Three new C-flavonoids from Corallodiscus flabellata

Three new C-glycosylflavones, named 5,7,4'-trihydroxy-6-methoxy-8-C-[beta-D-xylopyranosyl- (1 --> 2)]-beta-D-glucopyranosyl flavonoside (1), 5,7,4'-trihydroxy-8-methoxy-6-C-[beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl flavonoside (2), and 5,3',4'-trihydroxy-7,8-dimethoxy-6-C-[beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl flavonoside (3), along with two known compounds 5,4'-dihydroxy-7-methoxy-6-C-glucopyranosyl-flavonoside (4), 3-methoxy-4-hydroxymethyl benzoate (5) were isolated from 70% acetone extract of Corallodiscus flabellata. Their structures were identified on the basis of spectroscopic techniques and chemical methods.     

Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship

The flavonoid fraction from the leaves of Lantana montevidensis Briq. (Verbenaceae) showed antiproliferative activity against human gastric adenocarcinoma (MK-1, GI50: 12 microg/ml), human uterus carcinoma (HeLa, 5 microg/ml), and murine melanoma (B16F10, 5 microg/ml) cells in vitro. Bioactivity-guided chemical investigation of the fraction has resulted in the isolation of apigenin (10) and ten 5,6,7-oxygenated flavones: cirsilineol (1), eupatorin (2), 5,4'-dihydroxy-6,7,3',5'-tetramethoxyflavone (3), 5,6-dihydroxy-7,3',4'-trimethoxyflavone (4), 5,6,4'-trihydroxy-7,3',5'-trimethoxyflavone (5), 5,6,3'-trihydroxy-7,4'-dimethoxyflavone (6), 5,3',4'-trihydroxy-6,7,5'-trimethoxyflavone (7), cirsiliol (8), hispidulin (9), and eupafolin (11). Antiproliferative activity of the isolated flavones, some other related flavones (luteolin, baicalein, 6-hydroxyluteolin, pectolinarigenin, jaceosidin, desmethoxycentaureidin, eupatilin, and chrysin) from other plant materials, and synthetic 6- and 7-methoxyflavones was evaluated, and the structure-activity relationships were examined.     

Flavans from the leaf of Ilex centrochinensis

Phytochemical investigation of the leaf of Ilex centrochinensis led to the isolation and characterization of four flavans, one flavanone (5), and one flavone (6), including a new compound whose structure was elucidated as (2S)-5,3',4'-trihydroxy-7-methoxyflavan (1) and a new natural product whose structure was elucidated as (2S)-5-hydroxy-7,3',4'-trimethoxyflavan (4) on the basis of spectroscopic methods especially 1D and 2D NMR, CD, and mass spectral analyses. Compounds 1 and 4 exhibited weak cytotoxic activity against Huh7 cell line and no cytotoxic activity against Caco-2 cell line.     

Flavonoids from the leaves of Pleioblastus argenteastriatus

A new flavonoid, 5,7,3′-trihydroxy-6-C-β-d-digitoxopyranosyl-4′-O-β-d-glucopyranosyl flavonoside (1), along with four known flavonoids 5,7,4′-trihydroxy-3′,5′-dimethoxy flavone (2), 5,3′,4′-trihydroxy-7-O-β-d-glucopyranosyl flavonoside (3), 5,4′-dihydroxy-3′,5′-dimethoxy-7-O-β-d-glucopyranosyl flavonoside (4), 5,3′,4′-trihydroxy-6-C-[β-d-glucopyranosyl-(1 → 6)]-β-d-glucopyranosyl flavonoside (5) were isolated from 95% EtOH extract of the leaves of Pleioblastus argenteastriatus. Their structures were determined on the basis of spectroscopic techniques and chemical methods.     

中间锦鸡儿黄酮类成分的研究

目的研究中间锦鸡儿的化学成分。方法用溶剂法、色谱法分离化学成分，用波谱法鉴定其结构。结果从中间锦鸡儿中分离得到10个黄酮类化合物，分别鉴定为5,7,4′-三羟基-3,3′-二甲氧基黄酮(1)，3,5,7,8,4′-五羟基-3′-甲氧基黄酮(2),槲皮素(3),柠檬黄酮醇(4),槲皮素-3-甲醚(5)，2(S)-7,3′,5′-三羟基二氢黄酮(6)，5,7,3′,4′-四羟基-3,8-二甲氧基黄酮(7),紫铆查尔酮（8）,甘草素（9）和5,7,4′-三羟基-3,8二甲氧基黄酮（10）。结论化合物6为新化合物，其余皆首次从中间锦鸡儿中分离得到。     

Flavonoids from Inula viscosa

Phytochemical study of the aerial parts of INULA VISCOSA resulted in the isolation of sixteen flavonoids. One of them, 3- O-acetylpadmatin [(2 R,3 R)-3-acetoxy-5,3',4'-trihydroxy-7-methoxyflavanone], was isolated for the first time as a natural compound. Ferulic aldehyde, 2-methylphloroacetophenone, inuviscolide and 2-deacetoxyxanthinin were also isolated.     

Flavonoids and stilbenoids with COX-1 and COX-2 inhibitory activity from Dracaena loureiri

Fom the stem wood of Dracaena loureiri, a new homoisoflavanone named loureiriol (1) and eight known flavonoid and stilbenoid derivatives, including 5,7-dihydroxy-3-(4-hydroxybenzyl)-4-chromanone (2), 4,4'-dihydroxy-2,6-dimethoxydihydrochalcone (3), 2,4'-dihydroxy-4,6-dimethoxydihydrochalcone (4), 4'-hydroxy-2,4,6-trimethoxydihydrochalcone (5), 4,6,4'-trihydroxy-2-methoxydihydrochalcone (6), 4,3',5'-trihydroxystilbene (7), 4,3'-dihydroxy-5'-methoxystilbene (8) and 4-hydroxy-3',5'-dimethoxystilbene (9) were isolated. These compounds were evaluated for their inhibitory activity against the enzymes cyclooxygenase-1 and cyclooxygenase-2. Potent but non-selective activity was found for the stilbenoids 7-9 (IC(50) 1.29 - 4.92 microM) whereas weak or no activity was observed for the flavonoids 1-6.     

A new chromone from Ficus lyrata

A new chromone, named 5,6-dihydroxy-2-methylchromone (FL-2), along with seven known flavonoids, 5-hydroxy-7,3,3',4'-tetramethoxyflavone (FL-3), 5,4'-dihydroxy-6,7,8-trimethoxyflavone (FL-4), 5,4'-dihydroxy-7,8-dimethoxyflavone (FL-5), 4-methoxychalcone (FL-6), 7,4'-dimethoxyapigenin (FL-7), 5,7,4'-trihydroxy-2',3',6'-trimethoxyisoflavone (FL-8 a rare flavonoid), acacetin-7-O-glucoside (FL-9) and acacetin-7-O-neohesperidoside (FL-10), and beta-sitosterol-D-glucoside (FL-1) have been isolated from the leaves of Ficus lyrata. Their structures have been established on the basis of chemical and spectral evidence (IR, UV, 1H NMR, 13C NMR and mass spectra).     

穿心莲根的化学成分研究

为研究常用中药爵床科植物穿心莲(Andrographis paniculata)根的化学成分,运用各种色谱方法从安徽临泉产穿心莲根的80%乙醇提取物中分离并鉴定了28个化合物,其中20个黄酮:5,5'-二羟基-7,8,2'-三甲氧基黄酮(1)、5-羟基-7,8,2',6'-四甲氧基黄酮(2)、5,3'-dihydroxy-7,8,4',-trimethoxyflavone(3)、2'-羟基-5,7,8-三甲氧基黄酮(4)、5-羟基-7,8,2',3',4'-五甲氧基黄酮(6)、wightin(7)、5,2',6'-trihydroxy-7-methoxyflavone 2'-O-β-D-glucopyranoside(8)、5,7,8,2'-四甲氧基黄酮(10)、5-羟基-7,8-二甲氧基二氢黄酮(11)、5-羟基-7,8-二甲氧基黄酮(12)、5,2'-二羟基-7,8-二甲氧基黄酮(13)、5-羟基-7,8,2',5'-四甲氧基黄酮(14)、5-羟基-7,8,2',3'-四甲氧基黄酮(15)、5-羟基-7,8,2'-三甲氧基黄酮(16)、5,4'-二羟基-7,8,2',3'-四甲氧基黄酮(17)、二氢黄芩新...     

Three new C-flavonoids from Corallodiscus flabellata

Three new C-glycosylflavones, named 5,7,4′-trihydroxy-6-methoxy-8-C-[β-d-xylopyranosyl- (1 → 2)]-β-d-glucopyranosyl flavonoside (1), 5,7,4′-trihydroxy-8-methoxy-6-C-[β-d-xylopyranosyl-(1 → 2)]-β-d-glucopyranosyl flavonoside (2), and 5,3′,4′-trihydroxy-7,8-dimethoxy-6-C-[β-d-xylopyranosyl-(1 → 2)]-β-d-glucopyranosyl flavonoside (3), along with two known compounds 5,4′-dihydroxy-7-methoxy-6-C-glucopyranosyl-flavonoside (4), 3-methoxy-4-hydroxymethyl benzoate (5) were isolated from 70% acetone extract of Corallodiscus flabellata. Their structures were identified on the basis of spectroscopic techniques and chemical methods.     

Flavonoids from Artemisia gmelinii Web. ex Stechm.

Phytochemical investigation of Artemisia gmelinii Web. ex Stechm. led to the isolation of 11 known flavonoids. Their structures were identified as genkwanin (1), hispidulin (2), 3'-hydroxy-genkwanin (3), chrysoeriol (4), apigenin (5), 5,7,3',4'-tetrahydroxy-6,5'-dimethoxy-flavone (6), kumatakenin (7), quercetin (8), patuletin (9), quercetagetin-3,6,7-trimethylether (10) and 7,3',4'-trihydroxy-3-methoxy-flavone (11) by spectroscopic methods. Ten compounds (2-11)were isolated from this title plant for the first time, and five compounds (3, 6, 7, 10 and 11) were isolated from genus Artemisia for the first time.     

滇桂艾纳香化学成分的分离与鉴定

目的分离鉴定中药滇桂艾纳香的化学成分。方法利用硅胶柱色谱、葡聚糖凝胶(SephadexLH-20)柱色谱及HPLC等方法进行分离纯化,根据理化性质和波谱数据进行结构鉴定。结果得到10个化合物,分别鉴定为:原儿茶醛(1)、原儿茶酸(2)、对羟基苯甲醛(3)、β-谷甾醇(4)、豆甾醇(5)、山柰酚(6)、3,5,3′-三羟基-7,4′-二甲氧基黄酮(7)、3,5,3′,4′-四羟基-7-甲氧基黄酮(8)、槲皮素(9)、5-羟基-3,7,3′,4′-四甲氧基黄酮(10)。结论化合物3~10为首次从该植物中分离得到。     

显脉羊蹄甲的生物活性成分

目的对显脉羊蹄甲中具有抑制血小板聚集活性的有效部位的化学成分进行研究。方法从显脉羊蹄甲抑制血小板聚集活性部位中,利用溶剂分步萃取法和各种色谱手段(硅胶吸附柱色谱,聚酰胺柱色谱,Sephadex LH-20柱色谱,开放ODS柱色谱,液相色谱等)分离得到了10个化合物,根据其理化性质和光谱数据分析(1H-NMR、13C-NMR等)鉴定了它们的结构。结果从活性部位中分离鉴定的化合物为黄酮类,分别是:3,5,7,4'-四羟基-3'-甲氧基黄酮(3,5,7,4'-tetrahydroxy-3'-methoxyflavone,1)、5,7,3',4'-四羟基-3-甲氧基黄酮(5,7,3',4'-tetrahydroxy-3-methoxyflavone,2)、槲皮素(quercetin,3)、木樨草素(luteolin,4)、山柰酚(kaempferol,5)、5,7,4'-三羟基-3'-甲氧基黄酮(5,7,4'-trihydroxy-3'-methoxyflavone,6)、7,3',4'-三羟基-3-甲氧基黄酮(7,3',4'-trihydroxy-3-methoxyflavone,7)、杨梅苷(myricitrin,8)、槲皮素-3-O-α-L-吡喃阿拉伯糖苷(quercetin-3-O-α-Larabinopyranoside,9)、儿茶素(catechin,10)。结论化合物1-6、8-9均为首次从该植物中分离得到,化合物7为首次从羊蹄甲属植物中分离得到。     

Antifungal chalcones from Maclura tinctoria

Five prenylated flavonoids, including one new natural product, were isolated from an ethanol extract of the leaves of Maclura tinctoria (L.) Gaud. The new compound has been characterized as 2',4',4,2'-tetrahydroxy-3'-[3'-methylbut-3'-enyl]chalcone (1). The known compounds were identified as 2',4',4-trihydroxy-3'-[3'-methylbut-3'-enyl]chalcone (isobavachalcone) (2), 4,2'-dihydroxy-2'-[1-hydroxy-1-methylethyl]-2',3'-dihydrofurano[4',5':3',4']chalcone (bakuchalcone) (3), 4,4',5'-trihydroxy-6',6'-dimethyldihydropyrano[2',3':5',6']chalcone (bavachromanol) (4), and 5,7,3',4'-tetrahydroxy-6,8-diprenylisoflavone (6,8-diprenylorobol) (5). All the isolated compounds were evaluated against the AIDS-related opportunistic fungal pathogens, Candida albicans and Cryptococcus neoformans. Compound 2 was active against both yeasts.     

Methylated Flavones from Teucrium polium

The following four methylated flavones were obtained from the leaves of TEUCRIUM POLIUM L. (Labiatae). 4', 5-dihydroxy-6,7-dimethoxyflavone (cirsimaritin); 3', 5 dihydroxy-4',6,7-trimethoxyflavone (eupatorin); 5-hydroxy-4',7-dimethoxyflavone (apigenin-4', 7-dimethylether); 4', 5, 3'-trihydroxy-6,7-dimethoxyflavone (cirsiliol). One of these (4', 5-dihydroxy- 6,7-dimethoxyflavone) has been already reported in the same plant by Brieskorn and Biechele (1).     

Lignans from the flower buds of Magnolia liliflora Desr

Six new lignans, 1- 6, along with six known compounds were obtained from the flower buds of Magnolia liliflora Desr. The new lignans were elucidated as (1 S*,2 R*,5 S*,6 S*)-2-(3,5-dimethoxyphenyl)-6-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (1), (1 R*,2 R*,5 R*,6 S*)-2-(3,5-dimethoxyphenyl)-6-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (2), (1 R*,?2 R*,5 R*,6 S*)-2,6-bis (3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (3), (1 R*,2 S*,5 R*,6 R*)-2-(3,4-methylenedioxyphenyl)-6-(3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane ( 4), (7' S*,8 R*,8' R*)-3,5'-dimethoxy-3',4,9'-trihydroxy-7',9-epoxy-8,8'-lignan (5), and (7' R*,8' S*)-3,3',4,5'-tetramethoxy-7-en-7',9-epoxy-8,8'-lignan (6), by the analysis of 1D and 2D-NMR as well as HRESIMS data. The capacity of compound 1 to protect against damages to the DNA of rat lymphocyte cells induced by UV irradiation was assessed by the comet assay. It showed stronger antigenotoxicity than ascorbic acid from 6×10(-3)?mmol·L(-1) to 6×10(-6)?mmol·L(-1).     

Dihydrochalcones and benzoic acid derivatives from Piper dennisii

Two new dihydrochalcones (1, 2), as well as eight known compounds, piperaduncin C (3), 2',6'-dihydroxy-4'-methoxydihydrochalcone (4), 4,2',6'-trihydroxy-4'-methoxydihydrochalcone (5), 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoic acid (6), 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoic acid (7), 4-hydroxy-3-(3-methyl-2-butenoyl)-5-(3-methyl-2-butenyl)-benzoic acid (8), 2,2-dimethyl-8-(3-methyl-2-butenyl)-2H-1-chromene-6-carboxylic acid (9), and 3-(3',7'-dimethyl-2',6'-octadienyl)-4-methoxybenzoic acid (10) were isolated from the leaves of Piper dennisii Trelease (Piperaceae), using a bioassay-guided fractionation to determine their antileishmanial potential. Among them, compound 10 exhibited the best antileishmanial activity (IC50 = 20.8 μM) against axenic amastigote forms of Leishmania amazonensis, with low cytotoxicity on murine macrophages. In the intracellular macrophage-infected model, compound 10 proved to be more active (IC50 = 4.2 μM). The chemical structures of compounds 1-10 were established based on the analysis of the spectroscopic data.     

New abietane diterpenoids from the mangrove Avicennia marina

Phytochemical investigations of the twigs of Avicennia marina yielded three new abietane diterpenoids 11-hydroxy-8,11,13-abietatriene 12- O-beta-xylopyranoside ( 1), and a pair of inseparable epimers 6 Halpha-11,12,16-trihydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial 11,6-hemiacetal ( 2) and 6 Hbeta-11,12,16-trihydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial 11,6-hemiacetal ( 3), as well as the new lignan (7' S,8' R)-4,4',9'-trihydroxy-3,3',5,5'-tetramethoxy-7,8-dehydro-9-al-2,7'-cyclolignan ( 5), together with 6,11,12,16-tetrahydroxy-5,8,11,13-abitetetraen-7-one ( 4), lyoniresinol ( 6), lyoniresinol 9'- O-beta- D-glucopyranoside ( 7), and diacetylmartynoside ( 8). Structure elucidation of the new compounds was accomplished by analysis of their spectroscopic data. Compounds 2 - 4 showed moderate cytotoxic and antimicrobial activities.     

鸡血藤的化学成分研究

目的研究中药鸡血藤(Spatholobus suberectus Dunn)的化学成分。方法利用多种柱色谱方法进行分离纯化,根据光谱数据和化学方法进行结构鉴定。结果从鸡血藤70%乙醇浸膏的乙酸乙酯部分分离鉴定了8个化合物,分别是:密花豆素(1)、芒柄花素(2)、大豆苷元(3)、毛蕊异黄酮(4)、焦性粘液酸(5)、间苯三酚(6)、琥珀酸(7)、β-谷甾醇(8)。结论化合物1为7,3′,4′-三羟基-6-甲氧基二氢黄酮,是1个新化合物,命名为密花豆素,化合物4,5,6和7为首次从本属植物中得到。     

Antimycobacterial activity and cytotoxicity of flavonoids from the flowers of<Emphasis Type="Italic">Chromolaena odorata</Emphasis>

From the flowers of Chromolaena odorata (Eupatorium odoratum) four flavanones, isosakuranetin (5,7-dihydroxy-4'-methoxyflavanone) (1), persicogenin (5,3'-dihydroxy-7,4'-dimethoxyflavanone) (2), 5,6,7,4'-tetramethoxyflavanone (3) and 4'-hydroxy-5,6,7-trimethoxyflavanone (4), two chalcones, 2'-hydroxy-4,4',5',6'-tetramethoxychalcone (5) and 4,2'-dihydroxy-4',5',6'-trimethoxychalcone (6), and two flavones, acacetin (5,7-dihydroxy-4'-methoxyflavone) (7) and luteolin (5,7,3',4'-tetrahydroxyflavone) (8) were isolated and identified. Compound 1 exhibited moderate antimycobacterial activity against Mycobacterium tuberculosis with the MIC value of 174.8 microM, whereas compounds 4, 7, and 8 exhibited weak activity with the MIC values of 606.0, 704.2 and 699.3 microM respectively. Compound 7 showed moderate cytotoxicity against human small cell lung cancer (NCI-H187) cells with the MIC value of 24.6 microM, whereas compound 8 exhibited moderate toxicity against NCI-H187 cells and week toxicity against human breast cancer (BC) cells with the MIC values of 19.2 and 38.4 microM respectively.