New Flavonoids from Boldoa purpurascens Cav

Phytochemical analysis of the leaves of BOLDOA PURPURASCENS Cav. led to isolation of four flavone glycosides, three of which are new compounds. Their structures have been determined by mass spectrometry and by 1 D and 2 D NMR analysis, i. e., 4',5-dihydroxy-6,7-methylenedioxyflavonol 3- O-alpha- L-rhamnopyranosyl-(1-->2)-beta- D-xylopyranoside ( 1), 4',5-dihydroxy-6,7-methylenedioxyflavonol 3- O-beta- D-xylopyranoside ( 2), and 4',5-dihydroxy-6,7-methylenedioxyflavonol 3- O-alpha- L-rhamnopyranosyl-(1-->2)-beta- D-glucopyranoside ( 3). The known compound was 4',5-dihydroxy-6,7-methylenedioxyflavonol 3- O-beta- D-glucopyranoside ( 4). The aglycone 4',5-dihydroxy-6,7-methylenedioxyflavonol is known as gomphrenol. Compounds 1 and 2 failed to show antifungal activity when tested against three different strains of fungi, i. e., FUSARIUM CULMORUM, BOTRYTIS CINEREA, and ASPERGILLUS FLAVUS.     

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.     

Auriculatin 4'-O-Glucoside: A New Prenylated Isoflavone Glycoside from Erythrina eriotricha1

In addition to known compounds, sigmoidin C and 8-(3,3-dimethylallyl)-erythrinin C, also called senegalensin, a new isoflavone glycoside designated auriculatin 4'- O-glucoside was isolated from the chloroform extract of the stem bark of ERYTHRINA ERIOTRICHA. Its structure was elucidated as 7,6-(2',2'-dimethyl-2 H-pyrano)-2',5-dihydroxy-8-(3,3-dimethylallyl)-isoflavone 4'- O-beta- D-glucoside on the basis of spectroscopic methods and chemical evidence.     

Two new flavonoid glycosides from Artemisia frigida Willd

An investigation of the n-BuOH-soluble fraction from the aerial parts of Artemisia frigida has led to the isolation of two new flavonoid glycosides, named friginoside A and friginoside B. Their structures were characterized as 5,7-dihydroxy-3',4',5'-trimethoxy flavone 7-O-β-d-glucuronide (1) and 5,7-dihydroxy-3',4',5'-trimethoxyflavone 7-O-β-d-glucuronyl-(1?→?2)O-β-d-glucuronide (2) on the basis of 1D and 2D NMR spectral analysis.     

New cytotoxic flavonoids from Thelypteris torresiana

During our search for anti-tumor agents from pteridophytes, three new flavonoids, protoapigenone (1), 5',6'-dihydro-6'-methoxyprotoapigenone (2), and protoapigenin (3), along with four known compounds, protoapigenin 4'- O-beta- D-glucoside (4), apigenin 4'- O-beta- D-glucoside (5), kaempferol 3- O-alpha- L-rhamnopyranoside (6), kaempferol 3,7-di- O-alpha- L-rhamnopyranoside (7), were isolated from Thelypteris torresiana using bioactivity-guided fractionation methods . The structures of the new isolates were elucidated by 1D- and 2D-NMR spectral analysis. Among the 7 compounds, protoapigenone (1) exhibited significant anti-tumor activities toward Hep G2, Hep 3B, MCF-7, A549, and MDA-MB-231 with IC50 values of 1.60, 0.23, 0.78, 3.88 and 0.27 microg/mL, respectively.     

New Chalcones from Bidens pilosa

Okanin 4'- O-beta- D-(2',4',6'-triacetyl)-glucoside, okanin 4'- O-beta- D-(6'- TRANS-P-coumaroyl)-glucoside, both new natural compounds, and okanin 3'- O-beta- D-glucoside have been isolated from the leaves of BIDENS PILOSA L. Their structures have been elucidated by means of UV, FD-MS, (1)H-NMR, and (13)C-NMR spectroscopy. NMR spectral data for okanin 4'- O-beta- D-glucoside (marein) are given.     

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).     

Antitumor activity of flavones isolated from Artemisia argyi

The flavones 5,6-dihydroxy-7,3',4'-trimethoxyflavone ( 1), 5,6,4'-trihydroxy-7,3'-dimethoxyflavone ( 2), 5-hydroxy-3',4',6,7-tetramethoxyflavone, 5,7,3'-trihydroxy-6,4',5'-trimethoxyflavone, ladanein, and hispidulin were isolated from the methanolic extracts of the aerial parts of Artemisia argyi and structures of the compounds were elucidated on the basis of their spectral data. These flavones inhibited farnesyl protein transferase with IC 50 values of 25 - 200 microg/mL. Compound 2 inhibited proliferation of a couple of tumor cell lines and also inhibited neovascularization in a chick chorioallantoic membrane assay. Without loss of body weight of nude mice, compounds 1 and 2 inhibited growth of a colon tumor (SW620) by 44.6 % and 14.6 %, respectively.     

About the Bufadienolide Complex of "Red" Squill

Red coloured bulbs of plants of the URGINEA MARITIMA aggregate from the northern and southern Mediterranean area were shown to exhibit different bufadienolide compositions. Therefore, the bufadienolide complex of "red squill" samples from Tunesia and from Sardegna was investigated. Twelve bufadienolides were isolated from bulbs of tetraploid squill from Tunesia, sixteen from tetraploid samples from Sardegna. The Compounds were identified by means of FAB-MS, (1)H-NMR, and (13)C-NMR studies or comparison with authentic substances. Both of the samples contained scilliroside ( 14), scillarenin 3- O-beta- D-glucoside ( 2), proscillaridin A (1), scilliphaeosidin 3- O-beta- D-glucoside ( 5), scilliglaucoside ( 17), scilliphaeoside ( 4), and 12- EPI-scilliphaeoside ( 7); the bulbs from Tunesia contained additionally glucoscilliphaeoside ( 6) and the four new bufadienolides 12- EPI-glucoscilliphaeoside ( 10), 12beta-hydroxyscilliglaucosidin 3- O-beta- D-glucoside ( 21), 12- EPI-scilliphaeosidin 3- O-beta- D-glucoside ( 8), and 12- EPI-scilliphaeosidin 3- O-alpha- L-rhamnosido-alpha- L-rhamnoside ( 9). In the bulbs from Sardegna scülaren A ( 3), gamabufotalin 3- O-alpha- L-rhamnoside ( 20), scilliglaucoside ( 17), scillirubrosidin 3- O-alpha- L-rhamnoside ( 11), scillirubroside ( 12), 12beta-hydroxyscilliroside ( 15), 5alpha-4,5-dihydroscillirosidin 3- O-alpha- L-thevetosido-beta- D-glucoside ( 19), and deacetyl-scilliroside ( 8) besides the new Compounds 10-carb-oxy-5beta,14beta-dihydroxybufa-3,20,22-trienolide 5- O-beta- D-glucoside ( 18) and scilliglaucogenin ( 16) were found in addition. Not only quantitative but even qualitative differences in the bufadienolide pattern between the samples of the northern and the southern Mediterranean area were proved. By now it is not clear whether the investigated samples belong to different chemodemes of URGINEA NUMIDICA or are two different species of the URGINEA MARITIMA aggregate.     

Studies on the constituents of roots of Scutellaria planipes

From the roots of Scutellaria planipes (L.), three new flavonoids, 5,7,3',6'-tetrahydroxy-6,8,2'-trimethoxyflavone, (2 R,3 R)-3,5,7,2',5'-pentahydroxyflavanone and 7,2'-dihydroxy-5-methoxyflavone were isolated, together with ten known flavonoids, skullcapflavone I, wogonin, baicalein, norwogonin, viscidulin III, 5,7,2',6'-tetrahydroxy-flavone, 3,5,7,2',6'-pentahydroxyflavone, wogonin 7- O-beta- D-glucuronide, baicalin, baicalein 7- O-beta- D-glucopyranoside, and three phenethyl alcohol glycosides, acteoside, martynoside, and jionoside D. The structures were elucidated by spectroscopic methods.     

Isolation and structure elucidation of viscoazucine, a novel sesquiterpene from Polygonum viscosum

A new sesquiterpene, 1,4-dimethoxycarbonyl-7-(1-methylethyl)- 3,3a,6,7,8,8a-hexahydroazulene (viscoazucine) (1), and a known flavone, 3',5,7-trihydoxy-3,4',5'-trimethoxyflavone (4), have been isolated from Polygonum viscosum. The structures of these compounds were elucidated by spectroscopic analyses, notably UV, MS and NMR.     

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...     

Note: 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 β-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).     

大豆苷元在人肝微粒体中的单羟化代谢机制大豆苷元在人肝微粒体中的单羟化代谢机制

目的探讨大豆苷元在人肝微粒中羟基化代谢所涉及的肝细胞色素P450(CYP)同工酶，为研究其在人体内的代谢提供基础。方法通过分析大豆苷元在肝微粒体中和重组CYP酶中形成的单羟化代谢物的酶促动力学,分析其酶学模型，然后用不同CYP同工酶选择性抑制剂或底物进行抑制实验，初步筛选出介导大豆苷元单羟化代谢所涉及的CYP同工酶。结果代谢物的形成动力学符合米氏方程单酶模型。CYP1A2选择性抑制剂呋喃茶碱和CYP1A2单克隆抗体均能明显抑制3种单羟化代谢物的形成。而其他CYP选择性的抑制剂对3种代谢物的形成没有或较小产生抑制作用。用重组酶实验得出相同结果。结论体外肝微粒体研究表明，大豆苷元的单羟基代谢主要由CYP1A2所介导。     

Flavan-3-ols and flavonoids from Potentilla anserina

Roots/rhizomes and aerial parts of Potentilla anserina L. (Rosaceae) contain two flavan-3-ols: (+)-catechin and (+)-gallocatechin. The flavonol glycosides and glucuronides isolated from the herb were kaempferol 3- O-beta- D-glucoside, kaempferol 3- O-beta- D-(6'- O-( E)- P-coumaroyl)glucopyranoside, quercetin 3- O-beta- D-glucoside, quercetin 3- O-beta- D-xyloside, quercetin 3- O-alpha- L-rhamnoside, quercetin 3- O-beta- D-sambubioside, quercetin 3- O-beta- D-glucuronide, isorhamnetin 3- O-beta- D-glucuronide, myricetin 3- O-alpha- L-rhamnoside, and myricetin 3- O-beta- D-glucuronide. Herbacetin 8-methyl ether-3- O-beta- D-sophoroside (8-methoxykaempferol 3-sophoroside) was identified in the flowers. The 6'-methyl ester of quercetin 3- O-beta- D-galacturonide, which may be an artifact, was isolated from the herb. The total flavonoid content calculated as quercetin-3- O-beta- D-glucuronide was 1% in the lyophilized herb used in this study and 0.5% in a commercial drug, meeting DAC standards.     

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.     

粉枝莓中的两种新黄酮成分

为研究粉枝莓(Rubus biflorus Buch)的化学成分，经柱色谱分离，从粉枝莓中分离得到2个黄酮类化合物，光谱分析鉴定其结构为：8-甲基-6-异戊烯基-5,7-二羟基-5′-甲氧基-3′,4′-二氧亚甲基黄酮(A),和8-甲基-5′-异戊烯基-5-甲氧基-6,7-(2″,2″-二甲基吡喃)-3′,4′-二氧亚甲基黄酮(B)，分别命名为粉枝莓素A和粉枝莓素B。化合物A和B为新的黄酮类化合物。     

Antimicrobial constituents from goldenseal (the Rhizomes of Hydrastis canadensis) against selected oral pathogens

Two new C-methyl flavonoids, 6,8-di- C-methylluteolin 7-methyl ether (1) and 6- C-methylluteolin 7-methyl ether (2), were isolated from a commercially available sample of the roots of Hydrastis canadensis, along with seven known compounds, berberine (3), beta-hydrastine (4), canadine (5), canadaline (6), isocorypalmine (7), canadinic acid (8), and beta-sitosterol 3- O-beta- D-glucoside (9). The structures of the new compounds 1 and 2 were elucidated on the basis of their spectral data including 1D and 2D NMR techniques. Of these isolates, berberine (3) and, to a lesser extent, 1 and 2, showed antimicrobial activity when evaluated against the oral pathogens Streptococcus mutans and Fusobacterium nucleatum. Berberine (3) exhibited an additive antimicrobial effect when tested against S. mutans in combination with 1.     

2,3-Dihydrobiflavone from Ginkgo biloba

From the yellow leaves of Ginkgo biloba 2,3-dihydrosciadopitysin (5,5',7'-trihydroxy-7,4',4'-trimethoxy-3',8'-flavanone/flavone) was isolated as a mixture of two diastereomers. Its structure was elucidated employing 2D NMR techniques.     

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-beta-d-galactopyranoside (7), 3,5,3'-trihydoxy-7,4'-dimethoxy-flavone-3-O-beta-d-galactopyranoside (8), 3,5,3',4'-tetrahydroxy-7-methoxy-flavone-3-O-beta-d-galactopyranoside (9), 3,5,3',4'-tetrahydroxy-7-methoxy-flavone-3-O-beta-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.