NMR-guided isolation of undescribed triterpenoid saponins from Lysimachia atropurpurea L.

Phytochemical investigation on aerial parts of Lysimachia atropurpurea L. (Myrsinaceae), guided by NMR methods, resulted in the isolation and characterization of three previously undescribed triterpenoid saponins named stralysaponins A-C along with five known compounds. Their structures were elucidated by 1D and 2D NMR spectroscopy and HR-ESI-MS. Stralysaponins A-C were categorized into 13ß-28-epoxyoleanane-type triterpenoid saponins, reaffirming their prevalent presence of this type in the Myrsinaceae family and the genus Lysimachia. The identified derivatives share a common four-unit branched sugar chain, with rhamnose as the terminal sugar linked at C-3 of the aglycone. The presence of triterpenoid saponins in L. atropurpurea is reported herein for the first time. This study enriched the chemical diversity of triterpenoid saponins of the genus Lysimachia. Additionally, it demonstrates the effectiveness of NMR-profiling in isolating previously undescribed triterpenoid saponins from Lysimachia spp.

Chemometric Analysis Evidencing the Variability in the Composition of Essential Oils in 10 Salvia Species from Different Taxonomic Sections or Phylogenetic Clades.

Essential oil (EO) of Salvia spp. has been widely used for culinary purposes and in perfumery and cosmetics, as well as having beneficial effects on human health. The present study aimed to investigate the quantitative and qualitative variations in EOs in wild-growing and cultivated pairs of samples from members in four Salvia sections or three clades, namely S. argentea L. (Sect. Aethiopis; Clade I-C), S. ringens Sm. (Sect. Eusphace; Clade I-D), S. verticillata L. (Sect. Hemisphace; Clade I-B), S. amplexicaulis Lam., and S. pratensis L. (Sect. Plethiosphace; Clade I-C). Furthermore, the natural variability in EO composition due to different genotypes adapted in different geographical and environmental conditions was examined by employing members of three Salvia sections or two phylogenetic clades, namely S. sclarea L. (six samples; Sect. Aethiopis or Clade I-C), S. ringens (three samples; Sect. Eusphace or Clade I-D), and S. amplexicaulis (five samples; Sect. Plethiosphace or Clade I-C). We also investigated the EO composition of four wild-growing species of two Salvia sections, i.e., S. aethiopis L., S. candidissima Vahl, and S. teddii of Sect. Aethiopis, as well as the cultivated material of S. virgata Jacq. (Sect. Plethiosphace), all belonging to Clade I-C. The EO composition of the Greek endemic S. teddii is presented herein only for the first time. Taken together, the findings of previous studies are summarized and critically discussed with the obtained results. Chemometric analysis (PCA, HCA, and clustered heat map) was used to identify the sample relationships based on their chemical classes, resulting in the classification of two distinct groups. These can be further explored in assistance of classical or modern taxonomic Salvia studies.

Comparative phytochemical analysis of cultivated and wild Sideritis raeseri Boiss. & Heldr. subsp. raeseri infusions.

The present study focuses on the chemical composition of the infusions of Sideritis raeseri subsp. raeseri from cultivated and wild populations using NMR, LC-DAD, LC-HRESIMS, and GC-MS techniques, to reveal possible differences. Mainly carbohydrates, flavonoids, and phenylethanoid glycosides were detected in the 1H-NMR spectra of both infusions. In the GC-MS analysis, carbohydrates were shown to be the main constituents in both infusions. Caffeic acid was found in traces only in the cultivated sample, while quinic and chlorogenic acids were detected in both samples. Further investigation by LC-HRESIMS unveiled the same constituents with only slight differences in the amounts. Although the Sideritis samples originated from wild and cultivated populations, similar metabolic profiles were observed in the infusions.

Phytochemical Profiles and Biological Activities of Plant Extracts from Aromatic Plants Cultivated in Cyprus.

Medicinal and aromatic plants' properties, still an interesting research area, are attributed to the presence of various specialized products that possess important pharmacological activities. In the present study, six medicinal/aromatic plants (Sideritis cypria, Origanum dubium, Melissa officinalis, Mentha piperita, Thymus capitatus, and Salvia fruticosa) were evaluated for their phytochemical and nutritive composition, as well as their biological activities, including antioxidant, antimicrobial, and cytotoxic properties. The results obtained indicate that M. piperita was rich in proteins and minerals such as N and Mg, while S. cypria accumulated more K, Na, P, and Ca. The highest content of phenols and flavonoids was observed in M. piperita, followed by O. dubium and T. capitatus, which eventually influenced their high antioxidant capacity. NMR screening revealed the presence of (i) triterpenoids and hydroxycinnamic acid derivatives in M. officinalis; (ii) terpenoids, flavonoids, and phenolic acid derivatives in S. fruticosa; (iii) flavonoids and phenolic acid derivatives in M. piperita; (iv) phenolic monoterpenes in O. dubium and T. capitatus; and (v) terpenoids, flavones, and phenylethanoid glycosides in S. cypria. The results of the antimicrobial activity showed that the tested samples overall had quite good antimicrobial potential. High antibacterial activity was found in O. dubium and T. capitatus, while O. dubium and S. cypria exhibited great antifungal activities. The studied species also had an important effect on the viability of female-derived and colon cancer cells. In particular, in colon cancer cells, the extracts from T. capitatus, M. officinalis, M. piperita, and S. fruticosa exhibited a stronger effect on cell viability in the more metastatic cell line at significantly lower concentrations, indicating an important therapeutic potential in targeting highly metastatic tumors. This finding is worth further investigation. The present study unveiled interesting phytochemical profiles and biological properties of the six medicinal/aromatic plants, which should be further explored, contributing to green chemistry and the possible creation of natural health products for humans' health/nutrition and additives in cosmetics.