bluuebunny/crossref_metadata_2025 huggingface dataset:
The Leaf, Wood and Bark Oils of three Species of Myodocarpus (Myodocarpaceae) Endemic to New Caledonia
Authors: Lebouvier Nicolas , Lawes Douglas , Hnawia Edouard , Page Michael , Brophy Joseph , Nour Mohammed
Published: March 2019

The leaf, wood and bark oils of three species of Myodocarpus, M. viellardii Brongn. & Gris, M. fraxinifolius Brongn. & Gris and M. lanceolatus Dubard & R. Viguier have been examined. From the wood oil of M. viellardii the major components were α-pinene (22.4%) and a monoterpene methyl ester, methyl myodocarpate (methyl 3,7-dimethylbicyclo [4,1,0]hept-3-ene-7-carboxylate) (61%), based on the δ-3-carene skeleton. Also present in lesser amounts was the corresponding acid, myodocarpic acid (3,7-dimethylbicyclo[4,1,0]hept-3-ene-7-carboxilic acid) and the corresponding alcohol, myodocarpol (3,7-dimethylbicyclo[4,1,0]hept-3-en-7-yl) methanol), in lesser (<3%) amounts. The bark oil contained β-caryophyllene (13.8%) and a series of long chain fatty alcohols, dodecanol, tetradecanol, hexadecanol, octadecanol and octadec-9-en-1-ol in amounts of 1.4–15% (all but octadecanol >11%). The leaf oil of this species produced a sesquiterpenic oil with the principal components being β-caryophyllene (36%), α-humulene (11.1%) and bicyclogermacrene (10.6%). In M. fraxinifolius, both the wood and bark oils contained a series of long chain alcohols, tetradecanol (30–38%), hexadecanol (23–29%) and octadec-9-en-1-ol (12%) as principal components. In the leaf oil of this species the principal component was β-caryophyllene (63%), with lesser amounts of humulene oxide II (2.9%), isocomene (2.8%) and viridiflorol (1.4%). In M. lanceolatus, the leaf oil was dominated by the monoterpene hydrocarbons α-pinene (22.9%) and 5–3-carene (32.6%). In the wood oil of this species the principal components were geraniol (7.4%), citronellol (4.7%), germacrene-B (7.1%), zingiberine (6.8%) and linalool (6.7%), while in the bark oil they were geraniol (12.4%), citronellol (2.6%), germacrene-B (5.8%), and linalool (6.5%).
Iridoids and a Norsesquiterpenoid from the Leaves of Villaria odorata
Authors: Tan Mario A. , Villacorta Raychel Ann U. , Alejandro Grecebio Jonathan D. , Takayama Hiromitsu
Published: March 2019

Phytochemical investigation of Villaria odorata, a Philippine endemic Rubiaceae species, led to the identification of three iridoids, morindolide (1), hydrophylinA (2), hydrophylin B (3) and a norsesquiterpenoid, vomifoliol (4). This is the first report of compounds 1–4 from the genus Villaria. These classes of compounds proved to be important chemotaxonomic markers in the Rubiaceae family in combination with morphology and molecular data.
Diterpenoids from Fagonia mollis
Authors: Sallam Amal , Nugroho Alfarius Eko , Hirasawa Yusuke , Chin-Piow Wong , Kaneda Toshio , Shirota Osamu , Gedara Sahar R. , Morita Hiroshi
Published: March 2019

A new acyclic diterpenoid (1) and a new erythroxan diterpenoid (2), together with 4 erythroxan diterpenoids and 3 triterpenoids, have been isolated from the aerial parts of Fagonia mollis. Their structures were elucidated on the basis of 1D and 2D NMR data. The cytotoxic activity of the isolated compounds was investigated against HL-60 cancer cells.
Cytotoxicity of the Diterpene 14-O-Methyl-ryanodanol from Erythroxylum passerinum in an Astrocytic Cells Model
Authors: de Jesus Menezes-Filho Noélio , Souza Cleide dos Santos , Costa Tereza Cristina Silva , da Silva Victor Diógenes Amaral , de Oliveira Ribeiro Cátia Suse , Barreiros Marizeth Liborio , Costa Jose Fernando Oliveira , David Jorge Mauricio , David Juceni P.L. , Costa Silvia Lima
Published: March 2019

Plant secondary metabolites, such as, specifically, alkaloids and terpenes, may present psychoactive properties that modify the function of the central nervous system (CNS) and induce neurotoxicity. Neurotoxicity involves the response of glial cells, mainly astrocytes, which play a fundamental role in the control of homeostasis of the CNS. Some Erythroxylum species are indigenous to the state of Bahia in Brazil. This study investigated the cytotoxic activity of the diterpene AEP-1, extracted from the fruit of E. passerinum in a GL-15 cell line, astrocytic, glial cells model. The effects on cell viability, analyzed by the MTT assay, demonstrated a dose-dependent cytotoxic effect, with maximum effect at 500 μg/mL of AEP-1, and with a reduction of about 40 and 47% on cellular viability after 24 h and 72 h treatment, respectively. Evidence for induction of apoptosis by AEP-1 was first obtained when GL-15 glial cells were incubated with 250 μg/mL AEP-1 causing reniform and/or pyknotic nuclei and apoptotic bodies revealed by chromatin staining with Hoechst 33258. Increase in DNA fragmentation was also observed by comet assays in cells incubated with 500 μg/mL of AEP-1. Moreover, cells exposed to a sub toxic dose of AEP-1 (250 μg/mL) showed significant changes in morphology – contraction of the cytoplasm and expansion of cellular projections – signifying the presence of astrocytic cytoskeletal protein and glial fibrillary acidic protein (GFAP). These findings indicated astrocytic cells as the target for terpene AEP-1 and suggest the involvement of glial cells with psychoactive symptoms observed in humans and animals after consumption of fruits of plants of the genus Erythroxylum.
Absolute Configuration of Cembrane Diterpenoids from Bursera multijuga
Authors: Hernández-Hernández Juan D. , García-Gutiérrez Hugo A. , Román-Marín Luisa U. , Torres-Blanco Yunuen I. , Cerda-García-Rojas Carlos M. , Joseph-Nathan Pedro
Published: March 2019

The stems of Bursera multijuga afforded (-)-(1 S,3 E,7 R,8 R,11 E)-7,8-epoxycembra-3,11-dien-1-ol (1) and its acetate 2, together with cembrene A (3), nephthenol (4), and cembrenol (5). The structures of 1 and 2 were elucidated by 1D and 2D NMR, HRESIMS, and X-ray diffraction. The conformational preference of flexible 1 was studied by molecular modeling at the DFT B3LYP/DGDZVP level of theory. Good agreement between calculated and experimental vibrational circular dichroism curves established the absolute configuration of 1. This is the first time that cembrane derivatives have been isolated from the genus Bursera.
Three New Steroid Biglycosides, Plancisides A, B, and C, from the Starfish Acanthaster planci
Authors: Kicha Alla A. , Dinh Thi H. , Ivanchina Natalia V. , Malyarenko Timofey V. , Kalinovsky Anatoly I. , Popov Roman S. , Ermakova Svetlana P. , Tran Thi T. T. , Doan Lan P.
Published: March 2019

Three new steroid biglycosides, plancisides A-C (1-3), were isolated from the ethanolic extract of the starfish Acanthaster planci. The structures of 1-3 were determined by extensive NMR and ESI-MS techniques, as (24 S)-28- O-[β-D-galactofuranosyl-(1→5)-α-L-arabinofuranosyl]-24-methyl-5α-cholestane-3β,4β,6α,8,15β,16β,28-heptol (1), (24 S)-28- O-[α-L-fucopyranosyl-(1→2)-3- O-methyl-β-D-xylopyranosyl]–24-methyl-5α-cholestane-3β,4β,6α,8,15β,16β,28-heptol (2) and (24 S)-28- O-[2,4-di- O-methyl-β-D-xylopyranosyl-(1→2)-α-L-arabinofuranosyl]-24-methyl-5α-cholestane-3β,4β,6α,8,15β,16β,28-heptol 6- O-sulfate (3), respectively. Compound 2 is the first steroid glycoside containing an α-fucopyranose unit found from starfish. Compound 1 slightly inhibits cell proliferation of HCT-116, T-47D, and RPMI-7951 cancer cell lines, but has no effect on colony formation of these cells in a soft agar clonogenic assay.
Antimicrobial Metabolites from Endophytic Streptomyces sp. YIM61470
Authors: Yang Xueqiong , Liu Yun , Li Shuquan , Yang Fangfang , Zhao Lixing , Peng Li , Ding Zhongtao
Published: March 2019

Six compounds were isolated from Streptomyces sp. YIM61470, and their structures elucidated by spectral analysis as ( R)-1- O-(phenylacetyl)glycerol (1), 4′,5-dihydroxy-6-(3,3–dimethylallyl)-7-methoxyflavanone (2), (32 R,33 R,34 S)-32,33,34,35-bacteriohopanetetrol (3), MKN-003C (4), cyclo (L-Pro-L-Gly) (5), and cyclo(L-Pro-L-Tyr) (6). Compound 1, an chiral monoacylglycerol, was isolated from a natural source for the first time. Compound 2 was first found in microorganisms, and compound 3, a bacteriohopanoid, was found first in the genus Streptomyces. Compounds 1-6 showed weak anti-microbial activity.
Genkwanin 4′-O-glucosyl-(1→2)-rhamnoside from New Chemotype of Asplenium normale in Japan
Authors: Fujiwara Tao , Uehara Ayumi , Kitajima Junichi , Iwashina Tsukasa , Matsumoto Sadamu , Watano Yasuyuki
Published: March 2019

New flavone glycoside, genkwanin 4′- O-β-glucopyranosyl-(1→2)- O-α-rhamnopyranoside was isolated from the fronds of new chemotype of Asplenium normale D.Don, together with two known C-glycosylflavones, vicenin-2 and lucenin-2. The chemical structure of the isolated glycoside was established by UV, LC-MS, characterization of acid hydrolysates, and 1H and 13C NMR spectroscopy.
Potent SIRT1 Enzyme-stimulating and Anti-glycation Activities of Polymethoxyflavonoids from Kaempferia parviflora
Authors: Nakata Asami , Koike Yuka , Matsui Hirofumi , Shimada Tsutomu , Aburada Masaki , Yang Jinwei
Published: March 2019

The SIRT1 enzyme-stimulating and anti-glycation activities of Kaempferia parviflora extract and its main polymethoxyflavonoids were evaluated in vitro. K. parviflora extract elevated SIRT1 catalytic activity by eight- and 17-fold at 20 μg/mL and 100 μg/mL, respectively, compared with vehicle only. Two major polymethoxyflavonoids, 3,5,7,3′,4′-pentamethoxyflavone (4) and 5,7,4′-trimethoxyflavone (5), were isolated from this extract and are four- and fivefold more potent than resveratrol, hitherto the strongest known natural SIRT1 activator. In addition, the anti-glycation activity of K. parviflora extract was observed to be seven times more effective than aminoguanidine, a clinical anti-diabetes drug. 3,5,7,3′,4′-Pentamethoxyflavone (4) and 5,7,4′-trimethoxyflavone (5) showed the strongest anti-glycation activity among the tested polymethoxyflavonoids. Further comparison of the activity of these structurally related polymethoxyflavonoids revealed a possible structure-activity relationship, in particular, for the contribution of methoxy moieties.
Protective Activity of C-Geranylflavonoid Analogs from Paulownia tomentosa against DNA Damage in 137Cs Irradiated AHH-1Cells
Authors: Moon Hyung-In , Jeong Min Ho , Jo Wol Soon
Published: March 2019

Radiotherapy is an important form of treatment for a wide range of cancers, but it can damage DNA and cause adverse effects. We investigated if the diplacone analogs of P. tomentosa were radio-protective in a human lymphoblastoid cell line (AHH-1). Four geranylated flavonoids, diplacone, 3′- O-methyl-5′-hydroxydiplacone, 3′- O-methyl-5′- O-methyldiplacone and 3′- O-methyldiplacol, were tested for their antioxidant and radio-protective effects. Diplacone analogs effectively scavenged free radicals and inhibited radiation-induced DNA strand breaks in vitro. They significantly decreased levels of reactive oxygen species and cellular DNA damage in 2 Gy-irradiated AHH-1 cells. Glutathione levels and superoxide dismutase activity in irradiated AHH-1 cells increased significantly after treatment with these analogs. The enhanced biological anti-oxidant activity and radioprotective activity of diplacone analogs maintained the survival of irradiated AHH-1 cells in a clonogenic assay. These data suggest that diplacone analogs may protect healthy tissue surrounding tumor cells during radiotherapy to ensure better control of radiotherapy and allow higher doses of radiotherapy to be employed.
Anti-proliferation Effect on Human Breast Cancer Cells via Inhibition of pRb Phosphorylation by Taiwanin E Isolated from Eleutherococcus trifoliatus
Authors: Wang Hui-Chun , Tseng Yen-Hsueh , Wu Hui-Rong , Chu Fang-Hua , Kuo Yueh-Hsiung , Wang Sheng-Yang
Published: March 2019

Eleutherococcus trifoliatus has been used as a folk medicine since ancient times, especially as refreshing qi medicines. In our current study, taiwanin E, which possesses strong cytotoxicity, was isolated from the branches of E. trifoliatus by using a bioactivity guided fractionation procedure. Taiwanin E presented a potent anti-proliferation activity on the growth of a human breast adenocarcinoma cell line (MCF-7), with an IC50 value for cytotoxicity of 1.47 μM. Cell cycle analysis revealed that the proportion of cells in the G0/G1 phase increased in a dose-dependent manner (from 79.4% to 90.2%) after 48 h exposure to taiwanin E at a dosage range from 0.5 to 4μM. After treatment with taiwanin E, phosphorylation of retinoblastoma protein (pRb) in MCF-7 cells was inhibited, accompanied by a decrease in the levels of cyclin D1, cyclin D3 and cyclin-dependent kinase 4 (cdk4) and cdk6; in addition, there was an increase in the expression of cyclin-dependent kinase inhibitors p21WAF-1/Cip1 and p27Kip1. The results suggest that taiwanin E inhibits cell cycle progression of MCF-7 at the G0/G1 transition.
Bioactive Metabolites from Cnidoscolus souzae and Acmella pilosa
Authors: Zapata-Estrella Hiatzy E. , Sánchez-Pardenilla Azeret D. M. , García-Sosa Karlina , Escalante-Erosa Fabiola , de Campos-Buzzi Fátima , Meira-Quintão Nara Lins , Cechinel-Filho Valdir , Peña-Rodríguez Luis M.
Published: March 2019

The bioassay-guided purification of the ethanol extracts of Acmella pilosa and Cnidoscolus souzae, two plants of the native flora of the Yucatan Peninsula used in traditional medicine to treat inflammation and pain, resulted in the identification of rosmarinic acid (1) and caffeic acid (2) as the bioactive metabolites from A. pilosa, and of 7-deoxynimbidiol (4) as the major bioactive metabolite from C. souzae. Metabolites 1, 2, and 4 proved to be responsible for the antioxidant activity originally detected in the corresponding organic crude extracts; 7-deoxynimbidiol (4) showed good analgesic and anti-inflammatory activities, inhibiting the pain induced by PGE2 and reducing the edema induced by carrageenan, respectively.
Dipterostilbenosides A and B, Oligostilbene Glycosides from Dipterocarpus tuberculatus
Authors: Surapinit Serm , Jong-aramruang Jonkolnee , Siripong Pongpun , Khumkratok Suttira , Tip-pyang Santi
Published: March 2019

From the chemical investigation of the methanolic extract of the roots of the Thai dipterocarp, Dipterocarpus tuberculatus, two new oligostilbene glycosides, dipterostilbenes A (1) and B (2), were isolated together with four known stilbenes. Their structures and relative configurations were determined on the basis of spectroscopic data. From an evaluation of cytotoxic activity against KB and HeLa cell lines, α-viniferin (5) and (-)-hopeaphenol (6) showed potent activity, but less than that of doxorubicin.
Galactans of Gracilaria pudumadamensis (Gracilariales, Rhodophyta) of Indian Waters
Authors: Kondaveeti Stalin , Kumar Sanjay , Ganesan Meenakshi S. , Siddhanta Arup K.
Published: March 2019

Galactans from the Indian agarophyte Gracilaria pudumadamensis were extracted and characterized. The isolated native (GPNative) and alkali treated (GPAlkali) galactans were characterized by IR, 13C NMR, GC-MS and GPC. It was found that GPNative and GPAlkali were composed mainly of 3,6-anhydro L-galactose, 6- O-methylated D-galactose and galactose in various mole proportions (15.6:69.9:17.5 mole% for GPNative and 20.2:69.8:10.0 mole% for GPAlkali). The GPNative and GPAlkali exhibited low gel strengths (<100 g/cm2) and high melting points (~76 °C), which may be due to the presence of high 6- O-Me-galactose contents. The latter, having low sulfate (2.1%), was by far the greatest 6- O-Me-galactose containing polysaccharide in a Gracilaria spp. reported in the literature. This methylated agar contained very low heavy metal ions estimated by inductively coupled plasma spectrophotometry (ICP). The results of this investigation would be useful in bioprospecting of agarophytes, especially those occurring in Indian waters and would be potentially useful in food, personal care and related domains.
Comparative Anti-inflammatory Effects of Anti-arthritic Herbal Medicines and Ibuprofen
Authors: Kang Joshua J. , Samad Mohammed A. , Kim Kye S. , Bae Soochan
Published: March 2019

Non-steroidal anti-inflammatory drugs (NSAIDS), such as ibuprofen, are widely used over-the-counter drugs to treat arthritis, but they are often associated with side effects. Herbal medicines have been used to treat various diseases such as arthritis, but the scientific profiles are not well understood. In this study, we examined, in comparison with ibuprofen, the inhibitory effects on various inflammatory markers of the most commonly used herbal medicines to treat arthritis, boswellia (Boswellia sapindales), licorice (Glycyrrhiza glabra), guggul (Commiphora wightii), and neem (Azadirachta indica). To elicit inflammatory response, we exposed mouse myoblast C2C12 cells to lipopolysaccharide (LPS). Tumor necrosis factor-alpha (TNF-α) and monocyte chemotactic protein-1 (MCP-1), which are cytokines activated during an inflammatory response, were determined. The optimal non-toxic concentration was determined by exposing different concentrations of drugs (from 0.01 to 10 mg/mL). Cell death measurement revealed that the drug concentrations lower than 0.05 mg/mL were non-toxic concentrations for each drug, and these doses were used for the main experiments. We found that neem and licorice showed robust anti-inflammatory responses compared with ibuprofen. However, boswellia and guggul did not demonstrate significant anti-inflammatory responses. We concluded that neem and licorice are more effective than ibuprofen in suppressing LPS-induced inflammation in C2C12 cells.
Composition and Chemical Variability of Corsican Pinus halepensis Cone Oil
Authors: Nam Anne-Marie , Casanova Joseph , Tomi Félix , Bighelli Ange
Published: March 2019

The composition of the essential oil isolated from cones of Pinus halepensis grown in Corsica has been investigated by a combination of chromatographic (CC, GC) and spectroscopic (MS, 13C NMR) techniques. In total, 48 compounds that accounted for 95.5% of the whole composition have been identified. α-Pinene (47.5%) was the major component followed by myrcene (11.0%), ( E)-β-caryophyllene (8.3%) and caryophyllene oxide (5.9%). Various diterpenes have been identified by 13C NMR in the fractions of CC. Fifteen oil samples isolated from cones harvested in three forests have been analyzed and two groups of similar importance have been differentiated within the 15 compositions. Oil samples of the first group contained α-pinene (mean 45.0 g/100 g, SD = 5.5) as the major component. The composition of samples of the second group was dominated by myrcene (mean 30.3 g/100g, SD = 9.0) and α-pinene (mean 24.6 g/100 g, SD = 3.1).
Hawaiian Sandalwood: Oil Composition of Santalum paniculatum and Comparison with Other Sandal Species
Authors: Braun Norbert A. , Sim Sherina , Kohlenberg Birgit , Lawrence Brian M.
Published: March 2019

Four commercial qualities of Hawaiian sandalwood oil produced from wood of Santalum paniculatum originating from the island of Hawaii (“The Big Island”) were analyzed using GC and GC-MS. Main constituents of the oils were ( Z)-α-santalol (34.5–40.4%) and ( Z)-β-santalol (11.0–16.2%). An odor evaluation of the oils was carried out against East Indian sandalwood oil. In addition, the chemical composition of Hawaiian sandalwood oil was compared with four different Santalum species originating from East India, New Caledonia, Eastern Polynesia and Australia, respectively.
Aroma Compounds of Mountain Tea (Sideritis scardica and S. raeseri) from Western Balkan
Authors: Qazimi Bujar , Stefkov Gjoshe , Karapandzova Marija , Cvetkovikj Ivana , Kulevanova Svetlana
Published: March 2019

The composition of the volatile aroma components was defined in the dried and fresh aerial parts of Sideritis scardica Griseb. from R. Macedonia and S. raeseri Boiss. & Heldr. from R. Macedonia, Albania and Greece. Analysis was made by gas chromatography (GC/FID/MS) equipped with a headspace (HS) sampler. Thirty-two components (15 monoterpenes representing 33.2–62.8% and 17 sesquiterpenes representing 25.2–51.2% of the entire volatiles) were identified as aroma components of dried plant material of S. scardica. Thirty components {14 monoterpenes (19.3–74.2%), 2 alcohols (6.2–38.4%) and 14 sesquiterpenes (18.2–33.5%)} were identified as aroma components in the fresh aerial parts of S. scardica. The predominant components were trans-caryophyllene, β-pinene, α-pinene and 1-octen-3-ol, which were found only in the fresh samples. In the aerial parts of S. raeseri, 43 components were identified in the dried samples {22 monoterpenes (65.7–94.3%) and 21 sesquiterpenes (5.4–27.8%)} and 29 components {15 monoterpenes (77.3–90.7%) and 14 sesquiterpenes (6.3–18.2%)} in the respective fresh samples. Prevailing components in all tested samples of S. raeseri were β-pinene, α-pinene, α-copaene, sabinene and limonene. Only minor differences were revealed in the qualitative composition of the aroma volatiles between the dried and fresh plant material of both species. Furthermore there was almost no difference in the chemical profiles of the aroma compounds between S. scardica and S. raeseri, except for 1-octen-3-ol, which was present only in fresh S. scardica.
Compositional Analysis and in vitro Protective Activity against Oxidative Stress of Essential Oils from Egyptian Plants Used in Traditional Medicine
Authors: Eissa Tarek F. , González-Burgos Elena , Carretero M. Emilia , Gómez-Serranillos M. Pilar
Published: March 2019

The Sinai desert in Egypt contains great variability in plants extensively used for traditional medicines such as Achillea fragrantissima, Chiliadenus montanus, Mentha longifolia and Haplophyllum tuberculatum. The essential oils extracted by hydrodistillation from the aerial parts have been analyzed. Subsequently, their potential protective activity against oxidative stress has been evaluated, employing H2O2 as oxidant inductor and astrocytes as the cell model. The chemical composition of the essential oils was analyzed by GC/MS. Most of the compounds identified in A. fragrantissima and M. longifolia samples were oxygenated monoterpene derivatives, whereas for H. tuberculatum they were monoterpenes hydrocarbons and oxygenated compounds, and for C. montanus oxygenated monoterpenes and oxygenated sesquiterpenes predominated. The in vitro evaluation of antioxidant properties, using ORAC assay, revealed that M. longifolia essential oil possessed the highest scavenging activity against peroxyl radicals, following by H. tuberculatum, A. fragrantissima and C. montanus. Under oxidative stress conditions, M. longifolia and H. tuberculatum essential oils were the only ones that protected human astrocytoma U373-MG cells against H2O2 damage. Both essential oils prevented cell death and inhibited ROS production caused by H2O2. M. longifolia essential oil was the most active, suggesting an interesting prevention role in those CNS disorders associated with oxidative stress.
The Essential Oil Profiles and Antibacterial Activity of Six Wild Cinnamomum species
Authors: Vairappan Charles Santhanaraju , Nagappan Thilahgavani , Kulip Julius
Published: March 2019

The essential oil composition of six species of wild Cinnamomum found in Borneo was investigated. The oils were obtained from bark by hydrodistillation and the volatile chemical profile was obtained via Gas Chromatography-Mass Spectrometry (GCMS). A total of 65 volatile constituents were identified, where the essential oils of the studied specimens contained high contents of oxygenated monoterpenes. Eucalyptol (1.2~31.1 %), terpinen-4-ol (7.9~22.1 %), eugenol (0.4~37.9 %) and α-cadinol (0.4~1.8 %) were detected consistently in the specimens studied. The oils of C. cuspidatum and C. crassinervium exhibited significant inhibition against Listeria monocytogenes, specifically the latter, which displayed a lower minimum bactericidal concentration (MBC) value against Staphylococcus aereus and L. monocytogenes. This result had highlighted the possible usage of the essential oil derived from wild cinnamom species against food borne pathogens.
Diterpene Foliar Exudates of Blakiella bartsiifolia and Phytotoxicity of Clerodanes
Authors: Rodriguez-Hernandez Diego , Oliveros-Bastidas Alberto , Alonso-Amelot Miguel E. , Calcagno-Pissarelli Maria Pia
Published: March 2019

Blakiella bartsiifolia (S.F. Blake), an endemic and rare high altitude plant of the northern Andes, appears well adapted to the prevailing harsh environment owing in part to a thick glandular trichome cover. From foliar exudates, two new clerodanes, 15,16-epoxy-2-hydroxy-3,13(16),14-clerodatrien-20-oic acid (bartsiifolic acid) (2) and Z-15,16-dihydroxy-3,13-clerodien-20-oic acid (barthydrolic acid) (3), were isolated in addition to the known junceic acid (1). In addition, three new alicyclic furanoditerpenes: 1,20-epoxy-1,3(20),6( E),10( E),14-phytapentaen-18-methyl-19-oic acid (blakielic acid) (4), 1,20-epoxy-1,3(20),10( E),14-phytapentaen-18-methyl-19-oic acid (blakifolic acid) (5) and 1,20-epoxy-1,3(20),6,14-phytatetraen-19-methyl-18-oic acid (dihydrocentipedic acid) (6) were obtained in minor quantity. Seed germination and plantlet growth bioassays on Allium cepa and Lactuca sativa to monitor bioactivity during isolation procedures revealed compounds 1–3 with substantial inhibition comparable with synthetic linuron.
A New 1,6-Benzoxazocine-5-one Alkaloid isolated from the Aerial Parts of Peristrophe lanceolaria
Authors: Prapalert Wasana , Santiarworn Dammrong , Liawruangrath Saisunee , Liawruangrath Boonsom , Pyne Stephen G.
Published: March 2019

A new 1,6-benzoxazocine-5-one alkaloid has been isolated as its butyl acetal derivative (1) along with peristrophine from the n-BuOH and EtOAc fractions of the crude MeOH extract of the aerial parts of Peristrophe lanceolaria growing in Thailand. The structures of these compounds were elucidated on the basis of their spectroscopic data. These compounds were isolated for the first time from P. lanceolaria. The EtOAc and n-BuOH fractions also possessed significant antioxidant activity with IC50 values of 57 and 50 μg/mL, respectively (DPPH method), whereas 1 had an IC50 value of 23 μg/mL.
Comparative Analysis of Therapeutically Important Indole Compounds in in vitro Cultures of Hypericum perforatum Cultivars by HPLC and TLC Analysis Coupled with Densitometric Detection
Authors: Muszyńska Bożena , Ekiert Halina , Kwiecień Inga , Maślanka Anna , Zodi Rawad , Beerhues Ludger
Published: March 2019

Five indole compounds (5-hydroxy-L-tryptophan, L-tryptophan, indole-3-acetic acid, melatonin, serotonin) and hypericin were identified and quantified in methanolic extracts of shoot cultures of three Hypericum perforatum cultivars (Helos, Elixir, Topas) growing on two variants of Murashige -Skoog medium differing in concentrations of growth regulators (naphthalene-1-acetic acid and 6-benzylaminopurine). Extracts of the aboveground parts of field-grown plants ( Hyperici herba) were also analyzed by HPLC and TLC analysis coupled with densitometric detection. Determination of four compounds was based on our assay described earlier. The methods of determination of 5-hydroxy-L-tryptophan and hypericin were developed and validated in this study. The composition and contents of the metabolites under study differed between the cultivars cultured in vitro and between medium variants containing diverse contents of growth regulators. The contents of individual indole compounds in the biomass from in vitro cultures ranged from 39.6 to 343.2 mg/100 g dry mass. 5-Hydroxy-L-tryptophan was the dominating metabolite (from 78.2 to 343.2 mg/100 g dry mass). Extracts from shoots of the cultivar Helos also contained high contents of serotonin (319.9 and 197.4 mg/100 g dry mass). The contents of indole compounds in Hyperici herba were also diverse (from 7.1 to 55.3 mg/100 g dry mass). 5-Hydroxy-L-tryptophan was the dominating metabolite as well. Hypericin content of Hyperici herba, equaling 12.2 mg/100 g dry mass was from 3.3 to 10 times higher than in extracts from shoots cultured in vitro. The present report is the first analysis of endogenous accumulation of indole compounds in Hyperici herba which involves, apart from melatonin, four other compounds.
Monoterpene Indole Alkaloids from the Twigs of Kopsia arborea
Authors: Cheenpracha Sarot , Raksat Achara , Ritthiwigrom Thunwadee , Laphookhieo Surat
Published: March 2019

The phytochemistry of Kopsia arborea Blume has received considerable attention, which has resulted in the isolation of a number of new unusual indole alkaloids with intriguing structures. In this study, a new eburnane-type alkaloid, phutdonginin (1), together with eight known alkaloids: 19-OH-(-)-eburnamonine (2), melodinine E (3), kopsinine (4), kopsilongine (5), kopsamine (6), (-)-methylenedioxy-11,12-kopsinaline (7), decarbomethoxykopsiline (8), and vincadifformine (9), were isolated from the twigs of K. arborea. Their structures were characterized extensively by 1D and 2D NMR spectroscopy and HR-ESI-MS. All compounds were submitted to TLC screening for acetylcholinesterase inhibitory activities. Only kopsamine and decarbomethoxykopsiline showed AChE inhibition with MIR values of 12.5 and 6.25 μg, respectively, compared with galanthamine (positive control, 0.004 μg). In addition, compounds 1 and 2 inhibited moderate antibacterial activity against E. coli TISTR 780 with the MIC value of 32 μg/mL.
Isolation, Identification and Usefulness of Antifungal Compounds from Zuccagnia punctata for Control of Toxigenic Ear Rot Pathogens
Authors: Jimenez Cristina M. , Sampietro Diego A. , Sgariglia Melina A. , Soberón José R. , Vattuone Marta A.
Published: March 2019

Infusion, tincture and decoction of leaves of Zuccagnia punctata Cav. were assayed on growth of Fusarium verticillioides, F. graminearum sensu stricto, F. boothii, F. meridionale, F. subglutinans and F. thapsinum. The tincture showed the lowest IC50 on mycelial growth. A diethyl ether fraction of the tincture showed the highest antifungal activity in microdilution assays on F. verticillioides and F. graminearum. The antifungal constituents were separated by silica gel chromatography and identified as 2′,4′-dihydroxychalcone, 2′,4′-dihydroxy-3′-methoxychalcone and 7-hydroxy-3′,4′-dimethoxyflavone. These chalcones had the lowest MIC and MFC values on F. verticillioides and F. graminearum sensu stricto. 2′,4′-Dihydroxychalcone was mildly toxic and the remaining identified compounds were non-toxic in the brine shrimp assay. 2′,4′-Dihydroxychalcone in mixtures with commercial food preservatives showed additive effects on F. graminearum sensu stricto and synergistic ones on F. verticillioides. 2′,4′-Dihydroxy-3′-methoxychalcone showed synergistic effects in mixtures. Our results suggest that addition of chalcones to food preservatives allows reduction in the doses of the preservatives required for control of Fusarium species.
Identification and Evaluation of Flavone-glucosides Isolated from Barley Sprouts and their Inhibitory Activity against Bacterial Neuraminidase
Authors: Park Mi Jin , Ra Ji-Eun , Seo Kyung Hye , Jang Ki-Chang , Han Sang-Ik , Lee Jin-Hwan , Kang Young-Hwa , Nam Min-Hee , Seo Woo Duck
Published: March 2019

Neuraminidase (NA) is one of the key enzymes responsible for bacterial infection and pathogenesis. This study aimed to gain deeper insights into the inhibitory effects of flavone-glucosides (1–9) isolated from barley sprouts (BS) on neuraminidase activity. The isolated compounds were identified as, lutonarin (1), saponarin (2), isoorientin (3), orientin (4), isovitexin (5), isoscoparin-7- O-[6-sinapoyl]-glucoside (6), isoscoparin-7- O-[6-feruloyl]-glucoside (7), isovitexin-7- O-[6-sinapoyl]-glucoside (8), and isovitexin-7- O-[6-feruloyl]-glucoside (9). Among them, compounds 1–5 exhibited neuraminidase-inhibitory activities in a dose-dependent manner, with IC50 values ranging from 20.1 to 32.7 μM, in a non-competitive inhibition mode according to kinetic studies. Moreover, the individual flavone-glucoside levels differed notably, in particular, lutonarin (1) and saponarin (2) were shown to be present in the greatest amounts, according to UPLC analysis. Consequently, our results suggest that BS may be utilized as an effective NA inhibitor in human health food, additives, and feed.
Polyphenol Composition and Antioxidant Capacity of Three Lysimachia Species
Authors: Toth Anita , Toth Gergo , Kery Agnes
Published: March 2019

The polyphenol composition and antioxidant properties of three Lysimachia species ( L. nummularia L., L. vulgaris L. and L. punctata L.) and their column chromatographic fractions were investigated. The antioxidant activity of herb extracts and 54 different column chromatographic fractions was evaluated using in vitro DPPH• and ABTS•+ decolorization tests. The total polyphenol content was determined by spectrophotometric methods. The phenolic compounds of extracts of different Lysimachia species and their bioactive fractions were characterized by online chromatographic methods. For identification of the compounds, UV spectral data, accurate molecular mass and formula, as well as MS and fragmentation patterns given by LC-DAD-ESI/MS/MS and LC-ESI-TOF analyses were used. Quantification of the compounds was performed by LC-DAD using an external standard method. In the extracts, caffeic acid derivatives, chlorogenic acid, free flavonoid aglycones, and 11 various flavonoid glycosides were identified. Flavonoid composition of Lysimachia extracts showed significant differences. L. punctata extracts had the strongest DPPH• and ABTS•+ radical scavenger activity (IC50=43.3 μg/mL and 21.3 μg/mL), due to their high myricitrin and quercetin-hexoside content. Correlation between polyphenol content and radical scavenging activity of each column chromatographic fractions is also included.
Phenolic Content, Antioxidant and Astroprotective Response to Oxidative Stress of Ethanolic Extracts of Mentha longifolia from Sinai
Authors: Eissa Tarek F. , González-Burgos Elena , Carretero M. Emilia , Gómez-Serranillos M. Pilar
Published: March 2019

The aerial parts of Mentha longifolia L. are used as herbal remedies for curing different diseases through traditional Bedouin medicine. The antioxidant activity of the ethanolic extracts of M. longifolia was investigated measuring peroxyl radical-scavenging activity by ORAC assay, with Trolox (a water-soluble analogue of α-tocopherol) employed as reference compound. In addition, the total content of phenolic compounds estimated by the Folin-Ciocalteau method and the identification of the polyphenols using high-performance liquid chromatography coupled with mass spectrometry (HPLC-MS) have been performed. Furthermore, the effect of these extracts on cell viability and intracellular ROS production was assayed using the U373-MG human astrocytoma cell line in a H2O2-induced oxidative stress model. Results showed that the major type of polyphenols found were benzoic acids, cinnamic acids, flavones and flavanones. The total phenolic content was 37.7 mg gallic acid/g sample and the ORAC value was 1.355 μmol TE/mg sample. The data obtained in cellular assays demonstrated that these ethanolic extracts protected H2O2-induced astrocyte damage by increasing cell viability and inhibiting production of intracellular ROS. These results suggest that the investigated extracts obtained from the aerial parts of M. longifolia have antioxidant potential related to their phenol content which have important beneficial health effects, especially in those disease associated with ROS.
Antibacterial Compounds from the Roots of Cratoxylum formosum spp. pruniflorum
Authors: Raksat Achara , Laphookhieo Surat , Cheenpracha Sarot , Ritthiwigrom Thunwadee , Maneerat Wisanu
Published: March 2019

Phytochemical investigation of the roots of Cratoxylum formosum spp. pruniflorum led to the isolation and identification of a new xanthone, namely cratopruniforone (1), together with 13 known compounds (2–14). Some of these more abundant compounds were evaluated for their antibacterial activities.
Stimulation of Phosphorylation of ERK and CREB by Phellopterin and Auraptene Isolated from Citrus junos
Authors: Nakamura Mitsuhiro , Suzuki Tomoko , Takagi Mai , Tamura Hirotoshi , Masuda Toshiya
Published: March 2019

Bioactive compounds from citrus fruits contribute many benefits to human health. Extracellular signal-regulated kinase (ERK) signaling plays an important role in the regulation of multiple cellular processes. Activation of the ERK-cAMP response element binding protein (CREB) signaling is required for long-term memory formation. In this study, auraptene, phellopterin, thymol, coniferyl alcohol 9-methyl ether and methyl ferulate were isolated from Citrus junos. Among the five compounds isolated, auraptene and phellopterin increased the phosphorylation of ERK and CREB. This study provides, to our knowledge, the first evidence that phellopterin potently stimulates the phosphorylation of ERK and CREB. Phellopterin could be a novel neuroprotective agent.
A New Aggreceride Analogue and a Peltogynoid Isolated from the Stem Bark of Entada abyssinica (Fabaceae)
Authors: Melong Raduis , Kapche Deccaux G. F. W. , Feussi Michel T. , Laatsch Hartmut
Published: March 2019

A new monoglyceride, 1′,26′-bis-[( S)-2,3-dihydroxypropyl] hexacosanedioate (1a) and the new peltogynoid, entadanin (3), along with eight known compounds, were isolated from the stem bark of Entada abyssinica (Fabaceae). The structures of the new compounds were determined by detailed analyses of 1D and 2D NMR spectra, in combination with high-resolution mass spectrometry data, and by comparison with related data from the literature. The stereochemistry of 1a was derived by comparison of the optical rotation with reference data. Peltogynoids have been reported previously from other Fabaceae, however this is the first report of a peltogynoid from the genus Entada.
Chemical Composition of the Essential Oil of Ligularia hodgsonii and Free Radical Scavenging Activity of the Oil and Crude Extracts
Authors: Zhou Zihao , Tang Jun , Song Xueping
Published: March 2019

The chemical composition of the essential oil from roots and rhizomes of Ligularia hodgsonii was analyzed by gas chromatography (GC) and GC-mass spectrometry (MS). Forty-seven components were identified, representing 77.0% of the total oil. The main constituents were l-(+)-ascorbic acid 2,6-dihexadecanoate (15.7%), selina-6-en-4-ol (8.4%) and 9,10-dimethyl-1,2,3,4,5,6,7,8-octahydroanthracene (6.6%). The free radical scavenging activities of the essential oil, aqueous extract, ethanolic extract, and crude polysaccharides of L. hodgsonii, as well as some of their major components, were investigated using DPPH and ABTS assays. The essential oil displayed a lower capacity to quench free radicals than the extracts; the ethanolic and aqueous extracts showed considerably higher antioxidant potential that deserves further study.
Essential Oil from the Heartwood of Taiwan fir Ameliorates LPS-induced Inflammatory Response by Inhibiting the Activation of Mitogen-activated Protein Kinase
Authors: Liu May-Lan , Hua Kuo-Feng , Yang Tzu-Jung , Chiu Huan-Wen , Ho Chen-Lung
Published: March 2019

The essential oil from the heartwood of Taiwan fir (EOTC) was demonstrated to exhibit anti-inflammatory activity in lipopolysaccharide (LPS)-activated mouse macrophages. EOTC reduced nitrite oxide levels and inducible nitrite oxide synthase expression in, and tumor necrosis factor-α and interleukin-6 secretion by, LPS-activated macrophages without affecting cyclooxygenase-2 expression. EOTC reduced the levels of interleukin-1β precursor induced by LPS and decreased the NLRP3 inflammasome-derived interleukin-1β secretion induced by LPS and adenosine triphosphate. In addition, the phosphorylation levels of ERK1/2, JNK1/2, and p38 in LPS-activated macrophages were reduced by EOTC. Furthermore, EOTC was composed of oxygenated sesquiterpenes (68.4%), sesquiterpene hydrocarbons (28.9%) and diterpenes (0.9%). The major compounds of the oxygenated sesquiterpenes were τ-cadinol (23.9%), α-cadinol (21.1%) and cedrol (16.9%). These findings suggest that EOTC may be a candidate for the development of anti-inflammatory agents for preventing and ameliorating inflammation-related diseases.
Melissopalynological and Volatile Analysis of Honeys from Corsican Arbutus unedo Habitat
Authors: Yang Yin , Battesti Marie-José , Costa Jean , Paolini Julien
Published: March 2019

Thirty Corsican “autumn maquis” honeys were characterized by the typical combination of autumnal taxa: Arbutus unedo, Hedera helix, Smilax aspera, Rosmarinus officinalis, and two Asteraceae pollen forms. Corsican origin was characterized by the diversity of the taxa's biogeographical origins and significant presence of Castanea sativa and Quercus sp. Volatile fractions of “autumn maquis” honeys were dominated by isophorone and 3,4,5-trimethylphenol. The latter is reported in A. unedo honey for the first time. Otherwise, both A. unedo flower and “autumn maquis” honeys exhibited high contents of isophorone derivatives. H. helix honey exhibited phenylacetaldehyde, benzyl nitrile, 3-hydroxy-4-phenylbutan-2-one and nonanal as major compounds, which were scarcely represented in the studied “autumn maquis” honey samples.
Chemical Composition of the Essential Oils from Vietnamese Clausena indica and C. anisum-olens
Authors: Thai Tran Huy , Bazzali Ophélie , Hoi Tran Minh , Hien Nguyen Thi , Hung Nguyen Viet , Tomi Félix , Casanova Joseph , Bighelli Ange
Published: March 2019

The chemical composition of Vietnamese oil samples of the aerial parts of Clausena indica (Dalz.) Oliver and C. anisum-olens (Blanco) Merryll have been investigated using a combination of chromatographic and spectroscopic techniques. C. indica essential oil contained mainly terpinolene (53.9 and 56.1%), and myristicin (17.9 and 7.3%), whereas the major components of C. anisum-olens essential were citronellal (22.8%), geranial (21.4%) and neral (16.8%). The compositions of the investigated samples have been compared with those of essential oils from various origins.
Chemical Constituents from Sinningia canescens and S. warmingii
Authors: Verdan Maria Helena , Ehrenfried Carlos Augusto , Scharf Dilamara Riva , Cervi Armando Carlos , Salvador Marcos José , Barison Andersson , Stefanello Maria Elida A.
Published: March 2019

A new naphthoquinone, 6-methoxy-7-hydroxy-α-dunnione (1), along with four known compounds (2, 4, 10, and 11) were isolated from Snningia canescens (Mart.) Wiehler tubers, while S. warmingii (Hiern.) Chautems furnished eight known compounds (3–10). The known compounds were identified as 7-hydroxy-α-dunnione (2), lapachenole (3), tectoquinone (4), 7-methoxytectoquinone (5), 1-hydroxytectoquinone (6), 7-hydroxytectoquinone (7), aggregatin C (8), aggregatin D (9), halleridone (10), and cedrol (11). In addition, S. canescens yielded a volatile fraction, which was analyzed by GC/FID and GC/MS. This fraction was constituted mainly by sesquiterpene hydrocarbons (82.6%). The major components were β-santalene (14.6%), β-cedrene (10.4%), and trans-cadina-1(6)-4-diene (10.0%).
Sesinoside, a New Iridoid Glucoside from Sesame (Sesamum indicum) Seedlings
Authors: Takase Ryo , Hasegawa Tsuyoshi , Yamada Kosumi , Hasegawa Koji , Shigemori Hideyuki
Published: March 2019

A new iridoid glucoside, sesinoside (1), was isolated from the seedlings of Sesamum indicum. The structure of 1 was elucidated by spectroscopic analyses and by methanolysis of 1, which produced the known compounds, phlorigidosides C (2) and (6 Z)-foliamenthic acid methyl ester (3). This is the first report of an iridoid glucoside with 3.
Dammarane Terpenoids from the Fruits of Dysoxylum mollissimum
Authors: Tantapakul Cholpisut , Maneerat Wisanu , Sripisut Tawanun , Ritthiwigrom Thunwadee , Laphookhieo Surat
Published: March 2019

Two new dammaranes, dysomollisol (1) and dysomollisone (2), along with seven known compounds (3–9) were isolated and identified from the fruits of Dysoxylum mollissimum. The structures of these compounds were determined on the basis of spectroscopic analyses, including 1D and 2D NMR, UV, IR and mass spectrometry. The antibacterial activity and cytotoxicity against epidermoid carcinoma of oral cavity (KB) cell line of compounds 1–9 were evaluated.
Anti-tumor Activities of Triterpenes from Syzygium kusukusense
Authors: Bai Li-Yuan , Lin Wei-Yu , Chiu Chang-Fang , Weng Jing-Ru
Published: March 2019

In this study, we report the isolation from the stem of Syzygium kusukusense of five triterpenes, 2α-hydroxybetulinic acid (1), betulinic acid (2), platanic acid (3), ursolic acid (4), and hyptatic acid A (5). All were identified for the first time from this indigenous plant of Taiwan. Assessment of the cytotoxic activities of these compounds against a panel of human tumor cell lines, including MCF-7 breast, PC-3 prostate, and SCC2095 oral squamous cell cancers, revealed the high potency of compounds 1 (IC50, 5.7 – 7.6 μM) and, especially, 4 (IC50, 1.7 – 3.7 μM) in suppressing cell viability, which warrants further mechanistic investigations.
Profiling of Flavonols in Seeds and Sprouts of Luffa cylindrica
Authors: Shim Soon-Mi , Park Tae-Sik
Published: March 2019

Seeds of Luffa cylindrica (Luffa) have been considered as agricultural wastes. However, we hypothesized that the seeds and its sprouts may provide bioactive components that could provide health benefits for humans. The current study profiled the bioactive components in both seeds and sprouts of Luffa by using ultra-performance liquid chromatography-mass spectrometry (UPLC-MS/MSn). Apigenin was identified as a major component in the seeds of Luffa, with a concentration of 2.89 mg from 1 g fresh weight. The bioactive components in the sprouts were myricetin, luteolin, and quercetin, with concentrations of 32.4, 12.5, and 32.5 μg from 1 g fresh weight, respectively. Apigenin metabolites, such as apigenin-glucuronic acid and apigenin-acetyl glucuronic acid, were also identified in the sprouts. This implied that apigenin in the seeds, when sprouting, was changed to other flavonols having a flavone backbone. Results from the current study suggest that both seeds and sprouts of Luffa could be a bio-resource for health-promoting food materials.
PTP1B Inhibitory Effect of Alkyl p-Coumarates from Calystegia soldanella
Authors: Lee Jung Im , Kim In-Hye , Choi Youn Hee , Kim Eun-Young , Nam Taek-Jeong
Published: March 2019

In this report, the PTP1B inhibitory effect of Calystegia soldanella was investigated. Bioassay-guided fractionation of the crude extracts revealed that the n-hexane fraction had the strongest PTP1B inhibitory effect. Nine known alkyl p-coumarates were isolated from the n-hexane fraction, and each compound was evaluated for its effect on PTP1B. All compounds effectively inhibited PTP1B activity. The IC50 values of the compounds were 3 (10.8 μg/mL) > 2 (15.5 μg/mL) > 7 (26.6 μg/mL) > 1 (37.0 μg/mL) > 8 (41.2 μg/mL) > 9 (43.4 μg/mL) > 5 (44.7 μg/mL) > 4 (>50 μg/mL) > 6 (>50 μg/mL).
Identification of the Country of Growth of Sophora flavescens using Direct Analysis in Real Time Mass Spectrometry (DART-MS)
Authors: Fukuda Eriko , Uesawa Yoshihiro , Baba Masaki , Suzuki Ryuichiro , Fukuda Tatsuo , Shirataki Yoshiaki , Okada Yoshihito
Published: March 2019

In order to identify the country of growth of Sophora flavescens by chemical fingerprinting, extracts of plants grown in China and Japan were analyzed using direct analysis in real time mass spectrometry (DART)-MS. The peaks characteristic of each country of growth were statistically analyzed using a volcano plot to summarize the relationship between the p-values of a statistical test and the magnitude of the difference in the peak intensities of the samples in the groups. Peaks with a p value <0.05 in the t-test and a ≥2 absolute difference were defined as characteristic. Peaks characteristic of Chinese S. flavescens were found at m/z 439 and 440. In contrast, peaks characteristic of Japanese S. flavescens were found at m/z 313, 423, 437 and 441. The intensity of the selected peaks was similar in Japanese samples, whereas the m/z 439 peak had a significantly higher intensity than the other peaks in Chinese samples. Therefore, differences in selected peak patterns may allow identification of the country of growth of S. flavescens.