Anti-glycative and anti-inflammatory effects of macamides isolated from Tropaeolum tuberosum in skin cells.

Tropaeolum tuberosum, commonly known as Mashua, is an herbal remedy used on the skin in order to treat local pain and to heal wounds. This study aimed to evaluate the extracts and isolated compounds from T. tuberosum with anti-glycative and anti-inflammatory activities. Guided isolation by bioassay led to the isolation and characterisation by NMR and MS of (S)-(-)-N-(α-methylbenzyl)-oleamide (1) and (S)-(-)-N-(α-methylbenzyl)-linoleamide (2). Both compounds inhibited the production of TNF-α with IC50 values of 9.38 µM (NIH/3T3 cells) and 10.06 µM (PA317 cells) for compound 1, and 5.3 µM (NIH/3T3 cells) and 6.48 µM (PA317 cells) for compound 2. Compounds 1 and 2 showed the inhibitory effect on the BSA-MGO formation at concentrations of 9.38 µM (3.39%) and 5.30 µM (8.53%), respectively. Moreover, both compounds showed significant breaking properties on the MGO-AGE-protein crosslink with percent modification of 6.58% (9.38 µM) and 18.08% (5.30 µM), respectively.

Isolation and characterisation of antibacterial and anti-inflammatory compounds from Gnaphalium polycaulon.

ETHNO-PHARMACOLOGICAL RELEVANCE: Gnaphalium polycaulon commonly known as "cudweed" has been used throughout South America as an infusion to treat colds, bronchitis, fever or pneumonia. AIM OF THE STUDY: This study aimed to determine the antibacterial and anti-inflammatory activities of the aqueous extract of Gnaphalium polycaulon and identify the related compounds. MATERIALS AND METHODS: A bio-guided isolation of the active compounds of Gnaphalium polycaulon was carried out, selecting the fractions depending on their antibacterial, anti-inflammatory and cytotoxic activities. The antibacterial effect was studied against Haemophilus influenzae, Moraxella catarrhalis, Staphylococcus aureus and Streptococcus pneumoniae; and the anti-inflammatory study was performed by measuring the inhibition of NF-κB in BEAS-2B and IMR-90 cell cultures. RESULTS: Three compounds were obtained and characterised by nuclear magnetic resonance and mass spectrometry. These compounds are 2-(4-(1-H-tetrazol-1-yl) phenyl)-2-aminopropanoic acid (1), N-phenyl-4-(3-phenyl-1,2,4-thiadiazol-5-yl) piperazine-1-carboxamide (2) and N-(4-ethoxyphenyl)-4-(2-methylimidazo-[1,2-α] pyridine-3-yl) thiazol-2-amine (3). All compounds showed antibacterial activity with MIC values of 44.80-44.85, 0.017-0.021 and 0.0077-0.0079 µM, respectively, in the Haemophilus influenzae, Moraxella catarrhalis, Staphylococcus aureus and Streptococcus pneumoniae strains, while the positive control, Ofloxacin, had a MIC value of 27.64-27.67 µM. This was corroborated through a zone inhibition assay, where compound 3 (11.36-11.67 mm) was much more active than the positive control (Ofloxacin, 23.41-24.12 mm), while compounds 2 (26.47-27.64 mm) and 1 (28.39-29.76 mm) displayed similar antibacterial potential to the positive control. Finally, all the compounds presented NF-κB inhibitory activity, compounds 3 (IC50 = 0.0071-0.0073 µM) and 2 (IC50 = 0.016-0.019 µM) being the most promising. Compound 1 (IC50 = 44.24-44.26 µM) had less anti-inflammatory potential, being also the closest to the values displayed by the positive control (Celastrol, IC50 = 7.41 µM). CONCLUSION: In the present study, three compounds were isolated for the first time from the aqueous extract of Gnaphalium polycaulon. Their antibacterial and anti-inflammatory potential was tested and showcased.

Anti-inflammatory, pro-proliferative and antimicrobial potential of the compounds isolated from Daemonorops draco (Willd.) Blume.

ETHNO-PHARMACOLOGICAL RELEVANCE: Daemonorops draco (D. draco) commonly known as "Dragon's blood" is one of the most used plants by Momok, Anak Dalam and Talang Mamak tribes from Indonesia as a remedy for wound healing. AIM OF THE STUDY: This study aimed to identify the extract, fractions and compounds responsible for the anti-inflammatory and pro-proliferative activities of the D. draco resin. Additionally, the antimicrobial activity against two bacteria and one yeast species was analysed. MATERIALS AND METHODS: Bio-guided isolation of compounds with anti-inflammatory, pro-proliferative and antimicrobial activities from the D. draco resin was carried out by measuring: the inhibition of NF-κB and activation of Nrf2 in THP-1, HaCaT, NIH-3T3 cells; cell proliferation in NIH-3T3 and HaCaT cells; and the antimicrobial effect on E. coli, S. aureus and C. albicans. RESULTS: Guided isolation by bioassay gave rise to the isolation and characterisation by nuclear magnetic resonance and mass spectrometry of three compounds: 1 (Bexarotene), 2 (Taspine) and 3 (2-hydroxy-1-naphthaldehyde isonicotinoyl hydrazone). All compounds showed NF-κB inhibitory activity with IC50 values of 0.10-0.13, 0.22-0.24 and 3.75-4.78 µM, respectively, while the positive control, Celastrol, had an IC50 of 7.96 µM. Likewise, all compounds showed an activating effect of Nrf2 with EC50 values of 5.34-5.43, 163.20-169.20 and 300.82-315.56 nM, respectively, while the positive control, CDDO-Me, had an EC50 of 0.11 nM. In addition, concerning the pro-proliferative activity, compound 1 (IC50 = 8.62-8.71 nM) showed a capacity of 100%, compound 2 (IC50 = 166-171 nM) showed a capacity of 75%, and compound 3 (IC50 = 469-486 nM) showed a capacity of 65%, while FSB 10% (positive control) had a pro-proliferative activity of 100% in the NIH3T3 cell lines (fibroblasts) and HaCaT (keratinocytes). Finally, all the compounds showed antimicrobial activity with MIC values of 0.12-0.16, 0.31-0.39 and 3.96-3.99 µM, respectively, in S. aureus, E. coli and C. albicans strains, while the positive control, Ofloxacin, had a MIC of 27.65 µM. CONCLUSION: This study managed to isolate, for the first time, three compounds (Bexarotene, Taspine and 2-hydroxy-1-naphthaldehyde isonicotinoyl hydrazone) from the resin of D. draco, with anti-inflammatory, and pro-proliferative as well as antimicrobial activities.

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.