Biochemical Systematics and Ecology最新文献

We identified 3-hydroxy-2-methylpropylglucosinolate in foliage of Reseda luteola L, although the side chain stereochemistry was not resolved. The glucosinolates (GSLs) in R. luteola extracts were bound to an anion exchange column and enzymatically desulfated, followed by isolation by preparative HPLC of the desulfo derivatives, the structures of which were elucidated by NMR and/or MS/MS. Presence of intact 3-hydroxy-2-methylpropylGSL in extracts was supported by direct LC-MS detection and MS2 loss of HSO₄⁻. Prominent GSLs in R. luteola foliage were 3-hydroxy-2-methylpropylGSL as well as the previously known indol-3-ylmethylGSL and the 2R (minor) and 2S (major) isomers of 2-hydroxy-2-phenylethylGSL. Minor GSLs included the expected biosynthetic precursors 2-methylpropylGSL (tentative) and phenethylGSL, as well as 1-methylpropylGSL (tentative) and benzylGSL. The 3-hydroxy-2-methylpropylGSL matched a previously reported but so far unidentified constituent in Limnanthes alba (Limnanthaceae). The identity of investigated R. luteola was confirmed morphologically and from DNA barcoding, and a Reseda phylogeny was constructed. In conclusion, 3-hydroxy-2-methylpropylGSL occurs in at least two basal families of the Brassicales order.

Helichrysum italicum from the Asteraceae family is a small odorous shrub that is distributed in the Mediterranean region different altitudes. However, the species was not naturally found in the flora of Türkiye. Cultivation interest in H. italicum has grownsince its cosmetic and pharmaceutical usage. In the present study, H. italicum plants (seedlings were obtained from the same source) were cultivated in Hatay (Mediterranean, 149 m altitude) and Uşak (Continental, 906 m altitude) cities of Türkiye. Harvestings were done in the spring and autumn, at three different hours of the day (09.⁰⁰, 13.^00, and 18.⁰⁰) in both locations. Soil samples were analyzed to determine some soil properties in both locations. Harvested aerial plant samples were evaluated for essential oil content and composition with three replicates. The experimental field soils' pH values were similar, however there were differences in the ratio of soil lime and macro-microelements. The essential oil content varied between 0.29 and 0.59% in all examined variables. Generally, neryl acetate and α-pinene were found as a main component in all essential oils. Neryl acetate contents ranged between 8.07 and 36.66%, while α-pinene content was found between 13.93 and 31.18%. In the spring harvest, harvesting in the evening produced higher neryl acetate in the continental environment, whereas harvesting at any time of day did not affect the amount of neryl acetate in the Mediterranean climate. In the autumn harvest in the Mediterranean environment, the neryl acetate content was higher in the morning harvest, while neryl acetate content in autumn was comparatively low in the continental climate. Examining the seasons has shown that, in a Mediterranean environment, harvest time is not very significant, but in a continental climate, spring harvest could be favored.

In this study, two previously unreported lignans [4′-O-demetylsuchilactone-8′-ol (1), 7-O-(3-methyl-2,3-dihydroxy-butyl)isodaurinol] (2), four new alkaloids (haplomegalanthine (3), megalantin (4), megalanthamide (5), glycoisohaplopine (6) and thirty-five known compounds (7–41) were isolated from Haplophyllum megalanthum Bornm. (Rutaceae). Pinoresinol (23), epipinoresinol (24), indole-3-carbaldehyde (29), N-[2-(4-hydroxyphenyl)ethyl]-3-methylbut-2-enamide (34), 7,8-dimethoxyfuroquinoline-4-one (35), cis-khellactone (36), 4,4′-dihydroxy-3,3′,9-trimethoxy-9,9′-epoxylignan (37), ulopterol (39) and trans-decursidinol (40) were identified for the first time in the genus Haplophyllum. Also, 4′-O-demethylsuchilactone (16) and N-(4-hydroxyphenethyl)benzamide (32) were found for the first time within the family Rutaceae. Structures of the compounds were elucidated by the use of HRMS, UHPLC-MS and 1D/2D NMR analyses. Furthermore, cytotoxic activity of the crude extract and previously unreported compounds (1–3, 5, 6) on colon cancer cell line HT29 were tested by the MTT method. IC₅₀ values were determined for these five compounds and the crude extract as 18.48 ± 0.94 μg/ml, 52.62 ± 7.27 μg/ml, 23.15 ± 6.70 μg/ml, 21.45 ± 2.48 μg/ml, 5.06 ± 0.19 μg/ml and 2.82 ± 0.012 μg/ml, respectively.

The present report is the first detailed phytochemical investigation of the title plant pointing out that it comprises a rich source of diverse chemical constituents including new compounds with promising cytotoxic activity.

Citrus medica L. var. Sarcodactylis Swingle and C. medica L. were the subject of a chemotaxonomic inquiry using high-performance liquid chromatography (HPLC) fingerprint and multivariate data analysis, including hierarchical cluster analysis (HCA), principal component analysis (PCA), and orthogonal partial least squares-discriminant analysis (OPLS-DA). The results are in good agreement with current knowledge of the systematics of C. medica var. Sarcodactylis and C. medica. The analysis of Citri Sarcodactylis Fructus (CSF) and Citri Fructus (CF) showed that their chemical composition was highly similar except for the content; hesperidin (HP) and 5, 7-dimethoxycoumarin (DMC) were distinguishing markers for C. medica var. Sarcodactylis and C. medica; CSF had a significantly higher concentration of DMC than CF; additionally, the content ratio of HP to DMC in CSF was less than one (0.2401–0.7953), but in CF, it was more than one (2.5775–25.7800). The present work revealed the chemotaxonomic significance of HP and DMC for C. medica var. Sarcodactylis and C. medica and validated the traditional plant taxonomy regarding the two species at the chemical level.

Phytochemical investigation of Gentiana davidi led to isolation of a total of 21 compounds, including seven benzoic acid derivatives (1–7), one alkaloid compound (8), seven iridoids (9–15), and six flavonoids (16–21). The chemical structures of these compounds were characterized by spectroscopic analysis, and their NMR data were compared with those reported in the literature. Among them, compound 1 was identified as a new benzoic acid derivative, and compounds 2–21 are identified and reported for the first time from this plant. The chemotaxonomic significance of these isolated compounds from the G. davidi is discussed.

Toxoplasma gondii (T. gondii) poses significant risks, especially to those with weakened immune systems, highlighting the need for new, less toxic treatments. Laurus nobilis L. (L. nobilis), known for its beneficial properties including antiparasitic and antioxidant effects, offers potential for innovative therapies. This study assessed the anti-Toxoplasma, cytotoxic, antioxidant, and anti-hemolytic effects of L. nobilis's aqueous and ethanolic extracts both in vitro and in silico, including a phytochemical analysis. HPLC analysis identified a range of phenolic compounds, notably syringic acid, ferulic acid, gallic acid, caffeine, and quercetin. Both extracts exhibited an inhibitory effect on the growth of T. gondii tachyzoites in vitro and caused less cytotoxicity to host cells. In silico studies revealed that rutin and quercetin were the most potent compounds, with binding affinity scores for the DHFR enzyme of −10.6 and −9.3 kcal/mol, respectively. Antioxidant studies demonstrated that both extracts displayed antioxidant effects in the DPPH^•, ABTS^•+, NO^•, β-carotene-linoleic acid system, FRP, and TAC assays. Additionally, they provided significant protection to erythrocytes against H₂O₂-induced hemolysis. These findings, suggests that L. nobilis exhibits significant potential as a source of therapeutic agents for combating T. gondii infection and managing its associated adverse effects.

The genera Adenolobus, Cercis and Griffonia are closely related and classified within the subtribe Cercidinae of the Fabaceae family. Since no information exists on the secondary metabolites of the genus Adenolobus, this review focuses on the phytochemistry of Cercis and Griffonia. The genus Cercis is a source of interesting specialized metabolites including 82 phenolic compounds comprising 51 flavonoids, ten terpenoids, three cyanogenic glycosides, 54 volatile compounds, and some compounds from other compound classes. In the genus Griffonia, G. simplicifolia has been traditionally used for a variety of medicinal purposes, and research is mainly focused on this species. This review discusses the chemical structures of nine alkaloids reported from G. simplicifolia and compounds isolated from the genus Cercis along with their chemophenetic analysis. Finally, the review briefly mentions research gaps and potential directions for future investigations.

Global warming is responsible for increasing temperatures and reducing rainfall in many regions of the world. Due to insufficient rainfall or lack of water in the soil, plants experience a range of morphological and biochemical alterations when they are exposed to drought conditions. Interestingly, the cells of drought-stressed plants can serve as a potential source for discovering new drugs. These secondary metabolic products have important biological functions that determine how plants interact with the environment and help them accommodate alterations. Present research has shed light on the response of Pandanus tectorius induced drought stress at 8th and 16th days. The studies observed the levels of various secondary metabolites in plants under drought-induced stress. Among the secondary metabolites analyzed, total alkaloids exhibited the highest overall concentration at 26.19 ± 0.83^a. Furthermore, the observations found that drought stress had a significant impact on the plant's secondary metabolism. This resulted in increased levels of total alkaloids, saponins, tannins, and phenolics compared to the control plant. Especially the concentration of phenolics showed the most significant increase, with a remarkable 64.99% rise observed at the 16th day of treatment. The concentration of phenolics reached (20.52 ± 0.181^c) at this level. Moreover, compared to control, P. tectorius exhibits significant antioxidant, antidiabetic, anti-inflammatory, molecular docking, and anticancer effects against MDA-MB-231 human breast cancer cell line inhibitory concentration IC₅₀ values (48.91 ± 0.95 μg/mL) at 16th day treated plants. Consequently, the positive responses of P. tectorius drought stress enhance secondary metabolites. This research focus on drought stress stimulus prompts an urge in the production of secondary metabolites in P. tectorius, leading to an increase in its anticancer and anti-diabetic properties and treatments for type-2 diabetes and against fighting for cancer with minimal side effects and helping prevent diseases.

Through phytochemical research, the composition of diterpenoid alkaloids in Aconitum sessiliflorum was analyzed, and sixteen compounds were identified. Among them, there are seven napelline type C₂₀-diterpenoid alkaloids (1–4, 7–8, 15), three denudatine type C₂₀-diterpenoid alkaloids (5–6, 16), and six aconitine type C₁₉-diterpenoid alkaloids (9–14). On the basis of NMR spectroscopy, the structural analysis of the separated compounds was achieved by comparing with previous data. All sixteen compounds were isolated for the first time from the Aconitum sessiliflorum, of which five compounds (1, 6, 9, 13, 15) were isolated for the first time from series Brachypoda, where Aconitum sessiliflorum is classified. These diterpenoid alkaloids not only enrich the chemical diversity of Aconitum sessiliflorum, but also facilitate the analysis of their chemotaxonomic implications. Importantly, the diverse types and structural features of these diterpenoid alkaloids provide new insights into both the potential phylogenetic affiliations within the series Brachypoda and the varying degrees of evolutionary divergence among these related taxa.

Citrus peel essential oil (PEO) is utilized in the food and juice processing, pharmaceuticals, and aroma industries due to various nutritional, pharmaceutical and cosmaceutical properties. In this study, the PEO of five wild Citrus species (Citrus medica, C. indica, C. latipes, C. hystrix, and C. cavaleriei) from northeast India, has been extracted using the hydro-distillation method. The oil yield varied from 0.02% to 0.32% (w/w). Gas Chromatography-Mass Spectrometry (GC-MS) analysis of citrus PEO showed the presence of 36 compounds in the range of 84.63–95.9%. Limonene was the major compound in the PEO, with the highest percentage in C. cavaleriei (80.86%), followed by C. hystrix (75.7%), medica (66.9%), C. indica (63.03%), and C. latipes (23.95%). Other compounds present in a considerable percentage were γ-terpinene (C. latipes, 16.86%; C. indica, 14.72%; C. medica, 6.73%), myrcene (C. indica, 5.34%), β-pinene (C. latipes, 9.49%), 3-carene (C. medica, 6.38%), (E)- β-caryophyllene (C. latipes, 6.07%), and neryl acetate (C. latipes, 6.10%). Anti-inflammatory assay of PEO in the five Citrus species revealed the highest anti-inflammatory activity in C. indica. The study suggests that wild citrus fruits can be an important source of limonene and other bioactive compounds with potential pharmaceutical and industrial applications.