Phytochemical investigation of aerial parts of Woodsia ilvensis and its plasmin-inhibitory activity in vitro.

The fern plant Woodsia ilvensis (L.) R. Br. belongs to the Woodsiaceae family and its leaves are used to treat diarrhea, soft-tissue injuries, and external injuries. Investigations of the compounds obtained from the plasmin-inhibitory-active extracts of W. ilvensis led to the isolation of two undescribed maleimide N-glycosides, an undescribed stilbenoid glycoside, and five undescribed acetylated flavonol bisdesmosides, together with 19 known compounds. The chemical structures of the isolated compounds were determined using spectroscopy. The absolute configurations of the sugar moieties were determined via HPLC after acid hydrolysis. Among the isolated compounds, some flavonoids and stilbenoid glycosides exhibited plasmin-inhibitory activity.

Phytochemical investigation of Scutellaria scordiifolia and its trypanocidal activity.

Scutellaria scordiifolia Fisch. ex Schrank is used to treat various inflammatory diseases and other ailments in traditional and contemporary medicine. In this study, 10 undescribed compounds, including a flavanone (1), four chrysin C-glycosides (2-5), a phenanthrene glucoside (6), four iridoid glucosides (7-10) and 31 known compounds were identified from an extract of the aerial parts of S. scordiifolia. The absolute configurations of sugars in C-glycosides were determined by comparing electric circular dichroism spectra with calculated data. The flavanones (1 and 17), flavonols (11-13), flavone (14), and some of the flavone glucuronides (15, 16) exhibited trypanocidal activities against Trypanosoma congolense. The activity data and quantitative HPLC analysis of flavonoids from the aerial parts of S. scordiifolia suggest that they may effectively treat diseases caused by the aforementioned trypanosomes. Other compounds such as novel iridoids and phenanthrene glycosides, which may be useful for chemophenetic and chemoecological discussions, were also identified.

A new hexenoic acid glycoside with cytotoxic activity from the leaves of Psychotria luzoniensis.

A new hexenoic acid glycoside (1) together with known compounds, flavonol glycosides (2-4), iridoid glycoside (5), megastigmane glycoside (6), and amino acid (7) were isolated from the leaves of P. luzoniensis by resin column chromatography and preparative HPLC. Their structures were determined based on spectroscopic analysis, including HRFABMS and NMR (1H and 13C, 1H-1H COSY, HMQC, and HMBC) data. All compounds tested for cytotoxicity were active (IC50 < 50 µM) with IC50 values ranging from 1.97 to 32.85 µM against human colon adenocarcinoma cell line, compared to etoposide (IC50 1.19 µM).

Isolation and evaluation of trypanocidal activity of sesquiterpenoids, flavonoids, and lignans in Artemisia sieversiana collected in Mongolia.

Artemisia sieversiana is an annual herbaceous plant distributed throughout Central and East Eurasia and is regarded as an undesirable forage plant in Mongolia. It affects livestock, so information about its chemical composition is needed. We isolated three new sesquiterpenoids (1-3) and known compounds from A. sieversiana and investigated their activities. The absolute configuration of 1 was established using single-crystal X-ray diffraction crystallography, and its configuration differed from those of reported compounds with similar structures. Two additional new sesquiterpenoids (2 and 3) with similar structures were identified, and their configurations were determined. The trypanocidal activities of the isolated compounds (1-18) against Trypanosoma congolense and the pathogen responsible for fatal trypanosomosis in animals were estimated. Flavonoids and lignans were identified as active compounds with IC50 values ranging from 2.9 to 90.2 µM.

Hyaluronidase inhibitory saponins and a trypanocidal isoflavonoid from the aerial parts of Oxytropis lanata.

A chemical examination of an extract from the aerial part of Oxytropis lanata led to the isolation and identification of 36 compounds, including saponins, isoflavonoids, oxazoles, and glycosides. The three among them were previously unreported oleanane-type saponins. In trypanocidal screening, 5,7,4'-trihydroxyisoflavone showed inhibitory activity against Trypanosoma congolense (IC50 = 10.5 µM), the causative agent of African trypanosomosis in animals; this activity was similar to that of active compounds from the roots of this plant. O. lanata is known to be a traditional medicinal plant in Mongolia for the treatment of inflammatory diseases. The anti-hyaluronidase effect of saponins 3, 5, 8, and 9, (IC50 = 0.15-0.22 mM) was stronger than that of sodium cromoglicate, which was used as a reference drug (IC50 = 0.37 mM). The chemical structures of the new saponins were determined based on HRFABMS, 1H and 13C NMR, 1H-1H COSY, HMQC, HMBC, and ROESY spectroscopic data along with chemical procedures.

Acylated Lignans Isolated from Brachanthemum gobicum and Their Trypanocidal Activity.

Eight isovaleryllignans (1-4 and 8-11), three isovalerylphenylpropanoids (5-7), three known lignans (12-14), and four known compounds were isolated from an extract of the aerial part of Brachanthemum gobicum. The structures of the isolated compounds were elucidated based on NMR and MS data analyses. The enantiomers of compounds 1-3, 5, 8, and 9 were isolated using chiral-phase HPLC, and the absolute configurations of 1a/1b-3a/3b, 5a/5b, 8a/8b, and 9a/9b were elucidated from their optical rotations and ECD spectra; the other lignans were assumed to be racemic or scalemic by chiral-phase HPLC analyses and optical rotation data. Some of the acylated lignans (racemic mixtures) (1-4, 8, 9, and 12-14) exhibited moderate inhibitory activities against Trypanosoma congolense, the causative agent of nagana disease in animals.

Flavonoids isolated from the flowers of Pulsatilla flavescens and their anti-piroplasm activity.

Pulsatilla species are known as "Yargui", and their flowers are traditionally used in Mongolia as a tonic and for the treatment of inflammatory diseases. By chemical investigation of P. flavescens flowers, 21 flavonoids, including a new chalcone C-glucoside, chalconaringenin 2'-O-ß-D-glucopyranosyl-5'-ß-D-glucopyranoside, and two new flavanone C-glucosides, (2R)- and (2S)-naringenin 8-ß-D-glucopyranosyl-4'-O-ß-D-glucopyranoside, were isolated. The absolute configurations of the seven flavanone glucosides were elucidated by ECD spectra. For the isolated compounds, inhibitory activity against Babesia caballi and Theileria equi, which cause fatal diseases in horses, was estimated. Although most of the isolated chalcone and flavanone derivatives did not show any anti-piroplasm activity, all the isolated flavone and flavonol derivatives showed moderate effects against B. caballi and/or T. equi.

Trypanocidal Activity of 2,5-Diphenyloxazoles Isolated from the Roots of Oxytropis lanata.

Eleven 2,5-diphenyloxazole derivatives (1-11), together with six known isoflavonoid derivatives, were isolated from the roots of Oxytropis lanata. The 2,5-diphenyloxazole (1) obtained proved to be identical to a standard sample used as a scintillator and liquid laser dye. The other oxazole derivatives isolated were found to have one to four hydroxy and/or O-methyl groups in their phenyl rings. Seven of the oxazole derivatives obtained are new (3-9). The inhibitory activity of the isolated compounds was evaluated against Trypanosoma congolense, the causative agent of African trypanosomosis in animals. Oxazoles with di- and trihydroxy groups showed trypanocidal activity, and 2-(2',3'-dihydroxyphenyl)-5-(2″-hydroxyphenyl)oxazole (4) exhibited the most potent inhibitory activity (IC50 1.0 µM).