Indole alkaloid glycosides with a 1'-(phenyl)ethyl unit from leaves

Seven indole alkaloid glycosides containing a 1'-(4″-hydroxy-3″,5″-dimethoxyphenyl)ethyl unit (-) were isolated from an aqueous extract of leaves (da qing ye). Their structures were determined by spectroscopic data analysis combined with enzymatic hydrolysis as well as comparison of their experimental CD (circular dichroism) and calculated ECD (electrostatic circular dichroism) spectra. Based on analysis of and/or Cotton effect (CE) data of -, two simple roles to assign location and/or configuration of -glycopyranosyloxy and 1'-(phenyl)ethyl units in the indole alkaloid glycosides are proposed. Stereoselectivity in plausible biosynthetic pathways of - is discussed. Compounds and and their mixture in a 3:2 ratio showed activity against KCNQ2 in CHO cells. The mixture of and (3:2) exhibited antiviral activity against influenza virus H1N1 PR8 with IC 64.7 μmol/L (ribavirin, IC 54.3 μmol/L), however, the individual or was inactive. Preliminary structure-activity relationships were observed.

Phytochemical Constituents of Capsella bursa-pastoris and Their Anti-inflammatory Activity

Phytochemical investigation of 80% MeOH extract of the aerial parts of Capsella bursa-pastoris yielded fourteen compounds (1 – 14). The structures of the compounds were elucidated by spectroscopic methods to be methyl-1-thio-β-D-glucopyranosyl disulfide (1), 10-methylsulphinyl-decanenitrile (2), 11-methyl-sulphinyl-undecanenitrile (3), 1-O-(lauroyl)glycerol (4), phytene-1, 2-diol (5), (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (6), loliolide (7), β-sitosterol (8), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (9), 1-feruloyl-β-D-glucopyranoside (10), pinoresinol-4′-O-β-D-glucopyranoside (11), luteolin (12), quercetin-3-O-β-D-glucopyranoside (13), and luteolin 6-C-β-glucopyranoside (14). Although compound 1 was reported as synthetic compound, 1 was first isolated from natural source. NMR spectral data assignments of 1, 2 and 3 were reported for the first time, and compounds 1 – 14 were for the first time reported from this plant source. The anti-inflammatory effects of 1 – 14 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 12 exhibited strong inhibitory effects on nitric oxide production in LPS-activated BV-2 cells with IC50 values of 9.70 µM.

Sulfur-enriched alkaloids from the root of

Five new sulfur-enriched alkaloids isatithioetherins A-E (-), and two pairs of scalemic enantiomers (+)- and (-)-isatithiopyrin B ( and ) and isoepigoitrin and isogoitrin and ), along with the known scalemic enantiomers epigoitrin and goitrin ( and ), were isolated and characterized from an aqueous extract of the roots. Their structures were determined by extensive spectroscopic data analysis, including 2D NMR and theoretical calculations of electronic circular dichroism (ECD) spectra based on the quantum-mechanical time-dependent density functional theory (TDDFT). Compounds - represent a novel group of sulfur-enriched alkaloids, biogenetically originating from stereoselective assemblies of epigoitrin-derived units. Isolation and structure characterization of and support the postulated biosynthetic pathways for the diastereomers and a rare thio-Diels-Alder reaction. Compounds and showed antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2, IC 0.60 and 1.92 μmol/L) and the herpes simplex virus 1 (HSV-1, IC 3.70 and 2.87 μmol/L), and also inhibited Coxsackie virus B3 (IC 0.71 μmol/L).

Aromatic compounds from an aqueous extract of "ban lan gen" and their antiviral activities

A pair of new diphenyl glycerol ether enantiomers (-)-and (+)-and two new methyl benzamidobenzoatesand, named (-)-()- and (+)-()-isatindigotrioic acid [(-)-and (+)-] and isatindigoticamides A () and B (), respectively, were isolated from an aqueous decoction of the roots of(ban lan gen). Their structures were elucidated by spectroscopic data analysis including 2D NMR experiments. The absolute configurations of (-)-and (+)-were assigned based on the CD exciton chirality method. Compoundsandexhibited antiviral activities against HSV-1 with ICvalues of 4.87 and 25.87 μmol/L, respectively. Compoundwas also found active against Coxsackie virus B3 and LPS-induced NO production.

Indole alkaloid sulfonic acids from an aqueous extract ofroots and their antiviral activity

Six new indole alkaloid sulfonic acids (-), together with two analogues (and) that were previously reported as synthetic products, were isolated from an aqueous extract of theroot. Their structures including the absolute configurations were determined by spectroscopic data analysis, combined with enzyme hydrolysis and comparison of experimental circular dichroism and calculated electronic circular dichroism spectra. In the preliminary assay, compoundsandshowed antiviral activity against Coxsackie virus B3 and influenza virus A/Hanfang/359/95 (H3N2), respectively.

8,4'-Oxyneolignane glucosides from an aqueous extract of "ban lan gen" (root) and their absolute configurations

Three pairs of glycosidic 8,4'-oxyneolignane diastereoisomers, named isatioxyneolignosides A-F (-), were isolated from an aqueous extract ofroots. Their structures and absolute configurations were elucidated by comprehensive spectroscopic data analysis and enzyme hydrolysis. The validity of Δvalues to distinguishandaryl glycerol units and Cotton effects at 235±5 nm to determine absolute configurations at C-8 in-and their aglycones (-) are discussed.

Advances in Biosynthesis of Antiviral Active Components of Isatidis Radix / 世界科学技术-中医药现代化

Isatidis Radix,the root of Isatis indigotica Fort.(Cruciferae),is a representitive herb widely used for clearing away heat-toxin in traditional Chinese medicine (TCM).Lariciresinol is a representitive component of lignans and an important efficacious substance with the antiviral effect.This review elucidated the progress on its biosynthetic pathways,the screening of key regulatory genes and metabolic engineering of lignans components in Isatidis Radix,providing a favorable reference for the full understanding of biosynthesis of antiviral active components,the quality improvement of Isatidis Radix and the sustainable utilization of TCM resources.

Three pairs of alkaloid enantiomers from the root of Isatis indigotica

Three pairs of enantiomerically pure alkaloids with diverse structure features, named isatindigoticoic acid A and epiisatindigoticoic acid A [(-)-1 and (+)-1], phaitanthrin A and epiphaitanthrin A [(-)-2 and (+)-2], and isatindopyrromizol A and epiisatindopyrromizol A [(-)-3 and (+)-3], respectively, were isolated from an aqueous extract of the roots of Isatis indigotica. Racemic and scalemic mixtures of these enantiomers were separated by HPLC on a chiral semi-preparative column. Their structures including absolute configurations were determined by extensive spectroscopic analysis in conjunction with the calculation of electronic circular dichroism (ECD) spectra. The enantiomer pairs possess parent structures of 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid, indolo[2,1-b]quinazolinone, and 3-thioxohexahydro-1H-pyrrolo[1,2-c]imidazol-1-one, respectively. Except for phaitanthrin A [(-)-2] which the configuration was previously undetermined, these compounds are new enantiomeric natural products.

Chemical Constituents from Chemical Split Fractions of Seeds ofDescurainia sophia (L.) Webb. ex Prantl / 世界科学技术-中医药现代化

This article was aimed to study the chemical constituents of seeds of Descurainia Sophia (L.) Webb. ex Prantl., in order to lay the material foundation for further interpretation of seeds of D. Sophia and provide pharmacodynamic basis as well as the basis for attributing its nature and taste. The compounds were isolated and purified by Diaion HP-20, Toyopearl HW-40, MCI Gel CHP-20, ODS, Silica gel chromatography combining with Pre-HPLC. The structures were identified on the basis of spectral data and physicochemical properties. Twenty eight compounds were isolated and identified from 20% and 80% ethanol fraction. Thirteen compounds were identified from 20% ethanol fraction: kaempferol-3-O-β-D-glucopyranosyl-7-O-β-D-gentiobioside(1), quercetin-3-O-β-D-glucopyranosyl-7-O-β-D-gentiobioside (2), isorhamnetin-3-O-β-D-glucopyranosyl-7-O-β-D-gentiobioside (3), isorhamnetin-3,7-di-O-β-D-glucopyranoside (4), quercetin-3,7-di-O-β-D-glucopyranoside (5), kaempferol-3, 7-di-O-β-D-glucopyranoside (6), kaempferol-3-O-β-D-xylopyranosyl (1 → 2)-β-D-glucopyranoside (7), methyl sinapate (8), syringaldehyde (9), (S)-p- hydroxyphenyl lactate acid (10), (S)-2-hydroxy-phenylpropionic acid (11), scopoletin (12), sinapic acid (13). Fifteen compounds were identified from 80% ethanol fraction: isorhamnetin-3-O-β-D-glucopyranoside (14), quercetin-3-O-β-D-glucopyranoside (15), kaempferol-3-O-β-D-glucopyranoside (16), quercetin (17), kaempferol (18), isorhamnetin (19), syringic acids (20), quercetin-3-O-β-D-arabinopyranoside (21), quercetin-3-O-β-D-xylopyranoside (22), 6-O-[E]-Sinapoyl-(α- and β)-D-glucopyranoside (23), dimethyl (E, E)-4,4'-dihydroxy-3,3',5,5'-tetramethoxylign-7,7'-dien-9,9'-dioate (24), dimethylthomasidioate (25), 2-hydroxy-3-(1H-indol-3-yl) propanoic acid (26), 2-hydroxyl-3-(1H-indol-3-yl) propanoic acid methyl ester (27), 4'-O-methyl-dihydroquercetin (28). It was concluded that compounds 7-11 and 21-28 were isolated from seeds of D. sophia (L.) Webb. ex Prantl. for the first time.

Water-soluble constituents from of seeds Orychophragmus violaceus / 中国药学杂志

OBJECTIVE: To study water-soluble constituents from the seeds Orychophragmus violaceus. METHODS: The constituents were isolated and purified by silica gel chromatography repeatedly, and the structures were identified by spectral analysis and chemical methods. RESULTS: Fifteen water-soluble compounds were isolated from the seeds Orychophragmus violaceus and their structures were identified as blumenol A(1), 3', 5', 5, 7-tetrahydroxylflavanone(2), (+)-catechin(3), quercetin(4), adenosine(5), salicylic acid(6), 2'-deoxy adenosine(7), p-coumaric acid(8), vanillic acid(9), protocatechuic acid(10), caffeic acid(11), syringic acid(12), daucosterol(13), succinic acid(14) and azelaic acid(15). CONCLUSION: All compounds are isolated from Orychophragmus violaceus for the first time. This study can establish the foundation for the classification chemical composition this plant.

Use of cabbage leaves (Brassica oleracea var. acephala) in the stabilization of bone mass after menopause / Uso do suco das folhas da couve (Brassica oleracea var acephala), na estabilização da massa óssea pós-menopausa

This work evaluates the use of cabbage leaves, Brassica oleracea var acephala (Cruciferae family) to stabilize bone mass in 13 menopausal women. The mature leaves were used after removal of the midrib and petiole and taken as a juice and given to the patient once a day for 24 months. Densitometric exams were performed every six months. The measurement points were the Trocanter and Ward's triangle. According to the results found, the use of cabbage leaf juice results in bone mass stabilization at the points studied, with perspectives for its use as an important option in disease prevention.

Neste trabalho foi avaliado a utilização da folha da couve Brassica oleracea variedade acephala, pertencente à família Cruciferae, para estabilizar a massa óssea em 13 mulheres após a menopausa. As folhas da couve foram usadas após retirar a nervura principal e o peciolo, na forma de suco de uma folha ao dia, durante 24 meses. Foi realizado a cada seis meses o exame de densitometria óssea para avaliar os resultados. Os locais de medição foram o trocanter e o triângulo de Ward. De acordo com os resultados encontrados, podemos concluir que o uso da folha da couve foi capaz de estabilizar a massa óssea nos sítios estudados, com perspectivas do seu uso também como opção importante para prevenção da doença.