Lycopodium Alkaloids from Huperzia serrata and Their Anti-acetylcholinesterase Activities.

One new fawcettimine-type alkaloid (1), one new miscellaneous-type alkaloid (2), four new lycodine-type alkaloids (3-6), and eight known ones (7-14) were isolated from the whole plants of Huperzia serrata. Their structures and absolute configurations were elucidated based on spectroscopic data, X-ray diffraction, ECD calculation and Mosher's method. Compound 1 was a rare C18 N2 -type Lycopodium alkaloid, possessing serratinine skeleton with an amide side chain in C-5. The absolute configuration of the 18-OH of compounds 4-6 were first determined by Mosher's method. Moreover, compounds 1-14 were assayed anti-acetylcholinesterase effect in vitro, and compound 7 showed significant anti-acetylcholinesterase activity with an IC50 value of 16.18±1.64 µM.

How Closely Does Induced Agarwood's Biological Activity Resemble That of Wild Agarwood?

Continuous innovation in artificially-induced agarwood technology is increasing the amount of agarwood and substantially alleviating shortages. Agarwood is widely utilized in perfumes and fragrances; however, it is unclear whether the overall pharmacological activity of induced agarwood can replace wild agarwood for medicinal use. In this study, the volatile components, total chromone content, and the differences in the overall activities of wild agarwood and induced agarwood, including the antioxidant, anti-acetylcholinesterase, and anti-glucosidase activity were all determined. The results indicated that both induced and wild agarwood's chemical makeup contains sesquiterpenes and 2-(2-phenylethyl)chromones. The total chromone content in generated agarwood can reach 82.96% of that in wild agarwood. Induced agarwood scavenged 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals and 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS+) radicals and inhibited acetylcholinesterase activity and α-glucosidase activity with IC50 values of 0.1873 mg/mL, 0.0602 mg/mL, 0.0493 mg/mL, and 0.2119 mg/mL, respectively, reaching 80.89%, 93.52%, 93.52%, and 69.47% of that of wild agarwood, respectively. Accordingly, the results distinguished that induced agarwood has the potential to replace wild agarwood in future for use in medicine because it has a similar chemical makeup to wild agarwood and has comparable antioxidant, anti-acetylcholinesterase, and anti-glucosidase capabilities.

Baoshanmycin and a New Furanone Derivative from a Soil-Derived Actinomycete, Amycolatopsis sp. YNNP 00208.

Actinomycetes have being regarded as a treasure reservoir of various bioactive secondary metabolites and devoted many antibiotics in clinicals. Amycolatopsis sp. YNNP 00208 was isolated from a soil sample collected in Gaoligong Mountain area, Yunnan Province, China. Chemical investigation of its fermentation broth led to a new amide, baoshanmycin (1), and a new furanone derivative, 3-(1,3-dihydroxybutyl)-4-methylfuran-2(H)-one (2), together with eight known compounds, including two amides (3-4), four cyclic dipeptides (5-8), and two deoxyribonucleosides (9-10). Their structures were established on basis of the 1D- and 2D-NMR spectroscopic data, along with the HR-ESI-MS experiments. Baoshanmycin (1) showed moderate antimicrobial activities against Candida albicans, and weak activities against Staphylococcus aureus, multi-drug resistant Staphylococcus aureus, Bacillus subtilis, Listeria monocytogenes, fluconazole-resistant Candida albicans. Baoshanmycin (1) presented strong antioxidant activity and moderate anti-acetylcholinesterase activity. The other compound 3-(1,3-dihydroxybutyl)-4-methylfuran-2(H)-one (2) and the known compounds (3-10) showed moderate antioxidant activity.

Two New Picoline-Derived Meroterpenoids with Anti-Acetylcholinesterase Activity from Ascidian-Derived Fungus Amphichorda felina.

Amphichoterpenoids D (1) and E (2), two new picoline-derived meroterpenoids with a rare 6/6/6 tricyclic pyrano[3,2-c]pyridinyl-γ-pyranone scaffold, were isolated from the ascidian-derived fungus Amphichorda felina SYSU-MS7908. Their structures, including the absolute configurations, were established by extensive spectroscopic methods (1D and 2D NMR and high-resolution mass spectrometry) and ECD calculations. Compounds 1 and 2 showed anti-acetylcholinesterase (anti-AChE) activities with IC50 values of 12.5 µM and 11.6 µM, respectively. The binding interactions between 1, 2, and AChE were investigated using molecular docking analyses.

Mucuna pruriens Seed Aqueous Extract Improved Neuroprotective and Acetylcholinesterase Inhibitory Effects Compared with Synthetic L-Dopa.

L-dopa, a dopaminergic agonist, is the gold standard for the treatment of Parkinson's disease. However, due to the long-term toxicity and adverse effects of using L-dopa as the first-line therapy for Parkinson's disease, a search for alternative medications is an important current challenge. Traditional Ayurvedic medicine has suggested the use of Mucuna pruriens Linn. (Fabaceae) as an anti-Parkinson's agent. The present study aimed to quantify the amount of L-dopa in M. pruriens seed extract by HPLC analysis. The cytotoxicity and neuroprotective properties of M. pruriens aqueous extract were investigated by two in vitro models including the serum deprivation method and co-administration of hydrogen peroxide assay. The results showed the significant neuroprotective activities of M. pruriens seed extracts at a concentration of 10 ng/mL. In addition, the effects of L-dopa and M. pruriens seed extract on in vitro acetylcholinesterase activities were studied. M. pruriens seed extract demonstrated acetylcholinesterase inhibitory activity, while synthetic L-dopa enhanced the activity of the enzyme. It can be concluded that the administration of M. pruriens seed might be effective in protecting the brain against neurodegenerative disorders such as Parkinson's and Alzheimer's diseases. M. prurience seed extract containing L-dopa has shown less acetylcholinesterase activity stimulation compared with L-dopa, suggesting that the extract might have a superior benefit for use in the treatment of Parkinson's disease.

The chemical diversity, the attractant, anti-acetylcholinesterase, and antifungal activities of metabolites from biocontrol Trichoderma harzianum uncovered by OSMAC strategy.

Eight new compounds (1-8) were discovered from Trichoderma harzianum associated with edible mushroom by the one strain many compounds (OSMAC) strategy. Triharzianin A (1) is the first naturally scaffold characterized by a C13-prostaglandin skeleton. The configurations of 1-3, and 5 were determined by the Mosher's method, experimental and calculated ECD spectra, and plausible biosynthesis of stereospecific epoxidation. Most compounds indicated obvious feeding attractant activities to silkworm with attraction rates at 30-90%. Compound 7 showed anti-acetylcholinesterase (anti-AChE) activity with a ratio of 29% at a concentration of 50 µM for insecticidal potential. So 2,​3-​dialkylchromone (7) had potential of chemical entrapment and killing of insects. Compounds 2, 3 and 7-11 showed antifungal activities against Aspergillus fumigates, and Trichoderma sp. from mushroom with MICs ≤ 300 µM. The four fermentation extracts also indicated obvious feeding attractant activities to silkworm for the activities brought by active metabolites from T. harzianum. The material base of biocontrol induced by the interaction of host-fungal symbiont can be investigated by the antifungal metabolites against pathogen fungi.

Dynamic changes in chemical compositions and anti-acetylcholinesterase activity associated with steaming process of stem-leaf saponins of Panax notoginseng.

Stem-leaf saponins (SLSs), the total saponins from aerial part of P. notoginseng, are by-products of notoginseng, a famous traditional Chinese medicine. SLSs have been used as a health functional food in China, but its mild effects limited clinical applications in diseases. Inspired by steaming of notoginseng to enhance its pharmacological activity, a steaming protocol was developed to treat SLSs. SLSs were steamed at 100, 120, and 140°C for 1, 2, 3, and 4 h, respectively. The ultra-performance liquid chromatography coupled with quadrupole time-of-flight MS and ultra-performance liquid chromatography-tandem triple quadrupole mass spectrometry were applied to analyze the dynamic changes in chemical compositions. The anti-acetylcholinesterase activity of steamed SLS were assessed in vitro by directly determining the metabolic product of acetylcholine/choline. The components of SLSs were significantly changed by steaming. A total of 117 saponins and aglycones were characterized, and 35 of them were newly generated. The anti-acetylcholinesterase activity of steamed SLSs gradually increased with the extension of steamed time and the increase of steamed temperature and reached the maximum after 140°C for 3 h. Furthermore, ginsenosides Rk1 and Rg5, the main components of steamed SLSs, showed dose-dependent anti-acetylcholinesterase activities with half maximal inhibitory concentration (IC50 ) values of 26.88 ± 0.53 µm and 22.41 ± 1.31 µm that were only 1.8- and 1.5-fold higher than that of donepezil with IC50 values of 14.93 ± 4.17 µM, respectively.

Isolation and characterization of three pairs of indolediketopiperazine enantiomers containing infrequent N-methoxy substitution from the marine algal-derived endophytic fungus Acrostalagmus luteoalbus TK-43.

Three pairs of new N-methoxy-containing indolediketopiperazine enantiomers, acrozines A-C (1-3), were isolated from the culture extract of Acrostalagmus luteoalbus TK-43, an endophytic fungus obtained from the marine green alga Codium fragile. The optical resolution of compounds 1-3 by chiral HPLC successfully afforded individual enantiomers (+)-1/(-)-1, (+)-2/(-)-2, and (+)-3/(-)-3, respectively. The structures of all these compounds were established on the basis of detailed interpretation of their NMR and mass spectroscopic data. X-ray crystallographic analysis confirmed the structures of compounds 1-3, while the absolute configurations were determined by TDDFT-ECD calculations. All these compounds containing a N-methoxy group which is uncommon in indolediketopiperazines. The enantiomers, (+)-2/(-)-2, showed different antimicrobial activities against several plant-pathogenic fungi, while (+)-1 displayed better inhibitory activity against acetylcholinesterase than that of (-)-1.

Anti-Acetylcholinesterase Activities of Mono-Herbal Extracts and Exhibited Synergistic Effects of the Phytoconstituents: A Biochemical and Computational Study.

Alzheimer's disease (AD), a neurodegenerative disease, is the most common form of dementia. Inhibition of acetylcholinesterase (AChE) is a common strategy for the treatment of AD. In this study, aqueous, hydro-methanolic, and methanolic extracts of five potent herbal extracts were tested for their in vitro anti-AChE activity. Among all, the Tinospora cordifolia (Giloy) methanolic fraction performed better with an IC50 of 202.64 µg/mL. Of the HPLC analyzed components of T. cordifolia (methanolic extract), palmatine and berberine performed better (IC50 0.66 and 0.94 µg/mL, respectively) as compared to gallic acid and the tool compound "galantamine hydrobromide" (IC50 7.89 and 1.45 µg/mL, respectively). Mode of inhibition of palmatine and berberine was non-competitive, while the mode was competitive for the tool compound. Combinations of individual alkaloids palmatine and berberine resulted in a synergistic effect for AChE inhibition. Therefore, the AChE inhibition by the methanolic extract of T. cordifolia was probably due to the synergism of the isoquinoline alkaloids. Upon molecular docking, it was observed that palmatine and berberine preferred the peripheral anionic site (PAS) of AChE, with π-interactions to PAS residue Trp286, indicating that it may hinder the substrate binding by partially blocking the entrance of the gorge of the active site or the product release.

Polyphenolic Profiling, Quantitative Assessment and Biological Activities of Tunisian Native Mentha rotundifolia (L.) Huds.

Phenolic profiling of ten plant samples of Mentha rotundifolia (L.) Huds. collected from different bioclimatic areas of Tunisia, was for the first time carried out by using a fast ultra-high-performance liquid chromatography (UHPLC)-high resolution tandem mass spectrometry (HRMS/MS) method on a Q Exactive platform equipped with an electrospray ionization (ESI) source. An intraspecific, interpopulation variability was evidenced and a total of 17 polyphenolic metabolites were identified and quantified by using the UHPLC-HRESIMS/MS method, here validated for specificity, linearity, limit of detection, limit of quantitation, accuracy and precision. The quantitative method resulted sensitive at the nM level and reliable for rapid polyphenol quantification in vegetal matrices. The metabolomic study allowed us to identify a new compound, named salvianolic acid W, which was isolated and characterized mainly by NMR and MS analysis. A statistical correlation of the phenolic composition with antioxidant and anti-acetylcholinesterase activities was provided.

A novel skeleton alkaloid from Portulaca oleracea L. and its bioactivities.

A novel skeleton alkaloid was obtained from Portulaca oleracea L., which was identified as 10,11-dihydroxybenzo[5',6'] pentaleno[1',2':3,4]pyrrolo[2,1-b]oxazol-7(11bH)-one, named oleracone M, and its structure was determined using UHPLC-ESI-QTOF/MS, 1D NMR and 2D NMR spectroscopy, and circular dichroism. Then the bioactivities of the compound were investigated including the anti-inflammatory, anti-acetylcholinesterase and antioxidant activities. The results showed that the novel skeleton alkaloid exhibited the potent effect on inhibiting the secretion of IL-1ß at 10 µM, anticholinesterase activity with IC50 value of 49.58 µM, and antioxidant activity with IC50 value of 66.43 µM.

Synthesis, structural characterization and in vitro pharmacological properties of betanin-encapsulated chitosan nanoparticles.

Betanin, a natural food color and the only betalain, is approved for use in pharmaceutical and food industries as natural antioxidative and preservative agent, respectively. However, the antioxidant power and health-promoting properties of betanin have been disregarded due to its low stability in physiological conditions. Therefore, this study is designed to synthesize and evaluate in vitro pharmacological characteristics of betanin-encapsulated chitosan nanoparticles (ChBetNPs). ChBetNPs were synthesized by ionic gelation method and characterized by DLS, UV, FTIR, SEM and zeta potential analysis. The encapsulation efficiency (EE) and in vitro release kinetics were analyzed using spectrophotometric technique for quantifying the encapsulated amount of betanin in ChBetNPs as a function of time. The antioxidant activity of ChBetNPs was analyzed by DPPH and H2O2 radical scavenging assays, anti-inflammatory activity by protein denaturation and human RBCs stabilization assays, and anti-acetylcholinesterase activity using standard protocol with minor modifications. Unloaded chitosan nanoparticles (CSNPs) were found to be sized at 161.4 ± 5.75 nm while an increase in the size to 270.3 ± 8.50 nm was noticed upon encapsulating betanin. EE of ChBetNPs was measured to be ∼87.5%. The IC50 of ChBetNPs depicted significant free radical scavenging activities as compared to CSNPs. Similarly, a strong anti-inflammatory activity of ChBetNPs was noted. Significant decrease in acetylcholinesterase activity by ChBetNPs was measured (IC50 0.5255 µg/mL vs. control 26.09 µg/mL). The vegetables coated with 3% ChBetNPs showed decreased weight loss as compared to uncoated control. ChBetNPs was shown to exhibit strong antioxidant, anti-inflammatory and anti-acetylcholinesterase activities thus making it a significant therapeutic agent for the management of Alzheimer's disease.

Plants of the Genus Mahonia as a Potential Traditional Chinese Medicine for the Prevention and Treatment of Alzheimer's Disease.

Alzheimer's disease (AD), a prevalent multiple neurodegenerative disease, has gained attention, particularly in the aging population. However, presently available therapies merely focus on alleviating the symptoms of AD and fail to slow disease progression significantly. Traditional Chinese medicine (TCM) has been used to ameliorate symptoms or interfere with the pathogenesis of aging-associated diseases for many years based on disease-modifying in multiple pathological roles with multi-targets, multi-systems and multi-aspects. Mahonia species as a TCM present potential for anti-inflammatory activity, antioxidant activity, anti-acetylcholinesterase activity, and antiamyloid- beta activity that was briefly discussed in this review. They are regarded as promising drug candidates for AD therapy. The findings in this review support the use of Mahonia species as an alternative therapy source for treating AD.

Comparison of Various Solvent Extracts and Major Bioactive Components from Unsalt-Fried and Salt-Fried Rhizomes of Anemarrhena asphodeloides for Antioxidant, Anti-α-Glucosidase, and Anti-Acetylcholinesterase Activities.

The rhizome of Anemarrhena asphodeloides Bunge (AA, family Liliaceae) is a famous and frequently used herbal drug in the traditional medicine of Northeast Asia, under vernacular name "zhimu". A. asphodeloides has been used as an anti-inflammatory, antipyretic, anti-platelet aggregation, anti-depressant, and anti-diabetic agent in traditional Chinese medicine. We examined the antioxidant, anti-acetylcholinesterase (AChE), and anti-α-glucosidase activities of various solvent extracts and the main bioactive compounds from the rhizome of A. asphodeloides. Acetone extract exhibited comparatively high antioxidant activities by 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging, and ferric-reducing antioxidant power (FRAP) assays. A water extract exhibited relatively strong antioxidant activity by superoxide radical scavenging test. Furthermore, dichloromethane, chloroform, and n-hexane extracts showed significant anti-α-glucosidase activities. Finally, ethanol and dichloromethane extracts exhibited relatively strong AChE inhibitory activity. HPLC analysis was used to examine and compare various solvent extracts for their compositions of isolates. We isolated four major chemical constituents and analyzed their antioxidant, anti-α-glucosidase, and AChE inhibitory activities. The bioactivity assays showed that mangiferin displayed the most potential antioxidant activities via FRAP, ABTS, DPPH, and superoxide assays and also exhibited the most effective anti-AChE and anti-α-glucosidase activities among all the isolates. The present study suggests that A. asphodeloides and its active extracts and components are worth further investigation and might be expected to develop as a candidate for the treatment or prevention of oxidative stress-related diseases, AChE inhibition, and hyperglycemia.

Chemical composition, antibiofilm, cytotoxic, and anti-acetylcholinesterase activities of Myrtus communis L. leaves essential oil.

BACKGROUND: The potential of essential oils (EOs) and of their principal constituents for eradication of biofilm and at the same time the research of new potential acetylcholinesterase inhibitors is gaining increasing interest in last years. The aims of this study were to determine the chemical composition and to evaluate the antibacterial, cytotoxic, and anti-acetylcholinesterase properties of Myrtus communis leaves essential oil and its main constituents. METHODS: Essential oil was obtained by hydrodistillation of M. communis L. leaves and was analyzed by GC and GC-MS. The antimicrobial activity was carried out against both gram-negative and gram-positive bacteria. The microdilution method was used to estimate the minimum inhibitory concentrations (MICs). Then, the capacity of essential oil and its main constituent to inhibit biofilm growth, with the method of O'Toole and Kolterand, and the metabolic activity of biofilm cells through the MTT colorimetric method were evaluated at different times. Moreover, was studied the potential cytotoxic activity against SH-SY5Y cell line with MTT assay and the anti-acetylcholinesterase activity using Ellman's assay. RESULTS: Myrtenyl-acetate, 1,8 cineole, α-pinene, and linalool were the main components in the EO. The myrtle EO, at the minimum tested dose (0.4 mg/ml), inhibited S. aureus biofilm by 42.1% and was capable of inhibiting the biofilm cell metabolism in all tested strains, except Staphylococcus aureus. Moreover, the EO showed good cytotoxic and anti-acetylcholinesterase activities IC50 of 209.1 and 32.8 µg/ml, respectively. CONCLUSIONS: The results suggest that myrtle EO and its main constituents could be used as possible products that could act against the resistant pathogenic species E. coli, P. aeruginosa, L. monocytogenes and S. aureus, on the other hand, as possible coadjutants in the treatment of neurological diseases.

A new pyrrole alkaloid from the roots of Cissampelos pareira.

Phytochemical investigation of the roots of Cissampelos pareira Linn. led to the isolation of one new pyrrole alkaloid, cissampeline (1), together with ten known alkaloids, (-)-curine (2), (-)-cyclanoline (3), (+)-tetrandrine (4), (+)-obaberine (5), (+)-obamegine (6), (-)-oblongine (7), (+)-homoaromoline (8), (-)-nor-N׳-chondrocurine (9), trans-N-feruloyltyramine (10) and (+)-coclaurine (11). Their structures were elucidated by extensive NMR and MS spectroscopic analyses. Interestingly, compound 1 represents the first example of pyrrole alkaloid found in the genus Cissampelos. Moreover, compounds 5-11 were isolated for the first time from this genus. Among them, compound 6 showed the highest anti-acetylcholinesterase activity with an IC50 value of 3.26 µM, whereas compound 8 displayed the most potent cytotoxicity against human colon cancer (HT29) cells with an IC50 value of 7.89 µM.

Differentiation of Phenolic Composition Among Tunisian Thymus algeriensis Boiss. et Reut. (Lamiaceae) Populations: Correlation to Bioactive Activities.

: Twelve Tunisian Thymus algeriensis populations growing wild in different bioclimatic zones, extending from the subhumid to the upper-arid bioclimates, were compared regarding their phenolic composition and their ability to serve as antioxidant, anti-acetylcholinesterase, and antibacterial agents. A significant variation of phenol profile was observed between the analyzed populations, as assessed by ultra-high-performance liquid chromatography coupled with a diode array detector and an electrospray mass spectrometer (UHPLC-DAD-ESI/MSn) technique. Rosmarinic acid was the main phenolic compound in most populations (383.8-1157.8 µg/mL extract), but still, those from the upper-arid bioclimatic zone were distinguished by the presence of carvacrol (1374.7 and 2221.6 µg/mL extract), which was absent in the remaining ones. T. algeriensis methanolic extracts were found to possess a substantial antioxidant and anti-acetylcholinesterase activities, with significant variation observed between populations, which were correlated to their phenolic contents. The antibacterial activity of the extracts tested against seven bacteria was revealed only by populations collected from upper-arid bioclimate and mainly associated with the presence of carvacrol. Extracts revealed a bacteriostatic effect against all bacteria (MIC = 1.4 mg/mL). Yet, the bactericidal activity (MBC = 1.4mg/mL) was restricted to the gram-negative bacteria Escherchia coli.

Phytochemical composition and in vitro functional properties of three wild rose hips and their traditional preserves.

The aim of the present study was investigation of the phenolic profile, ascorbic acid content, antioxidant, anti-acetylcholinesterase, anti-inflammatory and cytotoxic activity of rose hips and the preserves (purée and jam) of three insufficiently examined Rosa species: Rosa dumalis Bechst., R. dumetorum Thuill. and R. sempervirens L. The liquid chromatography-tandem mass spectrometry analysis resulted in quantification of 14 of the 45 phenolic compounds examined, with ellagic acid as the most dominant. Notable antioxidant activity of all three species was confirmed through several assays. Moderate inhibition of acetylcholinesterase by extracts of all investigated Rosa species was observed. Several extracts of examined Rosa species demonstrated inhibition potency towards production of some monitored eicosanoids in cyclooxygenase-1 and 12-lipoxygenase pathways. Two R. sempervirens extracts exerted cytotoxic activity against HeLa and HT-29 cell lines, but were inactive towards MRC-5 and MCF7. The results support the potential of these rose hips as food with health-promoting properties.

Antioxidant and anti-acetylcholinesterase activities of extracts and secondary metabolites from Acacia cyanophylla.

OBJECTIVE: To investigate the antioxidant potential and anti-acetycholinesterase activity of compounds and extracts from Acacia cyanophylla (A. cyanophylla). METHODS: Three polyphenolic compounds were isolated from ethyl acetate extract of A. cyanophylla flowers. They have been identified as isosalipurposide 1, quercetin 2 and naringenin 3. Their structures were elucidated by extensive spectroscopic methods including 1D and 2D NMR experiments as well as ES-MS. The prepared extracts and the isolated compounds 1-3 were tested for their antioxidant activity using 1'-1'-diphenylpicrylhydrazyl (DPPH) and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) scavenging assays and reducing power. They have been also investigated for inhibitory effect against acetylcholinesterase using the microplate assay. RESULTS: In the DPPH test, the EtOAc extract of flowers exhibited the highest antioxidant effect (67.26 µg/mL). Isosalipurposide 1 showed a significant antiradical power against DPPH (81.9 µg/mL). All extracts showed a dose-dependent acetylcholinesterase inhibition. In terms of the IC50 value, the butanolic extract (16.03 µg/mL) was the most potent sample. Isosalipurposide 1 was found to be active against AChE with an IC50 value of 52.04 µg/mL. CONCLUSIONS: The results demonstrated the important antioxidant and anti-acetylcholinesterase activity of pure compounds and extracts from A. cyanophylla.

Chemical Compositionand Anti-acetyl cholinesterase Activity of Flower Essential Oils of Artemisiaannuaat Different Flowering Stage.

The chemical composition of the essential oils of flower at the pre-flowering, full-flowering and post-flowering stage of A. annua was analyzed by GC and GC/MS and sixty-two components were identified. The main compounds in the pre-flowering oil were ß-myrcene (37.71%), 1, 8-cineole (16.11%) and camphor (14.97%). The full-flowering oil contained predominantly caryophyllene (19.4%), germacrene D (18.1%), camphor (15.84%), 1, 8-cineole (10.6%) and (Z)-ß-farnesene (9.43%). The major constituents identified in the post-flowering oil were camphor (16.62%), caryophyllene (16.27%), ß-caryophyllene oxide (15.84%), ß-farnesene (9.05%) and (-)-spathulenol (7.21%). The variety of anti-AChE activity of flower oil of A. annua at three flowering stage might be a result of the variety of the content and interaction of those terpenoids with anti-AChE activity. The greatest acetylcholinesterase inhibitory activity (IC50 = 0.13 ± 0.02 mg mL(-1)) was exhibited by the essential oil of flower of A. annua at post-flowering stage.