八角莲的化学成分研究

目的研究八角莲Dysosma versipellis根茎的化学成分。方法运用硅胶、凝胶及RP-HPLC等多种色谱技术对八角莲根茎的化学成分进行分离纯化,并根据理化性质和波谱数据鉴定化合物的结构。结果从八角莲根茎95%乙醇提取物的醋酸乙酯和正丁醇萃取部位分离并鉴定了14个化合物,其中木脂素类化合物10个,分别为4′,5′-二去甲基鬼臼毒素(4′,5′-didemethylpodophyllotoxin,1)、鬼臼毒素(podophyllotoxin,2)、4′-去甲基鬼臼毒素(4′-demethylpodophyllotoxin,3)、山荷叶素(diphyllin,4)、鬼臼毒酮(podophyllotoxone,5)、苦鬼臼毒素葡萄糖苷(picropodophyllotoxin-4-O-β-D-glucoside,6)、4′-去甲基鬼臼毒素葡萄糖苷(4′-demethylpodophyllotoxin-4-O-β-D-glucoside,7)、山荷叶素葡萄糖苷(diphyllin-4-O-β-D-glucoside,8)、鬼臼毒素葡萄糖苷(podophyllotoxin-4-O-β-D-glucoside,9)、八角莲醇(dysosmarol,10);黄酮类化合物3个,分别为山柰酚(kaempferol,11)、槲皮素(quercetin,12)、山柰黄素-3-O-β-D-吡喃葡萄糖苷(kaempferol-3-O-β-D-glucoside,13);甾醇类化合物1个,为β-谷甾醇(β-sitosterol,14)。结论化合物1为新天然产物,化合物7和8为首次从该属植物中分离得到。     

液体振荡培养八角莲愈伤组织及其鬼臼毒素的含量测定

目的研究培养八角莲的愈伤组织。方法与结果在MS＋NAA 0.2 mg/L＋6-BA3.0 mg/L的液体培养基中,愈伤组织20 d平均增加重量达53.4 g。添加0.2g/L苯丙氨酸的培养基中,鬼臼毒素的含量可达0.5%。     

八角莲及其近缘植物中木脂素的分析

用二次展开薄层层析法定性分析了鬼臼毒素类木脂素在八角莲及其近缘植物中的存在,并用变色酸比色法分析了其总木脂素的含量,为八角莲及其近缘植物的资源利用提供科学依据。结果表明八角莲及其近缘植物的根茎、根、茎叶中皆含有多种鬼臼毒素类木脂素成分,其总木脂素含量可高达2％～7％。不同种间存在较大差异。商品八角莲总木脂素含量则与产地有较大关系。     

Isolation of coumarins and ferulate from the roots of Angelica purpuraefolia and the antitumor activity of khellactone

A new coumarin, hydroxylomatin (1), was isolated from the CHCl(3)-soluble fraction of the roots of Angelica purpuraefolia, along with one ferulate (2) and three other known coumarins (3-5) including khellactone (3). The structure of hydroxylomatin (1) was determined to be 3'beta,5'-dihydroxy-3',4'-dihydroseselin (1) by spectroscopic means including 2D-NMR. The modified Mosher's method was used to determine the chiral center at C-1 of compound 2. Khellactone (3) is a major compound of the roots of A. purpuraefolia. This study also examined the antitumor activity of khellactone (3) using a LLC mouse lung carcinoma in the BDF-1 mice and a NCI-H460 human lung carcinoma in a human tumor xenograft model in nude mice. This compound (3) inhibited LLC tumor growth with a T/C (mean value of treated group/mean value of control group) value of 12.9% at a dose of 5 mg/kg and 33.2% at a dose of 10 mg/kg, respectively, in a dose-dependent manner. In addition, it suppressed the growth of NCI-H460 tumor cells, accounting for 81.4% at a dose of 10 mg/kg in nude mice.     

Bioactive constituents of the roots of Cynanchum atratum

A novel biphenylneolignan, 2,6,2',6'-tetramethoxy-4,4'-bis(2,3-epoxy-1-hydroxypropyl)biphenyl (1), and two new glycosides named atratoglaucosides A (2) and B (3), were isolated from the roots of Cynanchum atratum, and their structures were determined on the basis of chemical and spectroscopic evidence. The aglycons of 2 and 3 were identified as glaucogenin C and 7-desoxyneocynapanogenin A, a new disecopregnane. A known compound, glaucogenin C 3-O-beta-D-cymaropyranosyl-(1-->4)-alpha-L-diginopyranosyl-(1-->4)-beta-D-thevetopyranoside (4), isolated from the same source, showed a significant cytotoxic effect against 212 cells. This substance also gave a significant inhibitory effect on TNF-alpha (tumor necrosis factor-alpha) formation from the RAW 264.7 mouse macrophage-like cell line stimulated with LPS (lipopolysaccharide) and on the N9 microglial cell line stimulated with LPS/IFN-gamma (interferon-gamma).     

Anti-inflammatory and anti-tumor-promoting effects of cucurbitane glycosides from the roots of Bryonia dioica

Seven new triterpene glycosides, bryoniosides A-G (1-7), have been isolated along with two known triterpene glycosides, cabenoside D (8) and bryoamaride (9), from a methanol extract of the roots of Bryoniadioica. The structures of 1-7 were determined on the basis of spectroscopic and chemical methods. Six compounds, 2, 3, 5, and 7-9, and 11 compounds, 1-9, bryodulcosigenin (10), and bryosigenin (11), respectively, were evaluated for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice and on Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA. All compounds tested showed marked anti-inflammatory effects, with 50% inhibitory doses (ID(50)) of 0.2-0.6 mg per ear. In addition, all of the compounds tested except for compound 5 showed potent inhibitory effects on EBV-EA induction (100% inhibition at 1 x 10(3) mol ratio/TPA).     

Lignans from the roots of Saururus chinensis

Four new lignans, saucerneol F (1), saucerneol G (2), saucerneol H (3), and saucerneol I (4), were isolated from the EtOAc extract of the roots of Saururus chinensis, together with one known compound, saucerneol D (5). The structures of compounds 1-4 were elucidated by spectroscopic analysis. These compounds showed cytotoxic activities against HT-29, MCF-7, and HepG-2 cell lines.     

荜茇根化学成分及其抗肿瘤活性

目的 研究荜茇PiperlongumL.根的化学成分及其抗肿瘤活性.方法 荜茇干燥根茎95％乙醇提取物采用硅胶、Sephadex LH-20、重结晶进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构.MTT法测定其中2种典型生物碱的抗肿瘤活性.结果 从中分离得到10个化合物,分别鉴定为β.谷甾醇(1)、胡萝卜苷(...     

八角莲丛生芽分化及试管苗移栽技术研究

目的探讨了八角莲的组织培养和快速繁殖技术。方法以八角莲的叶片作为外植体,接种在不同的培养基上,观察八角莲愈伤组织丛生芽的诱导率。结果以NAA1.0mg/L+6-BA0.2mg/L的激素配比最有利于新芽生根;苔藓+腐殖土的栽培基质中,八角莲试管苗的生长状况最好。结论通过合理筛选激素配比,可促进八角莲愈伤组织产生丛生芽并生根形成幼苗,为快速繁殖八角莲提供依据。     

Bioactive carbazole alkaloids from Clausena wallichii roots

Four new carbazole alkaloids, clausenawallines C-F (1-4), along with 18 known compounds (5-22) were isolated from the roots of Clausena wallichii. Compounds 3, 9, and 22 exhibited significant antibacterial activity against methicillin-resistant Staphylococcus aureus SK1 (MRSA SK1) and Staph. aureus TISTR 1466 with MIC values in the range 4-16 μg/mL, whereas compound 4 showed the highest cytotoxicity against oral cavity cancer (KB) and small-cell lung cancer (NCI-H187) with IC(50) values of 10.2 and 4.5 μM, respectively.     

Cytotoxic constituents of the roots of Ekmanianthe longiflora

Bioactivity-directed fractionation of the CHCl(3) extract of the roots of Ekmanianthe longiflora resulted in the isolation of three new natural products, (2R,3R,4R)-3,4-dihydro-3, 4-dihydroxy-2-(3-methyl-2-butenyl)-1(2H)-naphthalenone (1), (2S,3R, 4R)-3,4-dihydro-3, 4-dihydroxy-2-(3-methyl-2-butenyl)-1(2H)-naphthalenone (2), and (2R, 3aR,9R,9aR)-9-hydroxy-2-(1-hydroxy-1-methylethyl)-2,3,3a,4,9 , 9a-hexahydro-naphtho[2,3-b]furan-4-one (3), together with the known compounds 2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-quinone (4), 2-acetylnaphtho[2,3-b]furan-4,9-quinone (5), dehydro-iso-alpha-lapachone (6), alpha-lapachone (7), catalponol, and epi-catalponol. The structures of 1-3 were determined using a combination of NMR spectroscopic techniques, and the absolute configurations of compounds 1 and 2 were obtained using Mosher ester methodology. Compounds 4-6 showed significant cytotoxicity in a panel of human cancer cells. alpha-Lapachone (7) exhibited only marginal activity, and catalponol and epi-catalponol were inactive in this regard. When tested at 72 mg/kg/injection in an in vivo mouse P-388 leukemia system, compound 4 was inactive (110% T/C).     

Protective effect of steamed American ginseng (Panax quinquefolius L.) on V79-4 cells induced by oxidative stress

Heat-processed Asian ginseng roots (Panax ginseng C.A. Meyer), also known as "red ginseng" in Asia, are reported to have more bioactivity than the no-processed white ginseng roots. Therefore, American fresh ginseng roots (Panax quinquefolius L.) were processed to the red ginseng and examined changes in bioactivity during heating process. The fresh America ginseng roots were steamed at 100 degrees C for 30, 60, 90 and 120 min, and their bioactivities were examined by analyzing the content of ginsenosides and total phenolics, and measuring DPPH and superoxide radical scavenging acivity and their protective effects on V79-4 cells viability and lipid peroxidation. The heating treatment proportionally increased total ginsenosides (4.97%, w/w) content compared with white ginseng (3.27%) and total phenolics from 444.5 mg GAE/100 g to 489.6-574.2 mg GAE/100 g. The antioxidant activity also increased from 285 mg/100 g (vitamin C equivalent) to 353-487 mg/100 g. Heated ginseng showed high levels of DPPH radical scavenging activity (59.5-88.5%) and the high level of superoxide radical scavenging activity (44.2-90.9%). The heated ginseng protected cell viability against H2O2-induced oxidative damage, and enhanced the activities of superoxide dismutase and catalase by dose dependently in V79-4 cells.     

5alpha-steroidal glycosides from Parepigynum funingense

Four new 5alpha-steroidal glycosides with an unusual framework, funingenosides A (1), B (2), C (3), and D (4), were isolated from the roots of Parepigynum funingense. Their structures were elucidated on the basis of 1D and 2D NMR techniques. The structure and relative stereochemistry of compound 1 were demonstrated by X-ray crystallographic analysis.     

Norlignans, acylphloroglucinols, and a dimeric xanthone from Hypericum chinense

Two new norlignans, hyperiones A (1) and B (2), three new acylphloroglucinols, aspidinol C (3) and hyperaspidinols A (5) and B (6), the known compound aspidinol D (4), and the symmetrical dimeric xanthone hyperidixanthone (7) were isolated from Hypericum chinense. Their structures were established by spectroscopic analysis. In an antibacterial assay using a panel of multidrug-resistant (MDR) strains, compounds 3 and 4 exhibited promising activity against the NorA efflux protein overexpressing MDR Staphylococcus aureus strain SA-1199B with a minimum inhibitory concentration (MIC) of 2 μg/mL (8.4 μM) and 4 μg/mL (16.8 μM), respectively. The positive control antibiotic norfloxacin showed activity at MIC 32 μg/mL (100 μM).     

Cytotoxic pentacyclic and tetracyclic aromatic sesquiterpenes from Phomopsis archeri

Three new sesquiterpenes, named phomoarcherins A-C (1-3), and four known compounds, kampanol A (4), R-mevalonolactone, ergosterol, and ergosterol peroxide, were isolated from the endophytic fungus Phomopsis archeri. These structures were established on the basis of spectroscopic evidence. The structure and absolute configuration of 1 were confirmed by X-ray crystallographic analysis of its p-bromobenzoate derivative (1a). Compounds 1-4 showed cytotoxicity against five cholangiocarcinoma cell lines (0.1-19.6 μg/mL), while 1 and 2 exhibited weak cytotoxicity against the KB cell line with IC(50) values of 42.1 and 9.4 μg/mL, respectively. In addition, compound 2 showed antimalarial activity against Plasmodium falciparum with an IC(50) value of 0.79 μg/mL.     

Antibacterial iridoid glucosides from Eremostachys laciniata

Eremostachys laciniata (L) Bunge (family: Lamiaceae alt. Labiatae; subfamily: Lamioideae) is one of the 15 endemic Iranian herbs of the genus Eremostachys. A decoction of the roots and flowers of E. laciniata has traditionally been taken orally for the treatment of allergies, headache and liver diseases. Three antibacterial iridoid glucosides, phloyoside I (1), phlomiol (2) and pulchelloside I (3) have been isolated from the rhizomes of this plant. The structures of these compounds were elucidated unequivocally by a series of 1D and 2D NMR analyses. The antibacterial activity and brine shrimp toxicity of these compounds were assessed using the resazurin microtitre assay and the brine shrimp lethality assay, respectively. All three iridoid glycosides 1-3 exhibited from low to moderate levels (MIC = 0.05-0.50 mg/mL) of antibacterial activity. Of these compounds, compound 3 was the most active, and displayed antibacterial activity against 9 of 12 different strains tested. The most noteworthy activity of 3 was against Bacillus cereus, penicillin-resistant Escherichia coli, Proteus mirabilis and Staphylococcus aureus with an MIC value of 0.05 mg/mL.     

西藏胡黄连的苯乙醇糖苷类化学成分研究

目的 :对西藏胡黄连Picrorhizascrophulariiflora根的苯乙醇糖苷类化学成分进行研究。方法 :采用色谱技术进行分离 ,通过¹H ,¹³C-NMR等波谱技术确定化合物的结构。结果 :分离并鉴定了 6个苯乙醇糖苷类化合物 :2-(3,4-二羟基苯基 )乙基-O/i>-β-D-吡喃葡萄糖苷 (1) ,2-(3-羟基-4-甲氧基苯基 )乙基 -O/i>-β-D- 吡喃葡萄糖基 (1→ 3)-β-D-吡喃葡萄糖苷 (2 ) ,scrosideB (3) ,hemiphrosideA (4) ,plantainosideD (5 ) ,scrosideA (6 )。结论 :其中化合物 1,2 ,4和 5系首次从该植物中分离得到 ,2为新的天然产物。     

Activity of macrocyclic jatrophane diterpenes from Euphorbia kansui in a TrkA fibroblast survival assay

Three new macrocyclic diterpenes, kansuinins F (1), G (2), and H (3), together with four known jatrophane diterpenes, kansuinins D (4), E (5), and A (6) and 3beta,5alpha,7beta,15beta-tetraacetoxy-9alpha-nicotinoyloxyjatropha-6(17)-11E-dien-14-one, were isolated from the roots of Euphorbia kansui. Compounds 1 and 2 were assigned as 6(17)-en-11,12-epoxy-14-one-type jatrophane diterpenes, and compound 3 as a 6(17)-en-11,14-epoxy-12-one jatrophane diterpene. The structures of compounds 1-3 and the relative configurations of compounds 4 and 5 were determined by spectral data analysis. Kansuinin E (5) exhibited a specific survival effect on fibroblasts that expressed TrkA, a high-affinity receptor for nerve growth factor.     

Bioactive constituents of the roots of Polyalthia cerasoides

A new dimeric aporphine alkaloid, bidebiline E (1), and a new natural product, octadeca-9,11,13-triynoic acid (2), along with three known sesquiterpenes, alpha-humulene (3), caryophyllene oxide (4), and (-)-alpha-cadinol (5), and four known isoquinoline alkaloids, laudanosine (6), codamine (7), laudanidine (8), and reticuline (9), were isolated from the roots of Polyalthia cerasoides. The structures of compounds 1 and 2 were established on the basis of their 1D and 2D NMR spectroscopic data. Among these isolates, 1, 2, 4, 7, and 8 exhibited antimalarial activity against Plasmodium falciparum, while 1- 3 showed antimycobacterial activity against Mycobacterium tuberculosis using in vitro assays.     

Diterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of Xenopus

Twelve polycyclic diterpenes have been isolated from the roots of Euphorbia kansui. Nine were assigned with an ingenol skeleton, 20-O-(2'E,4'E-decadienoyl)ingenol (1), 20-O-(2'E,4'Z-decadienoyl)ingenol (2), 3-O-(2'E,4'Z-decadienoyl)ingenol (3), 3-O-(2'E,4'E-decadienoyl)ingenol (4), 3-O-(2'E,4'Z-decadienoyl)-5-O-acetylingenol (5), 3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol (6), 3-O-(2'E,4'E-decadienoyl)-20-O-acetylingenol (7), 20-O-(decanoyl)ingenol (8), and 5-O-(2'E,4'E-decadienoyl)ingenol (9), and three with a jatrophane skeleton, kansuinins A (12), B (11), and C (10). Compounds 1, 2, 5, 9, and 12 are new compounds, while 4 and 7 were assigned with new geometric configurations. Their structures were elucidated by spectroscopic and chemical analysis. In vitro treatment of cultured individual Xenopus cells at the blastular stage with 1-9 arrested cleavage significantly (0.5 microg/mL of each compound resulted in >75% cleavage arrest). Of the three jatrophane diterpenes (10-12), only kansuinin B (11) showed any activity, resulting in 87% cleavage arrest at 50 microg/mL.