iridoids and secoxyloganin

To study the chemical composition and their anti-inflammatory activities of honeysuckle (Lonicera japonica Thunb.) roots, seventeen compounds were isolated from the roots of L. japonica Thunb. by various chromatography, including silica gel, Sephadex LH-20 and preparative HPLC. Their structures were identified by MS, IR, and nuclear magnetic resonance spectra, as 1-oxo-(1H)-cyclopenta[b]benzofuran-7-carbaldehyde (1), 4-hydroxycinnamic acid (2), chlorogenic acid (3), loganin aglycone (4), caffeic acid (5), secologanin dimethyl acetal (6), korolkoside (7), coniferin (8), sweroside (9), secoxyloganin (10), 5-O-caffeoylquinic acid (11), chlorogenic acid methyl ester (12), chlorogenic acid ethyl ester (13), 3,5-O-dicaffeoylquinic acid (14), 4,5-O-dicaffeoylquinic acid (15), grandifloroside (16), and 4,5-O-dicaffeoylquinic acid (17). Among those, compound 1 is a new compound, and compound 8 is found in L. japonica for the first time. Compounds 1, 3, 14-17 showed significant anti-inflammatory activities against macrophage in zebrafish.

Topics: Animals; Anti-Inflammatory Agents; Chlorogenic Acid; Chromatography, High Pressure Liquid; Iridoid Glucosides; Iridoids; Lonicera; Macrophages; Plant Roots; Quinic Acid; Zebrafish

To study the chemical constituents from the flower of Lonicera fragrantissima.. The chemical constituents were isolated and purified by means of several chromatographic techniques, and their structures were elucidated by spectroscopic methods.. Nine compounds were isolated and identified as chlorogenic acid (1), caffeic acid (2), secologanoside (3), secoxyloganin(4), loganin (5), sucrose (6), myo-inositol (7), rutin (8), and chrysoeriol-7-O-β-D-glucoside (9).. Compounds 2-9 are obtained from this plant for the first time.

Topics: Caffeic Acids; Chlorogenic Acid; Flavones; Flowers; Glucosides; Inositol; Iridoid Glucosides; Iridoids; Lonicera; Rutin; Sucrose

The cytotoxic activity of crude extracts and their fractions from leaves and roots of G. pohliana was assessed against nine human cancer cell lines: melanoma (UACC-62), breast (MCF-7), breast expressing the multidrug resistance phenotype (NCI-ADR), lung (NCI-460), prostate (PCO-3), kidney (786-0), ovarian (OVCAR), colon (HT-29) and leukaemia (K-562). The hexane fraction from leaves (HL) and ethyl acetate (EAR), chloroform (CR) and hydromethanolic (HMR) fractions from roots were the most active fractions against K-562 with GI₅₀ values being lower than 1 μg mL⁻¹. Also, CR and HMR fractions were active against UACC-62 cell line in the same order of magnitude. The phytochemical study of the CR fraction allowed identifying the known iridoids secoxyloganin, sweroside and loganin.

Topics: Antineoplastic Agents, Phytogenic; Cell Line, Tumor; HT29 Cells; Humans; Iridoid Glucosides; Iridoids; Plant Extracts; Plant Leaves; Plant Roots; Rubiaceae

Allergy-preventive activity of flower buds of Lonicera japonica THUNB. was found in the 35% EtOH extract (LJ) using an in vivo assay, The assay system uses monitoring of a decrease in blood flow (BF) in the tail vein of mice subjected to sensitization with hen-egg white lysozyme (HEL). Bioassay-guided fractionation of the 35% EtOH extract led to isolation of chlorogenic acid (1) and three known iridoid derivatives, loganin (2), secoxyloganin (3) and sweroside (4), all of which inhibited the BF decrease. This suggested that the flower buds of L. japonica and compounds isolated from them have allergy-preventive properties. The structure-activity relationship of iridoid derivatives, morroniside (5), geniposide (6), asperuloside (7), aucubin (8) and catalpol (9), were also tested using the same bioassay method. Compounds 2-5 and 9 having the sp(3) atom at C-8 showed an allergy-preventive effect, while compounds 6, 7 and 8 having a double bond at C-7, C-8 did not.

Topics: Animals; Anti-Allergic Agents; Chickens; Chlorogenic Acid; Female; Flowers; Hypersensitivity; Iridoid Glucosides; Iridoids; Lonicera; Male; Mice; Mice, Inbred Strains; Muramidase; Phytotherapy; Plant Extracts; Structure-Activity Relationship; Veins

This study presents a new HPLC method for the simultaneous determination of seven major components, namely chlorogenic acid, caffeic acid, loganin, sweroside, secoxyloganin, rutin and luteolin 7-O-glucoside in Caulis Lonicerae Japonicae, a commonly used traditional Chinese medicinal herb derived from the caulis of Lonicera japonica Thunb. These seven compounds, belonging to the chemical types of phenolic acids, iridoids and flavonoids, were separated on a C18 column (250 x 4.6 mm, 5.0 microm) with the column temperature at 30 degrees C. The mobile phase was composed of (A) aqueous acetic acid (0.4%, v/v) and (B) acetonitrile using a gradient elution of 10% B at 0-12 min, 10-17% B at 12-25 min and 17% B at 25-35 min. The flow rate was 1.0 mL/min and detection wavelength was set at 245 nm. The limit of detection (S/N = 3) ranged from 0.10 to 0.23 microg/mL and the limit of quantification (S/N = 10) ranged from 0.69 to 3.56 microg/mL. All calibration curves showed good linear regression (r2 > 0.9990) within the test ranges. The intra- and inter-day precisions as determined from sample solutions were below 1.24 and 2.28%, respectively. The recoveries for seven compounds were found to range from 94.2 to 103.6%. This verified method has been successfully applied to evaluation of commercial samples of Caulis Lonicerae Japonicae from different markets in China.

Topics: Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Flavonoids; Glucosides; Hydroxybenzoates; Iridoid Glucosides; Iridoids; Linear Models; Lonicera; Luteolin; Molecular Structure; Reproducibility of Results; Rutin; Sensitivity and Specificity; Spectrophotometry, Ultraviolet

Three seco-iridoids 7-methoxydiderroside, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochemistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosoma cruzi, with IC(50) values of 59.0, 90.2, 74,2 and 84.9 microg/mL, respectively and were compared to the standard gentian violet (IC(50) 7.5 microg/ml).

Topics: Animals; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Magnetic Resonance Spectroscopy; Molecular Structure; Rubiaceae; Stereoisomerism; Trypanocidal Agents; Trypanosoma cruzi

A reinvestigation of the roots of Guettarda platypoda afforded in addition to morronoside and sweroside isolated previously further two iridoids, loganic acid and loganin and a rare secoiridoid, secoxyloganin. The structures were elucidated by NMR techniques. This is the first report of the isolation of such compounds from G.platypoda. Some chemotaxonomic conclusion can be drawn.

Topics: Chemical Phenomena; Chemistry; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Plants, Medicinal; Pyrans