Biochemical Systematics and Ecology最新文献

The objective of this study was to characterize the volatile compounds from the aerial part of Cistus ladanifer L., Pistacia lentiscus L., and Matricaria chamomilla L., members of Cistaceae, Anacardiaceae, and Asteraceae families, respectively; and assess their potential antioxidant, antimicrobial, and enzyme inhibitory properties. The essential oils were analyzed using gas chromatography-mass spectrometry (GC-MS-MS) analysis. The outcomes revealed distinct chemical profiles indicative of specific chemotypes within each species. Indeed, M. chamomilla essential oil (MCEO) contained sabinene (16.03 %), camphor (11.22 %), 3,6-dihydrochamazulene (14.22 %), and chamazulene (12.84 %) as its primary constituents. C. ladanifer essential oil (CLEO) prominently featured camphene (31.5 %), α-pinene (15.76%), and bornyl acetate (15.73 %), while P. lentiscus essential oil (PLEO) was rich in D-limonene (21 %), β-myrcene (14.89 %), α-pinene (13.93 %), and terpinen-4-ol (9.75 %). Remarkably, PLEO exhibited significant antioxidant activity across multiple assays, demonstrating inhibitory values of 72.07 ± 4.06 mg TE/g of extract (Cuprac), 45.74 ± 1.23 mg TE/g of extract (FRAP), 30.89 ± 1.69 mg EDTAE/g of extract (Chelating), 26.71 ± 1.84 mmol TE/g of extract (Phosphomolybdenum), 15.55 ± 0.84 mg TE/g of extract (ABTS), and 2.30 ± 0.22 mg TE/g of extract (DPPH). The results showed that the microorganisms under examination varied in their sensitivity to essential oils and the inhibitory zone ranged between 25 and 57 mm. The inhibitory effects of the essential oils were investigated against enzymes associated with human pathologies. As findings, CLEO demonstrated substantial inhibition of tyrosinase (10.22 ± 0.13 mg KAE/g of extract) and acetylcholinesterase (4.71 ± 0.97 mg GALAE/g of extract), outperforming other essential oils that displayed moderate activities. These important biological effects of the oils tested qualify these plants as an interesting source of phytochemicals with medicinal actions.

This research explores the therapeutic properties and medicinal potential of Mentha piperita L. (M. piperita) essential oil (EO) (MPEO) harvested in the province of Ouezzane, northwestern Morocco. We conducted a comprehensive chemical composition analysis of MPEO using gas chromatography-mass spectrometry (GC-MS) to identify its major components. The predominant constituents were pulegone (17.56%), mintlactone (10.62%), _D-carvone (9.24%), eucalyptol (7.53%), and thymol (6.06%). The antidiabetic effects were assessed by measuring the inhibition of two digestive enzymes (α-glucosidase and α-amylase). The dermatoprotective effect was evaluated based on the inhibition of elastase and tyrosinase, and neuroprotective activity was studied by examining the inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Additionally, molecular docking analysis was used to determine the interactions between the main MPEO compounds and the enzymes targeted. Antioxidant activity was estimated using in vitro FRAP, DPPH, and ABTS assays. Furthermore, the antibacterial potential was evaluated against pathogenic strains using the micro-broth dilution method. Our results indicate significant antioxidant and neuroprotective activities of MPEO, along with promising antidiabetic and dermatoprotective potential, surpassing references. Additionally, all bacterial strains tested were susceptible to MPEO, with MIC values lower than those of MBC for all bacteria except L. monocytogenes. These in vitro findings were supported by in silico analysis, showing that menthelactone and pulegone presented strong binding affinities with key enzymes involved in glucose regulation and pigmentation. MPEO, rich in bioactive compounds, has shown promising potential. The main components of this oil offer innovative prospects for the development of drugs and natural therapeutic applications.

A total of thirteen compounds consisting of nine xanthones; cowagarcinone C (1), doitunggarcinone C (2), nigrolineaxanthone E (3), nigrolineaxanthone Q (4), β-mangostin (5), 7-O-methylgarcinone E (6), dulcisxanthone F (7), ananixanthone (8) and nigrolineaxanthone N (9), two polycyclic polyprenylated acylphloroglucinols (PPAPs); garcinielliptone J (13) and garcinialone (14) as well as two terpenoids; 30-hydroxycycloartenol (15) and garcinane (16), were putatively identified with a good confidence level from dichloromethane extract of Garcinia griffithii T. Anderson using the ¹³C NMR-based dereplication and MixONat software. In addition, three xanthones; euxanthone (1,7-dihydroxyxanthone) (10), forbexanthone (11) and 1,5-hydroxy-3,6-dimethoxy-2,7-diprenylxanthone (12) were successfully isolated. The structure of the isolated compounds was confirmed through the analysis of spectroscopic data and comparison with reported data. The ¹³C NMR data of forbexanthone (11) was reported for the first time. Interestingly, the dichloromethane extract and 1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone (12) which were evaluated for their exhibited α-glucosidase inhibitory activity exhibited potent inhibition toward the enzyme with IC₅₀ values of 0.66 μg/mL and 3.02 μM, respectively as compared to the standard, acarbose (IC₅₀ = 392 μg/mL or 608 μM). Notably, ananixanthone (8) has not been reported from the genus Garcinia while compounds 1–7, 9, 11 and 13–16 being reported from Garcinia griffithii for the first time. In addition, the chemophenetic significance of all the compounds has also been discussed.

The chemical study of Centaurea granatensis Boiss. ex DC. allowed the isolation and structural elucidation of eighteen secondary metabolites (1–18) from ethyl acetate (EtOAc) and n-butanol (n-BuOH) extracts. These compounds are divided into one new epoxylignan glucoside (1) and seventeen known phytochemicals including seven flavonoids (2–8), four triterpenes (9–12), and six phytosterols (13–18). Structures of the isolates were identified using various spectroscopic methods, namely 1D NMR (¹H and ¹³C), 2D NMR (HSQC, ¹H–¹H COSY, HMBC, and NOESY), and mass spectrometry (HR-ESIMS), as well as by comparison with literature data. The obtained results showed the abundance of triterpenoids and flavonoids particularly flavones in C. granatensis. Apigenin (3) could be used as a chemotaxonomic marker of this genus due to its presence in approximately forty plant species. Furthermore, tiliroside (2) and stigmasteryl-3-O-β-D-glucoside-6′-palmitate (18) were first detected in Centaurea genus, but had previously been found in species of the Asteraceae family. Additionally, the chemotaxonomic significance of all isolated molecules was fully discussed.

The aim of the present study was to determine the phenolic profile, antioxidant capacities, inhibition of enzymes related to dermatological and neurodegenerative diseases, and cytotoxic properties of Acinos rotundifolius Pers. For this purpose, three different extraction methods were applied: Soxhlet extraction, ultrasonic-assisted extraction (UAE), and infusion (INF). The use of different solvents (ethyl acetate, methanol, water) has also been applied. The RP-HPLC-DAD data highlighted that Soxhlet extraction in MeOH/water is more effective at extracting flavonoids and phenolic acids. The UAE extract, which was richer in chlorogenic acid, exhibited a better scavenging capacity versus HO^•, NO^• and ABTS^•+ were determined by UAE, whereas the one obtained via Soxhlet extraction in water had a better efficacy to eliminate O₂^•. The greatest inhibitory effects on AChE and tyrosinase enzymes were demonstrated by the infusion. The different composition of the extracts obtained with the different methods also influences the cytotoxic properties which were investigated by MTT test on HepG2 and OE-33 cell lines.

In the present study, the caffeoylhexaric acids in Inuleae species of Asteraceae family as Geigeria alata Benth. & Hook.f. ex Oliv., Inula helenium L. and Telekia speciosa (Schreb.) Baumg. were profiled by ultra-high performance – liquid chromatography coupled with high resolution mass spectrometry. In the root methanol-aqueous extracts, 32 caffeoylhexaric acids were annotated. A variety of mono-, di-, tri- and terta-caffeoylhexaric acids, as well as their propionyl, isobutyryl, hydroxypropionyl, methylbutyryl/isovaleryl, hydroxybutyryl- and others derivatives were tentatively identified. The study is the first attempt to propose a fragmentation key of caffeoylhexaric acids derivatives by LC-HRMS. The chemophenetic significance of these compounds was discussed based on the results and literature data. The identification of leontopodic acid A and B in the studied Inuleae species highlighted T. speciosa as a new source of caffeoyl-D-glucaric acid derivatives, natural compounds with health-benefit promotion and cosmetic application.

Delphinium

L. (Ranunculaceae) is a taxonomically complex genus composed of approximately 365 species of perennial herbs. Chemical taxonomy is highly important for assisting and supplementing the taxonomy of this genus. In the present study, Delphinium tatsienense Franch., a Chinese endemic Delphinium species, was phytochemically investigated, which led to the discovery of two previously undescribed anthranilamide derivatives, tatsieamides A and B (1–2). The isolated anthranilamides possess chemotaxonomic value and could be utilized as good chemical markers to provide valuable information for the chemotaxonomy of D. tatsienense and related species.

The isolation of eight compounds from Elephantopus scaber L. through phytochemical studies yielded six lignans (1–6), two flavonoids (7–8), and two triterpenoids (9–10). The structures of these compounds were identified using thorough spectroscopic methods and compared with existing literature data. Notably, compounds 1–4, 6, and 8 were newly discovered in the Asteraceae family as per the analysis. Furthermore, the chemical classification of these isolated compounds was deliberated.

The comprehensive phytochemical investigation of the Callicarpa nudiflora resulted in the isolation of a new labdane diterpenoid 16(R/S)-3,4-seco-11E,13E-labdien-15,16-olide-3-al (2), together with sixteen known compounds: two sesquiterpenoids (1R,3S,4R,5S,9S)-3,4-epoxy-5-hydroxy-8(13)-caryophyllen (1), and 4β,10α-aromadendranediol (3), eight labdane analogues (4–11), a pimarane-type diterpenoid (12), three flavonoids (13–15), and two lignans (16, and 17). The structures were elucidated by extensive NMR and HRESIMS analysis. This marks the first comprehensive report of the NMR data of compound 1, as well as the absolute configurations of compounds 1 and 3. The chemotaxonomic significance of the isolated compounds was also discussed. Compounds 1, 3, 14, 16, and 17 were being reported from the genus Callicarpa for the first time, while 3,4-seco-labdane diterpenoids 4–11 were previously obtained only from C. nudiflora.

The phytochemical composition of Ficus tikoua Bur. was studied, from which fourteen compounds were isolated, including four phenolics (1-4), one aromatic alcohol glycoside (5), two benzofuran derivatives (6–7), five sesquiterpenes (8–12), one lignan (13) and one alkaloid (14). The structures of these compounds were determined by MS, NMR spectroscopy, and comparison with the published spectroscopic data. Compounds 1–3, 5, and 7–14 were firstly isolated from F. tikoua, and compounds 1, 5, 10, 11, 13 and 14 were reported from genus Ficus for the first time. Furthermore, the research discussed the taxonomic significance of the isolated compounds, and enriched the knowledge of the chemical classification of genus Ficus.