bluuebunny/crossref_metadata_2025 huggingface dataset:
Ovarian Cancer HO-8910 Cell Apoptosis Induced by Crocin in vitro
Authors: Xia Dan
Published: March 2019

The effect and mechanism of ovarian cancer HO-8910 cell apoptosis induced by crocin. MTT assay was performed to detect the inhibitory action of crocin on the proliferation of HO-8910 cells. Flow cytometry was used to test the cell cycle distribution and apoptosis rate of ovarian cancer HO-8910 cells. Western blot analysis was utilized to measure the levels of apoptotic proteins such as p53, Fas/APO-1, and Caspase-3. MTT analysis revealed that crocin significantly inhibited the growth of HO-8910 cells. Additionally, flow cytometry illustrated that crocin raised the proportion of HO-8910 cells in the G0/G1 phase and increased their apoptosis rate. Furthermore, Western blot analysis revealed that crocin up-regulated the expression of p53, Fas/APO-1, and Caspase-3. The results of this study showed that crocin can significantly inhibit the growth of HO-8910 cells and arrest them in the G0/G1 phase. Crocin can also promote ovarian cancer HO-8910 cell apoptosis, most likely by increasing p53 and Fas/APO-1 expression, and then activating the apoptotic pathway regulated by Caspase-3.
Cs2CO3-Catalyzed Synthesis of N-Sulfonyl-Substituted Allenamides
Authors: Zheqi Li
Published: March 2019

Several novel N-sulfonyl substituted allenamides were obtained in good yields via Cs2CO3-catalyzed isomerization of propargyl amides in THF at room temperature. The easily available starting materials and mild reaction conditions are features of this protocol.
Theoretical Studies on the Mechanism of the Azido-Tetrazole of Azido-s-triazine
Authors: Liang Xiao-Qin , Zhou Jin-Jun , Zheng Yan , Ma Feng
Published: March 2019

The B3LYP/aug-cc-pvDZ level of theory has been applied to the study of the molecular structures, electronic structures and the azido-tetrazole isomerization of 1-azido-s-triazine, 1,3-diazido-s-triazine and 1,3,5-triazido-s-triazine. NBO analysis was applied to investigate the atomic natural charge and stabilization interaction energies among molecules. The results showed that the reaction initially proceeds through the loss of the linearity of the azido group and the approaching of the terminal nitrogen atom of the azide group to the nitrogen atom of the ring. This is followed by an attack of the lone pairs on N atoms in the ring to the azido group, leading to the formation of the N-N bonds. Many factors, including bending of the bond angle, electrostatic attraction, orbital delocalization and the stabilization interaction give rise to a large free energy barrier for the cyclization process. The results also show that the second and third cyclization is relatively easier than the first one.
Hypotensive and Bradycardic Effects of Quinovic Acid Glycosides from Aspidosperma fendleri in Spontaneously Hypertensive Rats
Authors: Estrada Omar , González-Guzmán Juan M. , Salazar-Bookman María M. , Cardozo Alfonso , Lucena Eva , Alvarado-Castillo Claudia P.
Published: March 2019

The Aspidosperma genus (Apocynaceae) represents one of the largest sources of indole alkaloids widely associated with cardiovascular effects. Aspidosperma fendleri, a plant found mainly in Venezuela, has a single phytochemical report in which is revealed the presence of alkaloids in its seeds. This study explored the cardiovascular effects of an ethanolic extract of A. fendleri leaves (EEAF) in spontaneously hypertensive rats (SHR) and its potential bioactive compounds. Using bioguided fractionation, fractions and pure compounds were intravenously administered to SHR and their effects on mean arterial blood pressure (MABP) and heart rate (HR) monitored over time. EEAF induced hypotensive and bradycardic effects as shown by significant reductions in mean arterial blood pressure (MABP) and heart rate (HR), respectively. Bioactivity-guided fractionation led to the isolation of a mixture of two known isomeric triterpenoid glycosides identified by spectral evidence as quinovic acid 3- O-β-rhamnopyranoside and quinovic acid 3- O-β-fucopyranoside. This mixture of triterpenoid saponins induced reductions in MABP and HR similar to those induced by propranolol. Together, these findings indicate that the two quinovic acid glycosides are responsible for the hypotensive and bradycardic effects which suggest their potential use in cardiovascular therapy.
Chemical Composition and in vitro Cytotoxic and Antileishmanial Activities of Extract and Essential Oil from Leaves of Piper cernuum
Authors: Capello Tabata M. , Martins Euder G. A. , de Farias Camyla F. , Figueiredo Carlos R. , Matsuo Alisson L. , Passero Luiz Felipe D. , Oliveira-Silva Diogo , Sartorelli Patricia , Lago João Henrique G.
Published: March 2019

Fractionation of the MeOH extract from leaves of Piper cernuum Vell. (Piperaceae) afforded six phenylpropanoid derivatives: 3′,4′-dimethoxy-dihydrocinnamic acid (1), piplaroxide (2), methyl 4′-hydroxy-3′,5′-dimethoxy cinnamate (3), 3′,4′,5′-trimethoxydihydrocinnamic acid (3), dihydropiplartine (5), and piplartine (6). The structures of isolated metabolites were characterized by NMR and MS spectral data analysis. The chemical composition of essential oil from the leaves was determined using GC/LREIMS followed by the determination of Kovats indexes. This procedure allowed the identification of nineteen terpenoids, with β-elemene (7), bicyclogermacrene (8), germacrene D (9), and (E)-caryophyllene (10) as the main compounds. Compounds 1 and 3-6 displayed no in vitro cytotoxicity against cancer cell lineages B16F10-Nex2, U87, HeLa, HL-60, HCT, and A2058 while 2 showed moderate activity against B16F10-Nex2 and HL-60 lines. Otherwise, compounds 7-10 displayed high cytotoxic activity. Evaluation against non-tumorigenic HFF cells indicated a reduced selectivity of compounds 7-10 to tumoral cells. No antileishmanial activity on macrophages infected with L. (L.) amazonensis was found for the crude MeOH extract and compounds 1-6. The crude essential oil and compounds 7-10 reduced parasitism and eliminated the majority of infected and non-infected cells at 50μg/mL.
Phosphodiesterase Inhibitory Activity of the Flavonoids and Xanthones from Anaxagorea luzonensis
Authors: Sabphon Chalisa , Temkitthawon Prapapan , Ingkaninan Kornkanok , Sawasdee Pattara
Published: March 2019

Five flavonoids, one isoflavone and five xanthones were isolated from Anaxagorea luzonensis. Of these eleven isolated compounds, 1,3,5-trihydroxy-4-prenylxanthone (3) was a relatively potent inhibitor of phosphodiesterase type 5 (PDE5), with an IC50 value of 3.0 μM. This is the first report showing that natural xanthones can exhibit promising PDE5 inhibitory activity. Moreover, this study revealed that the presence of the C-4 prenyl residue attached to the xanthone core is correlated with the significant PDE5 inhibitory activity.
Xanthone Derivatives from the Fermentation Products of an Endophytic Fungus Phomopsis sp
Authors: Meng Yanlin , Yang Yuchun , Qin Ying , Xia Congfang , Zhou Min , Gao Xuemei , Du Gang , Hu Qiufen
Published: March 2019

Three new xanthones, 1-hydroxy-3-hydroxyethyl-5-methoxy-6-methoxycarbonylxanthone (1), 1,4-dihydroxy-3-hydroxyethyl-5-methoxy-6-methoxycarbonyl-xanthone (2), and 1-hydroxy-3-hydroxyethyl-4-methoxy-8-methoxycarbonylxanthone (3), together with five known xanthones (4–8) were isolated from the fermentation products of an endophytic fungus Phomopsis sp.. Their structures were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR spectroscopic techniques. Compounds 1–3 and 7 were also tested for their cytotoxicity against five human tumor cell lines (NB4, A549, SHSY5Y, PC3, and MCF7) by the MTT method, with paclitaxel used as the positive control. Compound 1 showed cytotoxicity against A549 and PC3 cells with IC50 values of 3.2 and 2.5 μM, respectively, 2 showed potential, with an IC50 value of 3.6 μM, and 3 showed cytotoxicity against A549 cells with an IC50 value of 3.5 μM.
Anti-inflammatory Anthraquinones from the Crinoid Himerometra magnipinna
Authors: Lin Yen-You , Tsai Su-June , Chiang Michael Y. , Wen Zhi-Hong , Su Jui-Hsin
Published: March 2019

Chemical investigation of a crinoid Himerometra magnipinna has afforded three anthraquinones (1–3), including one new metabolite, (+)-rhodoptilometrin (1). The structures of these compounds were elucidated on the basis of their spectroscopic data and the absolute configuration of 1 was further confirmed by single-crystal X-ray diffraction analysis. In the in vitro anti-inflammatory effects test, compound 2 was found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein of the LPS-stimulated RAW264.7 macrophage cells.
Arylalkanones from Horsfieldia macrobotrys are Effective Antidiabetic Agents Achieved by α-Glucosidase Inhibition and Radical Scavenging
Authors: Ramadhan Rico , Phuwapraisirisan Preecha
Published: March 2019

Horsfielda macrobotrys Merr has long been used by Dayak people in East Kalimantan of Indonesia, for diabetes therapy. Inspired by ethnopharmacological use and promising α-glucosidase and radical scavenging activities, an attempt to identify the active components was carried out. Bioassay-guided isolation yielded two related arylalkanones named 1-(2,4,6-trihydroxyphenyl)-9-phenylnonan-1-one (1) and malabaricone A (2). Arylalkanone 1 showed potent radical scavenging comparable with that of the standard antioxidant, ascorbic acid, and promising inhibition against α-glucosidases. Noticeably, arylalkanone 1 was 3-30 times more potent than malabaricone A (2) in all bioassays examined, thus suggesting the critical role in exerting bioactivities of the hydroxy group on the aryl moiety. This hypothesis was also supported by reduction in inhibitory effects of the methyl ether analogues 1a and 2a. Arylalkanone 1 inhibited yeast α-glucosidase in a mixed-type manner in which the noncompetitive pathway was dominant over competitive inhibition. This study is the first report of α-glucosidase inhibition of arylalkenone-type compounds and the first phytochemicals from H. macrobotrys.
Metabolomic Characterization of a Low Phytic Acid and High Anti-oxidative Cultivar of Turmeric
Authors: Tanaka Ken , Arita Masanori , Li Donghan , Ono Naoaki , Tezuka Yasuhiro , Kanaya Shigehiko
Published: March 2019

Turmeric, the rhizome of Curcuma longa, has a long history of use as a spice and also as a traditional medicine in many Asian countries. To reveal unique morphological features of a newly registered Curcuma cultivar, C longa cv. Okinawa Ougon (Ougon), non-targeted LC-MS and GC-MS analyses were conducted. The analysis revealed its distinctive chemical properties: lower amount of phytic acid and inorganic metals such as Fe, Mn, and Al, as well as higher concentrations of reduced derivatives of curcuminoids, such as dihydrobisdemethoxycurcumin, tetrahydrobisdemethoxycurcumin, dihydrodemethoxycurcumin, and tetrahydrodemethoxycurcumin. In addition, germacrane-type sesquiterpenes were almost absent although α-humulene and β-caryophyllene, generated by the same biosynthetic route, were present. Presumably the alternation of the metal ion content, serving as a cofactor of sesquiterpene synthase, modulates the resulting variation of the sesquiterpenes. In summary, the cultivar Ougon is considered a promising candidate for functional food additives.
The Cardioprotective Effects of Resveratrol in Rats with Simultaneous Type 2 Diabetes and Renal Hypertension
Authors: Mozafari Masoud , Nekooeian Ali Akbar , Mashghoolozekr Elaheh , Panjeshahin Mohammad Reza
Published: March 2019

This study aimed at examining the cardioprotective effects of resveratrol in rats with simultaneous type 2 diabetes and renal hypertension. Eight groups (8-10 each) of male Sprague-Dawley rats, including a control, a diabetic, a renal hypertensive, a sham, a simultaneously hypertensive–diabetic receiving vehicle, and 3 simultaneously hypertensive-diabetic receiving resveratrol at 5, 10 or 20 mg/kg/day were used. After 4 weeks of treatment, blood pressure and glucose, and serum markers of oxidative stress were measured, and animals’ hearts were used for isolated studies. Resveratrol prevented the increase of systolic blood pressure, serum malondialdehyde, fasting blood glucose, infarct size, coronary resistance, and coronary effluent creatine kinase-MB. Moreover, it prevented the decrease of serum superoxide dismutase and glutathione reductase, heart rate, left ventricular developed pressure, rate of increase of ventricular pressure, and rate of decrease of ventricular pressure. In conclusion, our findings show that resveratrol alleviates cardiac dysfunction in diabetic-hypertensive rats by virtue of antioxidant, antihypertensive, and coronary vasodilating activities.
A Specific Process to Purify 2-Methyl-D-Erythritol-4-Phosphate Enzymatically Converted from D-Glyceraldehyde-3-Phosphate and Pyruvate
Authors: Yang Shao-Qing , Deng Jian , Wu Qian-Qian , Li Heng , Gao Wen-Yun
Published: March 2019

A one-pot enzymatic cascade was established to synthesize MEP, one of the key intermediates in the MEP terpenoid biosynthetic pathway. D-GAP and sodium pyruvate were converted to MEP in a reaction catalyzed by DXP synthase and DXP reductoisomerase (DXR) in the presence of the coenzymes ThPP, NADPH, and Mg2+. The product was then isolated by using a specific two-step purification process and MEP was obtained in a yield of nearly 60% and high purity. Importantly, MEP prepared by this way was totally free from contamination by minor amounts of DXP that was not completely convertible by DXR.
Anti-inflammatory and Cytotoxic Compounds from Solanum macaonense
Authors: Lee Chia-Lin , Hwang Tsong-Long , Peng Chieh-Yu , Chen Chao-Jung , Kuo Chao-Lin , Chang Wen-Yi , Wu Yang-Chang
Published: March 2019

One new cerebroside, macaocerebroside A (1), and 15 known compounds (2–16) were isolated from Solanum macaonense for the first time. In an antineutrophilic inflammatory assay, four caffeic acid derivatives (2–5) were active against superoxide anion generation with IC50 values of 3.3–4.8 μM; especially, 3 inhibited elastase release with an IC50 value of 4.0 μM. Additionally, kaempferol (8) also showed inhibition against elastase release with an IC50 value of 4.0 μM. In a cytotoxic assay, rutin (14) had selective moderate cytotoxicity toward human lung (A549), bladder (NTUB1), and prostate (DU145) cancer cell lines with IC50 values of 34.6, 41.3, and 31.8 μM, respectively.
Using the Gene Expression Signature of Scutebarbalactone VN Isolated from Scutellaria barbata to Elucidate its Anticancer Activities
Authors: Thao Do Thi , Huang Chi-Ying , Lin Kuan-Ting , Phuong Do Thi , Nga Nguyen Thi , Trang Nguyen Thi , Cuc Nguyen Thi , Cuong Nguyen Xuan , Nam Nguyen Hoai , Van Minh Chau
Published: March 2019

Bioassay-guided fractionation led to the discovery of a novel neo-clerodane diterpenoid, scutebarbalactone VN (BalA: 8,13-epoxy-3-en-7-hydroxy-6,11- O-dibenzoyl-15,16-clerodanolide), from the methanol extract of the whole-plant of Vietnamese Scutellaria barbata D. Don. A microarray technique combined with bioinformatic analyses showed that BalA could inhibit cell cycle pathways by downregulating genes such as CDC25A and AURKA. BalA also showed the potential to reactivate downregulated genes in hepatocellular carcinoma cells and genes in antioxidant pathways such as HMOX1 and HSPA1A. Querying Connectivity map 2.0 resulted in a match of the BalA-modulated gene signature with that of 10 known compounds, most of which are currently marketed chemotherapy drugs. The highest matching scores belonged to lomustine, semustine, and withaferin A. Lomustine and semustine were found to alkylate DNA and RNA, while withaferin A inhibits nuclear factor kappa B (NF-κB) activity. A luciferase reporter assay was also conducted on 293/NF-κB human embryonic kidney cells that had been transfected with the NF-κB-luciferase plasmid to verify the anticancer activity of BalA. The assay showed that Ba1A effectively blocked NF-κB with an IC50 of 38.6 ± 0.05 μM.
Volatile Constituents of the Fruit and Roots of Cymbopogon olivieri
Authors: Asgarpanah Jinous , Bahrani Setareh , Bina Elham
Published: March 2019

The essential oil contents of the fruit and roots of Cymbopogon olivieri growing wild in south of Iran were found to be 0.7 % and 0.4% (v/w), respectively based on the fresh weight. The oils were analyzed by GC and GC–MS. Forty and twenty six constituents, representing 93.1 % and 93.4% of the oils were identified, respectively. The major components of the C. olivieri fruit oil were identified as piperitone (44.1%), α-terpinene (13.7%), neral (6.3%), elemol (5.6%) and β-eudesmol (5.3%). while the main components of that of roots were characterized as piperitone (20.6%), α-muurolol (9.5%), β-eudesmol (8.5%), selina-6-en-4-ol (7.9%), 5-epi-7-epi-α-eudesmol (6.8%) and elemol (5.8%).
Composition of Essential Oils Isolated from the Needles of Pinus uncinata and P. uliginosa Grown in Poland
Authors: Bonikowski Radosław , Celiński Konrad , Wojnicka-Półtorak Aleksandra , Maliński Tomasz
Published: March 2019

The compositions of mountain pine (Pinus uncinata) and peat-bog pine (P. uliginosa) needle essential oils were investigated. Enantiomeric compositions of selected monoterpene hydrocarbons were also examined. Respectively, fifty-three and seventy-six components of the essential oils were identified using GC-MS and retention indexes. The main group of essential oil components of mountain pine needles were monoterpenes, and bornyl acetate constituted approximately 30% (46.3g/100g) of the oil. In peat-bog pine essential oil, monoterpenes and sesquiterpenes exhibited a similar content (ca. 40%). Bornyl acetate and a-pinene were the main constituents of both essential oils. In the essential oil of P. uncinata needles, limonene, camphene, myrcene and ( E)-β-caryophyllene were also noticeable, while in the essential oil of P. uliginosa needles, Δ-car-3-ene, ( E)-β-caryophyllene, germacrene D, δ-cadinene, germacrene D 4-ol and α-cadinol were present in notable quantities. In both essential oils, borneol propionate, isobutyrate, 2-methylbutyrate and isovalerate were detected. Their presence was confirmed by synthesis and analysis of the standards; retention indexes on a non-polar column are published herein.
Extraction of Pinocembrin from Leaves of Different Species of Eucalyptus and its Quantitative Analysis by qNMR and HPTLC
Authors: Saraf Isha , Choudhary Alka , Sharma Ram Jee , Dandi Karthik , Marsh Karen J. , Foley William J. , Singh Inder Pal
Published: March 2019

Pinocembrin, a flavanone with a variety of biological activities was isolated from Eucalyptus sieberi leaves and quantified in several other Eucalyptus species using qNMR and HPTLC densitometry. The effect of different extraction procedures on the extraction of the compound from Eucalyptus sieberi was also studied. The methods were validated in terms of selectivity, specificity, linearity, recovery, precision and repeatability.
Convergent Synthesis of Moslosooflavone, Isowogonin and Norwogonin from Chrysin
Authors: Jing Lin-Lin , Fan Xiao-Fei , Jia Zheng-Ping , Fan Peng-Cheng , Ma Hui-Ping
Published: March 2019

A convergent synthesis route of moslooflavone, isowogonin and norwogoninis reported, starting from chrysin, an easily available flavone, by methylation, bromination, methoxylation and demethylation procedures. This synthetic route is convenient and can give the three rare flavones in good yield.
Tangeretin Triggers Melanogenesis through the Activation of Melanogenic Signaling Proteins and Sustained Extracellular Signal-Regulated Kinase in B16/F10 Murine Melanoma Cells
Authors: Yoon Hoon Seok , Ko Hee-Chul , Kim Sang Suk , Park Kyung Jin , An Hyun Joo , Choi Young Hun , Kim Se-Jae , Lee Nam-Ho , Hyun Chang-Gu
Published: March 2019

In order to test the effectiveness of tangeretin at ameliorating melanoma and melanoma-associated depigmentation, western blotting was used to assess the melanin content of treated melanoma cells. Tangeretin, a 4′,5,6,7,8-pentamethoxyflavone, was found to trigger intracellular melanin production in a concentration-dependent manner in B16/F10 murine melanoma cells. Melanin content increased 1.74-fold in response to treatment with 25 μM of tangeretin, compared to that in non-treated cells. Examination of melanogenic protein expression showed that tyrosinase, tyrosinase-related protein (TRP)-1, and extracellular signal-regulated kinase (ERK) 1/2 levels increased in a dose-dependent manner. Furthermore, the expression of cyclic adenosine monophosphate response element binding protein (CREB) and microphthalmia transcription factor (MITF) was increased by tangeretin in 1 h and 4 h, respectively. Tangeretin-upregulated melanogenesis was suppressed by ERK 1/2 inhibitor and not by ERK1 inhibitor. These results suggest that tangeretin has therapeutic potential for melanoma and melanoma-associated depigmentation because it can induce hyperpigmentation through the activation of melanogenic signaling proteins and initiation of sustained ERK2 expression.
Flavonoids from Artocarpus anisophyllus and their Bioactivities
Authors: Lathiff Siti Mariam Abdul , Jemaon Noraini , Abdullah Siti Awanis , Jamil Shajarahtunnur
Published: March 2019

Two new prenylated flavonoids, 4′,5-dihydroxy-6,7-(2,2-dimethylpyrano)-2′-methoxy-8-γ,γ-dimethylallylflavone 1 and 3′-hydroxycycloartocarpin 2 along with six known flavonoids, 5,7-dihydroxy-4′-methoxy-8-prenylflavanone 3, isobavachalcone 4, pyranocycloartobiloxanthone A 5, artocarpin 6, chaplashin 7 and cycloartocarpin 8 were isolated for the first time from the leaves and the heartwoods of Artocarpus anisophyllus Miq. The structures of isolated flavonoids were elucidated spectroscopically using 1D and 2D NMR, FTIR, MS, UV and also by comparison with literature data. These flavonoids were screened for their antioxidant and tyrosinase inhibitory activities. The dichloromethane and ethyl acetate crude extracts together with 3′-hydroxycycloartocarpin 2, pyranocycloartobiloxanthone A 5 and artocarpin 6 showed DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity with SC50 values of 80.2, 40.0, 152.9, 20.2 and 140.0 μg/mL in 30 min, respectively. Pyranocycloartobiloxanthone A 5 exhibited significant tyrosinase inhibitory activity against tyrosinase from mushroom with IC50 values of 60.5 μg/mL.
Quantitative Flavonoid Variation Accompanied by Change of Flower Colors in Edgeworthia chrysantha, Pittosporum tobira and Wisteria floribunda
Authors: Ono Megumi , Iwashina Tsukasa
Published: March 2019

The flavonoids in the flowers of Edgeworthia chrysantha, Pittosporum tobira and Wisteria floribunda were isolated and identified. Quercetin and kaempferol 3- O-glucosides and 3- O-rutinosides were found in E. chrysantha, and quercetin 3- O-rutinoside, 3- O-glucoside and 3- O-pentosylrhamnosylglucoside, kaempferol 3- O-robinobioside, 3- O-rutinoside, 3- O-glucoside and 3- O-pentosylrhamnosylglucoside, and isorhamnetin 3- O-rutinoside were isolated from P. tobira. Ten flavonoids, quercetin 3- O-sophoroside, 3- O-rutinoside, 3- O-glucoside, kaempferol 3- O-sophoroside and 3- O-glucoside, luteolin 5- O-glucoside, 7- O-glucoside and 7- O-hexoside, and apigenin 7- O-glucoside and 4′- O-hexoside were isolated from W. floribunda. The major pigments of E. chrysantha were carotenoids. Their content decreased with the change in flower color to white from yellow via cream, and total flavonoid content also slightly decreased by ca. 0.8 in cream and ca. 0.9 fold in white flowers. In contrast with E. chrysantha, white flowers of P. tobira turn to cream and then yellow in which the major pigments are also carotenoids. In this species, both carotenoid and flavonoid contents are gradually increased from white to yellow flowers. Though the petal color of Wisteria floribunda is mauve, due to anthocyanin pigments, the yellow areas are due to carotenoids; these turn to white in the late flowering stage. However, their flavonoid contents were essentially the same among the yellow, cream and white spots of flags. Thus, it was shown by HPLC analysis of the flower flavonoids of E. chrysantha, P. tobira and W. floribunda, although the visible pigments such as carotenoids and anthocyanins are quantitatively varied, the quantitative variation in UV-absorbing substances, such as flavones and flavonols, differs with plant species.
New Kaempferol 3,7-Diglycosides from Asplenium ruta-muraria and Asplenium altajense
Authors: Iwashina Tsukasa , Kitajima Junichi , Mizuno Takayuki , Smirnov Sergey V. , Damdinsuren Oyunchimeg , Kondo Katsuhiko
Published: March 2019

A flavonoid was isolated from the fronds of Asplenium ruta-muraria and A. altajense (Aspleniaceae) collected in the Altai Mountains and adjacent area. The compound was identified as kaempferol 3- O- β-[(6″′- E-caffeoylglucopyranosyl)-(1→3)-glucopyranoside]-7- O- β-glucopyranoside (1) by UV, 1H and 13C NMR spectroscopy, LC-MS, and acid and alkaline hydrolyses. Another flavonoid (2) was isolated from A. altajense, as a minor compound, together with 1 and identified as deacylated compound 1, i.e. kaempferol 3- O-laminaribioside-7- O-glucoside. They were found in nature for the first time.
New Flavonol Glycosides from the Leaves and Flowers of Primula sieboidii
Authors: Hashimoto Nana , Ohsawa Ryo , Kitajima Junichi , Iwashina Tsukasa
Published: March 2019

Three flavonol glycosides were isolated from the leaves of Primula sieboldii. They were identified as quercetin 3- O-β-[xylopyranosyl-(1→2)- β-glucopyranosyl-(1→6)- β-glucopyranoside] (1), kaempferol 3- O- β-[glucopyranosyl-(1→2)- β-glucopyranosyl-(1→6)- β-glucopyranoside] (2) and kaempferol 3- O- β-[xylopyranosyl-(1→2)- β-glucopyranosyl-(1→6)- β-glucopyranoside] (3). Their chemical structures were determined by UV, 1H and 13C NMR spectroscopy, LC-MS and acid hydrolysis. Compounds 1 and 3 are found in nature for the first time. They were also detected in the flowers, together with two anthocyanins, malvidin 3,5-di- O-glucoside and a minor petunidin dihexoside.
A New Triglycosyl Flavonoid Isolated from Leaf Juice of Kalanchoe gastonis-bonnieri (Crassulaceae)
Authors: Costa Sônia Soares , Corrêa Maria Fernanda Paresqui , Casanova Livia Marques
Published: March 2019

Kalanchoe gastonis-bonnieri R. Hamet & H. Perrier (Crassulaceae) is a succulent species empirically used as a vaginal contraceptive as well as to heal genitourinary infections. A phytochemical study of leaf juice prepared from specimens collected in the flowering season resulted in the isolation of the new flavonoid quercetin 3- O-α-rhamnopyranoside-7- O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranoside, as well as the already known 6- C-β-D-glucopyranosyl-8- C-β-D-glucopyranosylapigenin (vicenin-2). The NMR spectra of this flavonoid at room temperature exhibited broad and duplicated signals, suggesting the existence of rotameric conformers, which was confirmed by coalescence of the signals at 40°C. The structural elucidation was based on 1H and 13C NMR (HMQC and HMBC) analyses and MS data. This is the first report of a C-glycosyl flavonoid (vicenin-2) in the Crassulaceae family. Additionally, this is the first study in which atropoisomerism has been shown for vicenin-2.
Novel C-Xylosylflavones from the Leaves and Flowers of Iris gracilipes
Authors: Mizuno Takayuki , Kamo Tsunashi , Sasaki Nobuhiro , Yada Hiroshi , Murai Yoshinori , Iwashina Tsukasa
Published: March 2019

Two new C-glycosylflavones, apigenin 7,4′-dimethyl ether 6- C- β-[(4″′-acetyl-L-rhamnopyranosyl)-(1→2)-xylopyranoside] (1) and apigenin 7,4′-dimethyl ether 6- C- β-L-rhamnopyranosyl-(1→2)-xylopyranoside (2) were isolated from the leaves of Iris gracilipes (Iridaceae), along with two known flavonoids, swertiajaponin (3) and swertisin (4). C-Xylosylflavones 1 and 2 were elucidated by UV and NMR spectroscopy, mass spectrometry, and acid and alkaline hydrolyses. These novel compounds were also presented in the flowers.
Constituents of the Leaves of Verbascum blattaria
Authors: Youn I-Soo , Han Ah-Reum , Roh Mark S. , Seo Eun-Kyoung
Published: March 2019

Phytochemical investigation of the dried leaves of Verbascum blattaria L. (Scrophulariaceae) led to the isolation and identification of five known compounds, E-harpagoside, laterioside, kaempferol 3- O-β-D-glucopyranoside, bis(2-ethylhexyl)phthalate, and (2 S)-liquiritigenin. The structures of these compounds were determined by physical and spectroscopic data analysis. All compounds were isolated from V. blattaria for the first time.
Anthocyanins and Other Flavonoids as Flower Pigments from Eleven Centaurea Species
Authors: Mishio Tamaki , Takeda Kosaku , Iwashina Tsukasa
Published: March 2019

Anthocyanins and other flavonoids were isolated from the flowers of eleven Centaurea species, C. macrocephala, C. rupestotilis and C. suaveolens, which produce yellow flowers, and C. achtarovii, C. dealbata, C. montana, C. nigra, C. scabiosa, C. simplicicaulis, C. hypoleuca and C. triumfetti, which have cyanic flowers. Four anthocyanins, cyanidin 3,5-di- O-glucoside, cyanidin 3- O-(6″-malonylglucoside)-5- O-glucoside, cyanidin 3- O-(6″-succinylglucoside)-5- O-glucoside and cyanidin glycoside, were detected in the cyanic flowers of seven Centaurea species. Of these anthocyanins, the first two were found as major anthocyanins. In the cyanic species, four other flavonoids, apigenin 7- O-glucuronide-4′- O-glucoside, malonylated apigenin 7,4′-di- O-glucoside, apigenin 7- O-glucuronide and kaempferol glycoside, were also isolated. On the other hand, nine flavonols and four flavones were isolated from the three yellow-flowered species, and identified as quercetagetin, quercetagetin 7- O-glucoside, quercetagetin 3′-methyl ether 7- O-glucoside, patuletin, patuletin 7- O-glucoside, quercetin 7- O-glucoside, kaempferol 3-methyl ether, kaempferol 3-methyl ether 4′- O-glucuronide and isorhamnetin 3- O-galactoside, and apigenin, apigenin 7- O-glucuronide, luteolin 7- O-glucoside and apigenin 6,8-di- C-glucoside (vicenin-2). Of these flavonoids, the former five flavonols are “yellow flavonols”, and it was shown that their flower colors are due to these compounds.
Anthocyanins in the Bracts of Curcuma Species and Relationship of the Species Based on Anthocyanin Composition
Authors: Koshioka Masaji , Umegaki Naoko , Boontiang Kriangsuk , Pornchuti Witayaporn , Thammasiri Kanchit , Yamaguchi Satoshi , Tatsuzawa Fumi , Nakayama Masayoshi , Tateishi Akira , Kubota Satoshi
Published: March 2019

Five anthocyanins, delphinidin 3- O-rutinoside, cyanidin 3- O-rutinoside, petunidin 3- O-rutinoside, malvidin 3- O-glucoside and malvidin 3- O-rutinoside, were identified. Three anthocyanins, delphinidin 3- O-glucoside, cyanidin 3- O-glucoside and pelargonidin 3- O-rutinoside, were putatively identified based on C18 HPLC retention time, absorption spectrum, including λmax, and comparisons with those of corresponding standard anthocyanins, as the compounds responsible for the pink to purple-red pigmentation of the bracts of Curcuma alismatifolia and five related species. Cluster analysis based on four major anthocyanins formed two clusters. One consisted of only one species, C. alismatifolia, and the other consisted of five. Each cluster further formed sub-clusters depending on either species or habitats.
Acylated Cyanidin 3-sophoroside-5-glucoside in Purple-violet Flowers of Moricandia arvensis (Brassicaceae)
Authors: Tatsuzawa Fumi , Kato Kazuhisa , Sato Motoki , Ito Shun , Muraoka Hiroki , Takahata Yoshihito , Ogawa Satoshi
Published: March 2019

A new acylated anthocyanin was isolated as a major pigment, along with a known anthocyanin ( Moricandia arvensis anthocyanin 1: MAA-1), from a strain of Moricandia arvensis (Code No. MOR-ARV-3) with purple-violet flowers, and identified as cyanidin 3- O-[2- O-(2- O-(4- O-(6- O-(4- O-(β-glucopyranosyl)- trans-caffeoyl)-P-glucopyranosyl)- trans-caffeoyl)-β-glucopyranosyl)-6- O-( trans-sinapoyl)-β-glucopyranoside]-5- O-[6- O-(malonyl)-β-glucopyranoside].
Biological Activity of the Methanol and Water Extracts of the Fruits of Anthocyanin-Rich Plants Grown in South-West Poland
Authors: Strugala Paulina , Dudra Anna , Kucharska Alicja Z. , Sokół-Łętowska Anna , Wojnicz Dorota , Cisowska Agnieszka , Walkowski Stefan , Sroka Zbigniew , Gabrielska Janina , Hendrich Andrzej B.
Published: March 2019

In this study we focused on the chemical composition, antioxidant, anti-inflammatory and antibacterial properties of methanol and water extracts of fruits of six species grown in south-west Poland: blackberry, blackcurrant, chokeberry, cherry, gooseberry and raspberry. No general correlation could be drawn between extract chemical properties (i.e. antioxidant and free radical scavenging) and observed biological effects. However, blackcurrant and blackberry extracts (both methanol and water) appeared to be good antioxidants and free radical scavengers, as well as effective inhibitors of E. coli adhesion to the uroepithelial cells. On the other hand, the poorest antioxidants and free radical scavengers, cherry and gooseberry extracts, also poorly affected bacterial growth, swimming ability and adhesion to epithelial cells. Surprisingly, gooseberry extracts, which showed generally weak effects, appeared to be the most effective inhibitor of bacterial biofilm formation. Additionally, most of the studied extracts showed reasonably strong anti-inflammatory properties.
Investigation into the Antioxidant and Antidiabetic Potential of Moringa stenopetala: Identification of the Active Principles
Authors: Habtemariam Solomon
Published: March 2019

The fresh leaves of Moringa stenopetala (family, Moringaceae) are commonly eaten as cabbage while dried leaves are used as nutritional supplement and for treating a variety of disease conditions including diabetes. The present investigation into the therapeutic potential of the leaves and seeds of the plant revealed no inhibitory effect against α-glucosidase enzyme up to the concentration of 200 μg/mL but the leaves extract displayed potent DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging effect (IC50, 59.5 ± 4.1 μg/mL). An activity directed fractionation and isolation procedure resulted in the identification of the major antioxidant compound as rutin and minor active component, neochlorogenic acid. Both the crude extract (0.8–200 μg/mL) and rutin (0.8–200 μM) but not neochlorogenic acid displayed a concentration-dependent protection of human pancreatic β-cells (1.4E7 cells) from oxidant-induced cell death. The identification of these compounds along with their potential role in the nutritional and medicinal significance of the plant is discussed.
Dual Excitatory and Smooth Muscle-relaxing Effect of Sideritis montana Extract on Guinea-pig Ileum
Authors: Tóth Barbara , Bartho Loránd , Vasas Andrea , Sándor Zsolt , Jedlinszki Nikoletta , Pinke Gyula , Hohmann Judit
Published: March 2019

The neuronal and smooth muscle effects of a methanol extract prepared from the air-dried flowering aerial parts of Sideritis montana L. (SME) was tested in vitro on Guinea-pig ileum. The chemical composition of the investigated extract was analysed by HPLC-MS, and chrysoeriol, chlorogenic acid and caffeic acid were detected as main constituents. The isolated organ assay showed that S. montana extract caused an immediate contraction and a more slowly developing inhibitory response in the ileum. The SME-induced contractions were strongly inhibited by the acetylcholine muscarinic receptor antagonist atropine (0.5 μM), but not by either the Na+ channel blocker tetrodotoxin (TTX; 0.5 μM) or the histamine H1 receptor antagonist chloropyramine (0.5 μM). Selective desensitization of capsaicin-sensitive neurons by the sensory neuron stimulant and blocker capsaicin did not influence the contractile effect of SME. As to the spasmolytic effect, SME inhibited the effects of electrical field stimulation, exogenous acetylcholine, and histamine. These smooth muscle-relaxing effects were reversible in 40 min by repeated renewals of the bathing solution.
Analysis of Active Compounds and Antioxidant Activity Assessment of Six Popular Chinese Juhua Teas
Authors: Du Hui , Li Shan-Shan , Wu Qian , Ji Kui-Xian , Wu Jie , Liu Yang , Wang Liang-Sheng
Published: March 2019

Chrysanthemum is an important traditional Chinese medicine and is drunk daily as a herbal tea. Chlorogenic acids and flavonoids are generally considered as the bioactive compounds. In this work, six kinds of Juhua Tea were analyzed and their active compounds and antioxidant activities were compared. In total, 32 phenolic compounds were profiled and identified using HPLC-DAD/ESI-MSn, composed of chlorogenic acids (10), flavones (8), chalcones (8), flavanones (4) and flavonols (2). Chalcones were the main flavonoids in Kunlun Xueju ( Coreopsis tinctoria) extract, while flavones and chlorogenic acids were dominant in the five Chrysanthemum teas. Total chlorogenic acids content (TCA) was highest in Tai Ju ( Chrysanthemum morifolium cv. ‘ Tai Ju’) (8.59 ± 0.87 mg/g DW), and total flavonoids content (TF) was highest in Kunlun Xueju (87.2 ± 7.0 mg/g DW), which were both lowest in Ganye Ju ( Chrysanthemum eticuspe) (TCA 0.86 ± 0.26 mg/g DW, TF 1.43 ± 0.41 mg/g DW). Huangjin Ju ( Anthemis tinctoria) possessed the most flavones (19.7 ± 0.6 mg/g DW). Antioxidant capacity of each drink, assessed by Folin–Ciocalteu, DPPH, ABTS and FRAP assays, consistently showed that Kunlun Xueju extract possessed stronger antioxidant activity than the other five, suggesting that the flavonoids content accounted for the free radical scavenging. The present work provides a method for the characterization and quality control of Juhua Tea. Moreover, it is a guideline for consuming choice, due to the different biological functions resulting from chalcones, chlorogenic acids, and flavones.
Crocetenone, a New Rotenoid with an Unusual trans-fused Ring System from Iris crocea
Authors: Bhat Gulzar A. , Mir Fauzia , Shawl Abdul S. , Ganai Bashir A. , Kamili Azra N. , Masood Akbar , Tantry Mudasir A.
Published: March 2019

Crocetenone, a new rotenoid (1), along with five known compounds apocyanin (2), tectorigenin (3), 5,2′,3′-trihydroxy-7-methoxy flavanone (4), tectoridin (5) and tectoridin glycoside (6), were isolated from the methanolic extract of the root of Iris crocea. The structure of compounds was elucidated on the basis of 1D- and 2D-NMR spectroscopic and MS analysis. Antibacterial and antioxidant activities of compounds 1-6 were evaluated. Crocetenone (1) showed a prominent antibacterial activity.
Wood Colors and their Coloring Matters: A Review
Authors: Yazaki Yoshikazu
Published: March 2019

A number of colored specialty woods, such as ebony, rosewood, mahogany and amboyna, and commercially important woods, such as morus, logwood, Brazilwood, Japanese yellowwood, blackwood, kwila, red beech and myrtle beech, exhibit a wide range of colors from black, violet, dark red, reddish brown, to pale yellow. These colors are not only due to colored pigments contained in extractives from those woods but also to insoluble polymers. Wood and bark from many species of both hardwood and softwood trees contain many types of flavonoid compounds. Research on flavonoids has been conducted mainly from two points of view. The first is chemotaxonomy with flavonoid compounds as taxonomic markers, and the second relates to the utilization of woods for pulp and paper and the use of tannins from bark for wood adhesives. Most chemotaxonomic studies have been conducted on flavonoids in the extracts from softwoods such as Podocarpus, Pinus, Pseudotsuga, Larix, Taxus, Libocedrus, Tsuja, Taxodium, Sequoia, Cedrus, Tsuga, Abies and Picea. Hardwood chemotaxonomic studies include those on Prunus and Eucalyptus species. Studies on flavonoids in pulp and paper production were conducted on Eucalyptus woods in Australia and woods from Douglas fir in the USA and larch in Japan. Flavonoids as tannin resources from black wattle tannin and quebracho tannin have been used commercially as wood adhesives. Flavonoids in the bark from radiata pine and southern pine, from western and eastern hemlock, southern red oak and Quercus dentata are also discussed. In addition, the distribution of flavonoids among tree species is described, as is the first isolation of rare procyanidin glycosides in nature.
Flavonoids in Foods: A Review
Authors: Terahara Norihiko
Published: March 2019

The flavonoids in edible plants and foods are surveyed. The food materials rich in flavonoids, such as grape, tea, and cocoa receive particular attention. Also, the ingestion of flavonoids, the absorption and the bioavailability in vivo are discussed. Flavonoids have antioxidant and other living-body modulating activities. When expressing these functionalities, interactions between flavonoids and proteins are important. The interactions with various enzymes and receptors are described. Moreover, as an example of a processed food containing flavonoids, fermented red vinegar that we have investigated is highlighted. The structural determination, antioxidant activity and the generation mechanism of the new acylated polyphenols in red vinegar are described.
Contribution to Flower Colors of Flavonoids Including Anthocyanins: A Review
Authors: Iwashina Tsukasa
Published: March 2019

Flavonoids are one of the major pigments in higher plants, together with chlorophylls and carotenoids. Though ca. 8,000 kinds of flavonoids have been reported in nature, anthocyanins, chalcones, aurones and some flavonols act as major flower pigments. Flavonoids are present as major components in many flowers. On the other hand, flavones and flavonols, which are colorless or extremely pale yellow, function as copigment substances. Moreover, expression of the flower colors is diversified by inter-molecular and intra-molecular copigmentation, metal chelation, pH change and so on. In this review, I describe the distribution of the flavonoids which act as the pigments, and contribution to flower colors, e.g., yellow, scarlet, red, red-purple, violet, purple, blue and so on, of flavonoids, especially anthocyanins, chalcones, aurones and flavonols.
Synthesis of Chiral Hexasubstituted Cyclohexanediol, a Key Intermediate for the Synthesis of Verticillol, from (+)-Dihydrocarvone; Attempted Cyclization to 12-Membered Carbocycle in Verticillol using RCM Reaction
Authors: Nakashima Katsuyuki , Kondo Yuzuru , Yoshimasu Kosei , Sono Masakazu , Tori Motoo
Published: March 2019

A cyclohexane derivative with three chiral centers, a key intermediate for the synthesis of a diterpene verticillol, was prepared starting from (+)-dihydrocarvone. A further challenge to cyclize to a 12-membered carbocycle was attempted, although the products were dimeric derivatives presumably due to an undesirable conformation of the substrate.
Diterpenoid Derivatives of Kenyan Croton sylvaticus
Authors: Ndunda Beth , Langat Moses K. , Midiwo Jacob O. , Omosa Leonidah K.
Published: March 2019

Kenyan Croton sylvaticus Hochst. ex Krauss gave four clerodane diterpenoids, the new ent–3,13 E-clerodadiene-15-formate (1), the known 15-acetoxy- ent-3,13 E-clerodadiene (2), ent-3,13 E-clerodadien-15-ol (3) and hardwickiic acid (4), two known halimane diterpenoids, penduliflaworosin (5) and crotohalimaneic acid (6) and one labdane diterpenoid, labda-13 E-ene-8α,15-diol (7). The compounds, when tested for their anti-microbial activities against Bacillus subtilis, Xanthomonas campestris and Candida albicans, were found to be inactive.
A Novel Triterpene from the Roots of Paullinia pinnata: 6α-(3′-methoxy-4′-hydroxybenzoyl)-lup-20(29)-ene-3-one
Authors: Jackson Nora , Annan Kofi , Mensah Abraham Y. , Ekuadzi Edmund , Mensah Merlin L. K. , Habtemariam Solomon
Published: March 2019

Paullinia pinnata L. (Sapindaceae) is an endemic West African plant that is extensively used in traditional medicine to treat various diseases. Previous phytochemical analysis by various groups led to the isolation of several novel lupene-based triterpenene derivatives along with other classes of compounds. As part of our continued phytochemical studies on the roots of this plant, we have now identified yet another novel triterpene, 6α-(3′-methoxy-4′-hydroxybenzoyl)-lup-20(29)-ene-3-one. The identification of the compound through comprehensive spectroscopic studies is discussed.
Bioactive Oleanane Glycosides from Polyscias duplicata from the Madagascar Dry Forest [1]
Authors: Eaton Alexander L. , Brodie Peggy J. , Callmander Martin W. , Rakotondrajaona Roland , Rakotobe Etienne , Rasamison Vincent E. , Kingston David G. I.
Published: March 2019

As part of the International Cooperative Biodiversity Group (ICBG) program, in a search for antiproliferative compounds, an ethanol extract of Polyscias duplicata was investigated due to its antiproliferative activity against the A2780 human ovarian cell cancer line (IC50 6 μg/mL). Seven known oleanane glycosides, 3β-[(α-L-arabinopyranosyl)oxy]-16α-hydroxyolean-12-en-28-oic acid (1, IC50 8 μM), 3β-[(α-L-arabinopyranosyl)oxy]-16α,23-dihydroxyolean-12-en-18-oic acid (2, IC50 13 μM), 3β-[( O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]–16α-hydroxyolean-12-en-28-oic acid (3, IC50 7 μM), 3β-[( O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl)oxy]-16α-hydroxyolean-12-en-28-oic acid (4, IC50 2.8 μM), 3β-[( O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]–23-hydroxyolean-12-en-28-oic acid (5, IC50 10 μM), 3β-[( O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid (6, IC50 3.4 μM), and 3β-[(α-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid (7, IC50 3.4 μM) were isolated, and their structures determined using spectroscopic methods.
Design, Synthesis and Biological Evaluation of Caudatin and its Ester Derivatives as Novel Antitumor Agents
Authors: Tao Xuefen , Ma Yongmin , Chen Jing , Zhao Huajun
Published: March 2019

A series of caudatin ester derivatives were synthesized and tested for their activities against human lung cancer A549, human prostate cancer PC3, human liver cancer BEL-7402 and human gastric cancer SGC-7901 cell lines. All the compounds showed noticeable activities against the tested tumor cell lines, and the IC50s are all lower than that of caudatin. Among them, 5e and 5h are the most potent compounds. SAR study implies that introducing either a halogenated acyl group or amino aryl group to the C3β position of caudatin is beneficial to their anti-viability activities, and the lipophilicity affects the anti-viability activity of caudatin derivatives.
Elucidation of the Mass Fragmentation Pathways of Tomatidine and β1-Hydroxytomatine using Orbitrap Mass Spectrometry
Authors: Caprioli Giovanni , Cahill Michael , Logrippo Serena , James Kevin
Published: March 2019

Tomatoes, members of the Solanaceae plant family, produce biologically active secondary metabolites, including glycoalkaloids, which may have both adverse and beneficial biological effects. Using the linear ion trap (LIT) mass spectrometry, multi-stage collision induced dissociation (CID) experiments (MSn) were performed to elucidate characteristic fragmentation pathways of the glycoalkaloid, tomatidine and of β1-hydroxytomatine. High resolution with high accuracy mass analysis using an Orbitrap fourier transform MS with higher-energy collisional induced dissociation (HCD) was used to produce mass spectra data across a wide spectral range for confirmation of proposed ion structures and formulae.
Alkaloids from Peumus boldus and their Acetylcholinesterase, Butyrylcholinesterase and Prolyl Oligopeptidase Inhibition Activity
Authors: Hošt'álková Anna , Opletal Lubomír , Kuneš Jiří , Novák Zdeněk , Hrabinová Martina , Chlebek Jakub , Čegan Lukáš , Cahlíková Lucie
Published: March 2019

Eleven isoquinoline alkaloids (1–11) were isolated from dried leaves of Peumus boldus Mol. by standard chromatographic methods. The chemical structures were elucidated by MS, and 1D and 2D NMR spectroscopic analysis, and by comparison with literature data. Compounds isolated in sufficient amount were evaluated for their acetylcholinesterase, and butyrylcholinesterase inhibition activity using Ellman's method. In the prolyl oligopeptidase assay, Z-Gly-Pro- p-nitroanilide was used as substrate. Promising butyrylcholinesterase inhibition activities were demonstrated by two benzylisoquinoline alkaloids, reticuline (8) and N-methylcoclaurine (9), with IC50 values of 33.6 ± 3.0 μM and 15.0 ± 1.4 μM, respectively. Important prolyl oligopeptidase inhibition activities were shown by N-methyllaurotetanine (6) and sinoacutine (4) with IC50 values of 135.4 ± 23.2 μM and 143.1 ± 25.4 μM, respectively. Other tested compounds were considered inactive.