Plantago major L. which is a medicinal plant with important biological activities, commonly used as traditional medicine. Potential inhibitory activities of the aqueous extract and three isolated constituents calceorioside B (1), homoplantaginin (hispidulin-7-O-glucoside) (2) and plantamajoside (3) from the aerial parts of Plantago major subsp. major L. (Plantaginaceae) have been tested against hyaluronidase, collagenase, and elastase, which play critical roles in wound pathogenesis. Even though, the extract (27.04%), and among the isolated compounds, calceorioside B (41.16%) exerted significant inhibition against hyaluronidase enzyme, homoplantaginin and plantamajoside were found to be inactive. Similar results were obtained from collagenase enzyme inhibition test. The extract (21.92%) and calceorioside B (28.34%) also caused notable inhibition in this test. However, no remarkable inhibition was observed in the presence of elastase enzyme. The experimental data revealed that P. major subsp. major displayed remarkable inhibitory activity against hyaluronidase and collagenase enzymes. In vitro enzyme activity of P. major subsp. major is reported for the first time in the current study.

A new highly oxygenated iridoid glucoside, urphoside B (1) was isolated from the Veronica pectinata var. glandulosa together with seven known iridoid glucosides, aucubin, catalpol, veronicoside, catalposide, verproside, amphicoside and 6-O-veratroyl catalpol. The planar as well as the stereo structures of the isolated compounds were determined by means of extensive 1D- and 2D-NMR spectroscopy and confirmed by HR-Mass.

Two new phenylethanoid glycosides integrifoliosides A (2) and B (3), along with a known phenylethanoid glycoside alyssonoside (1) and a flavone glucoside chrysoeriol-7-O-β-ᴅ-glucopyranoside (4) were isolated from the aerial parts of Phlomis integrifolia. The structures of the new compounds were identified as 3,4-dihydroxy-β-phenylethoxy-O-β-ᴅ-apiofuranosyl- (1 →4)-α-ʟ-rhamnopyranosyl-(1 →3)-4-O-feruloyl-β-ᴅ-glucopyranoside (2) and 3-hydroxy-4-methoxy-β-phenylethoxy-O-β-ᴅ-apiofuranosyl-(154)-α-ʟ-rhamnopyranosyl-(1→3)-4-O-feruloyl-β-ᴅ-glucopyranoside (3), on the basis of spectroscopic (UV, IR, 1D- and 2D-NMR, and HR-FABMS) methods.

The genus Plantago (Plantaginaceae) is represented by 21 species in Turkey. Plantago species are used as folk medicine, especially for wound healing, antiinflammatory and anticancer effects. Iridoid glucosides, phenylethanoid and flavonoid glycosides, caffeic acid derivatives, polysaccharides and lipids are main components of Plantago species. In this study; aerial parts of Plantago holosteum Scop. were investigated by bioactivity guided fractionation via cytotoxic and antiinflammatory effects. For this purpose; aqueous extract of plant, fractions and compounds isolated from active fractions were tested for their cytotoxic effects against HEp-2 cancer, L929 and RAW 264.7 noncancerous cell lines using MTT assay while anti-inflammatory effects were monitorized by the level of nitric oxide (NO) on LPS stimulated RAW264.7 macrophages. Furthermore; DPPH, NO, SO and ABTS radical scavenging capacities were also investigated to support this study. According to our results; aqueous extract and fractions showed selective cytotoxic effect on HEp-2 cancer cells and reduced the NO level with their increasing concentrations. Moreover, acteoside and isoacteoside isolated from active fractions, showed selective cytotoxic activity against HEp-2 cells and decreased the level of NO not compatible with increasing concentrations; thus cytotoxic and anti-inflammatory activities of aqueous extract of P. holosteum can be attributed to these compounds.

The genus Plantago (Plantaginaceae) is widely distributed worldwide. The Plantago species are used in traditional medicine as wound healers, anti-inflammatory agents, antipyretics, and analgesics. This study aimed to investigate the phytochemical composition from the aerial parts of Plantago indica L. and to evaluate its biological activities. Isolation studies and in vitro investigations were conducted on an aqueous phase of 80% EtOH extract of Plantago indica. In addition, in vivo studies were carried out using the MeOH, 80% EtOH, and water extracts. Plantarenaloside (1), 3-oxo-α-ionol β-glucoside (2), martynoside (3), acteoside (4), feruloyl gardoside (5), and ursolic acid (6) were isolated from the extract. The structures of the compounds were elucidated using 1D- and 2D-NMR and ESI-MS analyses. The extract, fractions, and pure compounds were tested in vitro for cytotoxicity (MTT), anti-inflammatory activity (NO, IL-6, and TNF-α production), wound healing (scratch test), and antioxidant capacity (DPPH, ABTS, SO). Feruloyl gardoside (20.11–58.27%) significantly reduced NO levels at concentrations of 25–100 µM. It significantly reduced IL-6 levels (40.17%) at 100 µM. Additionally, the in vivo anti-inflammatory (acetic acid-induced vascular permeability) and wound healing (incision and excision models) effects of the extracts were investigated. The findings suggest that P. indica may be considered to be a potential therapeutic option for managing inflammation and for promoting wound healing.