Sesquiterpenoids from Ferula fukanensis and their inhibitory effects on nitric oxide production

Six sesquiterpene derivatives, 2,3-dihydro-7-methoxy-2S*, 3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]furo[3,2-c]coumarin (1) and 2,3-dihydro-7-methoxy-2R*,3R*-dimethyl-2-[4,8-dimethyl-3(E),7-nonadienyl]furo[3,2-c]coumarin (2), nerolidol (3), 1-(2,4-dihydroxyphenyl)-3,7,11-trimethyl-3-ninyl-6(E),10-dodecadien-1-one (4), 1-(2,4-dihydroxyphenyl)-3,7-dimethyl-3-vinyl-8-(4-methyl-2-furyl)-6(E)-octen-1-one (5) and dshamirone (6) were isolated from an 80% aqueous methanol extract of the roots of Ferula fukanensis. The sesquiterpenoids inhibited nitric oxide (NO) production and inducible NO synthase gene expression by a murine macrophage-like cell line (RAW 264.7) [1], which was activated by lipopolysaccharide and recombinant mouse interferon-.     

Antihepatotoxic, nephroprotective, and antioxidant activities of phenolic compounds from Satureja macrostema leaves against carbon tetrachloride-induced hepatic damage in mice

Satureja macrostema (SM) is used with culinary and medicinal purposes. Methanol extract from SM was investigated for its phenolic content, antioxidant, hepatoprotective, and kidney protective activities. Liver and kidney damage were induced in rats with CCl₄. Hepatoprotective efficacy was measured by the activity of aspartate aminotransferase, alanine aminotransferase, alkaline phosphatase, total bilirubin, cholesterol, high density lipoprotein and total protein, and lipid peroxidation. Kidney function was evaluated by measuring plasma urea and creatinine. Antioxidant activity was evaluated by measuring blood glutathione content, superoxide dismutase and catalase activities, and malondialdehyde equivalent; their activity was comparable to that of silymarin, a well-known hepatoprotective agent. Methanol extracts of S. macrostema showed potent antioxidant, kidney protective, and hepatoprotective activities; in-depth chromatographic investigation resulted in the identification of six new flavonoid glycosides: 5-hydroxy-3,6,4′-trimethoxyflavonol-7-C-α-l-rhamnopyranosyl-(1 → 3)-β-d-glucopyranoside (2), 4′-methoxy-5,7,3′,5′-tetra-hydroxyflavanone-3-O-β-d-rhamnopyranosyl-(1 → 2)-β-d-rhamnopyranoside (3), 5,4′-dimethoxy-7,3′,5′-trihydroxyflavanone-3-O-β-d-rhamnopyranoside (4), 5,3′,4′,5′-tetrahydroxyflavanone-7-O-β-d-rhamnopyranoside (5), 5,3′,4′,5′-tetramethoxyflavanone-7-O-β-d-rhamnopyranoside (6), and 5,4′-dimethoxy-3′-hydroxyflavone-7-β-d-rhamnopyranoside (8) along with three known compounds: 5-hydroxy-7,4′-dimethoxyflavone (1), prunin (7), and diosmin (9) that were isolated. Structural elucidation of the new compounds was established based on the spectral data. The present study revealed that S. macrostema leaves have a significant radical scavenging and hepatoprotective activity.     

C-glycosylflavones from the leaves of Iris tectorum Maxim.

A new C-glycosylflavone, 5-hydroxyl-4′,7-dimethoxyflavone-6-C-[O-(α-l-3′′′-acetylrhamnopyranosyl)-1→2-β-d-glucopyranoside] (1), along with five known C-glycosylflavones, 5-hydroxy-4′,7-dimethoxyflavone-6-C-[O-(α-l-2′′′-acetylrhamnopyranosyl)-1→2-β-d-glucopyranoside] (2), embinin (3), embigenin (4), swertisin (5) and swertiajaponin (6) were isolated from the leaves of Iris tectorum Maxim. Their structures were elucidated on the basis of extensive NMR experiments and spectral methods and their cytotoxic activities against A549 (lung cancer) human cell lines were determined.     

Two new chalcones from Clerodendrum phlomidis

Two new chalcones, 3,2′,3′-trihydroxy-4′-methoxychalcone (1) and 3,2′-dihydroxy-4′,6′-dimethoxychalcone (2), were isolated from the seeds of Clerodendrum phlomidis together with three known flavonoids, 5-hydroxy-7-methoxyflavanone (3), 5-hydroxy-7-methoxyflavone (4), and kaempferol-3-O-α-l-rhamnopyranoside (5). The structures of the new compounds 1 and 2 have been established mainly on the basis of 1D and 2D NMR studies.     

10-Carbethoxymethyl-3-phenyl-1,2,4-triazolo[4′,3′:2,3][1,2,4]triazino[5,6-b]indole and Derivatives at its 10-Position

Reaction of 3-phenyl-10H-1,2,4-triazolo[4′,3′:2,3][1,2,4]triazino[5,6-b]indole ( 4 ) with ethyl chloroacetate gave 10-carbethoxymethyl-3-phenyl-1,2,4-triazolo[4′,3′:2,3][1,2,4]triazino[5,6-b]indole ( 3 ). Condensation of 3 with hydrazine hydrate gave (3-phenyl-1,2,4-triazolo[4′,3′:2,3][1,2,4]triazino[5,6-b]indol-10-yl)acetylhydrazine ( 5 ). Reactions of 5 with a number of aromatic aldehydes, acetophenone, cyclohexanone and D-galactose gave the corresponding hydrazones 6 - 12 . Condensation of 5 with acetylacetone gave the pyrazole 15 . Cyclization of 5 with CS₂ gave (3-phenyl-1,2,4-triazolo[4′,3′:2,3][1,2,4]triazino[5,6-b]indol-10-yl)(2-thiol-1,3,4-oxadiazol-5-yl)methane ( 16 ). Reaction of 16 with ethyl chloroacetate gave the carbethoxy alkylated derivative (3-phenyl-1,2,4-triazolo[4′,3′:2,3][1,2,4]triazino[5,6-b]indol-10-yl)[2-(thiocarbethoxymethyl)1,3,4-oxadiazol-5-yl]methane ( 17 ).     

A new norlignan lignanoside from Selaginella moellendorffii Hieron

This study reports an investigation into the chemical constituents of the whole plant of Selaginella moellendorffii Hieron. Ten compounds, isolated and purified by column chromatography, were identified on the basis of spectral analysis and their physicochemical properties to be: (8R)-3,5-dimethoxy-4-hydroxyphenylpropylalcohol-8-(1-acetyl-3-methoxy-4-hydroxyphenyl)-9-O-β-d-glucopyranoside (moellenoside B) (1), amentoflavone (2), hinokiflavone (3), apigenin-7-O-β-neohesperidoside (4), apigenin-8-C-β-d-glucopyranoside (5), adenosine (6), uridine (7), 2,3,4,9-tetrahydro-1H-pyrido[3, 4-b]indole-3-carboxylic acid (8), vanillic acid (9), and lariciresinol (10). Compound 1 is a new norlignan lignanoside and compounds 4–10 were isolated from this plant for the first time.     

红松松针中木脂素类成分的分离与鉴定

目的研究红松松针中的木脂素类成分,为松属植物的化学分类学研究提供依据。方法采用反复硅胶、聚酰胺、ODS、Sephadex LH-20柱色谱等方法进行分离纯化,根据理化性质和波谱分析对分离得到的化合物进行结构鉴定。结果从红松松针中分离得到8个化合物,分别鉴定为(+)-异落叶松脂素-9-O-β-D-吡喃木糖苷((+)-isolariciresinol-9-O-β-D-xylopyranoside,1)、(+)-异落叶松脂素-9-O-β-D-吡喃葡萄糖苷((+)-isolariciresinol-9-O-β-D-glucopyranoside,2)、7S,8R-苏式-3′,4,9′-三羟基-3-甲氧基-7,8-二氢苯并呋喃-1′-丙醇基新木脂素-9-O-α-L-吡喃鼠李糖苷(7S,8R-threo-3′,4,9′-trihydroxy-3-methoxy-4′,7-epoxy-neolignan-9-O-α-L-rhamnopyranoside,3)、7S,8R-苏式-3′,9,9′-三羟基-3-甲氧基-7,8-二氢苯并呋喃-1′-丙醇基新木脂素-4-O-α-L-吡喃鼠李糖苷(7S,8R-threo-3′,9,9′-trihydroxy-3-methoxy-4′,7-epoxy-neolignan-4-O-α-L-rhamnopyranoside,4)、7R,8S-赤式-4,7,9-三羟基-3,3′-二甲氧基-8-O-4′-新木脂素-9′-O-α-L-吡喃鼠李糖苷(7R,8S-erythro-4,7,9-trihydrox-y-3,3′-dimethoxy-8-O-4′-neolignan-9′-O-α-L-rhamnopyranoside,5)、7S,8S-苏式-4,7,9-三羟基-3,3′-二甲氧基-8-O-4′-新木脂素-9′-O-α-L-吡喃鼠李糖苷(7S,8S-threo-4,7,9-trihydroxy-3,3′-dimethoxy-8-O-4′-neolignan-9′-O-α-L-rhamnopyranoside,6)、7S,8S-苏式-3′,4,7,9-四羟基-3-甲氧基-8-O-4′-新木脂素-9′-O-α-L-吡喃鼠李糖苷(7S,8S-threo-3′,4,7,9-tetrahydroxy-3-methoxy-8-O-4′-neolignan-9′-O-α-L-rhamnopyranoside,7)、7R,8S-赤式-3′,4,9,9′-四羟基-3-甲氧基-8-O-4′-新木脂素-7-O-β-D-吡喃葡萄糖苷(7R,8S-erythro-3′,4,9,9′-tetrahydroxy-3-methoxy-8-O-4′-neolignan-7-O-β-D-glucopyr-anoside,8)。结论化合物1~8均为首次从红松中分离得到。     

Flavonoids from Camptosorus sibiricus Rupr.

Three new flavonol glycosides, kaempferol-3-O-(6-trans-caffeoyl)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside (1), kaempferol-3-O-(6-trans-caffeoyl)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside-7-O-β-d-glucopyranoside (2), and kaempferol-3-O-(6-trans-p-coumaroyl)-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside-7-O-β-d-glucopyranoside (3), were isolated from the aerial part of Camptosorus sibiricus. Their structures were elucidated by spectroscopic methods, including 2D NMR spectral techniques.     

Two new dihydrobenzofuran lignans from Rabdosia lophanthoides (Buch.-Ham.ex D.Don) Hara

Two new dihydrobenzofuran lignanosides, (7R,8S)-4,3′,9′-trihydroxyl-3-methoxyl-7,8-dihydrobenzofuran-1′-propylneolignan-9-O-(6-O-syringoyl)-β-d-glucopyranoside, named lophanthoside B (1) and (7R,8S)-4,9,9′-trihydroxyl-3-methoxyl-7,8-dihydrobenzofuran-1′-propylneolignan-3′-O-β-d-glucopyranoside (2), an enantiomer of umbroside, along with four known dihydrobenzofuran lignans (3–6), were isolated from 50% acetone extract of Rabdosia lophanthoides (Buch.-Ham.ex D.Don) Hara. Their structures were elucidated by NMR and MS experiments.     

New flavonol glycosides and new xanthone from Polygala japonica

Three new flavonol glycosides and a new xanthone were isolated from Polygala japonica HOUTT. with eight known compounds. Their structures were identified as 1,7-dihydroxy-3,4-dimethoxy-xanthone (1), kaempferol-7,4′-dimethyl ether (2), physcion (3), guazijinxanthone (4), rhamnetin (5), polygalin A (6), 3,5,7-trihydroxy-4′-methoxy-flavone-3-O-β-d-galactopyranoside (7), 3,5,3′-trihydoxy-7,4′-dimethoxy-flavone-3-O-β-d-galactopyranoside (8), 3,5,3′,4′-tetrahydroxy-7-methoxy-flavone-3-O-β-d-galactopyranoside (9), 3,5,3′,4′-tetrahydroxy-7-methoxy-flavone-3-O-β-d-glucopyranoside (10), polygalin B (11), polygalin C (12). Among them, compound 4 is a new xanthone, and 6, 11 and 12 are new flavonol glycosides. Compounds 1, 4, 7 and 8 were tested for cytotoxic activity with MTT assays on five human tumor cell lines, K562, A549, PC-3M, HCT-8 and SHG-44. Compound 4 showed cytotoxic activity against all the five cell lines.     

西南山茶化学成分的分离与鉴定

目的研究西南山茶叶的化学成分。方法采用硅胶柱色谱、Sephadex LH-20柱色谱等方法进行分离纯化,根据波谱学数据和理化性质进行结构鉴定。结果从西南山茶叶体积分数95%乙醇提取物的乙酸乙酯萃取物中分离并鉴定了11个化合物,分别为槲皮素(quercetin,1)、芦丁(rutin,2)、槲皮素-3-O-α-D-阿拉伯糖苷(quercetin-3-O-α-D-arabinofuranoside,3)、槲皮素-3-O-β-D-半乳糖苷(quercetin-3-O-β-D-galactopyranoside,4)、槲皮素-3-O-β-D-鼠李糖苷(quercetin-3-O-β-D-rhamno-side,5)、山柰酚(kaempferol,6)、山柰酚-3-O-(2″,6″-二反式-对香豆酰基)-β-D-葡萄糖苷(kaempfer-ol-3-O-[2″,6″-di-(E)-p-coumaroyl]-β-D-glucopyranoside,7)、羽扇豆醇(lupeol,8)、齐墩果酸(olean-olic acid,9)、原儿茶酸(3,4-dihydroxybenzoic acid,10)和没食子酸乙酯(ethyl gallate,11)。结论化合物1~11均首次从西南山茶中分离得到,其中化合物7为首次从山茶属植物中分离得到。     

Two new compounds from Comastoma pedunlulatum

Two new compounds, a xanthonoid and a flavonoid C-glycoside, were isolated from the ethyl acetate extract of the dried herb of Comastoma pedunlulatum. The structures of the new compounds were elucidated, respectively, as 1,8-dihydroxy-3,5-dimethoxyxanthone 1-O-[2-(4′-hydroxy-3′,5′-dimethoxy-E-cinnamoyl)]-β-d-xylopyranosyl-(1-6)-β-d-glucopyranoside (1) and 6″-O-acetylisoorientin (2) on the basis of their spectroscopic and physicochemical properties.     

Two new neolignan glucosides from Arctii Fructus

Two new neolignan glucosides named (7S, 8R)-4,7,9,9′-tetrahydroxy-3,3′-dimethoxyl-7′-oxo-8-4′-oxyneolignan-4-O-β-d-glucopyranoside (1) and (7′S, 8′R, 8S)-4,4′,9′-trihydroxy-3,3′-dimethoxy-7′,9-epoxylignan-7-oxo-4-O-β-d-glucopyranosyl-4′-O-β-d-glucopyranoside (2), together with two small molecular peptides named 3-benzyl-6-(1-hydroxyethyl)-2,5-piperazinedione (3) and 3-benzyl-2,5-piperazinedione (4), were isolated from the extract of Arctii Fructus. Their structures and absolute configurations were elucidated by various spectroscopic methods (IR, HR-ESI-MS, 1D and 2D NMR, and CD).     

New anti-inflammatory flavonoids from Cadaba glandulosa Forssk

Three new flavonoids; kaempferol-4′-phenoxy-3,3′,5′-trimethylether (3), rhamnocitrin-4′-(4-hydroxy-3-methoxy)phenoxy-3-methyl ether (4), and rhamnocitrin-3-O-neohesperoside-4′-O-rhamnoside (6), along with three known compounds; 4-methoxy-benzyldehyde (1), kaempferol-3-methylether (2), and stachydrine (5) were isolated from the aerial parts of Cadaba glandulosa Forssk. Their chemical structures were established by physical, chemical, and spectral methods, as well as comparison with literature data. The antioxidant and anti-inflammatory activities of the isolated compounds were determined. Compounds 2–4, and 6 exhibited potent anti-inflammatory activity comparable with indomethacin and moderate antioxidant activity.     

Stilbenoids isolated from the roots of Rheum lhasaense under the guidance of the acetylcholinesterase inhibition activity

Four unknown stilbenoids, including one dimer, namely 4′-methoxy-scirpusin A (5) and three monomeric stilbene glycosides, namely piceatannol-3′-O-[2′′-(3,5-dihydroxy-4-methoxybenzoyl)]-β-d-glucopyranoside (13), piceatannol-3′-O-(2′′-galloyl)-β-d-glucopyranoside (14) and piceatannol-3′-O-(6″-p-coumaroyl)-β-d-glucopyranoside (16) together with 15 described compounds, were isolated from the ethyl acetate fraction of the ethanol extract of roots of Rheum lhasaense based on the guidance of the inhibitory effect on acetylcholinesterase. The structures of the unknown compounds were established by combined spectroscopic analysis and comparing their spectral data with compounds with similar structures. Some selected components were also investigated for their inhibitory abilities on acetylcholinesterase (AChE), indicating that compound 13 may be responsible for higher inhibitory activity of the ethyl acetate fraction on AChE.

     

A new isoflavone from Blepharis ciliaris of an Egyptian origin

A phytochemical study of the aerial parts of Blepharis ciliaris (L.) B.L. Burtt. led to the isolation of one new isoflavone glycoside caffeic acid ester: genistein-7-O-(6″-O-E-caffeoyl-β-d-glucopyranoside) (4), along with seven known compounds: methyl veratrate (1), methyl vanillate (2), protocatechuic acid (3), naringenin-7-O-(3″-acetyl-6″-E-p-coumaroyl-β-d-glucopyranoside) (5), naringenin-7-O-(6″-E-p-coumaroyl-β-d-glucopyranoside) (6), apigenin-7-O-(6″-E-p-coumaroyl-β-d-glucopyranoside) (7), and acteoside (8). Their structures were established on the basis of detailed analyses of physical, chemical, and spectral data. Compounds 1, 2, 3, 6, and 8 were isolated for the first time from this plant. The antioxidant activity of the different extracts as well as for some of the isolated compounds was evaluated.     

北沙参化学成分的分离与鉴定

目的对北沙参的化学成分进行研究,为进一步开发利用该植物资源提供依据。方法运用反复硅胶柱色谱、大孔树脂HP20、Sephadex LH-20柱色谱及开放ODS柱色谱进行化合物的分离纯化,并通过理化性质和光谱数据鉴定化合物的结构。结果从北沙参根的乙醇提取物中分离鉴定了9个化合物,分别鉴定为:3-羟基-1-(4-羟基-3-甲氧基苯基)-2-[4-(3-羟基-1-(E)-丙烯基)-2-甲氧基苯氧基]-丙基-β-D-吡喃葡萄糖(3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxy-1-(E)-propenyl)-2-methoxyphenoxy]propyl-β-D-glucopyranoside,1)、2,3-E-2,3-二氢-2-(3'-甲氧基-4'-羟基苯基)-3-羟甲基-5-(3″-羟基-丙烯基)-7-O-β-D-吡喃葡糖基-1-苯骈[b]呋喃(2,3E-2,3-dihydro-2-(3'-methoxy-4'-hydroxyphenyl)-3-hydroxymethyl-5-(3″-hydroxypropeyl)-7-O-β-D-glucopyranosyl-1-benzo[b]furan,2)、原儿茶酸甲酯(protocatechuic acid methyl ester,3)、七叶内酯(esculetin,4)、可来灵素J(glehlinoside J,5)、东莨菪苷(scopolin,6)、亥茅酚苷(sec-O-glucosylhamaudol,7)、(-)-开环异落叶松脂素4-O-β-D-吡喃葡萄糖苷[(-)-secoisolariciresinol 4-O-β-D-glucopyranoside,8]、可来灵素C(glehlinoside C,9)。结论 1-4和6、7共6个化合物为首次从珊瑚菜属中分离得到。     

Two new compounds from the dry leaves of Pleioblastus amarus (Keng) keng f.

Two new compounds, xylitol 1-O-(6′-O-p-hydroxylbenzoyl)-glucopyranoside (1) and bambulignan B (2), together with three known ones gastrodin (3), glucovanillin (4), and rel-(7S,7′R,8R,8′S)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7,7′-epoxyligna-9,9′-diol-9(or)9′-O-β-glucopyranoside (5), were isolated from the 95% EtOH extract of the dry leaves of Pleioblastus amarus (Keng) keng f. Their structures were determined by UV, IR, HR-ESI-MS, CD, and 1D and 2D NMR data analyses as well as GC experiments.     

Microbial transformation of naringenin derivatives

Microbial transformations of (±)-7-O-prenylnaringenin (7-PN, 1) and (±)-7-O-allylnaringenin (7-AN, 2) have isolated four metabolites (3–6). Structures of these novel compounds were identified as 5,4′-dihydroxy-7-O-[(2E)-4-hydroxy-3-methyl-2-buten-1-yl]flavanone (3), 5,4′-dihydroxy-7-O-(2,3-dihdroxy-3-methylbutyl)flavanone (4), 5,4′-dihydroxy-7-O-(2,3-dihdroxypropyl)flavanone (5), and 5-O-β-D-glucopyranosyl-7-O-allyl-4′-hydroxyflavanone (6) based on spectroscopy. Compounds 1–6 were evaluated for their radical scavenging capacity using DPPH (2,2-diphenyl-1-picrylhydrazyl). The derivatives 3–6 exhibited more potent antioxidant activity than their corresponding substrates 1 and 2.