bluuebunny/crossref_metadata_2025 huggingface dataset:
Chemical Compositions and Antimicrobial and Antioxidant Activities of the Essential Oils from Magnolia grandiflora, Chrysactinia mexicana, and Schinus molle Found in Northeast Mexico
Authors: Guerra-Boone Laura , Álvarez-Román Rocío , Salazar-Aranda Ricardo , Torres-Cirio Anabel , Rivas-Galindo Verónica Mayela , de Torres Noemí Waksman , González Gloria María González , Pérez-López Luis Alejandro
Published: March 2019

The essential oils from Magnolia grandiflora and Chrysactinia mexicana leaves, and from Schinus molle leaves and fruit, were characterized by gas chromatography/flame-ionization detection and gas chromatography/mass spectrometry. Twenty-eight compounds from M. grandiflora leaves were identified (representing 93.6% of the total area of the gas chromatogram), with the major component being bornyl acetate (20.9%). Colorless and yellow oils were obtained from the C. mexicana leaves with 18 (86.7%) and 11 (100%) compounds identified, respectively. In both fractions, the principal component was sylvestrene (36.8% and 41.1%, respectively). The essential oils of S. molle leaves and fruit were each separated into colorless and yellow fractions, in which 14 (98.2) and 20 (99.8%) compounds were identified. The main component was α-phellandrene in all fractions (between 32.8% and 45.0%). The M. grandiflora oil displayed antifungal activity against five dermatophyte strains. The oils from S. molle and M. grandiflora leaves had antimicrobial activity against Staphylococcus aureus and Streptococcus pyogenes, which cause skin infections that potentially may lead to sepsis. However, the antioxidant activities of all oils were small (half maximal effective concentration values >250 μg/mL).
Steroidal Saponins from Dracaena marginata
Authors: Rezgui Abdelmalek , Mitaine-Offer Anne-Claire , Pertuit David , Miyamoto Tomofumi , Tanaka Chiaki , Delemasure Stéphanie , Dutartre Patrick , Lacaille-Dubois Marie-Aleth
Published: March 2019

Three new steroidal saponins and ten known ones were isolated from the bark of Dracaena marginata, along with two known steroidal saponins from the roots. Their structures were elucidated on the basis of extensive 1D and 2D NMR experiments and mass spectrometry as (25R)-26-(β-D-glucopyranosyloxy)- 3β,22α-dihydroxyfurost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→-4)]-β-D-glucopyranoside (1), (25R)-26-(β-D-glucopyrano- syloxy)-3β,22α-dihydroxyfurost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1→-2)-4-O-sulfo-α-L-arabinopyranoside (2), and (25 S)-3β-hydroxyspirost-5-en-1β-yl O- α-L-rhamnopyranosyl-(1→2)-4-O-sulfo-α-L-arabinopyranoside (3).
Composition of Essential Oils from Seeds of Abies koreana
Authors: Wajs-Bonikowska Anna , Olejnik Karol , Bonikowski RadosJaw , Banaszczak Piotr
Published: March 2019

The essential oils from seeds of nine Abies koreana specimens have been studied using GC-MS-FID and NMR methods, leading to the determination of 96 volatiles, which constituted over 99% of the oils. The hydrodistilled oils of fresh, resinous scent were isolated with yields in the range of 3.8-8.5%. The results showed that the essential oil of Korean fir seeds contained 70-95% monoterpenes and 1-20% oxygenated monoterpenes as the dominant groups. The numerous sesquiterpenes, diterpenes and their oxygenated derivatives constituted only 2-8% of the oil. The major component of the seed essential oil was limonene (4172 g/100g); the laevorotary form of this terpene predominated. A. koreana seeds seem to be a rich source of both essential oil and (-)-limonene, whose average enantiomeric excess was above 95%.
Essential Oils from Five Species of Annonaceae from Vietnam
Authors: Thang Tran D. , Dai Do N. , Hoi Tran M. , Ogunwande Isiaka A.
Published: March 2019

The essential oils obtained by hydrodistillation from the leaves of five species of Annonaceace grown in Vietnam were analyzed by gas chromatography (GC) coupled with mass spectrometry (GC/MS). The main constituents of Artabotrys hongkongensis Hance were the sesquiterpenes spathulenol (13.1%), β-caryophyllene (6.6%), γ-elemene (6.3%) and δ-cadinene (6.3%). β-Caryophyllene (12.1%), bicycloelemene (11.2%) and bicyclogermacrene (11.6%) were the predominant components of the oil of Melodorum fruticosum Lour, whereas the oil of Polyalthia longifolia var. pendula Hort was comprised mainly of β-caryophyllene (30.0%), α-zingiberene (21.7%), aromadendrene (15.2%) and β-selinene (9.1%). The main constituents of Fissistigma maclurei Merr. were germacrene D (26.1%), α-terpinene (8.2%), spathulenol (10.0%), and bicyclogermacrene (6.6%), while α-santalene (14.3%), β-caryophyllene (6.3%), terpinen-4-ol (6.3%), caryophyllene oxide (5.7%), trans-α-bergamotene (5.3%) and allo-ocimene (5.3%) were identified in significant quantity from Fissistigma rufinerve (Hook.f. & Thomson) Merr.
TLC-Bioautographic Evaluation of In Vitro Anti-tyrosinase and Anti-cholinesterase Potentials of Sandalwood Oil
Authors: Misra Biswapriya B. , Dey Satyahari
Published: March 2019

Sandalwood oil, rich in sesquiterpenoid alcohols, has been used in traditional medicinal systems as a relaxant and coolant. Besides, sandalwood oil is used as an ingredient in numerous skin fairness enhancing cosmetics. However, there is no available information on biological activities that relate to the above applications. Hence, the anti-tyrosinase and anti-cholinesterase potentials of sandalwood oil were probed by both TLC-bioautographic and colorimetric methods. Results obtained from colorimetric assays indicated that sandalwood oil is a potent inhibitor of tyrosinase (IC50=171 μg mL−1) and cholinesterases (IC50=4.8-58 μg mL−1), in comparison with the positive controls used in the assays, kojic acid and physostigmine, respectively. The TLC-bioautographic assays indicated that α-santalol, the major constituent of the oil, is a strong inhibitor of both tyrosinase and cholinesterase. These in vitro results indicate that there is a great potential of this essential oil for use in the treatment of Alzheimer's disease, as well as in skin-care.
Plants from Northeast Mexico with Anti-HSV Activity
Authors: Silva-Mares David , Torres-López Ernesto , Rivas-Estilla Ana M , Cordero-Pérez Paula , Waksman-Minsky Noemí , Rivas-Galindo Verónica M
Published: March 2019

Based on chemotaxonomic and ethno-pharmacological criteria, three Mexican plants ( Jatropha dioica, Salvia texana and S. ballotaeflora) were studied for in vitro activity against HSV-1 and HSV-2. Hydro-methanolic extracts were initially evaluated for their toxicity to Vero cells. Both Salvia species displayed cytotoxicity at the lowest dose (125 μg/mL). The J. dioica extract showed only negligible cytotoxicity (CC50 644 μg/mL). Its anti-HSV activity was evaluated using the plaque reduction assay with HSV-1 and HSV-2 (from clinical isolates) infected Vero cells. The hydro-methanolic extract of J. dioica showed IC50s of 280 and 370 μg/mL against HSV-1 and HSV-2, respectively. The n-hexane liquid-liquid partition of J. dioica extract contained the majority of the active principle(s) with IC50 values of 300 and 270 μg/mL for HSV-1 and HSV-2, respectively. Bioassay-guided isolation led to the known diterpene, riolozatrione.
GC-MS Investigation of Amaryllidaceae Alkaloids in Galanthus xvalentinei nothosubsp. subplicatus
Authors: Sarikaya Buket Bozkurt , Berkov Strahil , Bastida Jaume , Kaya Gulen Irem , Onur Mustafa Ali , Somer Nehir Unver
Published: March 2019

A GC-MS analysis of alkaloids in the aerial parts and bulbs of Galanthus x valentinei nothosubsp. subplicatus was performed for the first time. Totally, twenty-six alkaloids were identified, of which tazettine and galanthindole were the major ones. Acetylcholinesterase inhibitory activity of the alkaloidal extracts was determined using modified in vitro Ellman's method. Significant anticholinesterase activity was observed in the tested samples (bulbs: IC50 = 21.3 μg/mL, aerial parts: IC50 = 16.3 μg/mL).
Geranyl Flavonoids from Robinia pseudoacacia
Authors: Zhang Lai-Bin , Lv Jie-Li , Zhang Hui
Published: March 2019

A new geranyl flavonol, robipseudin A (1), and a known geranyl flavone, kuwanon S (2), were isolated from the leaves of Robinia pseudoacacia. The structure of the new compound was determined by spectroscopic methods. Compounds 1 and 2 showed moderate antioxidant activities in the DPPH radical scavenging assay.
Effect of the Isoflavone Genistein on Tumor Size, Metastasis Potential and Melanization in a B16 Mouse Model of Murine Melanoma
Authors: Danciu Corina , Borcan Florin , Bojin Florina , Zupko Istvan , Dehelean Cristina
Published: March 2019

The isoflavonoid genistein, the aglycone of the heteroside genistin, possesses preventive effect on coronary heart disease and osteoporosis, antioxidant, anthelmintic, antineoplastic and anti-inflammatory properties. Much research has been undertaken regarding the action of genistein on cancer-preventing/treating effects, especially on breast and prostate cancer. The aim of this study was to analyze the effect of this compound in vivo by observing tumor size, metastasis potential and melanization in a mouse model of murine melanoma, employing the B164A5 melanoma cell line and C57BL/6J mice. Genistein decreased the tumor volume and weight by approximately 30%. Non-invasive measurements for both melanin and erythema showed that genistein reduced the quantity of melanin and the degree of erythema in direct proportion to the number of days of treatment. HE analysis diagnosed malignant melanoma in both groups, but no metastasis was recorded in the treated group compared with the liver metastasis in the untreated group after a period of 15 days of experiment at a dose of 15 mg/kg body weight of genistein. Genistein showed beneficial effects regarding tumor size, metastasis potential and melanization in a B16 mouse model of murine melanoma.
Antimicrobials from the Marine Algal Endophyte Penicillium sp
Authors: Flewelling Andrew J. , Johnson John A. , Gray Christopher A.
Published: March 2019

An endophytic fungus identified as Penicillium sp. was isolated from the brown alga Fucus spiralis collected from the Shetland Islands, United Kingdom. Bioassay-guided fractionation of an extract of the fungus led to the isolation of cladosporin, epiepoformin, phyllostine, and patulin, all of which showed antimicrobial activity against either Staphylococcus aureus or Pseudomonas aeruginosa. Cladosporin has not previously been identified from a fungus of the genus Penicillium, and, despite being biosynthetically related, epiepoformin, phyllostine and patulin have not been previously reported from one source.
Induction of Defensive Response in Eucalyptus globulus Plants and its Persistence in Vegetative Propagation
Authors: Troncoso Christian , Perez Claudia , Hernandez Victor , Sanchez-Olate Manuel , Rios Darcy , Martin Aurelio San , Becerra José
Published: March 2019

The expression of defensive compounds derived from secondary metabolism in plants of Eucalyptus globulus Labill, and the persistence of these in vegetative propagation was evaluated by gas chromatography with flame ionization (GC-FID) and mass spectrometry (MS). The plants were induced by attack from the insect Ctenarytaina eucalypti (“blue gum psyllid”) and by mechanical damage. Defense responses were activated in plants for the different types of tested induction. We identified four defensive compounds present in the leaves of plants induced in entomological form (β-terpineol, aromadendrene, caryophyllene-oxide and eremophilene); all remained in the vegetative propagation. After mechanical induction, we identified three compounds (β-terpineol, aromadendrene and ledol), of which ledol and aromadendrene persisted in the vegetative propagation. Virtually all the compounds detected, in addition to persisting in the vegetative propagation, showed specificity for the induction type, whether entomological or mechanical, except for aromadendrene, which was expressed in both types of induction.
Chemical Composition and Anti-Trypanosoma cruzi Activity of Essential Oils Obtained from Leaves of Xylopia frutescens and X. laevigata (Annonaceae)
Authors: da Silva Thanany Brasil , Menezes Leociley Rocha Alencar , Sampaio Marília Fernanda Chaves , Meira Cássio Santana , Guimarães Elisalva Teixeira , Soares Milena Botelho Pereira , do Nascimento Prata Ana Paula , de Lima Nogueira Paulo Cesar , Costa Emmanoel Vilaça
Published: March 2019

Essential oils from leaves of Xylopia frutescens (XFMJ) and two specimens of Xylopia laevigata (XLMC and XLSI) were obtained by hydrodistillation using a Clevenger-type apparatus, and analyzed by GC-MS and GC-FID. Sesquiterpenes dominated the essential oils. The main constituents of XFMJ were ( E)-caryophyllene (24.8%), bicyclogermacrene (20.8%), germacrene D (17.0%), β-elemene (7.9%), and ( E)-β-ocimene (6.8%). XLMC contained significant quantities of germacrene D (18.9%), bicyclogermacrene (18.4%), β-elemene (9.5%), 5-selinene (9.2%), ( E)-caryophyllene (8.5%), germacrene B (5.7%) and γ-muurolene (5.7%), while germacrene D (27.0%), bicyclogermacrene (12.8%), ( E)-caryophyllene (8.6%), γ-muurolene (8.6%), 5-cadinene (6.8%), and germacrene B (6.0%) were the main components of XLSI. The essential oils had trypanocidal activity against the Y strain of Trypanosoma cruzi. with IC50 values lower than 30 μg.mL−1 and 15 μg.mL−1 against epimastigote and trypomastigote forms of T. cruzi. respectively, and were also able to reduce the percentage in vitro of T. cruzi-infected macrophages and the intracellular number of amastigotes at concentrations that were non-cytotoxic to macrophages.
Methyl Carnosate, an Antibacterial Diterpene Isolated from Salvia officinalis Leaves
Authors: Climati Elisa , Mastrogiovanni Fabio , Valeri Maria , Salvini Laura , Bonechi Claudia , Mamadalieva Nilufar Zokirzhonovna , Egamberdieva Dilfuza , Taddei Anna Rita , Tiezzi Antonio
Published: March 2019

Ethanolic extracts of Salvia officinalis leaves demonstrated antibacterial activity against Bacillus cereus. Fractionation of the extracts led to the isolation of the most active antibacterial compound, which, from spectroscopic and LC-MS evidence, was proved to be the diterpene, methyl carnosate.
Antioxidative / Acetylcholinesterase Inhibitory Activity of Some Asteraceae Plants
Authors: Mekinić Ivana Generalić , Burčul Franko , Blaževieć Ivica , Skroza Danijela , Kerum Daniela , Katalinić Višnja
Published: March 2019

The extracts obtained by 80% EtOH from some Asteraceae plants ( Calendula officinalis, Inula helenium, Arctium lappa, Artemisia absinthium and Achillea millefolium) were studied. Rosmarinic acid, one of the main compounds identified in all extracts, was determined quantitatively by using HPLC. In addition, spectrophotometric methods were evaluated as an alternative for rosmarinic acid content determination. Total phenolic content was also established for all extracts. A. millefolium extract was found to have the highest content of rosmarinic acid as well as total phenols. All extracts were tested for antioxidant and acetylcholinesterase inhibitory activity. A. millefolium was shown to possess the best antioxidant activity (for all tested methods) as well as acetylcholinesterase inhibitory activity. Highly positive linear relationships were obtained between antioxidant/acetylcholinesterase inhibitory activity and the determined rosmarinic acid content indicating its significance for the observed activities.
Volatile Composition of Six Horsetails: Prospects and Perspectives
Authors: Fons Françoise , Froissard Didier , Bessière Jean-Marie , Fruchier Alain , Buatois Bruno , Rapior Sylvie
Published: March 2019

Six horsetails were investigated for volatile organic compounds (VOC) by GC-MS using organic solvent extraction. Seventy-five VOC biosynthesized from the shikimic, lipidic and terpenic pathways including isoprenoid derivatives were detected from these putative natural resources. E. palustre var. americana contained mainly lipidic derivatives, i.e., 1-octen-3-ol (mushroom-like odor), ( E)-2-hexenoic acid (fruity odor) and ( E)-2-hexenal (green odor). Many isoprenoid flavour precursors, i.e., 3-oxo-α-ionol (spicy odor) and ( E, E)-pseudoionone (balsamic odor), as well as odorous benzenic derivatives, i.e, phenylethanal (hyacinth, lilac note) and 2-phenylethanol (rose odor) contributed to the odor of E. arvense. The volatile pattern of E. telmateia is dominated by high amounts of isoprenoids and benzenic derivatives. The complex volatile profiles of E. hyemale and E. ramosissimum are based on ferulic acid isomers, along with either ( E)-2-heptenal (green vegetable-like odor) or 4-vinylguaiacol (spicy clove smoky odor) for E. hyemale and E ramosissimum, respectively. The broad spectrum of E. scirpioides shows the lowest VOC content with high amount of isoprenoids (46.9%), mainly ionone derivatives. Equisetum resources are of great interest as bioactive litter and new potential functional feed ingredients.
Chemical Composition and Antimicrobial Activity of Three Essential Oils from Curcuma wenyujin
Authors: Zhu Jingjing , Lower-Nedza Agnieszka D. , Hong Meng , Jiec Song , Wang Zhimin , Yingmao Dong , Tschiggerl Christine , Bucar Franz , Brantner Adelheid H.
Published: March 2019

Curcuma wenyujin is a traditional medicinal plant in China. The non-steamed rhizomes, steamed rhizomes and steamed roots of this plant are used as herbal medicines in three clinics, namely Pian-jiang-huang (PJH), Wen-e-zhu (WEZ), and Wen-yu-jin (WYJ), and are officially listed in the Chinese Pharmacopoeia. The purpose of this study was to conduct a comparative analysis of the three essential oils extracted from the C. wenyujin rhizomes and roots using GC-MS, and in doing so thirty compounds were identified. Principal component analysis (PCA) effectively distinguished the samples taken from the three different groups. Monoterpenoids, including camphene, linalool, camphor, isoborneol, borneol and eucalyptol, were characteristic components of the PJH oil, while β-elemene, β-elemenone, γ-elemene and δ-elemene were typical components of the WEZ oil, and propanenitrile, caryophyllene oxide, (-)-caryophyllene, germacrene B, pogostol and α-humulene were representative ingredients of the WYJ oil. The ratio of sesquiterpenoids to monoterpenoids in PJH, WEZ, and WYJ were 2:1, 5:1 and 7:1, respectively. The antimicrobial activities of the three essential oils and of the six main ingredients were tested against two bacterial and one fungal strains using agar diffusion and broth dilution methods. The essential oil of PJH was shown to present a higher antimicrobial activity than that of WEZ and WYJ. Based on the Partial Least Square Model (PLS), the correlation between the antimicrobial activity of the tested oils and the identified chemical components was discussed and potential components of the antimicrobial activity were predicted according to Variable Importance in the Project (VIP) Value. The tested monoterpenes eucalyptol and isoborneol demonstrated a higher inhibitory activity than the sesquiterpenes germacrone, curdione and β-elemene. Therefore, the potent inhibitory effect of the PJH oil might be attributed to its higher content of monoterpenes. The MIC values for the essential oils and their ingredients ranged from 62.5 to 500 μg/mL.
Cytotoxic Scalarane Sesterterpenoids from a Marine Sponge Hippospongia sp
Authors: Fuh Yuh-Ming , Lu Mei-Chin , Lee Chia-Hung , Su Jui-Hsin
Published: March 2019

A new scalarane sesterterpenoid, hippospongide C (1), along with four previously reported known scalarane–type sesterterpenes (2–5), were isolated from a sponge Hippospongia sp. The structure of 1 was elucidated on the basis of its spectroscopic data and comparison of its NMR data with those of known analogues. The cytotoxicity of 1–5 against DLD-1, HCT-116, T-47D and K562 cell lines was evaluated. The results showed that compound 4 exhibited potent activity against DLD-1, HCT-116 and T-47D cell lines with IC50 values of 1.3–2.0 μg/mL. Furthermore, metabolites 1–5 were also found to exhibit significant cytotoxicity towards the K562 cell line with IC50 values of 0.01–2.9 μg/mL.
Chemical Analysis of Flowers of Bombax ceiba from Nepal
Authors: Joshi Khem Raj , Devkota Hari Prasad , Yahara Shoji
Published: March 2019

From the flowers of Bombax ceiba L. (Family: Bombacaceae) twenty-four compounds were isolated and identified, including ten flavonoids, quercetin (1), quercetin-3- O-β-D-glucopyranoside (2), quercetin-3- O-β-D-glucuronopyranoside (3), rutin (4), sexangularetin-3- O-sophoroside (5), vitexin (6), isovitexin (7), vicenin 2 (8), kaempferol-3- O-rutinoside (18), and kaempferol-3- O-β-D-glucuronopyranoside (23); three xanthones, isomangiferin (9), mangiferin (10), and 7- O-methyl mangiferin (11); four coumarins, esculetin (12), scopoletin (13), fraxetin (14), and scopolin (21); and seven other compounds, blumenol C glucopyranoside (15), benzyl-β-D-glucopyranoside (16), phenylethyl rutinoside (17), protocatechulic acid (19), chlorogenic acid (20), methyl chlorogenate (22) and vanillic acid (24). Among these, 13 compounds (3, 5, 6, 9, 11, 14, 15, 16, 17, 18, 22, 23 and 24) were isolated for the first time from B. ceiba.
Two 2-Phenylbenzofuran Derivatives from Morus atropurpurea
Authors: Wang Wen-Jing , Wu Dong-Ling , Liao Sen-Tai , Fan Chun-Lin , Guo-Qiang Li , Zhang Xian-Tao , Wang Ying , Zhang Xiao-Qi , Ye Wen-Cai
Published: March 2019

Two new 2-phenylbenzofuran derivatives, atrofuran A (1) and atrofuran B (2), along with five known compounds, were isolated from the root bark of Morus atropurpurea. The structures of the new compounds were determined on the basis of extensive NMR spectroscopic and HR-ESI-MS analyses.
Comparing Different Solvent Extracts of Rhus semialata var. roxburghiana Stem against Ferrous Ion-Induced Lipid Peroxidation in Mice Liver Mitochondria
Authors: Lin Pei-Chin , Bi Wei-Fung , Lin Che-Hsuan , Lee Fei-Peng , Yang Ling-Ling
Published: March 2019

Rhus semialata Murr. var. roxburghiana DC. stem ( RSRS) is a Taiwanese native folk medicine for anti-inflammation and the treatment of diarrhea and liver disease. Five extracts and a main constituent, gallic acid, elucidated inhibitory effects on ferrous ion-induced lipid peroxidation (LPO) in mice liver mitochondria (IC50: 10.8 ± 0.7 −55.2 ± 0.6 and gallic acid: 36.1 ± 3.1 μg/mL). None of the samples tested induced LPO production. The IC50 values for antioxidant activities were 1) 1,1-diphenyl-2-picryl-hydrazyl (DPPH) scavenging: 1.5 ± 0.08 – 56.2 ± 1.1 μg/mL; 2) superoxide anion radical scavenging: 53.5 ± 0.7 – 226.6 ± 2.1 μg/mL; 3) hydrogen peroxide scavenging: ethyl acetate (EA) and acetone extracts 264.2 ± 4.7 and 208.0 ± 1.9 μg/mL, respectively; and 4) ferric-reducing antioxidant power (FRAP): EA extract, equivalent Trolox 116.4 ± 0.3 μM. The total phenolic content of the extracts was 82.0 ± 2.1 – 455.2 ± 9.3 μg gallic acid equivalents/mg. The highest flavonoid and flavanol contents of the extracts were acetone extract 30.9 ± 2.7 μg rutin equivalents/mg and water extract 10.9 ± 0.05 μg epicatechin equivalents/mg. Next, the gallic acid content of each extract was quantitatively analyzed using high-performance liquid chromatography (HPLC), which showed one main peak. Based on this evidence, RSRS and gallic acid may be used as a potential antioxidant and LPO inhibitor for developing a natural liver-protective phytochemical.
Establishment of a Phenotypic-based Sand Dollar Fellaster zelandiae Embryo Development Assay and its Application in Defining the Structure-Activity Relationship of Discorhabdin Alkaloids
Authors: Grkovic Tanja , Copp Brent R.
Published: March 2019

An embryo development assay using the common New Zealand intertidal species Fellaster zelandiae (sand dollar) is presented. The assay was validated by comparing activity profiles of a range of discorhabdin alkaloids, natural products sourced from Latrunculia spp. sponges containing a core pyrido[2,3- h]pyrrolo[4,3,2- de]quinoline tetracyclic skeleton bound to various spiro-substituents at the C-6 position. Structural features on the discorhabdin molecule that correlated to the greatest degree of F. zelandiae embryo developmental inhibition were the presence of a spiro-dienone moiety and a C-2 bromine substituent. Based on the sand dollar embryo development assay results, a mechanism for the activity of the discorhabdin alkaloids is proposed.
Sharing of Pyrazine Semiochemicals between Genera of Sexually Deceptive Orchids
Authors: Bohman Bjorn , Phillips Ryan D. , Flematti Gavin , Peakall Rod , Barrow Russell A.
Published: March 2019

It has recently been discovered that novel di-, tri- and tetra- substituted pyrazines are semiochemicals in Drakaea, an orchid genus that secures pollination by the sexual deception of male thynnine wasps. We examined if similar pyrazines were also present in the distantly related Caladenia barbarossa, a sexually deceptive orchid that is also pollinated by a thynnine wasp. Here we report for the first time the occurrence of two pyrazines, (3,5,6-trimethylpyrazin-2-yl)methyl 3-methylbutanoate (1) and 3-(3-methylbutyl)-2,5-dimethylpyrazine (2) in the orchid genus Caladenia. The former is known as a semiochemical involved in pollinator attraction in Drakaea livida. This convergence of floral odour between distantly related plants provides an exciting opportunity to understand the evolution and molecular basis of this sophisticated chemical mimicry.
HPLC-NMR Chemical Profiling and Dereplication Studies of the Marine Brown Alga, Cystophora torulosa
Authors: Urban Sylvia , Timmers Michael
Published: March 2019

A chemical profiling/dereplication exercise, involving the use of HPLC-NMR and mass spectrometry in combination with the MarinLit database, was conducted on the crude dichloromethane extract of the southern Australian marine brown alga Cystophora torulosa. This strategy was successful in identifying a total of nine secondary metabolites representing two principle structure classes, including seven resorcinol (1–7) and two polyene derivatives (8 and 9). Validation of this on-line dereplication strategy was supported by the isolation and complete 2D NMR assignment of the major secondary metabolite (1). This methodology was concluded to be suitable for the rapid on-line identification of the resorcinol and polyene structure classes that are frequently encountered in the genus Cystophora.
Dihydrotagetone, an Unusual Fruity Ketone, is Found in Enantiopure and Enantioenriched Forms in Additional Australian Native Taxa of Phebalium (Rutaceae: Boronieae)
Authors: Sadgrove Nicholas J. , Telford Ian R. H. , Greatrex Ben W. , Dowell Ashley , Jones Graham L.
Published: March 2019

Here we report for the first time hydrodistillation of leaf essential oils from Phebalium squamulosum subsp. verrucosum, P. glandulosum subsp. eglandulosum, P. glandulosum subsp. nitidum and P. glandulosum subsp. angustifolium (Rutaceae: Boronieae). Essential oils were analysed using gas-chromatography/mass spectrometry (GC-MS) and nuclear magnetic resonance spectroscopy (NMR). With the exception of P. glandulosum subsp. angustifolium, all taxa yielded essential oils in relatively high amounts (1–3%, w/w) made up predominantly of 2,6-dimethyloct-7-en-4-one (dihydrotagetone). The essential oil from P. squamulosum subsp. verrucosum contains either (+)-dihydrotagetone ( ee 94–100%) or (-)-dihydrotagetone ( ee 17–18%). Taxonomically, these results support the proposal that P. squamulosum subsp. verrucosum may be specifically misplaced, phytochemically resembling the P. glandulosum complex. Similarly, P. glandulosum subsp. angustifolium phytochemically resembles P. distans or P. longifolium and also appears to be assigned incorrectly to the P. glandulosum group.
Novel α-Glucosidase Activator from Pulicaria undulata
Authors: Rasool Nasir , Rashid Muhammad Abid , Khan Saleha Suleman , Ali Zulfiqar , Zubair Muhammd , Ahmad Viqar Uddin , Khan Shamsun Nahar , Choudhary M. Iqbal , Tareen Rasool Bakhsh
Published: March 2019

A new ent –kaurane type diterpene glucoside, pulicarside (1), together with three known terpenoids, paniculoside IV (2, diterpene), ent–16, 17-dihydroxy-(-)-kauran-19–oic acid (3, diterpene), and 2α–hydroxy alantolactone (4, sesquiterpene) have been isolated from Pulicaria undulata L. Their structures were determined with the help of spectral studies. Pulicarside (1) showed α-glucosidase activator activity, whereas its hydrolyzed product ent-16, 17-dihydroxy-(-)-kauran-19-oic acid (3) exhibited strong α-glucosidase inhibitory activity. Paniculoside IV (2) also shows high inhibitory potency compared with the standard drug acarbose.
Phytochemical, Antimicrobial and Antiplasmodial Investigations of Terminalia brownii
Authors: Machumi Francis , Midiwo Jacob O. , Jacob Melissa R. , Khan Shabana I. , Tekwani Babu L. , Zhang Jin , Walker Larry A. , Muhammad Ilias
Published: March 2019

Phytochemical investigation of the ethyl acetate-soluble fraction of stem bark extract of an African medicinal plant Terminalia brownii led to the isolation of a new oleanane-type triterpenoid, along with seven known triterpenoids, seven ellagic acid derivatives, and 3- O-β-D-glucopyranosyl-β-sitosterol. The new compound was identified using spectroscopic methods, notably 1D- and 2D NMR, as 3β,24- O-ethylidenyl-2α,19α-dihydroxyolean-12-en-28-oic acid. The isolated compounds were evaluated for their antimicrobial and antiplasmodial activities. Two compounds with a galloyl group (4 and 6) were found to be active against chloroquine sensitive (D6) and chloroquine resistant (W2) strains of Plasmodium falciparum, whereas three ellagic acid derivatives (5–7) were found active against three species of fungi and one species of bacteria.
A New Sulfated Triterpene Saponin from Gypsophila trichotoma
Authors: Krasteva Ilina , Yotova Maya , Jenett-Siems Kristina , Zdraveva Petranka , Nikolov Stefan
Published: March 2019

A new sulfated triterpeniod saponin, 3- O-sulfooleanolic acid 28- O-[ β-glucopyranosyl-(1→3)]-[ β-glucopyranosyl-(1→6)]- β-glucopyranosyl ester (1), along with three known Δ7-sterols: stigmast-7-en-3 β-ol (2), stigmast-7-en-3- O-β-D-glucopyranoside (3) and stigmast-7-en-3-on (4) were isolated from the roots of Gypsophila trichotoma Wend. (Caryophyllaceae). Their structures were elucidated by chemical and spectral methods. Compound 1 caused concentration-dependent inhibition of malignant cell proliferation against different human tumor cell lines.
Severibuxine, Isolated from Severinia buxifolia, Induces Apoptosis in HL-60 Leukemia Cells
Authors: Ito Chihiro , Murata Tomiyasu , Kato Midori , Suzuki Natsu , Wu Tian-Shung , Kaneda Norio , Furukawa Hiroshi , Itoigawa Masataka
Published: March 2019

In an ongoing search for cancer-preventing compounds derived from plant sources, we isolated the quinolin-2,4-dione alkaloid severibuxine from the root bark of Severinia buxifolia collected in Taiwan and then examined the apoptotic effect of this compound. Severibuxine showed cytotoxicity to leukemia HL-60 cells (IC50 = 12.3±0.6 μM). Fluorescence microscopic analysis of cells stained with Hoechst 33342 indicated that the percentage of apoptotic cells showing nuclear condensation and fragmentation increased in a time-dependent manner. In addition, the activities of caspase-9 and caspase-3 were also enhanced in a time-dependent manner upon treatment with severibuxine. The addition of caspase-9 and caspase-3 inhibitors blocked severibuxine-mediated apoptosis. Upon treatment with severibuxine, the mitochondrial membrane potential decreased in a time-dependent manner. Severibuxine induced apoptosis in HL-60 cells through activation of the caspase-9/caspase-3 pathway, which is triggered by mitochondrial dysfunction.
Isolation and Cholinesterase Inhibitory Activity of Narcissus Extracts and Amaryllidaceae Alkaloid
Authors: Cahlíková Lucie , Ločárek Miroslav , Benešová Nina , Kučera Radim , Chlebek Jakub , Novák Zdeněk , Opletal Lubomír
Published: March 2019

Alkaloid extracts of eleven Narcissus (Amaryllidaceae) species and varieties were studied with respect to their acetylcholinesterase (HuAChE) and butyrylcholinesterase (HuBuChE) inhibitory activity and alkaloid patterns. Forty-two alkaloids were determined by GC/MS, and thirty of them identified from their mass spectra, retention times and retention indexes. Promising HuAChE inhibition activity was demonstrated by nine Narcissus taxa and HuBuChE inhibition by Narcissus poeticus cv. Pink Parasol with an IC50 value of 3.3 ± 0.5 μg/mL. The alkaloid identified as (11C- S)-homolycorine was isolated in pure form from Narcissus Sir W. Churchill using preparative TLC and was tested for its biological activity. Homolycorine inhibited HuAChE and HuBuChE in a dose-dependent manner with IC50 values of 63.7±4.3 μM and 151.0±15.2 μM, respectively.
Antibacterial and Antioxidant Activities of Various Medicinal Plants Used in Oriental Medicine
Authors: Seo Junho , Kim Jiyeon , Go Geon , Sung Jung-Suk , Lee Kwang-Geun
Published: March 2019

The antibacterial activities of the ethanol extracts of 35 medicinal plants were screened against Escherichia coli, Bacillus cereus, and Staphylococcus aureus by following standard antimicrobial susceptibility testing procedures. The ethanol extracts of Coptis chinensis and Glycyrrhiza uralensis showed antibacterial activity against all three test bacterial species. The screened extracts were also tested for their antioxidant activities using the DPPH free radical scavenging activity assay, and for their cytotoxic and antioxidant activity in vitro using an assessment of cell viability on mouse embryonic fibroblast cells. The ethanol extracts of both C. chinensis and G. uralensis showed good radical scavenging antioxidant properties and attenuated the rate of cell death caused by oxidative damage. Our results showed that C. chinensis and G. uralensis are promising sources of natural products with good antibacterial and antioxidant activities.
Regioselective Hydroxylation and Glucosylation of Flavanones with Cultured Plant Cells of Eucalyptus perriniana
Authors: Hosoda Ryusuke , Horio Yoshiyuki , Shimoda Kei , Hamada Manabu , Hamada Hatsuyuki , Hamada Hiroki
Published: March 2019

Cultured plant cells of Eucalyptus perriniana catalyzed reduction regioselective hydroxylation and regioselective glycosylation of flavanones. (2 S)-Flavanone was converted into (2 S)-flavan-4-ol (2 S)-flavan-4,7-diol (2 S)-flavan-7-ol (2 S)-flavan-7-yl glucoside and (2 S)-flavan-7-yl gentiobioside. The cells glucosylated (2 S)-flavan-6-ol to (2 S)-flavan-6-yl glucoside. (2 S)-Flavan-2′-ol was transformed to (2 S)-flavan-2′,4-diol (2 S)-flavan-2′,7-diol (2 S)-flavan-2′-yl glucoside. In addition (2 S)-flavan-4′-ol was transformed to (2 S)-flavan-4,4′-diol (2 S)-flavan-4′,7-diol (2 S)-flavan-4′-yl glucoside.
Carvone as a Versatile Chiral Building Block for Total Syntheses of Heterocyclic Sesquiterpenoids
Authors: Hagiwara Hisahiro
Published: March 2019

This review article is focused on the total syntheses of heterocyclic sesquiterpenoids starting from carvone since 1996.
Stereocontrolled Total Synthesis of Tetrodotoxin from myo-Inositol and D-Glucose by Three Routes: Aspects for Constructing Complex Multi-Functionalized Cyclitols with Branched-Chain Structures
Authors: Sato Ken-ichi , Akai Shoji , Yoshimura Juji
Published: March 2019

This report describes the stereocontrolled total synthesis of the multi-functionalized cyclitol derivative tetrodotoxin containing eight asymmetric carbons and different types of branched-chains from myo-inositol and D-glucose using three different methods. The tetrodotoxin derivatives possess a relatively small molecular weight but unique structural and chemical properties. Selection of the appropriate synthetic method may be useful not only for compounds related to TTX (including related derivatives) but also for other highly complex multi-functionalized cyclitols containing branched-chains.
Natural Clovanes from the Gorgonian Coral Rumphella Antipathies
Authors: Chung Hsu-Ming , Wang Wei-Hsien , Hwang Tsong-Long , Wu Yang-Chang , Sung Ping-Jyun
Published: March 2019

Three natural clovane-related sesquiterpenoids, 2β-acetoxyclovan-9α-ol (1), 9α-acetoxyclovan-2β-ol (2) and clovan-2β,9β-diol (3), were isolated from the gorgonian coral Rumphella antipathies. The structures of clovanes 1–3 were elucidated by spectroscopic methods and by comparison of the spectral data with those of known clovane analogues. This is the first time that clovanes 1–3 have been isolated from a natural source. Clovanes 1 and 2 displayed inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.
Establishment of In Vitro Adventitious Root Cultures and Analysis of Andrographolide in Andrographis Paniculata
Authors: Sharma Shiv Narayan , Jha Zenu , Sinha Rakesh Kumar
Published: March 2019

Andrographolide is the principal bioactive component of the medicinal plant Andrographis paniculata, to which various diverse pharmacological properties are attributed. Traditionally, andrographolide was extracted from the leaves, stems and other parts of the plant. Leaves have the highest andrographolide content (2–3%) in comparison with the other plant parts. Adventitious root culture of leaf explants of A. paniculata was studied using different strength MS medium supplemented by different concentrations of auxins and a combination of NAA + kinetin for growth and andrographolide production. Among the different auxin treatments in adventitious root culture, only NAA was able to induce adventitious roots. Adventitious roots grown in modified strength MS medium showed the highest root growth (26.7±1.52), as well as the highest amount of andrographolide (133.3±1.5 mg/g DW) as compared with roots grown in half-and full-strength MS medium. Growth kinetics showed maximum biomass production after five weeks of culture in different strength MS liquid medium. The produced andrographolide content was 3.5- 5.5 folds higher than that of the natural plant, depending on the medium strength.
New Cycloartane-type Triterpenes from Marcetia Latifolia (Melastomataceae) and In Silico Studies on Candida Parapsilosis Protease
Authors: Leite Tonny C. C. , Leite Franco H. A. , Vieira Ivo J. C. , Filho Raimundo Braz , Branco Alexsandro
Published: March 2019

We have previously reported the antimicrobial activity of the ethyl acetate extract of Marcetia latifolia, particularly against Candida parapsilosis. In this work we describe the isolation of two new cycloartane-type triterpenes, 28,29- bis-norcycloartan-3β,4α-diol (1) and 28,29- bis-norcycloart-24-en-3β,4α-diol (2) from the same extract. These compounds were mainly characterized by one- (1H, 13C and APT) and two-dimensional (1H-1H-COSY, 1H-1H-NOESY, HMQC and HMBC) NMR spectroscopy, mass spectrometry and comparison with published structural data. In addition, the activity of triterpenes 1 and 2 on the Candida protease target was investigated by in silico methods using molecular docking.
New Metabolites from the Algal Associated Marine-derived Fungus Aspergillus Carneus
Authors: Zhuravleva Olesya I. , Afiyatullov Shamil Sh. , Yurchenko Ekaterina A. , Denisenko Vladimir A. , Kirichuk Natalya N. , Dmitrenok Pavel S.
Published: March 2019

The new oxepin-containing (1) and quinazolinone (2) alkaloids and new dihydrobenzofuran derivative (3) have been isolated from a marine strain of Aspergillus carneus KMM 4638. The structures of these metabolites were determined by HR-MS and 1D and 2D NMR, along with Marfey's method.
Flavonoids with Anti-HSV Activity from the Root Bark of Artocarpus Lakoocha
Authors: Sritularak Boonchoo , Tantrakarnsakul Kullasap , Lipipun Vimolmas , Likhitwitayawuid Kittisak
Published: March 2019

From the MeOH extract of the root bark of Artocarpus lakoocha, a new compound 5,7,2’,4’-tetrahydroxy-6-geranyl-3-prenyl-flavone (1) was isolated, along with three known flavonoids (+)-afzelechin-3- O-α-L-rhamnopyranoside (2), (+)-catechin (3) and cudraflavone C (4). Evaluation of these isolates for inhibitory effects against Herpes simplex virus (HSV) types 1 and 2 was carried out using the inactivation method. Compounds 1 and 4 showed moderate and weak activity against both types of HSV, respectively, whereas 2 and 3 were devoid of activity.
Dibenzylbutane Lignans from the Stems of Schisandra Bicolor
Authors: Chen Yinning , Li Na , Zhu Yuehui , Zhang Cuilan , Jiang Xiaofei , Yang Jianxiang , Xu Zhifang , Qiu Samuel X. , Huang Riming
Published: March 2019

Further investigation of the stems of Schisandra bicolor led to the isolation of a new dibenzylbutane lignan, named schibicolignan A (1), as well as five known compounds, namely bis[dibenzylbutane] (2), machilin A (3), macelignan (4), saururenin (5) and sphenanlignan (6). The structure of the new lignan was elucidated on the basis of extensive spectroscopic analysis. Antioxidant activity of 1–6 was also evaluated.
Smooth Muscle Relaxation Activity of an Aqueous Extract of Dried Immature Fruit of Poncirus Trifoliata (PF-W) on an Isolated Strip of Rat Ileum
Authors: Kim Kyu-Sang , Shim Won-Sik , dela Peña Ike Campomayor , Seo Eun-Kyung , Kim Woo-Young , Jin Hyo-Eon , Kim Dae-Duk , Chung Suk-Jae , Cheong Jae-Hoon , Shim Chang-Koo
Published: March 2019

We demonstrated that an aqueous extract of dried immature fruit of Poncirus trifoliate (PF-W) produces relaxation of intestinal smooth muscle using the ileac strips of a rat. Furthermore, the underlying mechanism of its relaxant activity was investigated. PF-W was prepared using the standard extraction protocol. A 1.5 – 2 cm long rat ileac strip was placed in an organ bath with Tyrode's solution and smooth muscle contractility was recorded by connecting it to a force transducer. Various compounds were added to the organ baths, and changes in muscular contractility were measured. PF-W concentration-dependently induced relaxation of rat ileac strips that were contracted both spontaneously and via acetylcholine treatment. Various potassium channel blockers did not inhibit the relaxation by PF-W. No difference in the effect of PF-W was observed between ileac strips treated with low (20 mM) and high concentrations (60 mM) of KCl. PF-W inhibited the contraction of rat ileac strips induced by extracellular calcium. PF-W acts as a potent smooth muscle relaxant, implicating its possible action as a rapid acting reliever for abdominal pains and a cure for intestinal convulsion. Considering that PF-W also exhibits prokinetic activity, its use in various gastrointestinal disorders seems promising.
Invertebrate Water Extracts as Biocompatible Reducing Agents for the Green Synthesis of Gold and Silver Nanoparticles
Authors: Han Lina , Kim Yeong Shik , Cho Seonho , Park Youmie
Published: March 2019

We report the use of water extracts of two invertebrates, snail body and earthworm, as biocompatible reducing agents for the green synthesis of gold and silver nanoparticles. The reaction conditions were optimized by varying the extract concentration, gold ion or silver ion concentration, reaction time, and reaction temperature. The gold and silver nanoparticles exhibited their characteristic surface plasmon resonance bands. Mostly spherical and amorphous shapes of the nanoparticles were synthesized. The average diameters of the gold and silver nanoparticles were 4.56 ± 1.81 nm and 11.12 ± 5.25 nm, respectively, when the extract of snail body was used as the reducing agent. The earthworm extracts produced gold and silver nanoparticles with average diameters of 6.70 ± 2.69 nm and 12.19 ± 4.28 nm, respectively. This report suggests that the invertebrate natural products have potential as biocompatible reducing agents for the green synthesis of metallic nanoparticles. This utility would open up novel applications of invertebrate natural products as nanocomposites and in nanomedicine.
Elemental Analysis of Ginkgo Biloba Leaf Samples Collected during One Vegetation Period
Authors: Czigle Szilvia , Háznagy-Radnai Erzsébet , Pintye-Hódi Klára , Tóth Jaroslav , Tekel'ová Daniela , Máthé Imre
Published: March 2019

The object of our work was the identification and quantification of inorganic elements in Ginkgo biloba L. leaves (Ginkgonis folium, Ginkgoaceae) by X-ray fluorescence analysis. The plant material was obtained from a 50-years-old female tree at the Comenius University Botanical Garden (Bratislava, Slovakia). Leaves were collected from early May to late September, with the last sample consisting of fallen leaves. The elements analyzed were: phosphorus, sulfur, potassium, calcium, scandium, iron, zinc, yttrium, molybdenum, tellurium, samarium, gadolinium, dysprosium, iridium, thallium and lead. The amounts of the monitored heavy metals were below the limits specified in Ph. Eur. 7 and PhS 1.
A New Bioactive Diterpene Glycoside from Molinaea Retusa from the Madagascar Dry Forest
Authors: Eaton Alexander L. , Harinantenaina Liva , Brodie Peggy J. , Cassera Maria B. , Bowman Jessica D. , Callmander Martin W. , Randrianaivo Richard , Rakotondrajaona Roland , Rakotobe Etienne , Rasamison Vincent E. , Kingston David G. I.
Published: March 2019

In a continuing collaboration in a search for new antiproliferative compounds in Madagascar as part of an International Cooperative Biodiversity Group (ICBG), an ethanol extract of Molinaea retusa Radlk. (Sapindaceae) was investigated on the basis of its moderate antiproliferative activity against the A2780 human ovarian cancer cell line (IC50 16 μg/mL). One new compound, 2″,3″,4″,6′-de- O-acetylcupacinoside (1, IC50 15.4 μM) and two known compounds, cupacinoside (2, IC50 9.5 μM) and 6-de- O-acetylcupacinoside (3, IC50 10.9 μM), were isolated by bioassay-directed fractionation using liquid-liquid partitioning, column chromatography, and HPLC. Compounds 2 and 3 also had moderate antiplasmodial activities, with IC50 values of 4.0 and 6.4 μM, respectively, against Plasmodium falciparum, Dd2 strain. The structures were determined using spectroscopic methods.
New Flavonol Glycosides from the Leaves of Triantha Japonica and Tofieldia Nuda
Authors: Iwashina Tsukasa , Tamura Minoru N. , Murai Yoshinori , Kitajima Junichi
Published: March 2019

Two new flavonol glycosides were isolated from the leaves of Triantha japonica, together with eight known flavonols, kaempferol 3- O-sophoroside, kaempferol 3- O-sambubioside, kaempferol 3- O-glucosyl-(1→2)-[glucosyl-(1→6)-glucoside], quercetin 3- O-sophoroside, quercetin 3- O-sambubioside, isorhamnetin 3- O-glucoside, isorhamnetin 3- O-sophoroside and isorhamnetin 3- O-sambubioside. The new compounds were identified as kaempferol 3- O-β-xylopyranosyl-(1→2)-[β-glucopyranosyl-(1→6)-β-glucopyranoside] (1) and isorhamnetin 3- O-β-xylopyranosyl-(1→2)-[β-glucopyranosyl-(1→6)-β-glucopyranoside] (3) by UV, LC-MS, acid hydrolysis, and 1H and 13C NMR spectroscopy. Another two new flavonol glycosides were isolated from the leaves of Tofieldia nuda, and identified as kaempferol 3- O-β-glucopyranosyl-(1→2)-[β-glucopyranosyl-(1→6)-β-galactopyranoside] (4) and quercetin 3- O-β-glucopyranosyl-(1→2)-[β-glucopyranosyl-(1→6)-β-galactopyranoside] (5). Though the genera Triantha and Tofieldia were treated as Tofieldia sensu lato, they were recently divided into two genera. It was shown by this survey that their flavonoid composition were also different to each other.
Biphenyl Derivatives from Garcinia Schomburgkiana and the Cytotoxicity of the Isolated Compounds
Authors: Ito Chihiro , Matsui Takuya , Noda Eri , Ruangrungsi Nijsiri , Itoigawa Masataka
Published: March 2019

Study of the chemical constituents of the stems of Garcinia schomburgkiana Pierre (Guttiferae), collected in Thailand, led to the isolation and identification of five known compounds and two new biphenyl derivatives, schomburgbiphenyl A (1) and B (2). Six phenolic compounds isolated from this plant were screened for their cell growth inhibition activity using several human leukemia cell lines. One compound, oblongifolin C (7), showed significant cytotoxic activity towards Jurkat, NALM6, K562 and HPB-ALL cells.