Sesquiterpene chromones from Ferula fukanensis and their nitric oxide production inhibitory effects

Five new sesquiterpene chromone derivatives, fukanefurochromones A-E (1-5), were isolated from a 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated on the basis of spectroscopic evidence, especially heteronuclear multiple-bond connectivity (HMBC) and high-resolution MS. The sesquiterpene chromone derivatives inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma).     

Sesquiterpene coumarins from Ferula fukanensis and nitric oxide production inhibitory effects

Six new sesquiterpene coumarin derivatives, 2,3-dihydro-7-hydroxy-2R,3R-dimethyl-2-[4,8-dimethyl-3(E),7-nonadien-6-onyl]furo[3,2-c]coumarin (4), fukanefuromarin A (5), fukanefuromarin B (6), fukanefuromarin C (7), fukanefuromarin D (8), and fukanemarin A (9), were isolated from a 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated on the basis of spectral evidence, especially heteronuclear multiple-bond connectivity (HMBC), nuclear Overhauser exchange spectroscopy (NOESY), and high-resolution MS. An extract of F. fukanensis (FFE) and the sesquiterpene coumarin derivatives inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma).     

Saponins from Cussonia bancoensis and their inhibitory effects on nitric oxide production

Two new triterpenoid saponins (1 and 2) were isolated from the stem bark of Cussonia bancoensis together with the known stigmasterol, ursolic acid, 23-hydroxyursolic acid (3), and 3beta-hydroxylup-20(29)-en-28-oic acid. On the basis of their spectroscopic data and on chemical transformations, the structures of the new saponins have been established as 3-O-(alpha-Ll-arabinopyranosyl)-23-hydroxyursolic acid (1) and 3-O-(beta-D-glucopyranosyl)-23-hydroxyursolic acid (2). In a nitric oxide (NO)-production bioassay, compound 3 exhibited significant NO inhibitory activity, while compounds 1 and 2 were less potent than 3.     

Kadsuralignans H-K from Kadsura coccinea and their nitric oxide production inhibitory effects

One new arylnaphthalene lignan named kadsuralignan H ( 1) and three new dibenzocyclooctadiene lignans, named kadsuralignans I ( 2), J ( 3), and K ( 4), respectively, were isolated from an EtOAc fraction of the 80% acetone extract of Kadsura coccinea. The structures were elucidated on the basis of spectroscopic evidence. Compound 1 is the second arylnaphthalene lignan isolated from the Kadsura genus. Compounds 1 and 3 showed inhibitory activity on nitric oxide (NO) production by the murine macrophage-like cell RAW264.7, which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (INF-gamma).     

云南石仙桃的化学成分及其抑制NO生成的作用

目的研究云南石仙桃全草的化学成分,并通过测定所得化合物抑制大鼠巨噬细胞中NO的生成量,以确定云南石仙桃中抑制NO生成的活性成分。方法采用多种柱色谱法进行分离纯化,并根据理化常数和光谱分析进行结构鉴定。利用微板紫外比色法,体外测定各化合物对脂多糖(LPS)和γ-干扰素(IFN-γ)诱导的RAW 264.7大鼠巨噬细胞NO的生成量。结果分离得到了7个化合物,分别为反式-3,3,′5-三羟基-2′-甲氧基二苯乙烯(trans-3,3,′5-trihydroxy-2′-m ethoxystilbene,Ⅰ)、顺式-3,3′-二羟基-5-甲氧基二苯乙烯(cis-3,3-′d ihydroxy-5-m ethoxystilbene,Ⅱ)、反式-3,3,′5-三羟基二苯乙烯(trans-3,3,′5-trihydroxystilbene,Ⅲ)、3,3′-二羟基-5-甲氧基联苄(3,3-′d ihydroxy-5-m ethoxyb ibenzy l,batatas in-Ⅲ,Ⅳ)、3,4′-二羟基-3,′5-二甲氧基联苄(3,4-′d ihydroxy-3,′5-d im ethoxyb ibenzy l,g igan to l,Ⅴ)、3,3,′5-三羟基联苄(3,3,′5-trihydroxyb ibenzy l,Ⅵ)、2,7-二羟基-4-甲氧基-9,10-二氢菲(贝母兰宁,2,7-d ihydroxy-4-m ethoxy-9,10-d ihydrophenan threne,coe lon in,Ⅶ)。结论化合物Ⅱ、Ⅳ、Ⅵ具有较强的抑制大鼠巨噬细胞NO生成的作用。化合物Ⅰ和Ⅱ为新化合物,化合物Ⅲ~Ⅶ为首次从该属植物中分离得到。     

Steroids and flavonoids from Physalis alkekengi var. franchetii and their inhibitory effects on nitric oxide production

Four new steroidal compounds possessing a rare 13,14-seco-16,24-cycloergostane skeleton, physalin Y ( 1), physalin Z ( 2), physalin I ( 6), and physalin II ( 7), were isolated from the 80% EtOH extract of calyces from Physalis alkekengi var. franchetii together with 11 known steroids ( 3- 5 and 8- 15) and eight flavonoids ( 16- 23). The structures of the new compounds were elucidated primarily on the basis of 1D and 2D NMR and mass spectroscopic studies. The relative configuration of the 3-OH group of 3, 4, and 5 was also established or re-established. The inhibitory effects of compounds 1- 23 on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated.     

Neoflavonoids and related constituents from Nepalese propolis and their nitric oxide production inhibitory activity

A methanolic extract of Nepalese propolis yielded 10 new open-chain neoflavonoids (1-10), a new chalcone (11), and eight previously reported compounds (12-19). Their structures were determined on the basis of spectroscopic data and chemical conversion. The isolated compounds other than 5, 8, and 16 showed dose-dependent inhibitory activities on nitric oxide production in lipopolysaccharide-activated macrophage-like J774.1 cells and were more active than a positive control, N(G)-monomethyl-L-arginine (IC(50), 27.1 microM). The most potent activities, of 6 and 7 (IC(50), 0.5 microM), were greater than another positive control, caffeic acid phenethyl ester (IC(50), 4.8 microM).     

Sesquiterpene coumarins from Ferula gumosa

A new sesquiterpene coumarin, gumosin (1), two new sesquiterpene coumarin glycosides, gumosides A (2) and B (3), and 10 known compounds, namely, cauferoside (4), feselol (5), conferoside, ferilin, ferocaulidin, ligupersin A, conferol, and daucosterol, and the phenolic compounds acantrifoside E and 4-hydroxybenzoic acid 4-(6-O-sulfo)glucopyranoside, were isolated from a methanolic extract of Ferula gumosa roots. The structures of 1-3 were elucidated by spectroscopic data interpretation. The cytotoxic activity of the sesquiterpene coumarin derivatives was evaluated against a small panel of cancer cell lines.     

Sesquiterpene lactones and phenylpropanoids from Cosmos pringlei

Activity-directed fractionation of a phytotoxic extract from Cosmos pringlei led to the isolation of three new compounds, namely, 1'-isovaleroyloxy-4-O-isobutyryleugenol (1), zaluzanin C isobutyrate (2), and zaluzanin C isovalerate (3). In addition, mokko lactone, 1'-isobutiroyloxy-4-O-isobutyryleugenol (4), dehydrocostus lactone (5), costunolide (6), 15-isovaleroyloxycostunolide (7), 15-isobutiroyloxycostunolide (8), 1',2'-epoxy-3',4'-di-isobutyryl-Z-coniferyl alcohol, and 3beta-hydroxy-5alpha-pregn-16-en-20-one were obtained. The structures of the new compounds were established by spectral methods. Compounds 5-7 caused inhibition of radicle growth of seedlings of Amaranthus hypochondriacus.     

Sesquiterpene lactones from the roots of Ferula varia and their cytotoxic activity

The ethyl acetate-soluble fraction from a MeOH extract of the roots of Ferula varia gave six new sesquiterpene lactones (1-6) and five known sesquiterpenes (7-11). Their structures were established on the basis of spectroscopic evidence. The cytotoxic activities of 1-11 were evaluated against selected human cancer cell lines. Compound 4 showed significant selective cytotoxicity against multidrug-resistant cancer cells (KB-C2). The cytotoxicities of compounds 1, 3, 5, 8, and 11 against KB-C2 cells were enhanced in the presence of nontoxic concentrations of colchicine.     

Sesquiterpene coumarins and related derivatives from Ferula pallida

Six new compounds-two sesquiterpene coumarins, pallidones A and B (1, 2), and four related derivatives, pallidones C-F (3-6), as well as two known sesquiterpene coumarins, feselol (7) and conferol (8), have been isolated from the EtOAc extracts of the roots of Ferula pallida. All structures of these compounds were determined on the basis of spectral evidence, especially 2D NMR ((1)H-(1)H COSY, HSQC, HMBC, and NOESY) and HRMS. The possible biosynthetic pathway of pallidones C-F (3-6) is discussed.     

Quinolone alkaloids with nitric oxide production inhibitory activity from Orixa japonica

Four new quinolone alkaloids, orixalone A (1), B (2), C (3), and D (4), together with 12 known compounds were isolated from the stems of Orixa japonica. Orixalone A (1) inhibited nitric oxide production in murine macrophage-like RAW 264.7 cells stimulated with interferon-gamma and lipopolysaccharide.     

Sesquiterpene phenylpropanoid and sesquiterpene chromone derivatives from Ferula pallida

Four novel compounds-two sesquiterpene phenylpropanoid derivatives, pallidones G (1) and H (2), and two sesquiterpene chromone derivatives, pallidones I (3) and J (4)-have been isolated from the roots of Ferula pallida. Their structures were determined on the basis of NMR and HREIMS evidence.     

羌活中的香豆素类成分及其抑制脂多糖诱导的RAW 264.7细胞NO生成活性的研究

目的研究羌活Notopterygium incisum的香豆素类成分及其抗炎活性。方法采用硅胶、HPLC等柱色谱方法进行分离纯化,通过质谱、核磁共振波谱数据鉴定化合物的结构;采用脂多糖(LPS)诱导的小鼠巨噬细胞RAW 264.7炎症反应模型,考察羌活中香豆素类成分对炎症反应模型一氧化氮(NO)生成的影响。结果从羌活甲醇提取物分离得到24个香豆素类化合物,分别鉴定为异欧前胡素(1)、川白芷素(2)、补骨脂素(3)、香柑内酯(4)、茵陈素(5)、欧芹酚(6)、5-去氢羌活醇(7)、环氧脱水羌活醇(8)、7″-O-甲基异羌活醇(9)、佛手柑素(10)、7-异戊烯氧基-6-甲氧基-香豆素(11)、栓翅芹烯醇(12)、羌活醇(13)、去甲呋喃羽叶芸香素(14)、异羌活醇(15)、蛇床夫内酯(16)、6-异戊烯氧基伞形花内酯(17)、紫花前胡苷元(18)、异虎耳草素(19)、紫花前胡苷(20)、前胡苷V(21)、前胡苷I(22)、印枳苷元-11-O-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖苷(23)、羌活苷(24)。化合物7～10、13和15抑制LPS诱导的RAW 264.7细胞NO生成活性最强,最大半数抑制浓度(IC_(50))值为8.50～35.12μmol/L。结论化合物7为新的天然产物,化合物17为首次从羌活中分离得到;C-5位上具有多烯烃结构的香豆素抑制LPS诱导的RAW 264.7细胞NO生成活性较强。     

Staminane- and isopimarane-type diterpenes from Orthosiphon stamineus of Taiwan and their nitric oxide inhibitory activity

From the MeOH extract of Taiwanese Orthosiphon stamineus, two new staminane-type diterpenes, staminols C (1) and D (2), and three new isopimarane-type diterpenes, orthosiphonone C (3) and D (4) and 14-deoxo-14-O-acetylorthosiphol Y (5), have been isolated together with 16 known diterpenes, orthosiphols A, B, D, K, M, N, O, X, and Y, nororthosiphonolide A, neoorthosiphol B, orthosiphonone A, secoorthosiphols B and C, 3-O-deacetylorthosiphol I, and 2-O-deacetylorthosiphol J. Their structures were determined on the basis of the spectroscopic data. All the newly isolated diterpenes exhibited dose-dependent inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophage-like J774.1 cells, and 2-O-deacetylorthosiphonone A showed the most potent activity, with an IC(50) value of 35.0 microM, comparable to that of the positive control N(G)-monomethyl-L-arginine (L-NMMA; IC(50), 35.7 microM).     

Butanolides from Machilus thunbergii and their inhibitory activity on nitric oxide synthesis in activated macrophages

In activated macrophages the inducible form of nitric oxide synthase (iNOS) generates high amounts of the toxic mediator, nitric oxide (NO), that contributes to the circulatory failure associated with septic shock. Three butanolides were isolated from Machilus thunbergii as active principles which inhibit the production of NO in lipopolysaccharide-activated RAW 264.7 cells, and their structures were identified as litsenolide A2 (1), B1 (2) and B2 (3). They showed dose-dependent inhibition of NO syntheses and the IC(50)s were 3.36, 3.70 and 6.19 micro m, respectively. These new inhibitors of iNOS may have potential in the treatment of endotoxaemia and inflammation accompanied by the overproduction of NO.     

板蓝根乙醇提取物化学成分及其抑制一氧化氮释放活性研究

目的 研究板蓝根Isatidis Radix的化学成分及其抑制一氧化氮（NO）释放活性。方法 采用硅胶、反相ODS C18、葡聚糖凝胶、半制备液相等色谱技术分离纯化,结合理化性质,NMR、MS等波谱数据解析结构,CCK-8法测定化合物抑制NO释放活性。结果 从板蓝根中共分离鉴定了17个化合物,分别为(7S,8R,7′S,8′R)-3,4,3′,4′-tetramethoxy-9,7-dihydroxy-8.8′,7.O.9′-lignan(1)、(-)-(7R,7′R,8S,8′S)-4-β-D-吡喃葡萄糖基-4′-羟基-3,3′,5′-三甲氧基-7,9′:7′,9-双环氧木脂烷（2）、liballinol(3)、2-amino-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol(4)、对羟基苯丙醇（5）、3-甲氧基-4-羟基苯丙醇（6）、3-羟基-1-(3-甲氧基-4-羟基-苯基)-丙基-1-酮（7）、 3,4,5-三甲氧基肉桂酸（8）、(E)-4-(3R,4S)-3,4-dihydroxy-2,6,6-trimethylcyclohex-1-...     

Potent cytotoxic lignans from Justicia procumbens and their effects on nitric oxide and tumor necrosis factor-alpha production in mouse macrophages

A new lignan glycoside, 4-O-alpha-L-arabinopyranosyl-(1' "-->2' ')-beta-D-apiofuranosyldiphyllin (2), named procumbenoside A, and 11 known compounds were isolated from the whole plant of Justicia procumbens. The structure of 2 was established by spectral analysis and chemical methods. The known compounds justicidin A (1), diphyllin (3), and tuberculatin (4) showed potent cytotoxic effects against a number of cancer cells in vitro. Compounds 1 and 4 also strongly enhanced tumor-necrosis factor-alpha (TNF-alpha) generation from mouse macrophage-like RAW 264.7 cells stimulated with lipopolysaccharide (LPS).     

Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production

A new prenylated chalcone, 3' ',3' '-dimethylpyrano[3',4']2,4,2'-trihydroxychalcone (1), was isolated from the heartwood of Artocarpus communis. Two flavonoid derivatives, (-)-cycloartocarpin (9) and (-)-cudraflavone A (10), were isolated as new isomers. In addition, eight known flavonoids, isobacachalcone (2), morachalcone A (3), gemichalcones B (4) and C (5), artocarpin (6), cudraflavone C (7), licoflavone C (8), and (2S)-euchrenone a(7) (11), were isolated and identified from this plant for the first time. Compounds 1-4, 6, and 11 exhibited potent inhibitory activity on nitric oxide production in RAW264.7 LPS-activated mouse macrophage cells with IC(50) values of 18.8, 6.4, 16.4, 9.3, 18.7, and 12.3 microM, respectively. The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments.     

Anti-angiogenic and inhibitory activity on inducible nitric oxide production of the mushroom Ganoderma lucidum

Fresh fruit bodies of Ganoderma lucidum were extracted with 70% ethanol at room temperature. The extract (GL) showed significant anti-angiogenic activity, which was detected using a chick embryo chorioallantoic membrane assay. GL significantly inhibited LPS-induced NO production in RAW 264.7 macrophages. These results support the anti-tumor effect of Ganoderma lucidum.