Iridoids from Scrophularia genus.

We report here an updated summary about iridoid composition of a series from the genus Scrophularia which have been investigated until now from a phytochemistry point of view. In addition a list is included about iridoids isolated in our laboratory from different plant parts of Scrophularia scorodonia L., which are compared with iridoids from some species of the Scrophularia genus. The present study may serve as a current information to researchers working on phytochemistry and pharmacological aspects from the Scrophularia genus and possibly to serve as a new starting point for future investigations.

Phytochemical analysis of Phillyrea latifolia L., a new source of oleuropeoside.

As a part of our studies on the biologically active substances from Spanish plants, we have undertaken an investigation of the chemical constituents of a typical mediterranean species, Phillyrea latifolia L. (Oleaceae). Two secoiridoid glycosides, three phenylpropanoid glycosides, one lignane and two triterpenic acids were isolated from the leaves of this species and identified. The phytochemical analysis of the aerial parts of P. latifolia revealed that it is a rich source of oleuropeoside.

Lignan and phenylpropanoid glycosides from Phillyrea latifolia and their in vitro anti-inflammatory activity.

Three phenylpropanoid glycosides (salidroside, syringin and coniferin) and one lignan (phillyrin) isolated from the leaves of Phillyrea latifolia L. (Oleaceae) were tested for interactions with the cyclo-oxygenase and 5-lipoxygenase pathways of arachidonate metabolism in calcium-stimulated mouse peritoneal macrophages and human platelets, and for their effects on cell viability. These compounds are capable of exerting inhibitory actions on enzymes of the arachidonate cascade. Phillyrin, salidroside and syringin exert a preferential effect on the cyclo-oxygenase pathway, inhibiting release of the cyclo-oxygenase metabolites prostaglandin E2 (IC50 values 45.6 microM, 72.1 microM and 35.5 microM, respectively) and to a lesser extent reducing thromboxane B2 levels (IC50 values 168 microM, 154 microM and 29.3 microM, respectively). In contrast, coniferin can be classified as a "dual inhibitor", since it produces reduction in generation of both cyclo-oxygenase (IC50 values 75.2 microM for prostaglandin E2 and 619 microM for thromboxane B2) and 5-lipoxygenase metabolites, but the effects are greater against leukotriene C4 (IC50 value 63.6 microM). Structure-activity relationships of the three phenylpropanoid glycosides are discussed. Thus, like some other compounds found in medicinal herbs, our molecules possess an array of potentially beneficial anti-eicosanoid properties which may, alongside other constituents, contribute to the claimed therapeutic properties of the plant from which they are derived.

Two new eudesmane alcohols from Jasonia glutinosa.

Two new sesquiterpene alcohols have been isolated from the aerial parts of Jasonia glutinosa D. C. The structure of these sesquiterpenes were characterized by 1D and 2D NMR techniques (DQCOSY. TOCSY, NOESY, HMQC and HMBC) as (11R)-eudesm-4-en-11,12-diol and (11R)-eudesmane-5alpha, 11,12-triol.

Sesquiterpene lactones from Inula montana L.

Aerial parts of Inula montana were investigated for its sesquiterpenoid composition. Five sesquiterpene lactones, isoinuviscolide, gaillardin, 1beta-hydroxy-3beta-acetoxy-eudesm-4(15), 11(13)-dien-12-8beta-olide, pulchellin-C and pulchellin-E were identified for the first time in this plant. One of them, 1beta-hydroxy-3beta-acetoxy-eudesm-4(15),11(13)-dien-1 2-8beta-olide, is a novel natural product. The structures of this compounds were established by 1D and 2D-NMR spectroscopy.

Four new triterpenoid saponins from the roots of Bupleurum rigidum.

Five triterpenoid saponins [buddlejasaponin IV, sandrosaponins VII (1), VIII (2), IX (3), and X (4)] were isolated from an n-BuOH extract of the roots of Bupleurum rigidum. Sandrosaponins VII-X (1-4) are new compounds, and their structures were established by 1D and 2D NMR techniques, FABMS, and chemical methods.

Minor sulfated saikosaponins from the aerial parts of Bupleurum rigidum L.

Five new sulfated saikosaponins (Sandrosaponins II-VI) were isolated as minor components from the aerial parts of Bupleurum rigidum L. Their structures have been established by 1D and 2D-NMR techniques, FABMS, and chemical methods. ,

Isoangoroside C, a phenylpropanoid glycoside from Scrophularia scorodonia roots.

A new phenylpropanoid glycoside isoangoroside C was isolated from the roots of Scrophularia scorodonia. Its structure was determined on the basis of spectral data as: 3-hydroxy-4-methoxy-beta-phenylethoxy-O-alpha-L-arabinopyranosy l-(1-->6)alpha L-rhamnopyranosyl-(1-->3)-4-O-Z-feruloyl-beta-D-glucopyranoside. Additionally, one known phenylpropanoid, angoroside C, and five known iridoid glycosides, harpagoside, bartsioside, 8-O-acetyl-harpagide, aucuboside and harpagide were isolated and identified.

Effects of some iridoids from plant origin on arachidonic acid metabolism in cellular systems.

Seven iridoid glycosides isolated from different extracts of Scrophularia scorodonia L., namely bartsioside, aucubin, harpagide, harpagoside, 8-acetylharpagide, scorodioside and scropolioside B, had been evaluated for their in vitro anti-inflammatory activity in cellular systems generating COX and LOX metabolites. Structure-activity relationships obtained from in vitro screening results were discussed. Most compounds assayed did not exhibit any significant effect on PGE2- and LTC4-release from calcium ionophore-stimulated mouse peritoneal macrophages. In the LTC4-assay, only aucubin showed a significant effect, with an IC50 value of 72 microM. Harpagoside and harpagide also inhibited release of LTC4, but neither effect reached statistical significance. The release of PGE2 by mouse peritoneal macrophages stimulated with calcium ionophore was inhibited by harpagoside and 8-acetylharpagide, but this effect is not statistically significant. However, most iridoids assayed showed a significant effect on TXB2-release from calcium ionophorestimulated human platelets, with inhibition percentages slightly lower than the reference drug ibuprofen. Only harpagide, scorodioside and scropolioside B had no significant effect on TXB2-release. Our results indicate that selective inhibition of the TX-synthase enzyme may be the primary target of action of most of these iridoids, and one of the mechanisms through which they exert their anti-inflammatory effects.

Polyphenolic compounds from Plantago lagopus L.

In the present study we report the isolation of a phenylpropanoid glucoside, plantamajoside, together with rosmarinic acid, chlorogenic acid and luteolin-7-O-monoglucoside. This is the first report of these compounds from Plantago lagopus.

Antiprotozoal activity of sesquiterpenes from jasonia glutinosa.

Two sesquiterpene alcohols, [11 R]-eudesm-4(14)-en-5ß,11,12-triol ( 1 ) and [11R]-eudesm-4(14)-en-5a,11-12-triol ( 2 ), from Jasonia glutinosa aerial parts (Asteraceae), have been tested using an in vitro technique against Leishmania donovani (promastigote forms) and Plasmodium falciparum . Sesquiterpene 1 was not effective at the assayed concentrations. Sesquiterpene 2 was found to be active against Leishmania donovani and Plasmodium falciparum .

Iridoids from plantago lagopus.

Catalpol ( 1 ), harpagoside ( 2 ), aucubin ( 3 ), 10-benzoylcatalpol ( 4 ) and 6-a-hydroxy-geniposide ( 5 ) were isolated from the aerial parts of Plantago lagopus L. for the first time. More generally, this is the first report of compound 5 being obtained from a plant extract.

Two new sulfated saponins from the roots of Gypsophila bermejoi.

Two new sulfated saponins (1 and 2) were isolated from a butanol-soluble extract of the roots of Gypsophila bermejoi and were identified by a combination of chemical degradation and spectral methods as the 3beta-sulfate ester of gypsogenin 28-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->6)]-beta -D-glucopyranoside (1), and the 23-sulfate ester of hederagenin 28-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->6)]-beta -D-glucopyranoside (2), respectively. Plants of the genus Gypsophila (Caryophyllaceae) are important industrially because of the capacity of their saponin constituents to behave like natural detergents.1 Saponins from this genus are based on oleanolic acid (3-hydroxyolean-12-en-28-oic acid), with gypsogenin being the main pentacyclic triterpenoidal aglycon found. In general, this aglycon is substituted at the C-3 hydroxyl and/or C-28 carboxylic acid groups by saccharide units.2

In vivo and in vitro antiinflammatory activity of saikosaponins.

Buddlejasaponin I and saikosaponin 1 and 2, biologically active compounds from Scrophularia scorodonia and Bupleurum rigidum respectively, exert potent in vivo antiinflammatory effects on mouse ear edema induced by phorbol myristate acetate (PMA). The effects of these compounds on swelling and other inflammatory parameters are described. In screening for in vitro effects of saikosaponins on cellular systems generating cyclooxygenase (COX) and lipoxygenase (LOX) metabolites, we observed that most saikosaponins showed a significant effect. The action is more marked on LOX metabolite LTC4. Our data support the inhibition of arachidonic acid metabolism as one of the biochemical mechanisms that might be the rationale for the putative antiphlogistic activity of these saikosaponins.

A saponin from the roots of Gypsophila bermejoi.

A new saponin was isolated from the methanol extract of the roots of Gypsophila bermejoi and identified by a combination of chemical degradation and spectral methods, which included negative FABMS and extensive 1D and 2D-NMR analysis (DQCOSY, TOCSY, ROESY, HMQC and HMBC), as gypsogenin 28-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl (1-->6)]-beta-D-glucopyranoside.

Saponins of the ivy plant, Hedera helix, and their leishmanicidic activity.

Antileishmanial activity is reported for the first time for saponins of ivy, Hedera helix L., in vitro on promastigote and amastigote forms of Leishmania infantum and Leishmania tropica. The compounds tested were an extract containing 60% of saponic complex (CS 60), the bidesmosides hederasaponin B, C, and D (saponin K10), their corresponding monodesmosides alpha-, beta-, and delta-hederin, and hederagenin. CS 60 and bidesmosides have shown no effect. Monodesmosides were found to be as effective on promastigote forms as the reference compound (pentamidine). Against amastigote forms only hederagenin exhibited a significant activity which was equivalent to that of the reference compound (N-methylglucamine antimonate).

[Flavonoids of 3 cultivars vine leaves, Vitis vinifera L. var. tinctoria (Alicante, Carignan, Grand noir). Value in chemical control]. / Mise au point sur les dérivés flavoniques des feuilles de trois cultivars de Vigne Vitis vinifera L. var. tinctoria (Alicante, Carignan, Grand noir). Intérêt dans le contrôle chimique.

Three flavonoids were isolated and identified from the leaves of 3 cultivars vine Vitis vinifera L. var. tinctoria (Alicante, Carignan and Grand noir): hyperin, isoquercitrin and quercetin 3-O-beta-D glucuronic acid. TLC analytic control and HPLC determination are proposed in this paper.