Theviridoside

Lantana canescens (Kunth) inhibits inflammatory and hyperalgesic responses in murine models

Ethnopharmacological relevance: Lantana canescens is popularly known in Brazil as "cidreirinha" or "chumbinho-branco". It is found in Pantanal biome and its flowers and leaves are used in traditional medicine to treat pain and inflammation. Information about this species is limited to the activity of isolated essential oils. Studies with different extracts, composition, and biological properties are still scarce. Aim of this study: The objective of this study was to evaluate the anti-inflammatory and anti-hyperalgesic activity of the hydroethanolic extract of L. canescens aerial parts. Materials and methods: The hydroethanolic extract L. canescens aerial parts (HELc) was analyzed using HPLC-DAD-EM. Male and female Swiss mice weighing 18-25 g were used in the in vivo assays. Acute toxicity was assessed (2000 mg/kg); anti-inflammatory activity through paw edema, mast cell degranulation and peritonitis, and anti-hyperalgesic activity through abdominal writhing assays induced by acetic acid and formalin sensitization, were evaluated using the doses of 3, 30 and 300 mg/kg. Results: The phytochemical characterization of HELc confirmed the presence of glycosylated iridoids (theveside, theviridoside), verbascosides and flavonoids. The HELc did not present toxicity in the evaluated dose. HELc reduced formation of paw edema, degranulation of peritoneal mast cells and infiltration of polymorphonuclear cells into the animals peritoneal cavity. In addition, HELc decreased the number of abdominal writhing induced by acetic acid and the time of paw licking in the evaluation of formalin sensitization. Conclusions: These results confirm the anti-inflammatory and anti-hyperalgesic effects of hydroethanolic extract of L. canescens, validating the use of this plant in folk medicine.

Iridoids and Amino Acid Derivatives from the Paraguayan Crude Drug Adenocalymma marginatum (ysypó h?)

The crude drug ysypó h? (Adenocalymma marginatum DC., Bignoniaceae) is used traditionally by the Guarani of Eastern Paraguayan as a male sexual enhancer. The aim of the present study was to identify the main constituents of the crude drug and to evaluate the in vitro inhibitory activity towards the enzyme phosphodiesterase-5 (PDE-5). The main compounds were isolated by counter-current chromatography (CCC). The metabolites were identified by spectroscopic and spectrometric means. The chemical profiling of the extracts was assessed by high-performance liquid chromatography coupled to mass spectrometry (HPLC-MS/MS). The crude extract and main isolated compounds were tested for their PDE-5 inhibitory activity using commercial kits. The iridoid theviridoside and 4-hydroxy-1-methylproline were isolated as the main constituent of the crude drug. Four chlortheviridoside hexoside derivatives were detected for the first time as natural products. Chemical profiling by HPLC-MS/MS led to the tentative identification of nine iridoids, six phenolics, and five amino acids. The crude extracts and main compounds were inactive towards PDE-5 at concentrations up to 500 ?g/mL. Iridoids and amino acid derivatives were the main compounds occurring in the Paraguayan crude drug. The potential of ysypó h? as a male sexual enhancer cannot be discarded, since other mechanisms may be involved.

Iridoid glycosides from the stems of Pithecoctenium crucigerum (Bignoniaceae)

Sixteen crude extracts from six Panamanian plants of the family Bignoniaceae were submitted to rapid TLC tests against DPPH and acetylcholinesterase. Pithecoctenium crucigerum (L.) A.H. Gentry, which showed interesting activity against DPPH, has been studied. The chemical investigation of the methanol extract from the stems afforded the iridoid glycoside theviridoside and three derivatives (6'-O-cyclopropanoyltheviridoside, 10-O-hydroxybenzoyltheviridoside and 10-O-vanilloyltheviridoside), along with five known phenylethanoid glycosides (verbascoside, isoverbascoside, forsythoside B, jionoside D and leucosceptoside B). These last compounds were all active against DPPH. The structures were determined by means of spectrometric and chemical methods, including 1D and 2D NMR experiments and MS analysis.

Cytotoxicity studies of semi-synthetic derivatives of theveside derived from the aqueous extract of leaves of 'suicide tree' Cerbera odollam

We report the isolation of two known iridoid glucosides theviridoside (1) and theveside (2) from the aqueous extract of leaves of Cerbera odollam and semi-synthetic derivatisation of theveside prepared in a single step under protection group-free conditions. Derivatives 2a-j were evaluated for cytotoxicity towards five human cancer cell lines of different origins, namely SKBR3 (breast), HeLa (cervical), A375 (skin), HepG2 (liver) and HCT-116 (colon), and IC50 values were determined. Derivatives 2b and 2h exhibited moderate cytotoxicity against HCT-116 and A375 cell lines, respectively.

[Studies on chemical constituents of the roots of Lantana camara]

Six oligosaccharides (I-VI) and six iridoid glucosides (VII-XII) isolated from the ethanolic extract of Lantana camara roots were identified as stachyose (I), verbascose (II), ajugose (III), verbascotetracose (IV), alpha-D-galac-(1-[-6)-alpha-D-galac(-1](3)-6-D-gluc(V ) , alpha-D-galac-(1-6)-alpha-D-galac(-1]-(4)6-D-)gluc(VI) , theveside (VII), 8-epiloganin (VIII), shanzhsid methyl ester (IX), theviridoside (X), lamiridoside (XI) and geniposide (XII), on the basis of spectral analysis (1H-NMR, 13C-NMR, FD-MS, GC-MS), physico-chemical constants and preparation of derivatives. V and VI were new compounds named lantanose A and lantanose B, respectively. The others were isolated from this plant for the first time.