (12), shikimic acid (13), (S)-1,2-propandiol-1-O-β-D-glucopyranoside (14), benzyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (15), 2-phenethyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (16), corchoionoside C (17), kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (18) by the analysis of the MS and NMR spectroscopic data and comparison with the literature. Compounds 1–2, 6–7, 10–12, and 14–16 were isolated from Cistus genus for the first time.     

Chemical constituents from Matricaria chamomilla L. (I)

In the present study, we aimed to perform a phytochemical investigation of the whole herb of Matricaria chamomilla L., a Uygur herbal medicine. A total of 18 phenolic compounds were isolated by silica gel and Sephadex LH-20 chromatography, together with preparative HPLC methods. By analysis of the MS and NMR spectroscopic data and comparison with those in literature, these 18 compounds were identified as apigenin (1), galangin (2), luteolin (3), kempherol (4), quercetin (5), hispidulin (6), 6-methoxykaempferol (7), eupafolin (8), 3-methylquercetin (9), ermanin (10), 5,7,4′-trihydroxy-3,6-dimethoxyflavonone (11),bracteoside (12), 7-O-(β-D-glucopyranosyl)-galactin (13), isochlorogenic acid B (14), isochlorogenic acid C (15), 4-hydroxybenzoic acid (16), 5-pentadecylbenzene-1,3-diol (17) and scopoletin (18). Among them, compounds 1–13 were identified as flavonoids. Compounds 2 and 6–17 were isolated from both the plant and the Matricaria genus for the first time.     

Chemical constituents from the red alga Symphyocladia latiuscula

The extraction and solvent fractionation of red alga Symphyocladia latiuscula, and repeated column chromatography led to isolation of 17 compounds: cholesterol (1), 3β,5β-dihydroxy-B-norcholestan-6β-carboxaldehyde(2),6β-hydroxy-cholest-4-ene-3-one(3), 1-O-myristoyl-3-O-(6′-sulfo-α-D-quinovopyranosyl)glycerol (4), 1-O-palmitoyl-3-O-(6′-sulfo-α-D-quinovopyranosyl)glycerol (5), 1-O-palmitoyl-3-O-[α–D-galactopyranosyl(1→6)β-D-galactopyranosyl] glycerol(6), 1-O-palmitoyl-3-O-β-D-galactopyranosylglycerol (7), methyl hexadecanoate (8), methyl stearate(9), hexadecanoic acid (10), γ-n-butyl cis-aconiate (11), α-n-Butyl cis-aconiate (12), phenethylamine (13),3,5-dibromo-L-tyrosine (14), 3-methylbutylamine (15),methyl pyroglutamate (16),n-butyl pyroglutamate (17).The structures of these compounds were identified by NMR spectroscopy and mass spectrometry, and compared with those reported in the literature. All the compounds were isolated from Symphyocladia genus for the first time.These compounds were investigated for their inhibitory effects on human recombinant aldose reductase in vitro. Of the compounds, 1-O-palmitoyl-3-O-β-D-galactopyranosylglycerol (7) demonstrated moderate enzyme inhibition.     

Synthesis and antitumor,antityrosinase, and antiplatelet aggregation activities of xanthone

In the present study, five fluorine substituted and three chlorine substituted 1,3-dihydroxyxanthones were synthesized in one step.The yields ranged from 48% to 72%. Among them, compounds 12 and 15–18 were reported for the first time. The antitumor, antityrosinase and antiplatelet aggregation activities of all or part of compounds 1–19 were evaluated. Compounds 1, 2, 4, 6–7, 10–15 and 19 exhibited enhanced cytotoxicity against certain cancer cells. Compound 10,containing 2,4-difluorophenyl at the C7 position, particularly exhibited superior antitumor activity. The inhibition rate of compound 18 against tyrosinase was approximately 22%. Compounds 1–3, 6, 9, 12 and 18, 19 exhibited obvious inhibitory platelet aggregation induced by ADP in rats. Moreover, the effects of compounds 2 and 3 were more pronounced. These results demonstrated that compounds 1–4, 6–7, 9–15 and 19 were promising leads for further structural modification.     

Neuroprotective coumarins from the root of<Emphasis Type="Italic">Angelica gigas</Emphasis>: Structure-activity relationships

An n-butanol-soluble fraction of the root of Angelica gigas Nakai (Umbelliferae) exhibited significant protection against glutamate-induced toxicity in primary cultured rat cortical cells. Using neuroprotective activity-guided fractionation, nine coumarins; marmesinin (1), nodakenin (2), columbianetin-O-beta-D-glucopyranoside (3), (S)-peucedanol-7-O-beta-D-glucopyranoside (4), (S)-peucedanol-3'-O-beta-D-glucopyranoside (5), skimmin (6), apiosylskimmin (7), isoapiosylskimmin (8) and magnolioside (9), were isolated from the n-butanol fraction. Of these nine coumarins, three dihydrofuranocoumarins; 1, 2 and 3, exhibited significant neuroprotective activities against glutamate-induced toxicity, exhibiting cell viabilities of about 50% at concentrations ranging from 0.1 to 10 microM. To explore the structure-activity relationships of coumarins, sixteen previously isolated compounds; 10-25, were simultaneously evaluated in the same system. Our results revealed that cyclization of the isoprenyl group, such as dihydropyran or dihydrofuran, or the furan ring at the C-6 position of coumarin, as well as lipophilicity played an important role in the neuroprotective activity of coumarins.     

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.     

The chemical constituents in the decoction of Urtica fissa rhizomes

Phytochemical investigation of the decoction of Urtica fissa rhizomes led to the isolation of 23 known compounds. Their structures were identified as medioresinol dimethyl ether (1), L-pyroglutamic acid methyl ester (2), nicotinic acid (3), L-pyroglutamic acid (4), erythritol (5), 6-methyl-2′-deoxy thymidine (6), 2-methyl-6-(2′,3′,4′-trihydroxybutyl)-pyrazine (7), 5-hydroxyl-2-hydroxymethyl pyridine (8) , adenine (9), uracil (10), thymine (11), adenosine (12), inosine (13), 2′-deoxyadenosine (14), 2′-deoxyguanosine (15), 2′-deoxyinosine (16), uridine (17), n-butyl-O-β-D-fructopyranoside (18), di-D-fructose (19), β-D-fructofuranosyl-α-D-galactopyranoside (20), bis (5-formyl-furfuryl) ether (21), chlorogenic acid (22), and 5-hydroxymethyl furaldehyde (23) by spectroscopic methods. In addition, a total of 20 compounds (1–20) were isolated from U. fissa for the first time. Meanwhile, compounds 1, 6, 7, 8, 19 and 20 were isolated from the Urticaceae plants for the first time.     

重齿毛当归中香豆素的进一步分离

重齿毛当归中香豆素的进一步分离柳江华，徐绥绪，姚新生，吴玉强（沈阳药科大学植化教研室，沈阳１１００１５；辽宁中医学院植化教研室，沈阳ｌ１００３２；哈尔滨中药二厂）重齿毛当归（ＡｎｇｅｌｉｃａｐｕｂｅｓｃｅｎｃｅＭａｘｉｍｆ．ｂｅｓｅｒｒａｔａＳｈａｎ...     

Coumarins from Coriaria nepalensis

Two new coumarins (1) and (2), along with seven known coumarins 3-9, were isolated from the leaves and stems of Coriaria nepalensis Wall. The two new compounds were established as 7-hydroxy-6-methoxy-3,8-bis(3-methyl-2-butenyl) coumarin (1) and 7-hydroxy-6-methoxy-3-(3-methyl-2-butenyl) coumarin (2), on the basis of 1D and 2D NMR techniques. The known compounds 3, 6-9 were isolated from this plant for the first time.     

Flavonoids, coumarins and triterpenes from the aerial parts of Cnidoscolus texanus

Phytochemical investigation on Cnidoscolus texanus led to the isolation of 26 compounds, which included 15 flavonoids (1-15), three coumarins (16-18), three coumaric acid derivatives (19-21), four triterpenoids (22-25), and one phytosterol (26). Among them, aromadendrin 7-O-(4'-O-P-E-coumaroyl-beta-glucopyranoside) (1), aromadendrin 7-O-(3',6'-di-O-P-E-coumaroyl-beta-glucopyranoside) (2), and naringenin 7-O-(4'-O-P-Z-coumaroyl-beta-glucopyranoside) (3) are new compounds. Their structures were determined by spectroscopic and chemical methods. All flavonoids were found to be inactive against DNA topoisomerase I.     

A new xanthone from Halenia elliptica D. Don

A new xanthone, 1,5-dihydroxy-2,3,4-trimethoxyxanthone (1), together with 15 known compounds (2-16), was isolated from an ethanolic extract of Halenia elliptica D. Don. Their structures were elucidated by spectroscopic methods. Among the known compounds, the (13)C NMR spectroscopic data of 2,3,4,5-tetramethoxyxanthone-1-O-gentiobioside (2) were reported for the first time.     

Cytotoxicity of compounds from the fruits of <Emphasis Type="Italic">Derris indica</Emphasis> against cholangiocarcinoma and HepG2 cell lines

Two new compounds, derrivanone (1) and derrischalcone (2), were isolated from the crude hexane extract of the fruits of Derris indica. In addition, 14 known compounds were isolated from the fruits of this plant. Chalcones 2–4 showed strong cytotoxicity against cholangiocarcinoma cell line (M156) and human hepatoma HepG2 cells. In addition, flavanones 15 and 16 exhibited potent and high cytotoxic efficacy.     

Antioxidant and cytotoxic isoprenylated coumarins from Mammea americana

Antioxidant-guided fractionation of Mammea americana L. seeds resulted in the identification of three new isoprenylated coumarins, mammea B/BA hydroxycyclo F (1), mammea E/BC (2), and mammea E/BD (3). In addition, twelve known isoprenylated coumarins, mammea A/AA (4), mammea A/AA cyclo D (5), mammea A/AA cyclo F (6), mammea A/AC cyclo D (7), mammea A/AD cyclo D (8), mammea B/BA (9), mammea B/BA cyclo F (10), mammea B/BB (11), mammea B/BC (12), mammea B/BD (13), mammea E/BA (14), and mammea E/BB (15), as well as two known flavanols, (+)-catechin (16) and (-)-epicatechin (17) were identified. The fifteen isoprenylated coumarins were screened for their cytotoxicity in the SW-480, HT-29, and HCT-116 human colon cancer cell lines and antioxidant capacities in the DPPH (1,1-diphenyl-2-picrylhydrazyl) free-radical assay. Compounds 1 - 15 exhibited significant cytotoxic activities in the SW-480, HT-29, and HCT-116 human colon cancer cell lines (IC50 ranges 13.9 - 88.1, 11.2 - 85.3, and 10.7 - 76.7 microM, in the three cell lines, respectively) at concentrations comparable to 5-fluorouracil (IC50 = 53.0, 46.1, and 45.1 microM), a drug frequently used for human colon cancer treatment. Compounds 2 - 4, 9, and 11 - 15 displayed high antioxidant activity in the DPPH assay (IC50 range 86 - 135 microM), compounds 1, 5 - 8, and 10, however, had no antioxidant activity (IC50 > 200 microg/mL) in the DPPH assay. The results of these assays were used to study the structure-activity relationships for this class of compounds. In the SW-480 cell line, the three new coumarins, 1 - 3, also exhibited dose-dependent increases in sub-diploid cells by flow cytometry, indicating that they induce apoptosis.     

In vitro antimicrobial and acetylcholinesterase inhibitory activities of coumarins from <Emphasis Type="Italic">Ferulago</Emphasis><Emphasis Type="Italic">carduchorum</Emphasis>

Ferulago carduchorum (Apiaceae) is an endemic plant of Iran. From the hexane and ethyl acetate extracts of F. carduchorum seven coumarins, one flavonoid and one steroid were isolated using column chromatography with silica gel and Sephadex LH₂₀ as the stationary phases. Antimicrobial activity of the isolated compounds was examined by a broth microdilution method. Acetylcholinesterase (AChE) inhibitory activity of isolated coumarins was also investigated. The isolated compounds were identified as suberosin, suberenol, bergapten, xanthotoxin, isopimpinellin, prantschimgin, β-sitosterol and hesperetin by comparison of their NMR and MS spectral data with those reported in the literature. Evaluation of the minimum inhibitory concentration (MIC) for each compound showed that hesperetin (flavonoid) was the most potent antimicrobial agent against a gram-positive bacterium (Staphylococcus aureus) and among the coumarins, bergapten had the best activity against S. aureus and Candida albicans. All coumarins inhibited AchE enzyme, in which xanthotoxin showed the most inhibitory among them (IC₅₀ = 39.64 µM). Our results indicate that isolated coumarins are effective against the tested bacterial strains and have AchE inhibitory activity suggesting their potential for commercial applications.     

A new coumarin from the stem of<Emphasis Type="Italic">Angelica dahurica</Emphasis>

One new and three known coumarins were isolated from the CHCl3 soluble fraction of Angelica dahurica stem. On the basis of spectral data, the structures of the isolated compounds were determined to be scopoletin, angelol I, angelol H and 6-[(1S), 2(R)-2, 3-dihydroxy-1-methoxy-3-methylbutyl]-7-methoxycoumarin; the latter being isolated for the first time from a plant source.     

裸花紫珠的脂溶性化学成分

目的 研究裸花紫珠(Callicarpa nudiflora Hook. Et Arn.)叶的脂溶性化学成分。方法 采用硅胶柱色谱、Sephadex LH-20柱色谱和大孔树脂HPD-100柱色谱分离化合物,通过理化性质和波谱分析确定化合物的结构。结果 从裸花紫珠叶的水提取物中分离得到8个已知化合物,分别鉴定为：5,4′-二羟基-3,7,3′-三甲氧基黄酮（1）、5-羟基-3,7,3′,4′-四甲氧基黄酮（2）、木犀草素（3）、木犀草素-7-O-β-D-吡喃葡萄糖苷（4）、七叶內酯（5）、乌苏-12-烯-3β-醇（6）、熊果酸（7）、β-谷甾醇（8）。结论 化合物5、6为首次从紫珠属植物中分离得到;化合物1~3、8为首次从该植物中分离得到;香豆素类化合物为首次从紫珠属植物中分得的化合物类型。     

Chemical constituents of the root ofDystaenia takeshimana and their anti-inflammatory activity

In our ongoing search for bioactive compounds originating from the endemic species in Korea, we found that the hexane and EtOAc fractions of the MeOH extract from the root of Dystaenia takeshimana (Nakai) Kitagawa (Umbelliferae) showed cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin D2 (PGD2) and leukotriene C4 (LTC4) in mouse bone marrow-derived mast cells. By activity-guided fractionation, five coumarins, viz. psoralen (2), xanthotoxin (3), scopoletin (4), umbelliferone (5), and (+)-marmesin (6), together with beta-sitosterol (1), were isolated from the hexane fraction, and two phenethyl alcohol derivatives, viz. 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7) and 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), three flavonoids, viz. apigenin (9), luteolin (10), and cynaroside (11), as well as daucosterol (12) were isolated from the EtOAc fraction using silica gel column chromatography. In addition, D-mannitol (13) was isolated from the BuOH fraction by recrystallization. Two of the coumarins, scopoletin (4) and (+)-marmesin (6), the two phenethyl alcohol derivatives (7, 8) and the three flavonoids (9-11) were isolated for the first time from this plant. Among the compounds isolated from this plant, the five coumarins as well as the three flavonoids showed COX-2/5-LOX dual inhibitory activity. These results suggest that the anti-inflammatory activity of D. takeshimana might in part occur via the inhibition of the generation of eicosanoids.