bluuebunny/crossref_metadata_2025 huggingface dataset:
Cytotoxic Effects of Air Freshener Biocides in Lung Epithelial Cells
Authors: Kwon Jung-Taek , Lee Mimi , Seo Gun-Baek , Kim Hyun-Mi , Shim Ilseob , Lee Doo-Hee , Kim Taksoo , Seo Jung Kwan , Kim Pilje , Choi Kyunghee
Published: March 2019

This study evaluated the cytotoxicity of mixtures of citral (CTR) and either benzisothiazolinone (BIT, Mix-CTR-BIT) or triclosan (TCS, Mix-CTR-TCS) in human A549 lung epithelial cells. We investigated the effects of various mix ratios of these common air freshener ingredients on cell viability, cell proliferation, reactive oxygen species (ROS) generation, and DNA damage. Mix-CTR-BIT and Mix-CTR-TCS significantly decreased the viability of lung epithelial cells and inhibited cell growth in a dose-dependent manner. In addition, both mixtures increased ROS generation, compared to that observed in control cells. In particular, cell viability, growth, and morphology were affected upon increase in the proportion of BIT or TCS in the mixture. However, comet analysis showed that treatment of cells with Mix-CTR-BIT or Mix-CTR-TCS did not increase DNA damage. Taken together, these data suggested that increasing the content of biocides in air fresheners might induce cytotoxicity, and that screening these compounds using lung epithelial cells may contribute to hazard assessment.
Assessment of the Chemical Composition and In Vitro Antimicrobial Potential of Extracts of the Liverwort Scapania Aspera
Authors: Bukvicki Danka R. , Tyagi Amit K. , Gottardi Davide G. , Veljic Milan M. , Jankovic Snezana M. , Guerzoni Maria E. , Marin Petar D.
Published: March 2019

The chemical composition of Scapania aspera extracts was determined by solid phase micro extraction gas chromatography–mass spectrometry (SPME GC-MS) and 96 constituents were identified. The dominant compounds in the methanol extract were β-barbatene (25.1%), o-cymene (14.0%), α-barbatene (5.7%), allo-aromadendrene (4.9%) and β-bourbonene, while in the ethanol extract, o-cymene (17.8%), β-barbatene (17.6%), α-thujene (6.7%), octen-1-ol acetate (4.9%) and β-bazzanene (2.4%) were the major components. In the ethyl acetate extract, β-barbatene (14.3%), undecane (11.8%), 2-methyldecane (11.2%), decane (10.9%) and o-cymene (3.6%) were major components. The antimicrobial activity of the different extracts was evaluated against pathogenic and food spoilage microorganisms using disc diffusion and micro-broth dilution methods. The minimal inhibitory concentration (MIC) of extracts of S. aspera varied from 0.4 to 1.5 mg/mL and 1 to 3 mg/mL for yeast and bacterial strains, respectively. The zone of inhibition of the methanol extract for yeast strains was higher than that for bacterial strains. The results suggest that S. aspera extracts have potential as natural antimicrobial agents.
Alkaloids from an Endophytic Streptomyces sp. YIM66017
Authors: Zhou Hao , Yang Yabin , Zhang Jucheng , Peng Tianfeng , Zhao Lixing , Xu Lihua , Ding Zhongtao
Published: March 2019

Three alkaloids, flavensomycinoic acid (1), a linear polyketide, alpiniamide (2), and cyclo (L-Trp-L-Ala) (3), were isolated from the culture filtrate of endophytic Streptomyces sp. YIM66017 from Alpinia oxyphylla. Their structures were elucidated by spectroscopic analysis and the structure of 1 was confirmed by X-ray crystallographic analysis. Compound 1 was isolated from a natural source for the first time, and compound 2 is a new compound. Compound 1 showed cytotoxicity to MCF-7 with an IC 50 value of 17.0 μM.
Identification of a Xanthine Oxidase-inhibitory Component from Sophora Flavescens using NMR-based Metabolomics
Authors: Suzuki Ryuichiro , Hasuike Yuka , Hirabayashi Moeka , Fukuda Tatsuo , Okada Yoshihito , Shirataki Yoshiaki
Published: March 2019

We demonstrate that NMR-based metabolomics studies can be used to identify xanthine oxidase-inhibitory compounds in the diethyl ether soluble fraction prepared from a methanolic extract of Sophora flavescens. Loading plot analysis, accompanied by direct comparison of 1H NMR spectra exhibiting characteristic signals, identified compounds exhibiting inhibitory activity. NMR analysis indicated that these characteristic signals were attributed to flavanones such as sophoraflavanone G and kurarinone. Sophoraflavanone G showed inhibitory activity towards xanthine oxidase in an in vitro assay.
HPLC-PDA Analysis and Anti-inflammatory Effects of Mori Cortex Radicis
Authors: Seo Chang-Seob , Lim Hye-Sun , Jeong Soo-Jin , Ha Hyekyung , Shin Hyeun-Kyoo
Published: March 2019

Mori Cortex Radicis (MCR, Moraceae) is used traditionally in the treatment of jaundice, hematemesis, edema, and pollakisuria in Korea. In this study, the anti-inflammatory effects of MCR extract were investigated using RAW 264.7 cells. The simultaneous analysis of five components present (neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, caffeic acid, and p-coumaric acid) in the MCR extract was performed using high-performance liquid chromatography (HPLC) coupled with photodiode array (PDA) detection. We determined the effects of MCR extract and its components on the production of nitric oxide (NO), prostaglandin E2 (PGE2), and mRNA expression of cyclooxygenase-2 (COX-2) in RAW 264.7 cells. MCR extract suppressed the production of NO and PGE2 in RAW 264.7 cells in a dose-dependent manner. None of the five components of the MCR extract had any influence on the production of NO. However, caffeic acid and p-coumaric acid inhibited the production of PGE2 and mRNA expression of COX-2 in RAW 264.7 cells. Our results suggest that MCR extract may offer potential as a therapeutic agent for the treatment of inflammation. The method we have established will help to improve the quality control of MCR extracts.
Development of HPLC Fingerprint for Quality Assessment of Bulbus Lilii
Authors: Qin Kunming , Cai Hao , Zheng Lijuan , Zhang Miao , Zhang Xinghai , Gu Jie , Cai Baochang
Published: March 2019

In this study, a simple, sensitive and reliable fingerprint analysis method by high-performance liquid chromatography coupled with diode array detection (HPLC-DAD) was developed for quality analysis of Bulbus Lilii, which is a famous traditional Chinese medicine and widely used as a restorative food. Then the developed method was subsequently applied to analyse 16 samples collected or purchased from different origins. Twelve common fingerprint peaks, including four definitely identified peaks, were found in total, and were involved for further characterisation and quality evaluation of Bulbus Lilii. The chemical quality of commercial samples collected from different origins varied obviously, indicating that more attention should be paid to the standardisation of the process of harvesting, manufacturing and storage of Bulbus Lilii. This is the first time that a new method has been established to control the quality of Bulbus Lilii through HPLC-DAD.
Juglans Regia and J. nigra, Two Trees Important in Traditional Medicine: A Comparison of Leaf Essential Oil Compositions and Biological Activities
Authors: Paudel Prajwal , Satyal Prabodh , Dosoky Noura S. , Maharjan Samjhana , Setzer William N.
Published: March 2019

The essential oils from the leaves of Juglans regia, collected from Kathmandu, Nepal, and Juglans nigra from Huntsville, Alabama, USA, were obtained by hydrodistillation and analyzed by GC-MS. A total of 69 compounds were identified in the J. regia oil, accounting for 99.0% of the eluting components of the oil while three different samples of J. nigra were analyzed identifying a total of 99.3%, 99.4% and 99.7% of the oils. The leaf essential oil of J. regia was dominated by the aromatic compounds eugenol (27.5%) and methyl salicylate (16.2%), and the sesquiterpenes germacrene D (21.4%) and ( E)-β-farnesene (8.2%). The essential oils from three different samples of J. nigra contained ( E)-caryophyllene (17.3%–20.4%) and germacrene D (7.1%–22.5%) with smaller amounts of juglone (1.0%–8.8%), α-hydrojuglone (1.0–9.5%), and δ-cadinene (3.8%–8.7%). J. regia leaf oil, devoid of juglone, showed allelopathic activity, while J. nigra leaf oil was less phytotoxic. The presence of eugenol and methyl salicylate in the leaves of J. regia are consistent with the traditional uses of this plant to treat toothache, rheumatism, and fungal infections.
Natural Compounds against Flaviviral Infections
Authors: Abubakr Md , Mandal Subhash C , Banerjee Sugato
Published: March 2019

Arthropod borne flaviviral diseases are a major public health concern in the tropics. However, the majority of cases are associated with Dengue virus (DENV), Yellow Fever virus (YFV), West Nile virus (WNV) and Chikungunya virus (CHIKV) infections. Despite their profound clinical and economic impact among large sections of the population there is a lack of effective treatment against these diseases. A large number of plants are available in nature, which may act as a source for lead molecules against various diseases including arthropod borne flaviviral infections. In this review we discuss various crude extracts as well as purified compounds from natural sources with promising anti-DENV, YFV, WNV and CHIKV activity.
Isolation, Characterization and Sensory Evaluation of a Hexa β-D-Glucopyranosyl Diterpene from Stevia rebaudiana
Authors: Prakash Indra , Chaturvedula Venkata Sai Prakash , Markosyan Avetik
Published: March 2019

From the extract of the leaves of Stevia rebaudiana Bertoni, a diterpene glycoside was isolated which was identified as 13-[(2- O-β-D-glucopyranosyl-3- O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-(2- O-β-D-glucopyranosyl-3- O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester (1). The complete 1H and 13C NMR assignment of 1 is reported for the first time, from extensive NMR (1H and 13C, COSY, HSQC, and HMBC) and mass spectral data. Also, we report the sensory evaluation of 1 against sucrose for the sweetness property of this molecule.
Ecology- and Bioassay-Guided Drug Discovery for Treatments of Tropical Parasitic Disease: 5α,8α-Epidioxycholest-6-en-3β-ol Isolated from the Mollusk Dolabrifera dolabrifera Shows Significant Activity against Leishmania donovani
Authors: Clark Kathryn E. , Capper Angela , Togna Gina Della , Paul Valerie J. , Romero Luz I. , Johns Timothy , Cubilla-Rios Luis , Capson Todd L.
Published: March 2019

An ecology- and bioassay-guided search employed to discover compounds with activity against tropical parasitic diseases and cancer from the opisthobranch mollusk, Dolabrifera dolabrifera, led to the discovery of antileishmanial properties in the known compound, 5α,8α-epidioxycholest-6-en-3β-ol (1). Compound 1 was identified through nuclear magnetic resonance spectroscopy (1H, 13C) and mass spectrometry. The compound was concentrated in the digestive gland of D. dolabrifera, but was not detected in other body parts, fecal matter or mucus. Compound 1 showed an IC50 of 4.9 μM towards the amastigote form of Leishmania donovani compared with an IC50 of 281 μM towards the control Vero cell line, a 57.3-fold difference, and demonstrated no measurable activity against Plasmodium falciparum, Trypanosoma cruzi, and the breast cancer cell line, MCF-7.
Further Evidence on the Intramolecular Lactonization in Rat Liver Microsomal Metabolism of 12-O-acetylated Retronecine-type Pyrrolizidine Alkaloids
Authors: Tang Jun , Wang Zhengtao , Akao Teruaki , Hattori Masao
Published: March 2019

We have previously found evidence of intramolecular lactonization in rat liver microsomal metabolism of isoline, a 12- O-acetylated pyrrolizidine alkaloid. In this study, the metabolism of another 12- O-acetylated pyrrolizidine alkaloid, acetylduciformine, by the proposed transformation pathway was investigated under the same incubation conditions. Two deacetylated metabolites from acetylduciformine were isolated and purified by chromatographic methods, and further characterized based on their physical properties and spectral data. One metabolite (lankongensisine A) was the lactone of another one (duciformine). Both compounds were first obtained as hydrolyzed metabolites from acetylduciformine by rat liver microsomes. More importantly, the present study provided further evidence for the intramolecular lactonization in the microsomal metabolism of 12- O-acetylated retronecine-type PAs.
Therapeutic Effect of Broussonetia papyrifera and Lonicera japonica in Ovalbumin-induced Murine Asthma Model
Authors: Hong Seong-Ho , Kwon Jung-Taek , Shin Ji-Young , Kim Ji-Eun , Minai-Tehrani Arash , Yu Kyeong-Nam , Lee Somin , Park Sung-Jin , Chang Seung-Hee , Jiang Hu-Lin , Vibin M , Han Kiwon , Son Kun-Ho , Kwak Wie-Jong , Chae Chanhee , Bang Sung-Hye , Cho Myung-Haing
Published: March 2019

Broussonetia papyrifera (L.) Vent. and Lonicera japonica Thunb. have been used in recent medicinal research for their antioxidative and anti-inflammatory properties. The present study investigated the therapeutic efficacy of B. papyrifera and L. japonica ethanolic extracts in a murine model of ovalbumin-induced asthma, in which intra-peritoneal (IP) injections and aerosol ovalbumin delivery were used to induce allergic asthma. Bronchioalveolar lavage fluid (BALF), serum samples, lungs and livers were collected from the experimental groups. In the groups treated with B. papyrifera and L. japonica extracts, CD3, CD4, serum IgE and IL-4 levels; activities of matrix metalloproteinase (MMP)-2 and MMP-9; and eotaxin levels in the BALF significantly decreased to near normal levels. Results of a histopathological analysis showed that the level of inflammation and mucous secretions reduced in the treated groups compared to the corresponding levels in the other groups. Moreover, results of a serum enzymatic analysis showed the non-toxic nature of the extracts in the B. papyrifera and L. japonica treated groups. Taken together, these results clearly indicate that the B. papyrifera and L. japonica extracts may be very effective against asthma and inflammation related diseases.
Volatile Constituents of Trifolium pratense spp. nivale Quantified at Different Growth Stages, and Evaluation of their Antimicrobial Activity
Authors: Cecotti Roberto , Carpana Emanuele , Bergomi Patrizia , Tava Aldo
Published: March 2019

The composition of the volatile fraction of Trifolium pratense L. ssp. nivale (Sieber) Asch. et Gr. from the southwestern Alps was investigated. Fresh aerial parts were collected in the summer at three different growth stages, namely vegetative, flowering and fruiting. The oils obtained by steam-distillation accounted for 0.006 to 0.011% of the fresh plant material and their composition was determined by GC/FID and GC/MS. Several classes of compounds were found, with a predominance of alcohols in all phases, followed by aldehydes, hydrocarbons, terpenes, phenolics, ketones, acids and esters. The oil composition varied both in quantity and quality; the most abundant compounds were oct-1-en-3-ol and phenylacetaldehyde in the vegetative and flowering phases, and phenylacetaldehyde and 2-phenylethanol in the fruiting phase. The essential oils obtained were tested for activity against two major bee pests, i.e. Paenibacillus larvae and Melissococcus plutonius, and against a reference bacterial species, Bacillus subtilis.
Cytotoxic Activity of Essential Oils of Aerial Parts and Ripe Fruits of Echinophora spinosa (Apiaceae)
Authors: Fraternale Daniele , Ricci Donata , Calcabrini Cinzia , Guescini Michele , Martinelli Chiara , Sestili Piero
Published: March 2019

The cytotoxic effects of the essential oils obtained from the flowering aerial parts (APO) and ripe fruits (RFO) of Echinophora spinosa L. (Apiaceae) from central Italy toward human U937 promonocytoid cells were studied; the contribution of each of the major constituents to the whole cytotoxic activity of either APO or RFO was also characterized. The major components of APO were β-phellandrene (34.7%), myristicin (16.5%), p-cymene (16.3%), δ3-carene (12.6%), α-pinene (6.7%) and α-phellandrene (6.2%); those of RFO p-cymene (50.2%), myristicin (15.3%), α-pinene (15.1%) and α-phellandrene (8.1%). Both oils tested were toxic to U937 cells, but RFO was much more cytotoxic: indeed, the IC50 values calculated from the linear regression curves of RFO and APO were 14.5 ± 0.85 and 43.4 ± 2.81 μg/mL, respectively. α-Pinene and α-phellandrene were identified as the most toxically relevant constituents: however, they did not completely account for the toxic effects of genuine APO and RFO. Interestingly, we found that p-cymene, although per se devoid of toxicity within the tested range of concentrations, was capable of significantly sensitizing U937 cells to the cytotoxic activity of α-pinene and α-phellandrene, and that specific mixtures of these three terpenes were as toxic as genuine APO and RFO.
Minor Triterpene Saponins from Underground Parts of Lysimachia thyrsiflora: Structure elucidation, LC-ESI-MS/MS Quantification, and Biological Activity
Authors: Podolak Irma , Żmudzki Paweł , Koczurkiewicz Paulina , Michalik Marta , Zajdel Paweł , Galanty Agnieszka
Published: March 2019

Two minor triterpene saponins, one previously not reported, were isolated from the underground parts of Lysimachia thyrsiflora L. The structures were determined based on a combination of one- and two-dimensional NMR techniques, and mass spectrometry, as 30- O-β-D-glucopyranosyl-3β,16α,30-trihydroxy-olean-12-en-28-yl acetate 3- O-β-D-glucopyranosyl-(1→4)- O-[β-D-glucopyranosyl-(1→2)-]- O-α-L-arabinopyranoside (denoted as thyrsiloside A), and davuricoside L. Quantitative determination of these two compounds, along with other saponins present in L. thyrsiflora underground parts, was performed by a developed UPLC-ESI-MS/MS method, validated according to the ICH guidelines. The relative total content of triterpene saponins amounted to 1.19 μg/mg dw. Both 4 and 5 were present in minor quantities, 0.031 and 0.077 μg/mg dw, respectively. Assays performed on a panel of human cancer cell lines showed antiproliferative activity against prostate carcinoma PC-3 (GI50 after 48 h = 20 and 24 μg/mL, respectively).
New Access to 7,17-seco C19-Diterpenoid Alkaloids via Vacuum Pyrolysis of N-Deethyl-8-acetyl Derivatives
Authors: Wang Ling , Chen Qi-Feng , Wang Feng-Peng
Published: March 2019

A novel access to 7,17-seco C19-diterpenoid alkaloids via vacuum pyrolysis of N-deethyl-8-acetyl derivatives is described.
Application of Mixture Analysis to Crude Materials from Natural Resources (IV)[1(a-c)]: Identification of Glycyrrhiza Species by Direct Analysis in Real Time Mass Spectrometry (II)
Authors: Fukuda Eriko , Uesawa Yoshihiro , Baba Masaki , Okada Yoshihito
Published: March 2019

In order to identify Glycyrrhiza species by chemical fingerprinting, the bark of the roots and stolons of Glycyrrhiza uralensis Fischer and G. glabra Linné were analyzed using DART (Direct Analysis in Real Time)-MS. The characteristic peaks of each species were determined statistically by volcano plot. This summarizes the relationship between the p-values of a statistical test and the magnitude of the difference in values of the samples in the groups. In this experiment, peaks that had a p value <0.05 in the t test and ≥2 absolute difference were defined as characteristic. As a result, characteristic peaks of G. uralensis were found at m/z 299, 315, 341, and 369. In contrast, characteristic peaks of G. glabra were found at m/z 323, 325, 337, 339, and 391. In conclusion, we found several characteristic peaks to distinguish G. uralensis and G. glabra by DART-MS using volcano plot. This method can be applied to identify the Glycyrrhiza species.
Rosmarinic Acid Interaction with Planktonic and Biofilm Staphylococcus aureus
Authors: Slobodníková Lívia , Fialová Silvia , Hupková Helena , Grančai Daniel
Published: March 2019

The subject of study was the evaluation of antibacterial activities of rosmarinic acid (RA) on clinical Staphylococcus aureus strains obtained from catheter-related infections. Minimal inhibitory (MIC) and minimal bactericidal concentrations (MBC) of RA were tested by broth microdilution assay. Biofilm-eradication activity was detected on 24-hour biofilm in microtiter plates using a regrowth technique; activity on biofilm formation was measured by a microtiter plate method after RA application to bacterial samples after 0, 1, 3 and 6 hours of biofilm development. RA had antimicrobial activity on all tested strains in concentrations from 625 to 1250 μg.mL−1 (MICs equal to MBCs). No biofilm-eradication activity on 24-hour biofilm was observed in the tested range of concentrations (from 156 to 5000 μg.mL−1). Subinhibitory RA concentrations suppressed the biofilm production, when applied at early stages of its development. Concentrations lower than subinhibitory stimulated the biofilm mass production in a concentration- and time-dependent manner. Considering our results, RA could be a candidate for a topical antimicrobial agent with killing activity on planktonic forms of bacteria and suppressing activity in the early stages of biofilm development, but probably not for the therapy of catheter-related infections as a sole agent.
Effect of Trehalose Addition on Volatiles Responsible for Strawberry Aroma
Authors: Kopjar Mirela , Hribar Janez , Simčič Marjan , Zlatić Emil , Požrl Tomaž , Piližota Vlasta
Published: March 2019

Aroma is one of the most important quality properties of food products and has a great influence on quality and acceptability of foods. Since it is very difficult to control, in this study the effect of addition of trehalose (3, 5 and 10%) to freeze-dried strawberry cream fillings was investigated as a possible means for retention of some of the aroma compounds responsible for the strawberry aroma. In samples with added trehalose, higher amounts of fruity esters were determined. Increase of trehalose content did not cause a proportional increase in the amount of fruity esters. However, results of our research showed that trehalose addition did not have the same effect on both γ-decalactone and furaneol.
Essential Oil Characterization of Two Azorean Cryptomeria japonica Populations and Their Biological Evaluations
Authors: Moiteiro Cristina , Esteves Teresa , Ramalho Luís , Rojas Rosario , Alvarez Sandra , Zacchino Susana , Bragança Helena
Published: March 2019

Essential oils from foliage, bark and heartwood of Cryptomeria japonica D. Don from Azores Archipelago (Portugal) were analyzed by GC and GC-MS. Two populations, of black and reddish heartwood color, were studied. The main compounds found in the foliage of both populations were α-pinene (9.6–29.5%), (+)-phyllocladene (3.5–26.5%), ent-kaur-16-ene (0.2–20.6%), sabinene (0.5–19.9%) and limonene (1.4–11.5%), with a large variation in individual compounds from each population. Heartwood oils were characterized by a high content of cubebol (2.8–39.9%) and epi-cubebol (4.1–26.9%) isomers, which were absent in the foliage. Elemol and eudesmol isomers were found in the foliage and heartwood oils, while (+)-phyllocladene was absent in heartwood. Black and reddish bark oils were composed of the diterpenes dehydroferruginol (1.9–5.1%) and ferruginol (2.6–11.5%), along with the sesquiterpenes δ-cadinene (10.4–15.9%), α-muurolene (3.3–5.4%), epi-zonarene (4.0–5.0%), cubenol (9.3–14.0%), τ-muurolol (4.8–10.7%), β-eudesmol (3.0–9.9%), γ-eudesmol (1.9–7.0%) and hedycariol (1.4–6.2%). Azorean C. japonica oils exhibited significant chemical differences compared with native plants from Asia.

The essential oils showed moderate antimicrobial activity against the pathogenic fungus Cryptococcus neoformans and human pathogenic bacteria (especially against multidrug-resistant Mycobacterium tuberculosis). The antimicrobial activity of the essential oils may be attributed to compounds such as ent-kaur-16-ene, (+)-phyllocladene, ferruginol and elemol, which are present in different proportions within the complex oil mixture. These results suggest a potential use for C. japonica oils obtained from wood industry leftovers.
Isolation of a New Anti-inflammatory 20, 21, 22, 23, 24, 25, 26, 27-Octanorcucurbitacin-type Triterpene from Ibervillea sonorae
Authors: Jardón-Delgado Angel , Magos-Guerrero Gil Alfonso , Martínez-Vázquez Mariano
Published: March 2019

A new cucurbitane-type triterpene, 20, 21, 22, 23, 24, 25, 26, 27-octanorcucurbita-5-ene-3, 11, 16-trione (1), named kinoin D, was isolated from the roots of the medicinal plant Ibervillea sonorae, (wereque). The structure of 1 was established on the basis of extensive NMR and MS studies. In addition, the known kinoins B (3) and C (5) were isolated, as were 16α-20,25-trihydroxy-3α-(2- O-α-L-rhamnopyranosiyl-D-glucopyranosyloxy)-(10α)-cucurbit-5-en-11,22-dione (6), (22 S)-16α,22-diacetoxy-20,25-dihydroxy-3α-[3,4,6-tri- O-acetyl-2- O-(2,3,4-tri- O-acetyl-α-L-rhamnopyranosyl)-β-glucopyranosyl]-(10α)-cucurbita-5,23t-dien-11-one (7) and 16α-acetoxy-20,25-dihydroxy-3α-[3,4,6-tri- O-acetyl-2- O-(2,3,4,-tri- O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-(10α)-cucurbita-5-ene-11,22-dione (8). Compound 1 exhibited anti-inflammatory activity in TPA-induced edema in mice.
Flavonoids Produced by Tissue Culture of Dracaena cambodiana
Authors: Wang Hui , Luo Guanyong , Wang Jiayuan , Shen Haiyan , Luo Ying , Dai Haofu , Mei Wenli
Published: March 2019

Dragon's blood is a traditional medicine used in many countries of many cultures because of its various therapeutic uses, and its main bioactive compounds are flavonoids, which mainly exhibit antitumor and antimicrobial activities. In the process of tissue culture of Dracaena cambodiana, one of its resource plants, red secretion was discovered in the culture when 6-benzylaminopurine was added. Analysis of its constituents by HPLC in comparison with dragon's blood and the standards proved that 17 compounds, including 10 flavonoids, are the same as those in dragon's blood. It is promising that flavonoids from dragon's blood could be produced by tissue culture of its resource plants for the development of new drugs.
Qualitative Identification of Dibenzoylmethane in Licorice Root (Glycyrrhiza glabra) using Gas Chromatography-Triple Quadrupole Mass Spectrometry
Authors: Mancia Marisela D. , Reid Michelle E. , DuBose Evan S. , Campbell James A. , Jackson Kimberly M.
Published: March 2019

Licorice root ( Glycyrrhiza glabra), an herbal Chinese medicine, has shown medicinal uses in therapeutics and cancer prevention. Dibenzoylmethane (DBM; 1, 3-diphenyl-1, 3-propadinedione), a small β-diketone, has been reported to be a minor constituent of licorice and a known deregulator of the human prostate cancer cell cycle. Characterization of the phytochemical profiles of licorice root forms including commercially available DBM will advance our search in identifying novel reagents for prostate cancer therapeutics. Gas chromatography- triple quadrupole-mass spectrometric analysis was used for detecting DBM in licorice root extracts. DBM and all licorice forms exhibited a component with a retention time of 14.5 minutes. The major fragment ions detected were at m/z 77, 105, 147, 223 and 224 at the identified retention time by selected reaction monitoring/SRM. These data confirm the presence of DBM from its natural source ( G. glabra), and the GC-MS/SRM method helps in the identification of this minor component in a complex biological matrix.
Anti-L. donovani Activity in Macrophage/Amastigote Model of Palmarumycin CP18 and its Large Scale Production
Authors: Ortega Humberto E. , Teixeira Eliane de Morais , Rabello Ana , Higginbotham Sarah , Cubilla-Ríos Luis
Published: March 2019

Palmarumycin CP18, isolated from an extract of the fermentation broth and mycelium of the Panamanian endophytic fungus Edenia sp., was previously reported with strong and specific activity against Leishmania donovani. Here we report that when the same strain was cultured on different solid media – Harrold Agar, Leonian Agar, Potato dextrose Agar (PDA), Corn Meal Agar, Honey Peptone Agar, and eight vegetables (V8) Agar – in order to determine the optimal conditions for isolation of palmarumycin CP18, no signal for this compound was observed in any of the 1H NMR spectra of fractions obtained from these extracts. However, one extract, prepared from the fungal culture in PDA contained significant amounts of CJ-12,372, a possible biosynthetic precursor of palmarumycin CP18. Edenia sp. was cultivated on a large scale on PDA and CJ-12,372 was converted to palmarumycin CP18 by oxidation of its p-hydroquinone moiety with DDQ in dioxane. Palmarumycin CP18 showed anti-leishmanial activity against L. donovani in a macrophage/amastigote model, with IC50 values of 23.5 μM.
Medelamine C, A New ω-Hydroxy Alkylamine Derivative from Endophytic Streptomyces sp. YIM 66142
Authors: Zhang Ju-Cheng , Yang Ya-Bin , Zhou Hao , Peng Tian-Feng , Yang Fang-Fang , Xu Li-Hua , Ding Zhong-Tao
Published: March 2019

A new alkylamine derivative and a common fatty acid were isolated from Streptomyces sp. YIM 66142. On the basis of spectral data, including HRMS, NMR and 2D NMR, their structures were determined as medelamine C (1) and isomyristic acid (2). The ω-hydroxyl group in structure 1 is rare in a natural alkylamine. The possible biosynthetic pathway in the genus Streptomyces from isomyristic acid (2) to medelamines is proposed. Compound 1 showed no obvious cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, SW480 cell lines. The ω-hydroxyl and the acetyl at NH in compound 1 decreased its cytotoxicity in comparison with that of medelamine.
Steroidal Aglycones from Stems of Marsdenia tenacissima that Inhibited the Hedgehog Signaling Pathway
Authors: Zhang Lin , Chen Feng-yang , Xu Shi-fang , Ye Yi-ping , Li Xiao-yu
Published: March 2019

Two novel steroidal aglycones, together with four known ones, were isolated from the hydrolysis extract of the CHCl3 soluble extract of the stems of Marsdenia tenacissima. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods, including 1D and 2D NMR spectroscopy. These compounds displayed inhibition of the Hedgehog signaling pathway in vitro.
Polyphenols in Representative Teucrium Species in the Flora of R. Macedonia: LC/DAD/ESI-MSn Profile and Content
Authors: Mitreski Ilija , Stanoeva Jasmina Petreska , Stefova Marina , Stefkov Gjoshe , Kulevanova Svetlana
Published: March 2019

In the present work, the polyphenolic profile and content of four Teucrium species ( T. chamaedrys L., T. montanum L., T. polium L., T. scordium L.) from the Macedonian flora were examined. A LC/DAD/ESI-MS n chromatographic method was optimized and 31 phenolic compounds were identified, quantified and classified into four groups: hydroxycinnamic acid derivatives (2), phenylethanoid glycosides (12), flavonoid glycosides (11) and flavonoid aglycones (6). The total phenolic content (mg/g dry herb) ranged from 28.2 ( T. montanum), 30.9 ( T. scordium), 35.1 ( T. polium) to 52.1 ( T. chamaedrys). Phenylethanoid glycosides were the predominant group of polyphenols in the studied samples contributing 60% of the total phenolic content for T. polium and T. scordium and around 90% for T. montanum and T. chamaedrys. The systematic analysis for identification and quantification of all present phenolic compounds contributes to the chemotaxonomy of the investigated Teucrium species and to the valorization based on their phenolic profiles and content.
A New Lignan Glycoside from Chamaecyparis obtusa var. breviramea f. crippsii
Authors: Xu Jian , Zeng Guang-Zhi , Chen Ke-Li , Liu Yi-Mei , Sun Zhang-Hua , Tan Ning-Hua , Zhang Yu-Mei
Published: March 2019

A new lignan glycoside, (-)-(8 S, 8′ R)-thujastandin-4- O-β-D-glucopyranoside (1), together with fourteen known lignanoids (2–15) and one coumarin (16) were isolated from the branches and leaves of Chamaecyparis obtusa var. breviramea f. crippsii. Their structures were elucidated by extensive spectroscopic and spectrometric analysis. Compound 16 exhibited cytotoxicity against A549, BGC-823 and Hela cell lines with IC50 values of 25.9, 20.9 and 18.5 μM, respectively.
An Expedient Synthesis of Linden Ether
Authors: Serra Stefano , Cominetti Alessandra A.
Published: March 2019

We here describe a comprehensive study on the preparation of the intensive flavor 3,9-epoxy- p-mentha-1,4(8)-diene (1). Key steps of the presented synthesis are the selective addition of MeLi to the keto-ester 7, the regioselective cyclization of the obtained triol to give the ethers 4 and 8 and the selective dehydration of ether 4 through the use of POCl3 and pyridine. It is worth noting that the presented synthesis represents the first expedient and reliable entry to ether 1. Being present in linden honey, 1 is also known as linden ether and it has been regarded as a potential marker for the authentication of the linden honey origin. Therefore, ether 1 can be used as a useful reference standard for the analysis of the natural flavors, as we demonstrated by means of its identification in a sample of unifloral linden honey.
A General Synthetic Approach to Hydroquinone Meroterpenoids: Stereoselective Synthesis of (+)-(S)-Metachromin V and Alliodorol
Authors: Serra Stefano , Cominetti Alessandra A. , Lissoni Veronica
Published: March 2019

A new general synthetic approach to hydroquinone meroterpenoids is here described. The framework of the aforementioned natural compounds was built up through the Li2CuCl4 catalysed cross coupling reaction of the 4-substituted-( E)-prenyl acetates 9 with 2,5-bis(benzyloxy)phenyl magnesium bromide 8 as a key step. The latter sp3-sp2 coupling affords the products in good chemical yields and in very high stereoisomeric purity. A further key step of the present synthetic method consists of the removal of the benzylic protecting groups by a very mild procedure based on the use of lithium naphthalenide. The latter reagent, in combination with aliphatic dialkylamines, is able to cleave all the benzylic protecting groups leaving unaffected the polyenic moieties. By these means, we devised a new synthesis of the natural hydroquinone geranylhydroquinone, farnesylhydroquinone, metachromin V and alliodorol. In addition, the marine meroterpenoid, (+)-( S)-metachromin V, was synthesized for the first time; its chemical structure was confirmed and its absolute configuration was unambiguously assigned.
Synthetic Approach to the Psoracorylifols
Authors: Kraus George A. , Dong Pengfei
Published: March 2019

Core analogs of the psoracorylifols were generated by a five-step route from 2,2-dimethyl-4-cyanobutanal.
Lactarane Sesquiterpenes from the European Mushrooms Lactarius aurantiacus, L. subdulcis, and Russula sanguinaria
Authors: Gilardoni Gianluca , Malagòn Omar , Tosi Solveig , Clericuzio Marco , Vidari Giovanni
Published: March 2019

The results of the first investigation of secondary metabolites occurring in intact and damaged fruiting bodies of the European mushrooms Lactarius aurantiacus, L. subdulcis, and Russula sanguinaria are reported. The pattern of sesquiterpenes in injured R. sanguinaria is dramatically different from that of Lactarius. The structure of the new furanolactarane 4, isolated from L. aurantiacus, was established on the basis of spectral data.
The First Isolation of Furanoeremophilane from Ligularia nelumbifolia
Authors: Hirota Hiroshi , Horiguchi Yurie , Kawaii Satoru , Hanai Ryo , Gong Xun , Kuroda Chiaki
Published: March 2019

Ligularol (1), a furanoeremophilane, was isolated together with eremophil-1(10)-en-11-ol (2) from one of eight collected samples of Ligularia nelumbifolia and L. kongkalingensis, a closely related species. It is proposed that the ability to produce the furanoeremophilane has been acquired through hybridization.
Antiproliferative Effects of 12-Oxoheteronemin vs Heteronemin
Authors: Kittiwisut Siriporn , Rohena Cristina C. , Yuenyongsawad Supreeya , Mooberry Susan L. , Plubrukarn Anuchit
Published: March 2019

The antiproliferative activities of 12-oxoheteronemin and heteronemin were evaluated in six cancer cell lines and IC50 values ranging from 0.66 to 1.35 μM were obtained. In four of the cell lines, 12-oxoheteronemin and heteronemin were equipotent; however, in two estrogenic receptor-positive cell lines, heteronemin showed a stronger potency. Both compounds had no overt effects on cell cycle distribution in HeLa cells, but did rapidly initiate apoptosis as evidenced by increased sub-G1 populations of cells and caspase-dependent PARP cleavage.
New Cembranoids from the Soft Coral Sinularia arborea
Authors: Wang Li-Hsueh , Chen Kuan-Hua , Dai Chang-Feng , Hwang Tsong-Long , Wang Wei-Hsien , Wen Zhi-Hong , Wu Yang-Chang , Sung Ping-Jyun
Published: March 2019

From the ethyl acetate extract of the soft coral Sinularia arborea, a new cembrane-type diterpenoid, arbolide C (1), along with (+)-sarcophytol T (2), an enantiomer of the known cembrane, sarcophytol T, were isolated. The structures of compounds 1 and 2 were established by spectroscopic methods and 1 was found to display an inhibitory effect on the release of elastase by human neutrophils.
New Schiartane-type Triterpene from Kadsura heteroclita and their Cytotoxic Activities
Authors: Minh Pham Thi Hong , Lam Do Tien , Tien Nguyen Quyet , Tuan Nguyen Ngoc , Nhung Vu Phuong , Van Hai Nong , Van Kiem Phan , Nhiem Nguyen Xuan , Van Minh Chau , Ju Park Seon , Hyun Kim Seung
Published: March 2019

One new schiartane- type triterpene, heteroclitalactone N (1), and four known compounds (2–5), seco-coccinic acid F, dihydroguaiaretic acid, schizanrin F, and kadsuralignan B were isolated from the stems of Kadsura heteroclita. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D-, 2D-NMR, and CD spectra as well as by comparing with the NMR data reported in the literature. The cytotoxic activities of all isolated compounds were evaluated on three human cancer cell lines. Compound 3 exhibited moderate to weak cytotoxic activities on three human cancer cell lines, OVCAR, HT-29, and A-549, with IC50 values ranging from 16.2 to 36.4 μM.
C-Lactam Derivatives of Oleanolic Acid. Hydrolysis and Further Acylation of Methyl Acetyloleanolate C-Lactam and C-Thiolactam
Authors: Bednarczyk–Cwynar Barbara , Zaprutko Lucjusz
Published: March 2019

Acetyl methyl oleanolate was transformed into a seven-membered C-lactam derivative (2) using Beckmann rearrangement of the corresponding C-oxime during the last step of the synthesis. The C=O group of the lactam system was transformed into a C=S group by Lavesson's reagent. The resulting acetylthiolactam 3 and initial acetyllactam 2 were subjected to alkaline hydrolysis to obtain lactam 4 and thiolactam 5 with an unsubstituted C-3 hydroxyl group. Subsequently, compounds 4 and 5 were acylated with either succinic or acetic anhydride in pyridine. Various acylating conditions were tested for hydroxythiolactam 5. The structures of the newly obtained compounds were supported by spectral and mass spectrometric data.
Cucurbitane-type Triterpene Glycosides from the Fruits of Momordica charantia
Authors: Yen Pham Hai , Dung Duong Thi , Nhiem Nguyen Xuan , Le Tuan Anh Hoang , Hang Dan Thi Thuy , Yen Duong Thi Hai , Cuc Nguyen Thi , Ban Ninh Khac , Van Minh Chau , Van Kiem Phan
Published: March 2019

Four new cucurbitane- type triterpene glycosides, charantosides D-G (1–4) were isolated from a methanol extract of Momordica charantia fruits. The structures of these compounds were determined by chemical and spectroscopic methods to be (19 R)-5 β,19-epoxy-25-methoxycucurbita-6,23-diene-3 β,19-diol 3- O-β-D-glucopyranoside, (19 R)-5 β,19-epoxy-25-methoxycucurbita-6,23-diene-3 β,19-diol 3- O-β-D-allopyranoside, 7 β-methoxycucurbita-5,23 E,25-triene-3 β-ol 3- O-β-D-allopyranoside, and 3 β,7 β-dihydroxycucurbita-5,23 E,25-triene-19-al 3- O-β-D-allopyranoside.
Terpenoids and Sterols from Some Japanese Mushrooms
Authors: Yaoita Yasunori , Kikuchi Masao , Machida Koichi
Published: March 2019

Over the past twenty years, our research group has been studying the chemical constituents of mushrooms. From nineteen species, namely, Amanita virgineoides Bas (Amanitaceae), Daedaleopsis tricolor (Bull.: Fr.) Bond. et Sing. (Polyporaceae), Grifola frondosa (Fr.) S. F. Gray (Polyporaceae), Hericium erinaceum (Bull.: Fr.) Pers. (Hericiaceae), Hypsizigus marmoreus (Peck) Bigelow (Tricholomataceae), Lactarius piperatus (Scop.: Fr.) S. F. Gray (Russulaceae), Lentinula edodes (Berk.) Sing. (Pleurotaceae), Lyophyllyum connatum (Schum.: Fr.) Sing. (Tricholomataceae), Naematoloma sublateritium (Fr.) Karst. (Strophariaceae), Ompharia lapidescens Schroeter (Polyporaceae), Panellus serotinus (Pers.: Fr.) Kuhn. (Tricholomataceae), Pholiota nameko (T. Ito) S. Ito et Imai in Imai (Strophariaceae), Pleurotus eringii (DC.: Fr.) Quel. (Pleurotaceae), Polyporus umbellatus Fries (Polyporaceae), Russula delica Fr. (Russulaceae), Russula sanguinea (Bull.) Fr. (Russulaceae), Sarcodon aspratus (Berk.) S. Ito (Thelephoraceae), Tricholoma matsutake (S. Ito et Imai) Sing. (Tricholomataceae), and Tricholoma portentosum (Fr.) Quel. (Tricholomataceae), we isolated eight new sesquiterpenoids, six new meroterpenoids, three new triterpenoids, and twenty eight new sterols. In this review, structural features of these new compounds are discussed.
Phytochemicals and Biological Activities of Poisonous Genera of Ericaceae in China
Authors: Wang Xiaohong , Jiang Rui , Liu Zizhen , Liu Weirui , Xie Meng , Wei Shengli , She Gaimei
Published: March 2019

The family Ericaceae is comprised of about 70 genera of which about 20 are found throughout China. Of these Ledum, Rhododendron, Enkianthus, Pieris, Craibiodendron, Gaultheria, Vaccinium, and Leucothoe are regarded as poisonous. Many species of these poisonous genera are used as Chinese herbal medicines for the treatment of, for example, inflammation, asthma, and coughs. Modern research has demonstrated that the toxic ingredients of these poisonous genera are chiefly tetracyclic diterpenes, which have adverse effects on the digestive, cardiovascular and nervous systems. Because various species of these poisonous genera also have medicinal functions, extensive studies of these plants have led to the identification of many kinds of compound. This paper compiles 306 compounds from the eight poisonous genera, reported in 141 references.
Decorosides A and B, Cytotoxic Flavonoid Glycosides from the Leaves of Rhododendron decorum
Authors: Rateb Mostafa E. , Hassan Hossam M. , Arafa El-Shaimaa A. , Jaspars Marcel , Ebel Rainer
Published: March 2019

Bioassay and NMR-guided fractionation of the methanolic extract of Rhododendron decorum leaves resulted in the isolation of two new flavonoid glycosides, 5,7-dihydroxy-6,8-dimethyldihydroflavanone-7-O-α-L-arabinopyranosyl(l→6)-β-D-glucopyranoside (decoroside A, 1) and its 3-hydroxy congener (decoroside B, 2), along with five known compounds myricitrin (3), afzelin (4), (-)-epicatechin (5), (+)-catechin (6), and ampeloptin (7). The structures of the isolated compounds were elucidated by extensive interpretation of their spectral data. Biological evaluation using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay revealed promising cytotoxic activities of these compounds against different cancer cell lines.
In Vitro Antioxidant Activity and Phenolic Content of Cedrus brevifolia Bark
Authors: Cretu Elena , Salminen Juha-Pekka , Karonen Maarit , Miron Anca , Charalambous Christiana , Constantinou Andreas I. , Aprotosoaie Ana Clara
Published: March 2019

A raw extract and four extractive fractions were obtained from Cedrus brevifolia (Cyprus cedar) bark. They were all studied regarding the phenolic content and profile using spectrophotometry and HPLC-DAD-ESI-MS. The antioxidant activity was investigated using in vitro assays: DPPH and ABTS radicals scavenging and reducing power assays. The ethyl acetate fraction had the highest total phenolic and proanthocyanidin contents; a taxifolin-O-hexoside, catechin, epicatechin and procyanidin oligomers (three dimers, two trimers) were identified in this fraction. The ethyl acetate fraction was found to possess the highest DPPH and ABTS radicals scavenging effects (EC50=13.9 ± 0.3 and 2.3 ± 0.0 μg/mL, respectively) and reducing capacity (EC50=9.1 ±0.1 μg/mL). Antioxidant effects were highly correlated with total phenolic and proanthocyanidin contents (r=0.89-0.99). These results suggest that Cedrus brevifolia bark is a new source of antioxidants.
A New Coumarin and Cytotoxic Activities of Constituents from Cinnamomum cassia
Authors: Ngoc Tran Minh , Nhiem Nguyen Xuan , Khoi Nguyen Minh , Son Doan Cao , Hung Tran Viet , Van Kiem Phan
Published: March 2019

A new coumarin derivative, coumacasia (1) and eight known compounds, coumarin (2), cinnamaldehyde (3), 2-methoxycinnamaldehyde (4), 2-hydroxycinnamaldehyde (5), coniferaldehyde (6), cinnamic acid (7), 2-hydroxycinnamic acid (8), and cinnamic alcohol (9), were isolated from the methanol extract of Cinnamomum cassia. Their structures were elucidated by spectral data and by comparison with the reported literature. The cytotoxic activities of compounds 1-9 were evaluated with two human cancer cell lines, HL-60 and A-549. Compound 1 showed growth inhibitory effects in the HL-60 and A-549 cell lines with IC50 values of 8.2 ± 0.5 and 11.3 ±1.1 μM, respectively. Compounds 3-6, and 8 exhibited moderate cytotoxicity with IC50 values ranging from 20.5 to 65.6 μM.
Coumarin Compounds in Coronilla scorpioides Callus Cultures
Authors: Piovan Anna , Filippini Raffaella , Innocenti Gabbriella
Published: March 2019

Coronilla scorpioides (L.) W.D.J. Koch is known for producing several compounds with pharmaceutical interest, such as the hydroxycoumarins umbelliferone, scopoletin and daphnoretin, the dihydrofuranocoumarin marmesin, and the furocoumarin psoralen. In vitro callus cultures of C. scorpioides were established from hypocotyl, leaf, stem internode and root explants in order to evaluate the possibility of in vitro production of these active secondary metabolites. Calli were obtained with high frequency from all the explant types both in B5 and MS medium. However, after the third subculture, B5 medium, giving the best results, was selected for subsequent transfers. Homogeneous calli were kept either in darkness or in light. Chemical analyses showed that scopoletin and the intermediate products of the biogenetic pathway of psoralen, umbelliferone and marmesin, were always present in the calli and excreted into the media, while daphnoretin was never detected. Light seems to be a prerequisite for psoralen biosynthesis. Root-derived calli produced a significantly higher amount of psoralen (137.5 μg g−1 DW). Principal component analysis showed that umbelliferone, marmesin and psoralen contents are related to variables associated with different explant types.
A New Isocoumarin from Cajanus cajan (Fabaceae)
Authors: Rodrigues Virginia F. , Oliveira Rodrigo R. , Vega Maria Raquel G.
Published: March 2019

A new isocoumarin, 3-phenyl-8-hydroxy-6-methoxy-5-γ, γ-dimethylallyl-isocoumarin, named cajavilmina (1) and eight known compounds: α-amirenone (2), β-amirenone (3), lupenone (4), 5-hydroxy-7-methoxydihydroflavone (5), longistilin C (6), 3-hydroxy-5-methoxystilbene (7), β-sitosterol (8) and stigmasterol (9) were identified in a dichloromethane fraction from Cajanus cajan leaves. Structures were elucidated by analysis of spectral data, mainly those afforded by 1H, NOEDIFF and 13C NMR (1D and 2D NMR HMQC, HMBC and COSY) and mass spectra.
Potent Acetylcholinesterase Inhibitory Compounds from Myristica fragrans
Authors: Cuong To Dao , Hung Tran Manh , Han Hyoung Yun , Sik Roh Hang , Seok Ji-Hyeon , Lee Jong Kwon , Jeong Ja Young , Choi Jae Sue , Kim Jeong Ah , Min Byung Sun
Published: March 2019

The anti-cholinesterase activity was evaluated of the ethyl acetate fraction of the methanol extract of Myristica fragrans Houtt (Myristicaceae) seeds and of compounds isolated from it by various chromatographic techniques. The chemical structures of the compounds were determined from spectroscopic analyses (NMR data). Thirteen compounds (1—13) were isolated and identified. Compound 8 {[(7S)-8′-(4′-hydroxy-3′-methoxyphenyl)-7-hydroxypropyl]benzene-2,4-diol} showed the most effective activity with an IC50 value of 35.1 μM, followed by compounds 2 [(8R,8′S)-7′-(3′,4′-methylenedioxyphenyl)-8,8′-dimethyl-7-(3,4-dihydroxyphenyl)-butane] and 11 (malabaricone C) with IC50 values of 42.1 and 44.0 μM, respectively. This is the first report of significant anticholinesterase properties of M. fragrans seeds. The findings demonstrate that M. fragrans could be used beneficially in the treatment of Alzheimer's disease.