A new irregular diterpenoid from Opopanax chironium

The ethereal extract of the roots of Opopanax chironium yielded peucelinenoxide acetate (1), a new natural product with an irregular diterpene skeleton, besides the known coumarins gaudichaudin, columbianadin, peucedanin and officinalin isobutyrate.     

Dihydrochalcones and coumarins of Esenbeckia grandiflora subsp. brevipetiolata

Six furoquinolines and five coumarins have been isolated from the roots of Esenbeckia grandiflora subsp. brevipetiolata. The leaves yielded two dihydrochalcones and two flavonol rhamnosides. One of the coumarins (5-senecioyl-xanthotoxin) and the dihydrochalcones are novel compounds and their structures were elucidated by spectroscopic methods. The comparison with the dihydrochalcones previously isolated from another subspecies, E. grandiflora subsp. grandiflora is also provided.     

Grapefruit: the last decade acquisitions

This review reports the last decade acquisitions on grapefruit. New coumarins and limonoids were isolated and characterised. The bioavailability of many drugs was tested with grapefruit juice (GJ) coadministration; the inhibition on cytochrome P450 seems due to a synergic action between flavonoids and coumarins. Antimicrobial, antifeeding, insecticidal, and antitumour activities were also reported.     

New coumarins from Cedrelopsis grevei

Two new coumarins, 7-methoxy-5-prenylcoumarin (isocedrelopsin) (1) and 3',4'-dihydrobraylin (2), were isolated from the trunk bark of Cedrelopsis grevei, along with five known coumarins, microfolicoumarin (6,7-dimethoxy-5-prenylcoumarin, (3), obliquin (4), 8-methoxyobliquin (5), aesculetin (6), cedrelopsin (7) and scoparone (8).     

Two new coumarins from Euonymus hamiltonianus

Two new coumarins, named Euonidiol (1) and Euoniside (2) were isolated from the aerial parts of Euonymus hamiltonianus.     

Coumarins from the aerial part of Halocnemum strobilaceum

Four known coumarins, coumarin (1), 7-hydroxy-3-methylcoumarin (2), oreoselone (3) and heraclenin (4), were isolated from aerial part of Halocnemum strobilaceum. Their structures were determined by 1 and 2-D NMR techniques.     

Two new O-geranyl coumarins from the resinous exudate of Haplopappus multifolius

From the resinous exudate of leaves of Haplopappus multifolius two new coumarins were isolated and assigned the structures 6-hydroxy-7-(5'-hydroxy-3',7'-dimethylocta-2',6'-dien)-oxycoumarin (1) and 6-hydroxy-7-(7'-hydroxy-3',7'-dimethylocta-2',5'-dien)-oxy coumarin (2).     

蚬壳花椒中性亲脂性成分的抑菌活性及其化学成分

Effects of bacteriostasis of the Neutral Lipophilic Components in Zanthoxylum dissitum were studied. The neutral lipophilic extract was fractionated through SiO_2 column and the products were identified by ~1H-NMR,~ 13 C-NMR and MS. The results showed that the fraction exhibited strong bacteriostasis activity to Staphylococcus aureus and Salmonella sp. and also showed more or less inhibition on Escherichia coli. Six components were obtained,namely triacontane,1-hexadecanol,β-sitosterol,ursolic acid,isopimpi...     

Hepatoprotective and TNF-α inhibitory activity of Zosima absinthifolia extracts and coumarins

Zosima absinthifolia (ZA) extracts and the coumarins (+)-columbianadin and (-)-deltoin were evaluated for their potential hepatoprotective and antiinflamatory effects in a CCl(4)-induced hepatotoxicity assay in rats and by the inhibition of TNF-α production on LPS-stimulated THP-1 macrophages, respectively. Both the ZA extracts and the coumarins showed hepatoprotective activity confirmed by monitoring the ALT/AST levels and by histopathological examination. The antiinflamatory activity, proved by the inhibition of TNF-α production, was found to be higher for the n-hexane root extract than for coumarins, suggesting synergic potential of the extract. The concentration of (-)-deltoin and (+)-columbianadin in extracts was determined by HPLC analysis.     

紫椴花和果实化学成分及其地理变异

采集不同地点紫椴花和果实,通过系统预试验,检测出紫椴花及花蕾中含有较多的酚类、糖和甙类,还检测到黄酮类化合物、蛋白质、香豆素及强心甙等,在花蕾中还含有少量鞣质.紫椴果实中含有酚类、糖和甙类,还含有少量黄酮化合物、香豆素和鞣质.对不同纬度和海拔紫椴花和果实中可溶性糖、总酚和黄酮的含量进行分析,发现3类化学成分含量随纬度、海拔的变化存在一定的变化规律.除花中总酚含量差异不显著外,紫椴花和果实中其他化学成分含量随着纬度升高而降低,随着海拔升高而增高.紫椴花中可溶性糖含量明显高于果实,其他化学成分在花和果实中的含量接近.化学成分含量聚类分析与遗传距离聚类分析比较表明:化学成分含量变异在纬度上是不连续的,在海拔梯度上是连续的.     

Chemical components of Fraxinus species

A wide range of chemical components including coumarins, secoiridoids, phenylethanoids, flavonoids, and lignans has been isolated from Fraxinus species. Extracts and metabolites have been found to possess antiinflammatory, immunomodulatory, antimicrobial, antioxidative, skin regenerating, photodynamic damage prevention, liverprotecting, diuretic and antiallergic activities. Some species find application in contemporary medicine. In the present review the literature data on the phytochemical and biological investigations on the genus Fraxinus are summarized up to the middle of 2004.     

Antimicrobial activity of 10-isobutyryloxy-8,9-epoxythymol isobutyrate

10-Isobutyryloxy-8,9-epoxythymol isobutyrate was found to be a major constituent of Inula helenium and Inula royleana root cultures. The compound showed moderate antimicrobial activity against Staphylococcus aureus, Enterococcus faecalis, Escherischia coli, Pseudomonas aeruginosa and Candida albicans.     

Flavonoids with antiplasmodial and cytotoxic activities of Macaranga triloba

A new flavanone derivative, malaysianone A (1), four prenylated flavanones, 6-prenyl-3'-methoxyeriodictyol (2), nymphaeol B (3), nymphaeol C (4) and 6-farnesyl-3',4',5,7-tetrahydroxyflavanone (5), and two coumarins, 5,7-dihydroxycoumarin (6) and scopoletin (7), were isolated from the dichloromethane extract of the inflorescences of Macaranga triloba. The structures of these compounds were elucidated based on spectroscopic methods including nuclear magnetic resonance (NMR-1D and 2D), UV, IR and mass spectrometry. The cytotoxic activity of the compounds was tested against several cell lines, with 5 inhibiting very strongly the growth of HeLa and HL-60 cells (IC(50): 1.3 μg/ml and 3.3 μg/ml, respectively). Compound 5 also showed strong antiplasmodial activity (IC(50): 0.06 μM).     

小叶臭黄皮的化学成分研究

从小叶臭黄皮(Clausena excavata Burm F.)的茎和叶中分离得到10个单萜基香豆素,分别鉴定为7-((E)-3'-甲基-4'-(8'-羰基-7',9'-烯-呋喃)-2'-烯)-香豆素(1)、7-((E)-3'-甲基-4'-(7'-甲基-8'-羰基-6'-烯-呋喃)-2'-烯)-香豆素(2)、7-((E)-3'-甲基-4'-(7'-甲基-6'-亚甲基-8'-羰基-呋喃)-2'-烯)-香豆素(3)、7-((E)-3'-甲基-4'-(9'-羟基-8'-羰基-6'-烯-呋喃)-2'-烯)-香豆素(4)、7-(3'-甲基-4'-(7'-甲基-8'-羰基-6'-烯-呋喃)-2',3'-环氧丁烷)-香豆素(5)、7-(3'-甲基-4'-(9'-羟基-8'-羰基-6'-烯-呋喃)-2',3'-环氧丁烷)-香豆素(6)、7-(3'-甲基-4'-(7'-甲基-7'-羟基-8'-羰基-6'-烯-呋喃)-2',3'-环氧丁烷)-香豆素(7)、7-(3'-甲基-4'-(7'-甲基-8'-羰基-呋喃)-2',3'-环氧丁烷)-香豆素(8)、5'-羟基葡萄内酯(9)和7-((E)-7'-羟基-3',7'-二甲基-2',5'-二烯)-香豆素(10),2个四降三萜,鉴定为11β-羟基-1α-乙酰基黄柏酮(11)、11β-羟基黄柏酮(12)和1个木脂素,鉴定为(-)-丁香脂素(13)。其中化合物11和13为首次从该植物中分离得到。测定了化合物1、2、3、11和12对癌细胞株A549、Hela和BGC-823的细胞毒活性,及其对白色念珠菌(Candida albicans)、金黄色葡萄球菌(Staphylococcus aureus)的抑菌活性。结果显示,化合物1对Hela和A549均有细胞毒活性,其半数抑制质量浓度(IC_(50))值分别为11.26和13.55 mg/L,化合物3对BGC-823有细胞毒活性,其IC_(50)值为16.65 mg/L,5个化合物对白色念珠菌和金黄色葡萄球菌均没有抗菌活性。     

3,4-seco-Lupanes and other constituents from Platypodium elegans

The isolation and NMR data of seco-lupane triterpenes and coumarins from Platypodium elegans are reported.     

蝙蝠葛茎叶中化学成分的研究

初步确定了蝙蝠葛茎叶所含化学成分，结果表明，其中含有生物碱、甾体成分、内酯、香豆素及其甙类、酸性成分、鞣质、油脂、糖类及氨基酸、蛋白质。并对其粗总生物碱含量进行测定，生物碱含量达0.69%。     

Pharmacokinetic study of eight coumarins of Radix Angelicae Dahuricae in rats by gas chromatography–mass spectrometry

A sensitive, specific gas chromatography–mass spectrometry (GC–MS) method was established for the quantitative determination of eight coumarins of Radix Angelicae Dahuricae including coumarin, isopsoralen, psoralen, xanthotoxin, bergapten, osthole, imperatorin and oxypeucedanin in rat plasma. Nitrendipine was used as the internal standard (IS). The plasma samples were extracted by acetonitrile. GC separation was accomplished on a DB-5MS column with temperature programmed from 160 °C (17 min) to 190 °C (10 min) at the rate of 20 °C/min, then to 240 °C (5 min) at 20 °C/min, and finally to 280 °C (14 min) at 20 °C/min. The detection was performed on a quadrupole mass spectrometer detector operated by full-scan mode (m/z 50–500). The lower limit of quantitation was 5–10 ng/mL for eight coumarins, and the linear range was 5–1000 ng/mL for the coumarins (R² > 0.9990). All the validation data were within the required limits. After oral administration, the plasma concentration–time curves showed that the time for maximum concentration (T_max) was 1.29 for coumarin, 1.83 for isopsoralen, 1.93 for psoralen, 1.30 for xanthotoxin, 2.04 for bergapten, 0.64 for osthole, 1.41 for imperatorin and 0.51 h for oxypeucedanin. The plasma concentration of the eight coumarins was low, with a mean maximum plasma concentration (C_max) < 6.41 μg/mL. Pharmacokinetic data analysis showed that the eight coumarins had different pharmacokinetic characteristics after oral administration. The method was successfully applied to pharmacokinetic studies of eight coumarins after oral administration in rats.     

Identification of non-alkaloid acetylcholinesterase inhibitors from Ferulago campestris (Besser) Grecescu (Apiaceae)

Inhibition of Acetylcholinesterase (AChE) is still considered as a strategy for the treatment of neurological disorders such as Alzheimer's disease. Many plant derived alkaloids (such as galantamine and rivastigmine) are known for their AChE inhibitory activity. Recently, other classes of natural compounds such as terpenoids, sesquiterpene glycosides and coumarins have been studied as new AChE inhibitors, with the aim to discover less toxic compounds compared to alkaloidal ones. The Ferulago campestris roots dichloromethane extract was used for a bioassay-guided fractionation for the search of AChE inhibitors. Three coumarin derivatives (umbelliprenin 1, coladonin 2 and coladin 3), three daucane ester derivatives (siol anisate 4, ferutinin 5 and 1-acetyl-5-angeloyl lapiferol 6), two phenol derivatives (2-epilaserine 7 and epielmanticine 8) and one polyacetylene (9-epoxyfalcarindiol 9) were isolated by the bioassay-guided approach. Their structures were characterized on the basis of spectral methods (1D and 2D NMR, and MS spectroscopy). All the isolated compounds were able to inhibit the AChE (IC₅₀ 1.2–0.1 mM) although at higher doses if compared to galantamine (6.7 μM) measured in the same conditions. The most active compounds were the daucane derivative siol anisate 4 and the epielmanticine 8, with IC₅₀ of 0.172 and 0.175 mM respectively.     

Antibacterial activity of Clausena heptaphylla.

The antibacterial activity of different crude extracts of Clausena heptaphylla leaves as well as three purified coumarins, obtained from the cold methanol extract, is reported.     

NorA efflux pump inhibitory activity of coumarins from Mesua ferrea

The purpose of this investigation was to study the modulator and efflux pump inhibitor activity of coumarins isolated from Mesua ferrea against clinical strains as well as NorA-over expressed strain of Staphylococcus aureus 1199B. Seven coumarins were tested for modulator activity using ethidium bromide (EtBr) as a substrate. Compounds 1, 4–7 modulated the MIC of EtBr by ≥ 2 fold against wild type clinical strains of S. aureus 1199 and S. aureus 1199B, whereas compounds 4–7 modulated the MIC of EtBr by ≥ 16 fold against MRSA 831. Compounds 1, 4–7 also reduced the MIC of norfloxacin by ≥ 8 fold against S. aureus 1199B, and 4–6 reduced the MIC of norfloxacin by ≥ 8 fold against MRSA 831 at half of their MICs. Inhibition of EtBr efflux by NorA-overproducing S. aureus 1199B and MRSA 831 confirmed the role of compounds 4–6 as NorA efflux pump inhibitors (EPI). Dose-dependent activity at sub-inhibitory concentration (6.25 μg/mL) suggested that compounds 4 and 5 are promising EPI compared to verapamil against 1199B and MRSA 831 strains.