Records of Natural Products Articles

Volatile organic compounds (VOC) from dried aerial parts (flowers, leafs, leafy branches and stems) of fourty five Salvia species, harvested from different regions of Turkey, were determined using thermal desorption technique coupled to gas chromatography-mass spectrometer (TD-GC-MS). Total percentages of the detected volatile organic compounds of the Salvia species ranged from 70.30 to 99.65% . Total yield of VOC was found to be highly variable among Salvia species, and the percentage of each component also exhibited high variation. While sesquiterpene hydrocarbons represented 0.90-45.02% of the volatile organic compounds, the others were found to be monoterpene hydrocarbons 0.00-32.25%, monoterpenoids 0.94- 53.60%, sesquiterpenoids 0.00- 31.45% and hydrocarbons and derivatives 2.99-46.87%. The rest of the composition consisted of diterpene alcohols, fatty acids, phenolics and triterpenes. In total, 108 volatile compounds were identified from studied 45 Anatolian Salvia species.

Ipomoea aquatica Forsk is a green leafy vegetable that is a rich source of amino acids and vitamins. Antioxidant and α-glucosidase inhibitory activities of the hexane (IAHE) and methanol (IAME) fractions of the vegetable portion of I. aquatica were investigated. The IAME fraction exhibited a strong scavenging effect of the 2,2-diphenyl-2-picryl hydrazyl (DPPH) free radicals, and this fraction contained the highest phenolic contents. Phytochemical investigation of the IAME fraction yielded three known compounds, namely 3,5-di-O-caffeoylquinic acid (1), 4,5-di-O-caffeoylquinic acid (2) and quercetin 3-O-β-D-glucoside (3). The structures were unambiguously elucidated based on 1D and 2D-NMR analyses (1H, 13C, COSY, HSQC, HMBC) and mass spectrometry data. Compound 3 was isolated for the first time from this plant.

A new sesquiterpenoid derivative, named aspergiketone (1), along with seven known compounds (2-8) were isolated from the coastal saline soil fungus Aspergillus fumigatus. Their structures were elucidated by spectroscopic analysis, and by comparison of experimental and reported data. The absolute configuration of compound 1 was defined by X-ray diffraction analysis. Compound 1 was cytotoxic towards HL-60 and A549 cell lines with IC 50 values of 12.4 and 22.1 μ M , respectively.

Four new guaiane-type sesquiterpene glycosides (1-4), 4α-hydroxy-guai-1(10)-en-12,8α-olide 2β-O-β-D-glucopyranoside (1), 4α-hydroxy-guai-1(10)-en-12,8α-olide 2β-O-(6΄-trans-caffeoyl)-β-D-glucopyranoside (2), 10α-hydroxy-guai-1(2)-en-12,8α-olide 4α-O-β-D-glucopyranoside (3) and 10α-hydroxy-guai-12,8α-olide 4β-O-β-D-glucopyranoside (4) and three known guaiane-type sesquiterpenes (5-7), 4α,6α-dihydroxy-1β,5α,7αH-guaia-9(10),11(13)-dien-12,8α-olide (5), 6α-acetoxy-4α-hydroxy-1βH-guaia-9(10),11(13)-dien-12,8α-olide (6), and 4β-10α-Dihydroxy-5α-guai-1(2),11(13)-dien-12,8α-olide (7) were isolated from the aerial parts of Chrysophthalmum montanum (DC) Boiss. The structures of the compounds were elucidated by extensive 1D- and 2D-NMR spectroscopic analysis in combination with MS experiments.

Opuntia dillenii (Nagphana) traditionally used against inflammation and also possess analgesic effect. Thus in the present study analgesic properties of O. dillenii cladode methanol extract, its fractions obtained via vacuum liquid chromatography along with isolated α-pyrones, opuntiol and its glucoside, opuntioside were analyzed. The acetic acid-induced writhes were reduced by O. dillenii test agents with opuntioside being most effective (IC 50 26 ± 0.9 mg/kg) and equipotent to diclofenac and β-sitosterol. Consistently, it also elicited most potent effect (IC 50: 28 ± 1.1 and 24 ± 1.2 mg/kg) during early and late phases of formalin-induced paw licking, producing effect similar to diclofenac and indomethacin. It was also most effective in hot plate test. Naloxone (opioid antagonist) reversed the analgesic effects of extract and fractions but failed to antagonize the opuntiol and opuntioside analgesic effects. In conclusion, edible O. dillenii extract, its fractions, opuntiol and opuntioside reduced peripheral and centrally mediated pain via opioid dependent and independent systems. Among them opuntioside emerged as most effective analgesic possibly due to the presence of glucose moiety at position 7 of its α-pyrone ring. This is the first report of opuntiol and opuntioside analgesic effect which may serve as lead compounds in designing of new analgesics.

The endophytic strain Xylaria papulis was originated from the stem of Taiwanese Lepidagathis stenophylla C. B. Clarke ex Hayata (Acanthaceae) growing in the Hengchun Peninsula of southern Taiwan. Bioassay-guided fractionation of an EtOAc -soluble fraction of the liquid fermentate of this strain resulted in the isolation of two new isopimarane-type diterpene glycosides compounds, i.e., xylapapusides A & B (1 & 2), along with five previously identified compounds, 3–7. The structures of 1 and 2 were elucidated by detailed spectroscopic analysis including 1H- and 13C-NMR, COSY, HSQC, HMBC, and HR-ESI-MS, while the structures of the known compounds 3–7 were deduced from comparison of their spectral data with those in the literature. The effects of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages were evaluated. Xylapapuside A (1) showed most potent of NO inhibition with E maxvalue of 34.3 μM.

The aim of the study is to explore the inhibitory potential of extract/fractions, and compounds of Monotheca buxifolia fruit against urease enzyme. Crude hydro-ethanolic extract showed a mild inhibitory activity against urease, among fractions ethylacetate fraction was more active followed by n-butanol fraction while there was no inhibitory activity in n-hexane soluble fraction. Ethylacetate fraction was subjected to activity guided isolation yielding four pure compounds, among them two were new i.e. buxifoline-A (1) (First time isolated from natural sources) and buxilide (2) while the other two were first time isolated from the fruit that are isoquercetin (3)and oleanolic acid ­(4). Their structures were elucidated using spectroscopic and spectrometric techniques. Among the isolated compounds compound 3 showed maximum inhibition. In order to understand the binding interactions of the compound 3, it was docked into the active site of urease enzyme. Our study validates the traditional use of the fruit in the treatment of gastritis and urinary tract infections, which is strongly supported by the isolated compound isoquercetin (3).

Aerial parts of Satureja montana L. (Lamiaceae) were collected from seven growing wild populations (four populations in Kosovo, two in Albania and one in Montenegro) in 2013 with the aim of assessing the natural variation in the chemical composition of the essential oils, total flavonoids, total phenolics and the antioxidant activity of their methanolic extracts. Essential oils were obtained by steam distillation and analysed using GC-FID and GC-MS, whereas total flavonoids, total phenolics and antioxidant activities were determined using spectrophotometric methods. Sixty-one volatile constituents were identified. The main constituents were myrcene, p-cymene, γ-terpinene, linalool, thymol, carvacrol and viridiflorol. Total phenolics ranged from 68.1 to 102.6 mg/g dry mass, the total flavonoid content ranged from 38.3 to 67.0 mg/g dm, and the antioxidant activity according to the DPPH assay ranged from 253.3 to 342.9 mg TE/g dm and according to the FRAP assay ranged from 8.9 to 11.4 mg TE/g dm. Hierarchical cluster analysis and principal component analyses were used to assess the geographical variations in the essential oil composition. Statistical analysis revealed that the analysed populations are grouped into four main clusters that appear to reflect the environmental impact on the chemical composition, which is influenced by differences in habitat composition, altitude and microclimatic conditions.

Calotroposide S (1), a new oxypregnane oligoglycoside has been isolated from the n-butanol fraction of Calotropis procera (Ait) R. Br. root bark. The structure of 1 was assigned based on various spectroscopic analyses. Calotroposide S (1) possesses the 12-O-benzoylisolineolon aglycone moiety with eight sugar residues attached to C-3 of the aglycone. It showed potent anti-proliferative activity towards PC-3 prostate cancer, A549 non-small cell lung cancer (NSCLC), and U373 glioblastoma (GBM) cell lines with IC 50 0.18, 0.2, and 0.06 µM, respectively compared with cisplatin and carboplatin.

Thymus praecox subsp. grossheimii (Ronniger) Jalas is (TPGJ) an aromatic and medicinal plant used as folk medicine and exhibits a variety of biological activities. Aerial part of plant material was boiled in water then extracted with hexane and ethyl acetate sequentially. Flash column chromatography (Sephadex LH-20) and HPLC were used for ethy acetate extract to isolate rosmarinic acid (1), apigenin 7-O-glucoside (2), chrysoeriol (3), apigenin (4), naringenin (5 ), eriodictiol (6), luteolin (7) and globoidnan A (8). The structures of isolated compounds were elucidated by spectroscopic techniques basically 1D, 2D-NMR and LC-TOF/MS/MS. Antiproliferative activity, cytotoxicity of compounds and extract were investigated in vitro on C6 (rat brain tumor), HeLa (human cervix carcinoma), HT29 (human colon carcinoma) and Vero (African green monkey kidney epithelium) cells lines by using BrdU cell proliferation ELISA and lactate dehydrogenase (LDH) assays. Extract and some compounds exhibited significant antiproliferative effects against various cancerous cell lines.

Piper betle L. can be a valuable proposal for the prevention and treatment of several disorders. In fact, i ts leaves are largely consumed as mouth freshener and masticator, being known for their biological properties. This material possesses several kinds of bioactive natural products. Considering that diabetes is a worldwide disease with strong impact on human health, this work intended to explore the in vitro α-glucosidase inhibitory capacity of P. betle leaves, as well as to improve the knowledge on their metabolic pattern. Thus, a targeted metabolite analysis of the aqueous and ethanolic extract was performed by GC-MS, a similar qualitative profile of both extracts being observed. Fourteen metabolites were determined in P. betle leaves, five of them for the first time. Alanine and β-sitosterol were the main amino acid and sterol, respectively. Stearic and palmitic acids were the predominant fatty acids. A strong capacity to inhibit α-glucosidase was noticed, ethanol extract being more active than the positive control (acarbose) tested under the same conditions. Taking into account the results obtained, this work further extends the potential application of this herbal medicine, suggesting that its consumption may have a positive impact in the prevention and treatment of diabetes disease.

The Monotheca A. DC. is a monotypic genus of the family Sapotaceae, which is widely distributed in Afghanistan, Djbouti, Northern Somalia, Oman, Pakistan and Southern Ethiopia. North-west Pakistan is the main region where Monotheca buxifolia (Falc.) A. DC., the only species of this genus, locally known as “Gurgura”, grows abundantly. It is an evergreen, fruit-producing medicinal tree. Bioassay-guided fractionation of the aerial parts of M. buxifolia afforded lupeol (1), lupeol acetate (2), betulin (3), oleanolic acid (4) andβ-amyrin (5) from the n-hexane and the chloroform fractions. This is the first report on the isolation, and identification of triterpenes (1-5) as the major compounds in the active fractions with antiproliferative property, and also on the antiproliferative activity of M. buxifolia extract and fractions against the human lung cancer cell line NCI-H460 in vitro.

Wedelia trilobata is a noxious invasive weed that has been widely cultivated as a decorative and groundcover plant. The plant has been reported to contain diverse bioactive compounds with a broad spectrum of biological activities including allelochemicals. Allelochemicals contribute to allelopathy interactions that suppress the growth and development of nearby plants. Several studies have reported the allelopathic potential of W. trilobata and its negative effects to crop plants. However, relatively little is known about the allelochemicals’ composition and how allelochemicals contribute to the allelopathic behavior of this plant. In order to prove allelopathy, the identification of the causative allelochemicals is required. The identification of potential allelochemicals that serve as biomarkers could be useful for assessing allelopathy interactions. In this study, a liquid chromatography (LC) based metabolomics approach was applied to find biomarkers with allelopathic effects from W. trilobata. Ethanol and water were used to extract metabolites from the leaves of W. trilobata and analyzed using liquid chromatography coupled with quadrupole high-resolution time of flight mass spectrometry (LC-QTOF-MS). Using multivariate statistical analysis (MVA), we identified eight Rt-m/z pairs as candidate marker compounds for assessing allelopathy interactions of W. trilobata. The results highlight the application of metabolomics for understanding of the role of allelochemicals in allelopathy interactions of W. trilobata .

Grape pomace contains high levels of valuable antioxidants such as anthocyanins and phenolic compounds that help prevent chronic diseases such as cardiovascular problems and cancers. In this study, Concord grape pomace was soaked in acidic solutions at different time intervals and pHs in a water bath at 80 oC. Five kinds of anthocyanins were released and identified in the pomace after acid hydrolysis. The releasing rate of anthocyanins and antioxidant activities of the acid hydrolyzed pomace extracts were determined by multitest systems. Different antioxidant assays including total antioxidant capacity (TAC), total phenolic content (TPC) and free radical scavenging activity (RSA) were used to evaluate the antioxidant properties of the acid hydrolyzed pomace extracts. The change in antioxidant capacity of the pomace extracts during hydrolysis was correlated with total phenolic content and free radical scavenging activity but had little relationship with anthocyanin contents.

Since the essential oil of Salvia sclarea is used as a flavouring agent, the effect of different extraction techniques (hydrodistillation & HS-SPME) and duration of hydrodistillation (2, 3 and 4 h) with respect to yield, composition and identification rate of extracted essential oils from Greek cultivated S. sclarea aerial blooming parts were investigated. Linalool and linalyl acetate levels seemed to decrease with increasing duration of hydrodistillation, while diterpenes increased dramatically, while the head space analysis showed significantly lower levels of linalool in comparison to its ester. Thus, linalool (5.1-35.8%), linalyl acetate (11.3-37.6%) and sclareol (0.0-41.8%), concerning the oils obtained by hydrodistillation, were the most important metabolites. Solid-phase microextraction yielded mainly oxygenated monoterpenes, especially linalyl acetate (59.3%), followed by cis-linalool oxide (8.6%) and linalool (7.8%).

The chemical composition of volatiles from the leaves of three different Illicium species has been studied. The essential oils were obtained by hydrodistillation and analyzed by GC (FID) and GC-MS. The components by identified by MS libraries and their LRIs. The essential oil contents vary between 0.12% and 0.21% (v/w), calculated on a dry weight basis. Illicium majus J. D. Hooker & Thomson afforded oil whose major constituents were aromadendrene (13.0%), cuparene (8.2%), 1,8-cineole (8.1%) and calamenene (7.8%). However, 1,8-cineole (8.4%), linalool (7.7%), (E)-nerolidol (7.6%) and sabinene (7.1%) were the quantitatively significant compounds of the leaf oil of Illicium micranthun Dunn. The leaf oil of Illicium tsaii A. C. Smith comprised mainly of (E)-nerolidol (15.5%), β-caryophyllene (8.1%), β-cedrene (6.5%), 1,8-cineole (6.3%) and calamenene (6.3%). The chemical composition of the leaf essential oils of these plants from are being reported for the first time.

In a previous study, the total ethanol extract of Bauhinia hookeri  showed a significant hepatoprotective effect in CCl 4-induced toxicity model in mice. However, the active components responsible for the activity were not identified. Therefore, this study was undertaken to determine if the activity of B. hookeri extract is due to its flavonoid content. The hepatoprotective activity of B. hookeri flavonoids was determined by measuring the activities of alanine aminotransferase (ALT) and aspartate aminotransferase (AST) in the culture medium of HepG2 cells challenged with CCl 4. The lipid peroxidation and antioxidant parameters, superoxide dismutase (SOD) and glutathione (GSH) were estimated in the cell lysates. The isolated flavonoids were identified by mass, UV and NMR spectral data. This study revealed that B. hookeri flavonoid fraction and its pure compounds ( kaempferol 3-O-β- D-glucoside, quercetin 3-O-β- D-glucoside and c atechin 3-O-α- L-rhamnoside) possess a promising hepatoprotective activity as evidenced from the normalized levels of ALT and AST. This was attributed partly to their potent antioxidant activity as demonstrated by the increased GSH levels, SOD activity and reduced lipid peroxidation. The whole flavonoid fraction showed the highest cytoprotective activity and was more effective than silymarin. This study highlights a promising natural hepatoprotective remedy derived from B. hookeri.

Composition and antibacterial activity of the hydro-distilled essential oil from aerial parts of Tanacetum hololeucum from Iran were investigated. The oil of T. hololeucum was analyzed by GC-FID and GC-MS. The major compounds were found to be artemisia alcohol (22.8%), yomogi alcohol (19.4%), artemisyl acetate (12.9%), γ-eudesmol (12.1%) and camphor (10.5%). The antibacterial activity of the oil was tested against four bacteria (Staphylococcus aureus, Bacillus cereus, KlebsiellaPneumoniae and Escherichia coli) by disk diffusion and determination of MIC and MBC values. The results showed that Gram-positive bacteria were highly inhibited by the oil with MIC values of 2 mg/mL. The most resistant strain was KlebsiellaPneumoniae with the highest MIC and MBC values of 16 and >32 mg/mL, respectively. Considering sensitivity screening it is notable that the antibacterial property of the oil from T. hololeucum could be attributed mainly to the synergistic property of main compounds.