Antioxidative constituents from the leaves of Hypericum styphelioides

Two new compounds have been isolated from the leaves of Hypericum styphelioides. Their structures have been established on the basis of mass spectrometry and 2D NMR techniques as 1,3,5-trihydroxy-2-(2',2'-dimethyl-4'-isopropenyl)cyclopentanylxanthone (1) and 3,5-dihydroxybenzophenon-4-beta-d-glucoside (2). Known compounds 5-O-demethylpaxanthonin (3) and 3-geranyl-1-(3-methylbutanoyl)phloroglucinol (4) were also isolated and characterized. Compounds 1-4 were evaluated for their antioxidative properties in Trolox equivalent antioxidant activity (TEAC) and chemiluminescence (CL) assays.     

光肺衣的化学成分研究

从地衣植物光肺衣中分离得到6个化合物,经光谱数据分析鉴定它们的结构分别为ergosterol(1),stict-an-3β,22α-diol(2),ethyl orsellinate(3),3-O-methyl-1,2∶5,6-bis-O-(1-methylethylidene)-d-chiro-inositol(4),retigericacid B(5)和retigeric acid A(6)。化合物1~4均系首次从本植物中分离得到。     

Antiviral phloroglucinols from New Zealand Kunzea species.

Four acyl-phloroglucinol derivatives showing antiviral activity have been isolated from Kunzea sinclairii and Kunzea ericoides (Myrtaceae) from New Zealand. The structures of these compounds were deduced from analysis of spectral data. Two of these compounds, 1 and 2, are the isomers of isobutyryl methoxyresorcinol. The two new compounds, 3 and 4, were isolated as a mixture and determined to be 4-cyclohexene-1,3-dioxo-5-hydroxy-2,2,6,6-tetramethyl-4- (1-[2,6-dihydroxy-4- methoxy-3-(3-methyl-1-oxobutyl)phenyl]-3-methylbutyl) and its 2-methyl-1-oxopropyl analogue, respectively.     

New lignans from the roots of Valeriana prionophylla with antioxidative and vasorelaxant activities

Two new 7,9':7',9-diepoxylignan glycosides have been isolated from the roots of Valeriana prionophylla. Their structures have been established on the basis of 1D and 2D NMR experiments as prinsepiol-4-O-beta-D-glucopyranoside (1) and fraxiresinol-4'-O-beta-D-glucopyranoside (2). In addition, 8-hydroxypinoresinol-4'-O-beta-d-glucopyranoside (3), 8-hydroxypinoresinol (4), prinsepiol (5), and chlorogenic acid were isolated. Compounds 1, 3, 4, and 5 were evaluated for their antioxidative properties in Trolox equivalent antioxidant activity (TEAC) and chemiluminescence (CL) assays. The same compounds were tested for their vascular activity in rat aorta rings. The aglycones 4 and 5 displayed powerful antioxidant activity; in addition, aglycone 4 showed a higher vasorelaxant activity than compounds 1, 3, and 5.     

新疆一枝蒿化学成分研究Ⅱ

目的：研究新疆一枝蒿Artemisia rupestris全草的化学成分。方法：采用硅胶柱色谱,聚酰胺柱色谱,Sephadex LH-20等方法进行分离纯化,采用光谱分析和理化常数对照等方法对所得化合物进行结构鉴定。结果：从新疆一枝蒿的丙酮部位分离鉴定了11个化合物,分别为洋槐苷(1),槲皮素(2),蒙花苷(3),木犀草素(4),蔗糖(5),田蓟苷(6),木犀草素-7-O-葡萄糖苷(glucoteolin,7),阿魏酸-4′-O-葡萄糖苷(β-D-3′-methoxy-4′-O-P-coumaroylglucoside,8),陆地棉苷(9),甲基香豆酸乙酯,［3-(4-methoxyphenyl)-(E)-2-propenoic acid ethyl ester,10］,芦丁(11)。结论：所有化合物为首次从该植物中分离得到。     

Macrophage activating activity of pyrrole alkaloids from Morus alba fruits

Ethnopharmacological relevance

The fruits of Morus alba have been traditionally used as a tonic to enhance immune responses.

Materials and methods

The macrophage activating constituents of Morus alba fruits were purified using various column chromatography techniques. The structures of isolated compounds were determined on the basis of spectroscopic data interpretation such as 1D and 2D NMR analysis. The macrophage activating activities of isolated compounds were evaluated by measuring the production of nitric oxide, TNF-α and IL-12 in RAW 264.7 cells. The phagocytic activity was also evaluated.

Results

Five pyrrole alkaloids, 5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde (1), 2-formyl-1H-pyrrole-1-butanoic acid (2), 2-formyl-5-(hydroxymethyl)-1H-pyrrole-1-butanoic acid (3), 2-formyl-5-(methoxymethyl)-1H-pyrrole-1-butanoic acid (4) and Morrole A (5) were isolated from the fruits of Morus alba. Morrole A (5) is first reported in nature and other pyrrole alkaloids (1–4) are first reported from Morus species. Among the isolated compounds, compounds 3 and 4 significantly activated macrophage activity by the enhancement of nitric oxide, TNF-α and IL-12 production, and the stimulation of phagocytic activity in RAW 264.7 cells.

Conclusion

Pyrrole alkaloids, including a new compound, were isolated from Morus alba fruits. These compounds activated macrophage activity in RAW 264.7 cells.     

网胰藻Hydroclathrus clathratus中次级代谢物的分离与结构鉴定

从中国南海网胰藻Hydroclathrus clathratus中分离得到4个化合物，经MS、^1H NMR、^13C NMR等方法鉴定其结构分别为软酯酸-1-甘油酯(1)、N-(2‘-羟基-1’-羟甲基十五烷基)二十脂肪酸酰胺(2)、尿嘧啶(3)、甘露醇(4)。其中化合物1、2、3均为首次从该藻中分离得到。     

5,6:8,9-diepoxy and other cytotoxic sterols from the marine sponge Homaxinella sp

Four new (1, 2, 4, and 5) and 14 known (3 and 6-18) polyoxygenated sterols have been isolated from the MeOH extract of the marine sponge Homaxinella sp. by bioactivity-guided fractionation. The planar structures of the sterols were established by 1D and 2D NMR and MS spectroscopic analysis. 5,6:8,9-Diepoxy sterols (1-3) were isolated from a marine organism for the first time. The isolated sterols were tested against a panel of five human solid tumor cell lines and exhibited varying degrees of cytotoxicity.     

Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria

Four chalcone glycosides (1-4), including three new natural products, and three flavanones (5-7) were isolated from the methanol extract of stem bark of Maclura tinctoria. The new compounds have been characterized as 4'-O-beta-D-(2' '-p-coumaroyl)glucopyranosyl-4,2',3'-trihydroxychalcone (1), 4'-O-beta-D-(2' '-p-coumaroyl-6' '-acetyl)glucopyranosyl-4,2',3'-trihydroxychalcone (2), and 3'-(3-methyl-2-butenyl)-4'-O-beta-D-glucopyranosyl-4,2'-dihydroxychalcone (3); the known derivatives were elucidated as 4'-O-beta-D-(2' '-acetyl-6' '-cinnamoyl)glucopyranosyl-4,2',3'-trihydroxychalcone (4), eriodictyol 7-O-beta-D-glucopyranoside (5), naringenin (6), and naringenin 4'-O-beta-D-glucopyranoside (7). Their structures were determined by 1D and 2D NMR and ESIMS. The antioxidant activity of all the isolated compounds was determined by measuring free-radical-scavenging effects using two different assays, namely, the Trolox Equivalent Antioxidant Capacity (TEAC) assay and the coupled oxidation of beta-carotene and linoleic acid (autoxidation assay). The results showed that compound 3 was the most active in both antioxidant assays.     

滇重楼的抗肿瘤活性成分研究

目的：研究滇重楼Paris polyphylla Smith var. yunnanensis根茎中具有抗肿瘤作用的活性成分。方法：利用硅胶柱色谱,Sephadex LH-20,反相制备HPLC等手段进行分离纯化,并通过波谱技术进行结构鉴定。采用MTT法对分离到的化合物进行抗肿瘤活性筛选。结果：从醋酸乙酯和正丁醇层中分离得到了6个化合物,鉴定为薯蓣皂苷元-3-O-α-L-呋喃阿拉伯糖基(1→4)-β-D-葡萄糖苷(1)、偏诺皂苷元-3-O-α-L-呋喃阿拉伯糖基(1→4)-β-D-葡萄糖苷(2)、异鼠李素-3-O-β-D-葡萄糖苷(3)、乙基-α-D-呋喃果糖苷(4)、偏诺皂苷元-3-O-α-L-吡喃鼠李糖基(1→4)-［α-L-吡喃鼠李糖基(1→2)］-β-D-葡萄糖苷(5)、偏诺皂苷元-3-O-α-L-吡喃鼠李糖基(1→4)-α-L-吡喃鼠李糖基(1→4)-［α-L-吡喃鼠李糖基(1→2)］-β-D-葡萄糖苷(6)。结论：化合物1～4为首次从滇重楼中分离得到,化合物3和4为首次从重楼属植物中分离得到,化合物5为首次从滇重楼的根茎中分离得到。药理实验表明,化合物1～3,5和6对小鼠肺腺癌细胞LA795都显示出一定的抑制作用,其中化合物5和6最显著。