Two new ent-kaurane diterpenes from the stems of Eurya chinensis

Abstract

Two new ent-kaurane diterpenes (1–2), together with five known analogs, were isolated from the stems of Eurya chinensis. The structures of new compounds were established by extensive analysis of mass spectrometric and 1D and 2D NMR spectroscopic data. Compound 3 exhibited noticeable anti-inflammatory activity as denoted by inhibiting LPS-induced nitric oxide (NO) production in RAW264.7 cells with an IC₅₀ value of 7.82 μM. Compound 4 showed potent cytotoxic activity against human cancer cell lines NCI-H46, HepG2 and SW480 with IC₅₀ values ranging from 7.45 to 8.54 μM.     

Anti-inflammatory amide alkaloids from the stems of Clausena emarginata

Two new amide alkaloids, clauemaramide A (1) and clauemaramide B (2), and three known analogs were isolated from the stems of Clausena emarginata. Their structures were determined on the basis of spectroscopic analyses. The absolute configurations of 1 and 2 were confirmed by CD spectroscopy. Compound 3 showed moderate inhibitory effects on LPS-induced NO production (IC₅₀ value = 4.9 μM).     

Three new coumarin glycosides from the stems of Hydrangea paniculata

Three new coumarin glycosides (1-3), together with three known compounds (4-6), have been obtained from the stems of Hydrangea paniculata Sieb. Their structures were elucidated based on spectroscopic data and chemical evidence. In addition, compounds 1-3 were screened for their neuroprotective effects against serum deprivation-induced PC12 cell damage, hepatoprotective activities against DL-galactosamine-induced toxicity in HL-7702 cells and their ability to inhibit LPS-induced nitric oxide production in the murine microglia BV2 cell line, but they were inactive.     

一种中华稻蝗成虫抗菌蛋白质的初步分离

目的提取中华稻蝗成虫中的抗菌蛋白质并测定其抗菌活性。方法对中华稻蝗成虫经针刺损伤和菌液浸泡相接合的方法处理,粗提液经沸水浴热变性、凝胶过滤色谱、高效液相色谱分析,初步分离中华稻蝗成虫中的抗菌蛋白质,以金黄色葡萄球菌为指示菌,抑菌圈法检测其抗菌活性。结果经高效液相色谱分析表明中华稻蝗成虫中能产生抗菌蛋白质,其相对分子质量约为3 600。结论首次从直翅目昆虫中华稻蝗中分离到对革兰阳性菌有较强活性的抗菌蛋白质。     

Anti-oxidative and photo-protective effects of coumarins isolated fromFraxinus chinensis

Free radicals and reactive oxygen species (ROS), which are generated by UV irradiation, may cause serious injury to skin cell membranes, DNA and functional proteins. In addition, these agents stimulate the expressions of matrix metalloproteinases (MMPs), which can degrade most components of the extracellular matrix (ECM), including collagen. In order to develop new anti-photoaging agents, five major components from the extract of Fraxinus chinensis extract (FCE) were identified. Two of the major components of FCE were found to be esculin (11.2%) and esculetin (1.9%). FCE (IC50: 50.0 microg/mL 1, 1-diphenyl-2-picrylhydrazyl (DPPH); 19.8 microg/mL, superoxide anion radical) and esculetin (IC50: 2.1 microg/mL DPPH; 0.6 microg/mL, superoxide anion radical) showed strong antioxidative activities. Of the compounds tested, esculetin showed the strongest scavenging activity against DPPH radicals, followed by superoxide anions from the xanthine/xanthine oxidase system. The intracellular ROS scavenging activity showed that oxidation of 5-(6-)-chloromethyl-2', 7'-dichlorodihydrofluorescein diacetate (CM-H2DCFDA) was effectively inhibited by esculetin, with potent free radical scavenging activity was also shown in UVB-irradiated human dermal fibroblasts (HDFs). Moreover, treatment of UVA-irradiated HDFs with esculetin resulted in dose-dependent decreases in the expression levels of MMP-1 mRNA and protein. From these results, FCE and one of its components, esculetin, were predicted to be potentially useful as ingredients in cosmetics for protecting against photoaging.     

Highly oxygenated triterpenoids from the roots of Schisandra chinensis and their anti-inflammatory activities

A new highly oxygenated triterpenoid, schinchinenlactone D (1), and three known compounds (2–4) were isolated from the roots of Schisandra chinensis. Their structures were determined by combining the spectroscopic analysis with the theoretical computations. The anti-inflammatory activities of compounds 1–4 were evaluated, and compound 3 exhibits the most significant activity in the inhibition of NO production with an IC₅₀ value of 10.6 μM.     

Two new unsaturated fatty acids from the whole plant of Pothos chinensis

Two new unsaturated fatty acids, (Z)-octadec-13-en-11-ynoic acid (1) and (Z)-octadec-16-en-12,14-diynoic acid (2), along with six known compounds were isolated from the whole plant of Pothos chinensis. The structures of these compounds were elucidated by detailed spectroscopic analysis, including 1D and 2D NMR data. Compound 2 showed moderate antibacterial activity against Staphylococcus aureus.     

Anti-inflammatory isoflavonoids from the stems of Derris scandens

Fractionation of the aqueous extract of Derris scandens stems extract using tests for eicosanoid inhibition resulted in the isolation of three isoflavonoids, genistein, its 7- O-alpha-rhamno(1-->6)-beta-glucosyl glycoside, a new compound, and two known isoprenyl derivatives 3'-gamma,gamma-dimethylallylweighteone and scandenin. The isoprenylated compounds showed a high inhibitory effect on eicosanoid production in vitro but HPLC analysis showed that the genistein accounted for most of the activity of the total extract. Antioxidant studies showed that genistein and the isoprenylated compounds showed activity comparable to standard antioxidants. Genistein and its glycoside demonstrated no cytotoxicity in the MTT test but the prenylated compounds showed some toxicity and also increased LDH release from polymorphonucleocytes, at concentrations much greater than would be encountered in an aqueous extract of D. scandens.     

白花蛇舌草总黄酮的抗炎及抗菌作用

目的观察白花蛇舌草总黄酮抗炎及抗菌作用。方法采用二甲苯诱导小鼠耳肿胀模型、大鼠松节油气囊肉芽增生模型、新鲜蛋清诱导大鼠足爪肿胀模型、醋酸所致小鼠毛细血管通透性增高试验和体外抗菌试验,观察白花蛇舌草总黄酮的抗炎及抗菌作用。结果白花蛇舌草总黄酮(15、30、60mg·kg-1)对二甲苯诱导的小鼠耳肿胀和醋酸所致小鼠毛细血管通透性增高有一定的抑制作用;白花蛇舌草总黄酮(12、24、48mg·kg-1)对大鼠松节油气囊肉芽增生和新鲜蛋清诱导大鼠足爪肿胀亦有明显的抑制作用;在体外,白花蛇舌草总黄酮对球菌和杆菌均具有不同程度的抑菌和杀菌作用,且对球菌的作用优于杆菌。结论白花蛇舌草总黄酮具有抗炎及抗菌作用。     

Chrysoeriol isolated from Eurya cilliata leaves protects MC3T3-E1 cells against hydrogen peroxide-induced inhibition of osteoblastic differentiation

Chrysoeriol is a flavonoid compound found in several tropical medicinal plants. To elucidate the protective effects of chrysoeriol isolated from Eurya cilliata on the response of osteoblasts to oxidative stress, osteoblastic MC3T3‐E1 cells were incubated with chrysoeriol and/or H₂O₂, and markers of osteoblast function and oxidative damage were examined. Chrysoeriol treatment significantly (P < 0.05) reversed the cytotoxic effect of H₂O₂ and increased collagen content, alkaline phosphatase activity and calcium deposition of osteoblasts in the presence of H₂O₂. These effects were blocked by ICI182780, suggesting that chrysoeriol's effect might be partly involved in estrogen action. Moreover, H₂O₂‐induced reduction of osteocalcin was recovered in the presence of chrysoeriol. Chrysoeriol significantly (P < 0.05) decreased the production of receptor activator of nuclear factor‐κB ligand, interleukin‐6, protein carbonyl and malondialdehyde of MC3T3‐E1 cells in the presence of H₂O₂. These results demonstrate that chrysoeriol isolated from E. cilliata can protect osteoblasts from oxidative stress‐induced toxicity. Copyright © 2010 John Wiley & Sons, Ltd.     

Chemical constituents from the roots and stems of Litsea cubeba

A new monoterpene and a new lignan, named litsecols A and B (1 and 2), respectively, together with nine known compounds (3–11), were isolated in a continuous investigation on the roots and stems of Litsea cubeba. Their structures were elucidated on the basis of extensive spectroscopic data analysis, and the absolute configuration of 1 was resolved by X-ray diffraction analysis. Compounds 2–5 and 7–9 showed significant inhibitory activity against nitric oxide (NO) production in lipopolysaccharide (LPS)-induced murine microglial (Bv-2) cell line. Compounds 10 and 11 exhibited significant neuroprotective effect against hydrogen peroxide-induced oxidative damage in rat adrenal pheochromocytoma (PC12) cell line.     

杠板归抗炎及抑菌活性部位研究

目的研究杠板归抗炎及体外抑菌作用以确定其有效部位。方法采用二甲苯诱发小鼠耳廓炎症、采用新鲜鸡蛋清致小鼠足肿胀评价其抗炎作用；采用试管二倍稀释法评价其抑菌作用。结果杠板归总提部位具有显著的抗炎作用，正丁醇部位有一定的抗炎作用；体外抑菌实验表明，杠板归乙酸乙酯部位对金黄色葡萄球菌、大肠杆菌、粪链球菌、铜绿假单孢菌有明显的抑菌作用，对白色念球菌有一定的抑菌作用。结论杠板归总提部位具有显著的抗炎活性，正丁醇部位有一定抗炎活性，杠板归乙酸乙酯部位抑菌作用明显，证实了杠板归用于炎症治疗的科学性。     

香豆素苯并三唑的合成、抗微生物活性及其与氯霉素和氟康唑协同作用研究

以间苯二酚为起始原料,经过环化、醚化、N-烷化等多步反应合成了一系列新型香豆素苯并三唑类化合物,其结构经1H NMR、IR、MS和元素分析证实。体外考察了合成的香豆素类化合物抗革兰阳性菌、革兰阴性菌及真菌活性。结果表明香豆素苯并三唑能有效抑制细菌和真菌的生长,其中化合物11a～11e和13a～13c抗普通变形杆菌ATCC 6896活性强于氯霉素(chloromycin)。化合物11a和11b抑制金葡菌ATCC 25923和藤黄微球菌ATCC 4698的生长能力与氯霉素相当。化合物11a～11d抗烟曲霉菌ATCC 96918活性优于氟康唑(fluconazole)。此外,氯霉素或氟康唑与香豆素苯并三唑联用后,不仅减少了用药剂量,还拓宽了抗微生物谱,尤其增强了抑制耐甲氧西林的金葡菌N 315和氟康唑不敏感的烟曲霉菌的生长能力。     

Anti-inflammatory pterocarpanoids from the roots of Pongamia pinnata

A phytochemical study on the roots of Pongamia pinnata afforded 11 pterocarpanoids, including three new compounds. The structures of the isolated compounds were determined by 1D and 2D NMR and HRESIMS data. The absolute configurations of the new compounds were assigned via analysis of the specific rotations and electronic circular dichroism (ECD) spectra. The isolates were evaluated for their inhibitory effects on nitric oxide (NO) production in LPS-stimulated BV-2 microglial cells. Six compounds exhibited inhibitory effects against NO production, and compound 5 showed the best activity with an IC₅₀ value at 12.0?μM.     

Antimicrobial constituents from the flowers of Trollius chinensis

A new 1-aryl-isochroman, trolliusol A (1), was isolated from the flowers of Trollius chinensis, along with seven known phenolic compounds in an antimicrobial activity-directed phytochemical investigation. The structures of these compounds were elucidated by spectroscopic methods, and their inhibitory activities against one fungus and four bacterial strains were measured.     

柽柳花挥发性成分研究

目的:定性分析柽柳花中的挥发性成分。方法:采用固相微萃取技术提取柽柳花的挥发性成分,采用气相色谱-质谱联用技术结合保留指数法鉴定其成分。结果:从柽柳花的挥发油中共鉴定出36个化合物,其中含量最高的是十五烷(9.80%),其次为6,10,14-三甲基-2-十五烷酮(7.61%)、5,6-二氢-6-戊基-2H-吡喃-2-酮(6.83%)、十六烷(6.25%)和二氢猕猴桃内酯(5.13%)。结论:本研究可为进一步开发利用柽柳资源提供科学依据。     

A new benzofuranone and anti-HIV constituents from the stems of Rhus chinensis

A new benzofuran lactone, rhuscholide A (1), was isolated from the stems of RHUS CHINENSIS, together with six known compounds: 5-hydroxy-7-(3,7,11,15-tetramethylhexadeca-2,6,10,11-tetraenyl)-2(3 H)-benzofuranone (2), betulin (3), betulonic acid (4), moronic acid (5), 3-oxo-6 beta-hydroxyolean-12-en-28-oic acid (6) and 3-oxo-6 beta-hydroxyolean-18-en-28-oic acid (7). Based on 1D, 2D NMR (COSY, HMQC, HMBC) and mass (EI-MS, HR-EI-MS) spectral data, the structure of rhuscholide A was deduced to be 5-hydroxy-3-(propan-2-ylidene)-7-(3,7,11,15-tetramethylhexadeca-2,6,10,11-tetraenyl)-2(3 H)-benzofuranone (1). Anti-HIV-1 bioassays IN VITRO revealed that compound 1 possesses significant anti-HIV-1 activity with an EC50 value of 1.62 microM and a therapeutic index (TI) of 42.40. Compounds 2, 4, 5 and 7 showed moderate anti-HIV-1 activities with EC50 values of 3.70, 5.81, 7.49 and 13.11 microM, respectively.     

香豆素类化合物药理和毒理作用的研究进展

香豆素类化合物是自然界重要的一类天然有机化合物,存在于不同种属的植物中,具有广泛的用途。实验研究发现香豆素具有抗HIV、抗肿瘤、抗氧化、抗炎等多种药理活性,在临床上广泛用于抗凝血和淋巴管性水肿的治疗。近年来的研究发现,香豆素类化合物在啮齿类动物中存在着明显的毒性作用,且具有种属和位点特异性,这与其代谢途径和CYP2A6酶的多态性有关。另外,毒性作用还与给药剂量和给药途径密切相关,口服和高剂量给药更容易产生毒性反应。该文综述了近年来有关香豆素及其衍生物在药理和毒理方面的研究进展,以期为香豆素类化合物的研发和临床应用提供帮助。     

茯苓总三萜的抗炎作用研究

目的研究茯苓总三萜对急、慢性炎症的抑制作用。方法采用二甲苯诱导的小鼠耳肿胀、冰醋酸诱导的小鼠腹腔毛细血管通透性实验、角叉菜胶诱导的大鼠足爪肿胀、棉球诱导的大鼠肉芽肿模型,观察茯苓总三萜的抗炎作用。结果茯苓总三萜（50、150、450mg·kg-1）灌胃（ig）给药对二甲苯诱导的小鼠耳肿胀和冰醋酸引起的腹腔毛细血管渗出有明显的抑制作用;能明显减轻角叉菜胶诱导的大鼠足爪肿胀、棉球诱导的大鼠肉芽肿。结论茯苓总三萜具有良好的抗炎作用。     

New ecdysteroid and ecdysteroid glycosides from the roots of Serratula chinensis

Three new ecdysteroid glycosides (1–3) and one new ecdysteroid (4), were isolated from the roots of Serratula chinensis. Their structures were established on the basis of extensive spectroscopic analysis and chemical methods.