Startseite Two new polypodane-type bicyclic triterpenoids from mastic
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Two new polypodane-type bicyclic triterpenoids from mastic

  • Xuerui An , Junlong Wang , Xuehui Yu , Hao Wu und Wei Liu EMAIL logo
Veröffentlicht/Copyright: 24. März 2022
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Open Chemistry
Aus der Zeitschrift Open Chemistry Band 20 Heft 1

Abstract

Pistacia lentiscus L. is an evergreen shrub belonging to the Anacardiaceae family, cultivated exclusively in the southern area of Chios Island. Mastic gum as a unique natural resin of the tree Pistacia lentiscus L. has been used extensively in functional foods and traditional medicine. The biological properties of Pistacia resins may be influenced by different chemical constituents. Herein the present work is aimed to further explore the diverse triterpenoids of mastic, and evaluate their anti-inflammatory activity. Two undescribed polypodane-type bicyclic triterpenoids were isolated from the Pistacia resins, their structures were elucidated using ultraviolet, infrared, high resolution electrospray ionization mass spectroscopy (HRESIMS), and nuclear magnetic resonance data. LPS-stimulated RAW264.7 macrophages were incubated with various concentrations of isolated compounds, and results showed that compounds 1 and 2 inhibited nitric oxide production in LPS-induced RAW264.7 cells with IC50 values of 28.1 and 32.6 µM, respectively.

Keywords: Pistacia lentiscus ; mastic; polypodane-type bicyclic triterpenoids; anti-inflammation

1 Introduction

Terpenes are a group of natural compounds which act on many steps of pathophysiological processes, and their chemical diversity is well suited to provide skeleton for anti-inflammatory remedies [1]. Several terpenes’ natural and synthetic derivatives showed anti-inflammatory activities in vitro and in vivo via inhibiting pro-inflammatory cytokine production, such as nitric oxide (NO), tumor necrosis factor-alpha (TNF-α), prostaglandin E2 (PGE2), and interleukin-6 (IL-6) [2].

Mastic is a globular, pale yellow, resinous exudate of the evergreen shrub Pistacia lentiscus L. of the Anacardiaceae family, grown only in southern part of the island of Chios [3]. It has been widely used both as a food supplement and as a traditional medicine in the Mediterranean and Middle Eastern countries [4,5]. Clinically, mastic has been effective in the treatment of gastrointestinal disorders with less side effects [6,7,8]. Up to now, various beneficial pharmaceutical properties have been found in mastic, including antimicrobial, anti-inflammatory, anti-ulcer, antioxidant, antitumor, etc. [3,5]. Because of those wide spectrum of biological activities, which are mainly attributed to triterpenes and volatile compounds, mastic has been rediscovered and attracted much attention [3]. More than 120 chemical compounds, including some identified by GC-MS, were reported so far from the 1980s. The gum resins contain triterpenes (constituting 65–70%) comprising tetracyclic and pentacyclic triterpenes which are derivatives of tirucallane, dammarane, oleanane, and lupane skeletons [9], essential oil containing the major components α-pinene and β-myrcene [10], and a range of dicyclic triterpenes (1–2% of the total resin) [11]. Multiple lines of evidence suggest that Pistacia resins can inhibit the production of both NO and PGE2 in lipopolysaccharide (LPS)-activated RAW264.7 cells [12], decrease the IL-6, and C-reactive protein (CRP) plasma levels [13], and limit an increase in plasma free amino acids for maintenance and recovery of intestinal functions [14].

Our preliminary experiments revealed that terpenoids were abundant in mastic [15], and the crude extract of mastic could improve disease active index and colonic pathological changes in dextran sulfate sodium salt-induced ulcerative colitis mice. To further explore the chemical diversity of triterpenoids, two new polypodane-type bicyclic triterpenoids were isolated and identified. In addition, their inhibitory effects against NO production in LPS-induced RAW264.7 cells were assayed.

2 Materials and methods

2.1 General experimental procedures

The equipment used in extraction and isolation of compounds include semi-preparative HPLC equipped with 5110 pump coupled to a 5430 diode array detector, a 5210 autosampler (Hitachi Limited, Tokyo, Japan), and Chiralpak AD-H (5 µm, 10 mm × 250 mm, Daicel, Tokyo, Japan). Instruments for structural characterization include Nuclear magnetic resonance Avance Ⅱ 400 MHz (Bruker Co., Germany), Autopol IV automatic polarimeter (Rudolph Research Analytical, USA), Q-Exactive tandem mass spectrometer (Thermo Fisher Scientific, Waltham, USA), and JASCO J-720W spectrophotometer (Jasco, Japan). All reagents (HPLC or analytical-grade) were bought from Sigma-Aldrich and Tansoole (Shanghai, People’s Republic of China).

2.2 Plant material

Pistacia resins were purchased from Xinjiang Uyghur Medicine Hospital (People’s Republic of China) and identified by Prof. Yan Wei, Xinjiang Agricultural University. A voucher specimen (MG-201810) was deposited in the University and College Key Lab of Natural Product Chemistry and Application in Xinjiang, Yili Normal University.

2.3 Extraction and isolation

Extraction and isolation were carried out according to the method previously described [15]. Briefly, a quantity of a crude methanol extract (175 g) was extracted successively with petroleum ether, ethyl acetate, and n-butanol. An MCI gel column was eluted with a gradient of MeOH/H2O (60:40‒100:0) to separate the ethyl acetate extract into nine fractions (Fr. A‒Fr. I). Fr. E (28.0 g) was subjected to column chromatography (CC) over ODS eluting with MeOH/H2O (50:50‒100:0) to give eight subfractions (Frs. E1–E8). Frs. E4 (2.3 g) was chromatographed on silica gel CC, eluted successively with CH2Cl2/MeOH (50:1‒0:1) to obtain subfraction E4b (523.2 mg). Following the purification by Sephadex LH-20 CC using MeOH, subfraction E4b3 (23.3 mg) were obtained and further separated by semi-preparative RP-HPLC (78:22, MeOH/H2O, 3.0 mL/min) to yield E4b3a (12.6 mg). Subfraction E4b3a via chiral-phase HPLC (AD-H column, n-hexane/isopropanol, 81:19; 3.0 mL/min) afforded 1 (3.7 mg, t R = 12.82 min) and 2 (3.8 mg, t R = 14.05 min).

2.3.1 3β,8β,21-Trihydroxypolypoda-22-methoxy-13(E),17(E)-diene (1)

Colorless amorphous solid; [ α ] D 25 + 20 ° (c 0.1, MeOH); UV(MeOH) λ max 204 nm; IR ν max 3,440, 2,953, 2,849, 2,353, 2,324, 1,635, and 1,456 cm−1; 1H (400 MHz) and 13C (100 MHz) NMR spectral data in CDCl3, Table 1; HRESIMS: m/z 515.4056 [M + Na]+ (calcd for C31H56O4Na, 515.4076).

Table 1

1H NMR (400 MHz) and 13C NMR (100 MHz) data of 1 (in CDCl3)

No. δ H (mult, J, Hz) δ C No. δ H (mult, J, Hz) δ C No. δ H (mult, J, Hz) δ C
1 1.71 m, 1.17 m 38.0 12 2.06 m 2H 31.4 23 0.76 s 3H 15.5
2 1.65 m, 1.59 m 27.3 13 5.17 t (7.1) 125.1 24 0.99 s 3H 19.1
3 3.25 dd (11.2, 4.8) 79.0 14 135.5 25 0.80 s 3H 15.7
4 39.0 15 2.08 m 2H 27.0 26 1.13 s 3H 23.9
5 0.91 m 55.2 16 2.00 m 2H 39.8 27 1.61 s 3H 16.4
6 1.67 m, 1.35 m 20.4 17 5.17 t (7.1) 124.7 28 1.61 s 3H 16.2
7 1.87 m, 1.36 m 44.6 18 135.1 29 1.12 s 3H 20.9
8 74.0 19 2.26 m, 2.03 m 37.0 30 1.10 s 3H 19.1
9 1.02 t (4.0) 61.4 20 1.50 m, 1.42 m 29.8 OMe 3.22 s 3H 49.2
10 39.0 21 3.42 dd (10.2 2.0) 76.4
11 1.42 m, 1.31 m 25.7 22 77.6

Bold font represents carbon atom serial number.

2.4 Cytotoxicity assay

The RAW264.7 cell line purchased from the American Type Culture Collection (ATCC) were cultured in DMEM with 10% FBS. The cell viability assays of the isolated triterpenoids to RAW264.7 cells were evaluated by cell counting kit 8 (CCK-8, Dojindo, Japan) as described previously [16]. The cells at a density of 1.5 × 104 cells/well were seeded in 96-well microplates with 100 μL of DMEM containing 10% FBS and 1% penicillin-streptomycin in 5% CO2 at 37°C for 24 h. The compounds and positive controls doxorubicin were dissolved in DMSO to afford a series of concentrations of solutions (10, 20, and 40 μM). The supernatant was replaced by FBS-free DMEM containing the stocks solutions and incubated for another 24 h. After that, the supernatant was removed, and CCK8 (10%, 100 μL) reagent was added into each well and incubated at 37°C for 2 h. The optial density (OD) at 450 nm was measured using a microplate reader, and IC50 values were calculated by Graphpad Prism software (version 8.0).

2.5 NO assay

Detection of accumulated nitrites was performed using Griess reagent (Beyotime, Shanghai, China) as described previously [17]. Briefly, the RAW264.7 cells at approximately 1.5 × 104 cells/well were incubated for another 24 h, the cells were pretreated with different compounds and dexamethasone (10, 20, and 40 μM) for 2 h, followed by LPS (1.0 μg/mL) for 18 h. After incubation, 50 μL of the supernatant were added to Griess reagent (100 μL, Reagent A and Reagent B). The OD at 540 nm was measured using a microplate reader, and IC50 values were calculated by Graphpad Prism software (version 8.0).

2.6 Statistical analysis

Data are expressed as mean value ± SD and analyzed by Graphpad Prism software (version 8.0).

3 Results and discussion

Compound 1 was isolated as a colorless oil with positive optical rotation (20, (c 0.1, MeOH). Its molecular formula was determined as C31H56O4Na by HRESIMS at m/z 515.4056 [M + Na]+, together with its 13C NMR (Table 1) data, suggesting 4 degrees of unsaturation. The 1H NMR spectrum (Table 1) of 1 exhibited 8 methyl groups at (δ H 1.14, 1.12, 1.10, 0.99, 0.80, 0.76, each 3H, s; δ H 1.61, 6H, s), two olefinic protons at δ H 5.17 (2H, t, J = 7.1 Hz), two oxygenated methines at δ H 3.42 (dd, J = 10.2, 2.0 Hz) and 3.24 (dd, J = 11.2, 4.8 Hz), and a methoxy at δ H 3.22 (3H, s). The 13C NMR and HSQC spectra displayed the presence of 31 carbons comprising eight methyls, ten methylenes, six methines (including three oxygenated and two sp2 carbons), and six quaternary carbons (including two oxygenated and two sp2 carbons), and one methoxy. The abovementioned data together with literature research [18,19] implied that 1 is likely a polypodane-type bicyclic triterpenoid.

Further analysis of 1 using HSQC and H1-H1 COSY data revealed that compound 1 shared the same A and B rings with those of (8R)-3β,8-dihydroxypolypoda- 13E,17E,21-triene [20]. The notable difference was that the double bond Δ21 group signal observed in (8R)-3β,8-dihydroxypolypoda-13E,17E,21-triene was absent in 1, while the presence of an additional methoxy at δ H 3.22 (3H, s), δ C 49.2, and one oxygenated methine at δ H 3.42 (dd, J = 10.2, 2.0 Hz), δ C 76.4, which were confirmed by the 1H–1H COSY correlations (Figure 1) between H-21 and H-19, H-20, and HMBC correlations (Figure 1) from H3-29/H3-30 to C-21 (δ C 76.4), and C-22 (δ C 77.6), and methoxy proton signal (δ H 3.22) to C-22. The large coupling constant of H-3 (dd, J = 11.2, 4.8 Hz) suggested that 3-OH was β-oriented [21], and the NOESY correlation from H-3 to H-5, and H3-24 supported this assignment. Therefore, the structure of 1 was proposed as 3β,8β,21-trihydroxypolypoda-22-methoxy-13(E),17(E)-diene.

Figure 1 Structure, key 1H–1H COSY (▬) and HMBC correlations (H → C) of compound 1.
Figure 1

Structure, key 1H–1H COSY (▬) and HMBC correlations (H → C) of compound 1.

We attempted to determine the absolute configurations of 1 using X-ray diffraction, circular dichroism (CD), and mosher’s method, but unfortunately all attempts have failed. In addition, compound 2 shows very similar data to 1, such as 1H NMR and 13C NMR spectra, HRESIMS and CD data. The most obvious difference was that compound 1 gave positive optical rotation, while compound 2 gave negative optical rotation. As the absolute configurations of rings A and B of natural polypodane-type bicyclic triterpenoid are affirmatory, the difference between 1 and 2 is speculated to stereo-isomerization at C-21. However, the absolute configuration of two compounds still needs further study.

The cell viability of RAW264.7 was kept more than 80% with the concentration of compounds and positive control dexamethasone from 10 to 40 µM (Figure 2), which excludes false positive results caused by the cytotoxicity. As shown in Figure 2, compounds 1 and 2 exhibited concentration-dependent manner at 10 to 40 µM, and they showed moderate inhibitory abilities against the production of NO with IC50 values at 28.1 and 32.6 µM, for comparison, dexamethasone had an IC50 value of 19.7 µM. Considering the anti-inflammatory effects previously reported for the source material [12,15,22], the isolated compounds were evaluated for inhibitory activity against NO production in LPS-induced RAW264.7 cells. The result showed that the isolated compounds possess potential inhibitory activity, which were comparable to that of positive control dexamethasone. Inhibition of NO production via MAPKs and NF-κB signaling pathways is a key anti-inflammatory approach. Bicyclic triterpenoids present in mastic contribute to the anti-inflammatory activity, but the potential mechanism of action was unclear and further research would be required to confirm this.

Figure 2 Concentration-response curve of samples on the NO inhibition and cell viability in RAW264.7 cells. Data are presented as mean value ± SD, n = 3.
Figure 2

Concentration-response curve of samples on the NO inhibition and cell viability in RAW264.7 cells. Data are presented as mean value ± SD, n = 3.

4 Conclusion

Inflammation is a defensive response to damaging factors in the host. While moderate inflammation exerts health beneficial effects, excessive produced pro-inflammatory cytokines will cause some adverse reactions. Mastic gum, which act as a traditional herbal medicinal product with good therapeutic effect on inflammation, is a complex mixture comprising different bioactive compounds in which each chemical constituent contributes to their overall bioactivity. Numerical results obtained from this research work have indicated two new polypodane-type bicyclic triterpenoids exhibited moderate inhibitory effects on anti-inflammatory activities in vitro through against NO release by LPS-stimulated RAW264.7 macrophages. These findings provide a foundation for illustrating the anti-inflammatory components, but underlying mechanisms still require further study.

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  1. Funding information: This work was financially supported by the National Natural Science Foundation of China (82060774) and University and College Key Lab of Natural Product Chemistry and Application in Xinjiang (2020YSHXZD02).

  2. Author contributions: An XR performed the separation and wrote the original draft; Wang JL performed the data analysis; Yu XH proofread the manuscript; Wu H carried out the biological tests; Liu W supervised the phytochemical experiments and revised the manuscript.

  3. Conflict of interest: The authors declare no conflict of interest.

  4. Ethical approval: The conducted research is not related to either human or animal use.

  5. Data availability statement: All data supporting the findings of this study are available within the article.

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Received: 2022-01-02
Revised: 2022-03-01
Accepted: 2022-03-02
Published Online: 2022-03-24

© 2022 Xuerui An et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  73. Activated partial thromboplastin time maybe associated with the prognosis of papillary thyroid carcinoma
  74. Treatment of rat brain ischemia model by NSCs-polymer scaffold transplantation
  75. Lead and cadmium removal with native yeast from coastal wetlands
  76. Characterization of electroless Ni-coated Fe–Co composite using powder metallurgy
  77. Ferrate synthesis using NaOCl and its application for dye removal
  78. Antioxidant, antidiabetic, and anticholinesterase potential of Chenopodium murale L. extracts using in vitro and in vivo approaches
  79. Study on essential oil, antioxidant activity, anti-human prostate cancer effects, and induction of apoptosis by Equisetum arvense
  80. Experimental study on turning machine with permanent magnetic cutting tool
  81. Numerical simulation and mathematical modeling of the casting process for pearlitic spheroidal graphite cast iron
  82. Design, synthesis, and cytotoxicity evaluation of novel thiophene, pyrimidine, pyridazine, and pyridine: Griseofulvin heterocyclic extension derivatives
  83. Isolation and identification of promising antibiotic-producing bacteria
  84. Ultrasonic-induced reversible blood–brain barrier opening: Safety evaluation into the cellular level
  85. Evaluation of phytochemical and antioxidant potential of various extracts from traditionally used medicinal plants of Pakistan
  86. Effect of calcium lactate in standard diet on selected markers of oxidative stress and inflammation in ovariectomized rats
  87. Identification of crucial salivary proteins/genes and pathways involved in pathogenesis of temporomandibular disorders
  88. Zirconium-modified attapulgite was used for removing of Cr(vi) in aqueous solution
  89. The stress distribution of different types of restorative materials in primary molar
  90. Reducing surface heat loss in steam boilers
  91. Deformation behavior and formability of friction stir processed DP600 steel
  92. Synthesis and characterization of bismuth oxide/commercial activated carbon composite for battery anode
  93. Phytochemical analysis of Ziziphus jujube leaf at different foliar ages based on widely targeted metabolomics
  94. Effects of in ovo injection of black cumin (Nigella sativa) extract on hatching performance of broiler eggs
  95. Separation and evaluation of potential antioxidant, analgesic, and anti-inflammatory activities of limonene-rich essential oils from Citrus sinensis (L.)
  96. Bioactivity of a polyhydroxy gorgostane steroid from Xenia umbellata
  97. BiCAM-based automated scoring system for digital logic circuit diagrams
  98. Analysis of standard systems with solar monitoring systems
  99. Structural and spectroscopic properties of voriconazole and fluconazole – Experimental and theoretical studies
  100. New plant resistance inducers based on polyamines
  101. Experimental investigation of single-lap bolted and bolted/bonded (hybrid) joints of polymeric plates
  102. Investigation of inlet air pressure and evaporative cooling of four different cogeneration cycles
  103. Review Articles
  104. Comprehensive review on synthesis, physicochemical properties, and application of activated carbon from the Arecaceae plants for enhanced wastewater treatment
  105. Research progress on speciation analysis of arsenic in traditional Chinese medicine
  106. Recent modified air-assisted liquid–liquid microextraction applications for medicines and organic compounds in various samples: A review
  107. An insight on Vietnamese bio-waste materials as activated carbon precursors for multiple applications in environmental protection
  108. Antimicrobial activities of the extracts and secondary metabolites from Clausena genus – A review
  109. Bioremediation of organic/heavy metal contaminants by mixed cultures of microorganisms: A review
  110. Sonodynamic therapy for breast cancer: A literature review
  111. Recent progress of amino acid transporters as a novel antitumor target
  112. Aconitum coreanum Rapaics: Botany, traditional uses, phytochemistry, pharmacology, and toxicology
  113. Corrigendum
  114. Corrigendum to “Petrology and geochemistry of multiphase post-granitic dikes: A case study from the Gabal Serbal area, Southwestern Sinai, Egypt”
  115. Corrigendum to “Design of a Robust sliding mode controller for bioreactor cultures in overflow metabolism via an interdisciplinary approach”
  116. Corrigendum to “Statistical analysis on the radiological assessment and geochemical studies of granite rocks in the north of Um Taghir area, Eastern Desert, Egypt”
  117. Corrigendum to “Aroma components of tobacco powder from different producing areas based on gas chromatography ion mobility spectrometry”
  118. Corrigendum to “Mechanical properties, elastic moduli, transmission factors, and gamma-ray-shielding performances of Bi2O3–P2O5–B2O3–V2O5 quaternary glass system”
  119. Erratum
  120. Erratum to “Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies”
  121. Special Issue on Applied Biochemistry and Biotechnology (ABB 2021)
  122. Study of solidification and stabilization of heavy metals by passivators in heavy metal-contaminated soil
  123. Human health risk assessment and distribution of VOCs in a chemical site, Weinan, China
  124. Preparation and characterization of Sparassis latifolia β-glucan microcapsules
  125. Special Issue on the Conference of Energy, Fuels, Environment 2020
  126. Improving the thermal performance of existing buildings in light of the requirements of the EU directive 2010/31/EU in Poland
  127. Special Issue on Ethnobotanical, Phytochemical and Biological Investigation of Medicinal Plants
  128. Study of plant resources with ethnomedicinal relevance from district Bagh, Azad Jammu and Kashmir, Pakistan
  129. Studies on the chemical composition of plants used in traditional medicine in Congo
  130. Special Issue on Applied Chemistry in Agriculture and Food Science
  131. Strip spraying technology for precise herbicide application in carrot fields
  132. Special Issue on Pharmacology and Metabolomics of Ethnobotanical and Herbal Medicine
  133. Phytochemical profiling, antibacterial and antioxidant properties of Crocus sativus flower: A comparison between tepals and stigmas
  134. Antioxidant and antimicrobial properties of polyphenolics from Withania adpressa (Coss.) Batt. against selected drug-resistant bacterial strains
  135. Integrating network pharmacology and molecular docking to explore the potential mechanism of Xinguan No. 3 in the treatment of COVID-19
  136. Chemical composition and in vitro and in vivo biological assortment of fixed oil extracted from Ficus benghalensis L.
  137. A review of the pharmacological activities and protective effects of Inonotus obliquus triterpenoids in kidney diseases
  138. Ethnopharmacological study of medicinal plants in Kastamonu province (Türkiye)
  139. Protective effects of asperuloside against cyclophosphamide-induced urotoxicity and hematotoxicity in rats
  140. Special Issue on Essential Oil, Extraction, Phytochemistry, Advances, and Application
  141. Identification of volatile compounds and antioxidant, antibacterial, and antifungal properties against drug-resistant microbes of essential oils from the leaves of Mentha rotundifolia var. apodysa Briq. (Lamiaceae)
  142. Phenolic contents, anticancer, antioxidant, and antimicrobial capacities of MeOH extract from the aerial parts of Trema orientalis plant
  143. Chemical composition and antimicrobial activity of essential oils from Mentha pulegium and Rosmarinus officinalis against multidrug-resistant microbes and their acute toxicity study
  144. Special Issue on Marine Environmental Sciences and Significance of the Multidisciplinary Approaches
  145. An insightful overview of the distribution pattern of polycyclic aromatic hydrocarbon in the marine sediments of the Red Sea
  146. Antifungal–antiproliferative norcycloartane-type triterpenes from the Red Sea green alga Tydemania expeditionis
  147. Solvent effect, dipole moment, and DFT studies of multi donor–acceptor type pyridine derivative
  148. An extensive assessment on the distribution pattern of organic contaminants in the aerosols samples in the Middle East
  149. Special Issue on 4th IC3PE
  150. Energetics of carboxylic acid–pyridine heterosynthon revisited: A computational study of intermolecular hydrogen bond domination on phenylacetic acid–nicotinamide cocrystals
  151. A review: Silver–zinc oxide nanoparticles – organoclay-reinforced chitosan bionanocomposites for food packaging
  152. Green synthesis of magnetic activated carbon from peanut shells functionalized with TiO2 photocatalyst for Batik liquid waste treatment
  153. Coagulation activity of liquid extraction of Leucaena leucocephala and Sesbania grandiflora on the removal of turbidity
  154. Hydrocracking optimization of palm oil over NiMoO4/activated carbon catalyst to produce biogasoline and kerosine
  155. Special Issue on Pharmacology and metabolomics of ethnobotanical and herbal medicine
  156. Cynarin inhibits PDGF-BB-induced proliferation and activation in hepatic stellate cells through PPARγ
  157. Special Issue on The 1st Malaysia International Conference on Nanotechnology & Catalysis (MICNC2021)
  158. Surfactant evaluation for enhanced oil recovery: Phase behavior and interfacial tension
  159. Topical Issue on phytochemicals, biological and toxicological analysis of aromatic medicinal plants
  160. Phytochemical analysis of leaves and stems of Physalis alkekengi L. (Solanaceae)
  161. Phytochemical and pharmacological profiling of Trewia nudiflora Linn. leaf extract deciphers therapeutic potentials against thrombosis, arthritis, helminths, and insects
  162. Pergularia tomentosa coupled with selenium nanoparticles salvaged lead acetate-induced redox imbalance, inflammation, apoptosis, and disruption of neurotransmission in rats’ brain
  163. Protective effect of Allium atroviolaceum-synthesized SeNPs on aluminum-induced brain damage in mice
  164. Mechanism study of Cordyceps sinensis alleviates renal ischemia–reperfusion injury
  165. Plant-derived bisbenzylisoquinoline alkaloid tetrandrine prevents human podocyte injury by regulating the miR-150-5p/NPHS1 axis
  166. Network pharmacology combined with molecular docking to explore the anti-osteoporosis mechanisms of β-ecdysone derived from medicinal plants
  167. Chinese medicinal plant Polygonum cuspidatum ameliorates silicosis via suppressing the Wnt/β-catenin pathway
  168. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part I
  169. Investigation of improved optical and conductivity properties of poly(methyl methacrylate)–MXenes (PMMA–MXenes) nanocomposite thin films for optoelectronic applications
  170. Special Issue on Applied Biochemistry and Biotechnology (ABB 2022)
  171. Model predictive control for precision irrigation of a Quinoa crop
https://doi.org/10.1515/chem-2022-0144
Schlagwörter für diesen Artikel
Pistacia lentiscus; mastic; polypodane-type bicyclic triterpenoids; anti-inflammation
Creative Commons
BY 4.0

Artikel in diesem Heft

  1. Regular Articles
  2. Photocatalytic degradation of Rhodamine B in aqueous phase by bimetallic metal-organic framework M/Fe-MOF (M = Co, Cu, and Mg)
  3. Assessment of using electronic portal imaging device for analysing bolus material utilised in radiation therapy
  4. A detailed investigation on highly dense CuZr bulk metallic glasses for shielding purposes
  5. Simulation of gamma-ray shielding properties for materials of medical interest
  6. Environmental impact assesment regulation applications and their analysis in Turkey
  7. Sample age effect on parameters of dynamic nuclear polarization in certain difluorobenzen isomers/MC800 asphaltene suspensions
  8. Passenger demand forecasting for railway systems
  9. Design of a Robust sliding mode controller for bioreactor cultures in overflow metabolism via an interdisciplinary approach
  10. Gamma, neutron, and heavy charged ion shielding properties of Er3+-doped and Sm3+-doped zinc borate glasses
  11. Bridging chiral de-tert-butylcalix[4]arenes: Optical resolution based on column chromatography and structural characterization
  12. Petrology and geochemistry of multiphase post-granitic dikes: A case study from the Gabal Serbal area, Southwestern Sinai, Egypt
  13. Comparison of the yield and purity of plasma exosomes extracted by ultracentrifugation, precipitation, and membrane-based approaches
  14. Bioactive triterpenoids from Indonesian medicinal plant Syzygium aqueum
  15. Investigation of the effects of machining parameters on surface integrity in micromachining
  16. The mesoporous aluminosilicate application as support for bifunctional catalysts for n-hexadecane hydroconversion
  17. Gamma-ray shielding properties of Nd2O3-added iron–boron–phosphate-based composites
  18. Numerical investigation on perforated sheet metals under tension loading
  19. Statistical analysis on the radiological assessment and geochemical studies of granite rocks in the north of Um Taghir area, Eastern Desert, Egypt
  20. Two new polypodane-type bicyclic triterpenoids from mastic
  21. Structural, physical, and mechanical properties of the TiO2 added hydroxyapatite composites
  22. Tribological properties and characterization of borided Co–Mg alloys
  23. Studies on Anemone nemorosa L. extracts; polyphenols profile, antioxidant activity, and effects on Caco-2 cells by in vitro and in silico studies
  24. Mechanical properties, elastic moduli, transmission factors, and gamma-ray-shielding performances of Bi2O3–P2O5–B2O3–V2O5 quaternary glass system
  25. Cyclic connectivity index of bipolar fuzzy incidence graph
  26. The role of passage numbers of donor cells in the development of Arabian Oryx – Cow interspecific somatic cell nuclear transfer embryos
  27. Mechanical property evaluation of tellurite–germanate glasses and comparison of their radiation-shielding characteristics using EPICS2017 to other glass systems
  28. Molecular screening of ionic liquids for CO2 absorption and molecular dynamic simulation
  29. Microwave-assisted preparation of Ag/Fe magnetic biochar from clivia leaves for adsorbing daptomycin antibiotics
  30. Iminodisuccinic acid enhances antioxidant and mineral element accumulation in young leaves of Ziziphus jujuba
  31. Cytotoxic activity of guaiane-type sesquiterpene lactone (deoxycynaropicrin) isolated from the leaves of Centaurothamnus maximus
  32. Effects of welding parameters on the angular distortion of welded steel plates
  33. Simulation of a reactor considering the Stamicarbon, Snamprogetti, and Toyo patents for obtaining urea
  34. Effect of different ramie (Boehmeria nivea L. Gaud) cultivars on the adsorption of heavy metal ions cadmium and lead in the remediation of contaminated farmland soils
  35. Impact of a live bacterial-based direct-fed microbial (DFM) postpartum and weaning system on performance, mortality, and health of Najdi lambs
  36. Anti-tumor effect of liposomes containing extracted Murrayafoline A against liver cancer cells in 2D and 3D cultured models
  37. Physicochemical properties and some mineral concentration of milk samples from different animals and altitudes
  38. Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies
  39. Diagnostic and therapeutic radioisotopes in nuclear medicine: Determination of gamma-ray transmission factors and safety competencies of high-dense and transparent glassy shields
  40. Calculation of NaI(Tl) detector efficiency using 226Ra, 232Th, and 40K radioisotopes: Three-phase Monte Carlo simulation study
  41. Isolation and identification of unstable components from Caesalpinia sappan by high-speed counter-current chromatography combined with preparative high-performance liquid chromatography
  42. Quantification of biomarkers and evaluation of antioxidant, anti-inflammatory, and cytotoxicity properties of Dodonaea viscosa grown in Saudi Arabia using HPTLC technique
  43. Characterization of the elastic modulus of ceramic–metal composites with physical and mechanical properties by ultrasonic technique
  44. GC-MS analysis of Vespa velutina auraria Smith and its anti-inflammatory and antioxidant activities in vitro
  45. Texturing of nanocoatings for surface acoustic wave-based sensors for volatile organic compounds
  46. Insights into the molecular basis of some chalcone analogues as potential inhibitors of Leishmania donovani: An integrated in silico and in vitro study
  47. (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity
  48. On the relative extraction rates of colour compounds and caffeine during brewing, an investigation of tea over time and temperature
  49. Characterization of egg shell powder-doped ceramic–metal composites
  50. Rapeseed oil-based hippurate amide nanocomposite coating material for anticorrosive and antibacterial applications
  51. Chemically modified Teucrium polium (Lamiaceae) plant act as an effective adsorbent tool for potassium permanganate (KMnO4) in wastewater remediation
  52. Efficiency analysis of photovoltaic systems installed in different geographical locations
  53. Risk prioritization model driven by success factor in the light of multicriteria decision making
  54. Theoretical investigations on the excited-state intramolecular proton transfer in the solvated 2-hydroxy-1-naphthaldehyde carbohydrazone
  55. Mechanical and gamma-ray shielding examinations of Bi2O3–PbO–CdO–B2O3 glass system
  56. Machine learning-based forecasting of potability of drinking water through adaptive boosting model
  57. The potential effect of the Rumex vesicarius water seeds extract treatment on mice before and during pregnancy on the serum enzymes and the histology of kidney and liver
  58. Impact of benzimidazole functional groups on the n-doping properties of benzimidazole derivatives
  59. Extraction of red pigment from Chinese jujube peel and the antioxidant activity of the pigment extracts
  60. Flexural strength and thermal properties of carbon black nanoparticle reinforced epoxy composites obtained from waste tires
  61. A focusing study on radioprotective and antioxidant effects of Annona muricata leaf extract in the circulation and liver tissue: Clinical and experimental studies
  62. Clinical comprehensive and experimental assessment of the radioprotective effect of Annona muricata leaf extract to prevent cellular damage in the ileum tissue
  63. Effect of WC content on ultrasonic properties, thermal and electrical conductivity of WC–Co–Ni–Cr composites
  64. Influence of various class cleaning agents for prosthesis on Co–Cr alloy surface
  65. The synthesis of nanocellulose-based nanocomposites for the effective removal of hexavalent chromium ions from aqueous solution
  66. Study on the influence of physical interlayers on the remaining oil production under different development modes
  67. Optimized linear regression control of DC motor under various disturbances
  68. Influence of different sample preparation strategies on hypothesis-driven shotgun proteomic analysis of human saliva
  69. Determination of flow distance of the fluid metal due to fluidity in ductile iron casting by artificial neural networks approach
  70. Investigation of mechanical activation effect on high-volume natural pozzolanic cements
  71. In vitro: Anti-coccidia activity of Calotropis procera leaf extract on Eimeria papillata oocysts sporulation and sporozoite
  72. Determination of oil composition of cowpea (Vigna unguiculata L.) seeds under influence of organic fertilizer forms
  73. Activated partial thromboplastin time maybe associated with the prognosis of papillary thyroid carcinoma
  74. Treatment of rat brain ischemia model by NSCs-polymer scaffold transplantation
  75. Lead and cadmium removal with native yeast from coastal wetlands
  76. Characterization of electroless Ni-coated Fe–Co composite using powder metallurgy
  77. Ferrate synthesis using NaOCl and its application for dye removal
  78. Antioxidant, antidiabetic, and anticholinesterase potential of Chenopodium murale L. extracts using in vitro and in vivo approaches
  79. Study on essential oil, antioxidant activity, anti-human prostate cancer effects, and induction of apoptosis by Equisetum arvense
  80. Experimental study on turning machine with permanent magnetic cutting tool
  81. Numerical simulation and mathematical modeling of the casting process for pearlitic spheroidal graphite cast iron
  82. Design, synthesis, and cytotoxicity evaluation of novel thiophene, pyrimidine, pyridazine, and pyridine: Griseofulvin heterocyclic extension derivatives
  83. Isolation and identification of promising antibiotic-producing bacteria
  84. Ultrasonic-induced reversible blood–brain barrier opening: Safety evaluation into the cellular level
  85. Evaluation of phytochemical and antioxidant potential of various extracts from traditionally used medicinal plants of Pakistan
  86. Effect of calcium lactate in standard diet on selected markers of oxidative stress and inflammation in ovariectomized rats
  87. Identification of crucial salivary proteins/genes and pathways involved in pathogenesis of temporomandibular disorders
  88. Zirconium-modified attapulgite was used for removing of Cr(vi) in aqueous solution
  89. The stress distribution of different types of restorative materials in primary molar
  90. Reducing surface heat loss in steam boilers
  91. Deformation behavior and formability of friction stir processed DP600 steel
  92. Synthesis and characterization of bismuth oxide/commercial activated carbon composite for battery anode
  93. Phytochemical analysis of Ziziphus jujube leaf at different foliar ages based on widely targeted metabolomics
  94. Effects of in ovo injection of black cumin (Nigella sativa) extract on hatching performance of broiler eggs
  95. Separation and evaluation of potential antioxidant, analgesic, and anti-inflammatory activities of limonene-rich essential oils from Citrus sinensis (L.)
  96. Bioactivity of a polyhydroxy gorgostane steroid from Xenia umbellata
  97. BiCAM-based automated scoring system for digital logic circuit diagrams
  98. Analysis of standard systems with solar monitoring systems
  99. Structural and spectroscopic properties of voriconazole and fluconazole – Experimental and theoretical studies
  100. New plant resistance inducers based on polyamines
  101. Experimental investigation of single-lap bolted and bolted/bonded (hybrid) joints of polymeric plates
  102. Investigation of inlet air pressure and evaporative cooling of four different cogeneration cycles
  103. Review Articles
  104. Comprehensive review on synthesis, physicochemical properties, and application of activated carbon from the Arecaceae plants for enhanced wastewater treatment
  105. Research progress on speciation analysis of arsenic in traditional Chinese medicine
  106. Recent modified air-assisted liquid–liquid microextraction applications for medicines and organic compounds in various samples: A review
  107. An insight on Vietnamese bio-waste materials as activated carbon precursors for multiple applications in environmental protection
  108. Antimicrobial activities of the extracts and secondary metabolites from Clausena genus – A review
  109. Bioremediation of organic/heavy metal contaminants by mixed cultures of microorganisms: A review
  110. Sonodynamic therapy for breast cancer: A literature review
  111. Recent progress of amino acid transporters as a novel antitumor target
  112. Aconitum coreanum Rapaics: Botany, traditional uses, phytochemistry, pharmacology, and toxicology
  113. Corrigendum
  114. Corrigendum to “Petrology and geochemistry of multiphase post-granitic dikes: A case study from the Gabal Serbal area, Southwestern Sinai, Egypt”
  115. Corrigendum to “Design of a Robust sliding mode controller for bioreactor cultures in overflow metabolism via an interdisciplinary approach”
  116. Corrigendum to “Statistical analysis on the radiological assessment and geochemical studies of granite rocks in the north of Um Taghir area, Eastern Desert, Egypt”
  117. Corrigendum to “Aroma components of tobacco powder from different producing areas based on gas chromatography ion mobility spectrometry”
  118. Corrigendum to “Mechanical properties, elastic moduli, transmission factors, and gamma-ray-shielding performances of Bi2O3–P2O5–B2O3–V2O5 quaternary glass system”
  119. Erratum
  120. Erratum to “Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies”
  121. Special Issue on Applied Biochemistry and Biotechnology (ABB 2021)
  122. Study of solidification and stabilization of heavy metals by passivators in heavy metal-contaminated soil
  123. Human health risk assessment and distribution of VOCs in a chemical site, Weinan, China
  124. Preparation and characterization of Sparassis latifolia β-glucan microcapsules
  125. Special Issue on the Conference of Energy, Fuels, Environment 2020
  126. Improving the thermal performance of existing buildings in light of the requirements of the EU directive 2010/31/EU in Poland
  127. Special Issue on Ethnobotanical, Phytochemical and Biological Investigation of Medicinal Plants
  128. Study of plant resources with ethnomedicinal relevance from district Bagh, Azad Jammu and Kashmir, Pakistan
  129. Studies on the chemical composition of plants used in traditional medicine in Congo
  130. Special Issue on Applied Chemistry in Agriculture and Food Science
  131. Strip spraying technology for precise herbicide application in carrot fields
  132. Special Issue on Pharmacology and Metabolomics of Ethnobotanical and Herbal Medicine
  133. Phytochemical profiling, antibacterial and antioxidant properties of Crocus sativus flower: A comparison between tepals and stigmas
  134. Antioxidant and antimicrobial properties of polyphenolics from Withania adpressa (Coss.) Batt. against selected drug-resistant bacterial strains
  135. Integrating network pharmacology and molecular docking to explore the potential mechanism of Xinguan No. 3 in the treatment of COVID-19
  136. Chemical composition and in vitro and in vivo biological assortment of fixed oil extracted from Ficus benghalensis L.
  137. A review of the pharmacological activities and protective effects of Inonotus obliquus triterpenoids in kidney diseases
  138. Ethnopharmacological study of medicinal plants in Kastamonu province (Türkiye)
  139. Protective effects of asperuloside against cyclophosphamide-induced urotoxicity and hematotoxicity in rats
  140. Special Issue on Essential Oil, Extraction, Phytochemistry, Advances, and Application
  141. Identification of volatile compounds and antioxidant, antibacterial, and antifungal properties against drug-resistant microbes of essential oils from the leaves of Mentha rotundifolia var. apodysa Briq. (Lamiaceae)
  142. Phenolic contents, anticancer, antioxidant, and antimicrobial capacities of MeOH extract from the aerial parts of Trema orientalis plant
  143. Chemical composition and antimicrobial activity of essential oils from Mentha pulegium and Rosmarinus officinalis against multidrug-resistant microbes and their acute toxicity study
  144. Special Issue on Marine Environmental Sciences and Significance of the Multidisciplinary Approaches
  145. An insightful overview of the distribution pattern of polycyclic aromatic hydrocarbon in the marine sediments of the Red Sea
  146. Antifungal–antiproliferative norcycloartane-type triterpenes from the Red Sea green alga Tydemania expeditionis
  147. Solvent effect, dipole moment, and DFT studies of multi donor–acceptor type pyridine derivative
  148. An extensive assessment on the distribution pattern of organic contaminants in the aerosols samples in the Middle East
  149. Special Issue on 4th IC3PE
  150. Energetics of carboxylic acid–pyridine heterosynthon revisited: A computational study of intermolecular hydrogen bond domination on phenylacetic acid–nicotinamide cocrystals
  151. A review: Silver–zinc oxide nanoparticles – organoclay-reinforced chitosan bionanocomposites for food packaging
  152. Green synthesis of magnetic activated carbon from peanut shells functionalized with TiO2 photocatalyst for Batik liquid waste treatment
  153. Coagulation activity of liquid extraction of Leucaena leucocephala and Sesbania grandiflora on the removal of turbidity
  154. Hydrocracking optimization of palm oil over NiMoO4/activated carbon catalyst to produce biogasoline and kerosine
  155. Special Issue on Pharmacology and metabolomics of ethnobotanical and herbal medicine
  156. Cynarin inhibits PDGF-BB-induced proliferation and activation in hepatic stellate cells through PPARγ
  157. Special Issue on The 1st Malaysia International Conference on Nanotechnology & Catalysis (MICNC2021)
  158. Surfactant evaluation for enhanced oil recovery: Phase behavior and interfacial tension
  159. Topical Issue on phytochemicals, biological and toxicological analysis of aromatic medicinal plants
  160. Phytochemical analysis of leaves and stems of Physalis alkekengi L. (Solanaceae)
  161. Phytochemical and pharmacological profiling of Trewia nudiflora Linn. leaf extract deciphers therapeutic potentials against thrombosis, arthritis, helminths, and insects
  162. Pergularia tomentosa coupled with selenium nanoparticles salvaged lead acetate-induced redox imbalance, inflammation, apoptosis, and disruption of neurotransmission in rats’ brain
  163. Protective effect of Allium atroviolaceum-synthesized SeNPs on aluminum-induced brain damage in mice
  164. Mechanism study of Cordyceps sinensis alleviates renal ischemia–reperfusion injury
  165. Plant-derived bisbenzylisoquinoline alkaloid tetrandrine prevents human podocyte injury by regulating the miR-150-5p/NPHS1 axis
  166. Network pharmacology combined with molecular docking to explore the anti-osteoporosis mechanisms of β-ecdysone derived from medicinal plants
  167. Chinese medicinal plant Polygonum cuspidatum ameliorates silicosis via suppressing the Wnt/β-catenin pathway
  168. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part I
  169. Investigation of improved optical and conductivity properties of poly(methyl methacrylate)–MXenes (PMMA–MXenes) nanocomposite thin films for optoelectronic applications
  170. Special Issue on Applied Biochemistry and Biotechnology (ABB 2022)
  171. Model predictive control for precision irrigation of a Quinoa crop
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