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No. 8 Phytotoxic Activity of Flavonoids from Dicranostyles ampla 1233 - 1237
Amaya Castroa*, Charles L. Cantrellb, Amber L. Haleb and Stephen O. Dukeb aIQAC-CSIC, Jordi Girona 18-26, 08034 Barcelona, Spain bUSDA-ARS, Natural Products Utilization Research Unit, University, MS 38677, USA amaya[email protected].
Received: September 22nd, 2009; Accepted: July 20th, 2010
Crude extracts from over 16 species of plants from the family Convolvulaceae were evaluated for phytotoxic activity against Agrostis stolonifera (bentgrass) and Lactuca sativa (lettuce) at 1000 μg/mL. Ethanol extracts of Dicranostyles ampla Ducke were among the most active of those species tested. Systematic bioassay-guided fractionation of the ethanol extract of the aerial parts from this species was performed to identify specifically the phytotoxic compounds. Two phytotoxic flavonoids, dihydromyricetin (1) and myricetin-3-O-α-rhamnoside or myricetrin (2), were found to be responsible for much of the activity of the extract as a whole in the A. stolonifera and L. sativa bioassay. In a Lemna paucicostata bioassay, 1 and 2 had no activity at 100 μM.
Keywords: flavonoids, Dicranostyles ampla, dihydromyricetin, myricitin-3-O-α-rhamnoside, phytotoxicity.
Current agricultural practices involved in weed tricolorin A as the major compound, showed high management depend strongly on the use of synthetic phytotoxic activity, as well as inhibition of herbicides. Most biologically active natural products are Staphylococcus aureus growth and cytotoxity against partially water-soluble and some of them can exhibit cultured P-388 and human breast cancer cells [11]. bioactivity at very low concentrations [1]. Furthermore, Total synthesis of tricolorin A, a promising compound they may have different modes of action from synthetic from Ipomoea tricolor, was accomplished five years herbicides, making natural products a promising source later [12,13]. Extracts from the Convolvulaceae species of new useful compounds to counter evolved herbicide Argyreia speciosa [14] and some Ipomoea species [15] resistance. Some of these mechanisms have been are also reported to be phytotoxic. described by Dayan et al. [2]. Flavonoids has been reported for this family The Convolvulaceae family consists of about 85 genera [8,9,16-18], but the genus Dicranostyles has thus far and 2800 species, which are widely distributed in never been studied. The potential phytotoxic activity of tropical, subtropical, and temperate regions. In China, flavonoids has been reported for some molecules: this family is well known as a source of food plants, hispidulin [19], eriodictyol-7-O-glucuronide [20], ornamentals, medicinal plants and noxious weeds [3]. wogonin [21] and (+)-catechin [22]; while no structure- Morning glory is a common name used to describe over activity studies have yet been reported. 1000 species of Convolvulaceae, the seeds of which are reported to contain alkaloids. For this reason they are Aerial parts of 16 Convolvulaceae species were the most studied compounds and considered chemo- evaluated against both the monocot Agrostis markers for different Convolvulaceae genera [4-6]. stolonifera (bentgrass) and the dicot Lactuca sativa (lettuce) at 1 mg/mL, where 0 = no effect and 5 = no Different bioactivities regarding other types of growth or no germination of the seeds (Table 1). molecules from Convolvulaceae have also been Species tested were: Aniseia martinicensis, Convolvulus described. Recently reported activities include arvensis, Dicranostyles ampla, D. holostyla, Evolvulus moderately antioxidant saponins [7] and flavonoids [8], nummularis, Ipoema acuatica, I. batatoides, I. nil, anti-stress phenolic compounds [9], and antinociceptive I. ophioides, I. pandurata, I. purpurea, I. quamoclit, I. caffeoylquinic acids [10]. Regarding allelopathic squamosa, I. triloba, I. batatas and Maripa paniculata. potential, a mixture of so called "resin glycosides", with D. ampla afforded one of the highest levels of 1234 Natural Product Communications Vol. 5 (8) 2010 Castro et al.
Table 1: Phytotoxicity screening results for 16 Convoluvulaceae species. which showed high activity (50% methanol) against species (aerial part extracted) L. sativa* A. stolonifera* bentgrass and moderate activity against lettuce. This Aniseia martinicensis (leaf-stem) 3 1 fraction was further purified using preparative HPLC to Convolvulus arvensis (whole plant) 0 1 yield four pure compounds, two of them unstable and Dicranostyles ampla (leaf-stem) 4 4 showing quick decomposition within one hour of Dicranostyles holostyla (stem-bark) 0 1 isolation. Dicranostyles holostyla (leaf-twig) 1 1 Evolvulus nummularius (whole plant) 2 1 Ipoema aquatica (whole plant) 0 1 Compounds 1 and 2 were stable and their structures I. batatoides (whole plant) 3 0 were established based on one- and two-dimensional I. nil (leaf-stem) 2 0 NMR experiments. Bioassay results are shown in Table I. ophioides (leaf-stem) 2 0 I. ophioides (whole plant) 2 1 3 for 1 and 0.1 mg/mL concentrations. I. pandurata (shoot) 4 1 1 13 I. pandurata (whole plant) 2 1 The H and C NMR spectroscopic data of 1 matched I. purpurea (whole plant) 3 1 those for dihydromyricetin (ampelopsin) [23], while a I. quamoclit (whole plant) 1 1 few re-assignments are proposed in this article for I squamosa (whole plant) 0 0 compound 2, myricetin-3-O-α-rhamnoside (myricitrin) I. triloba (leaf-stem) 1 0 1 13 Maripa paniculata (leaf-twig) 2 2 [24,25]. H- C HMBC cross-peaks from δ 6.90 ppm to M. paniculata (leaf-twig) 1 3 δ 157.6 points this value to C-2, which was previously M. paniculata (stem-bark) 3 2 switched with C-9 at δ 156.5. Correlation between I. batatas (shoot) 0 0 δ 6.39 and δ 156.5 confirms the assignment for C-2 and 0 = no effect, 5 = no growth or no germination of the seeds C-9 proposed in this paper. * 10% acetone used as solvent Due to the 1H-13C HSQC cross-peaks observed, the phytotoxic activity and was further studied using a 13C chemical shifts for the rhamnoside have also been bioassay-guided isolation approach. Aerial parts were re-assigned. Chemical shifts at δ 3.98, δ 3.55 and δ 3.36 sequentially extracted, as described below, and extracts present cross-peaks with carbons at δ 70.0, δ 70.7 and subjected to phytotoxicity assay (Table 2). The ethanol δ 70.4, respectively. A 1H-1H COSY spin system extract showed activity against both species, while all from the anomeric proton at δ 5.20, allows the remaining extracts were inactive against both bentgrass establishment of protons at 3.98, 3.55 and 3.36 as and lettuce at 1 mg/mL. chemical shifts for H-2’’, H-3’’ and H-5’’, respectively. C-1’’ stereochemistry for 2, showed as myricetin-3-O- The EtOH extract was further fractionated using C-4 α-rhamnoside, is thermodynamically preferred due to column chromatography, producing six fractions, one of
Table 2: Phytotoxicity screening results for Dicranostyles ampla bioassay-guided fractions. Fractiona,b L. sativa A. stolonifera Solvent Hx Extract 0 0 DCM DCM Extract 0 0 DCM EtOH Extract 4 4 EtOH Hx Partition 2 0 10% acetone CLF Partition 1 4 10% acetone EtOAc Partition 1 3 10% acetone C-4 Water 1 2 Water C-4 25% MeOH 0 1 MeOH C-4 50% MeOH 2 4 10% acetone C-4 75% MeOH 1 3 10% acetone C-4 MeOH 1 1 10% acetone C-4 DCM 0 1 10% acetone Water Partition 0 0 MeOH Water Extract 0 0 Water a Hx = n-hexanes, DCM = dichloromethane, EtOH = ethanol, CLF = chloroform, MeOH = methanol; b Fractions tested at 1 mg/Ml; 0 = no effect, 5 = no growth or no
Table 3: Phytotoxicity results for pure compounds 1 and 2. Compounda,b Solvent Concentration 1 mg/mL Concentration 0.1 mg/mL L. sativa A. stolonifera L. sativa A. stolonifera Dihydromyricetin (1) Water 1 2 0 0 Myricitrin (2) 10% Acetone 1 5 0 1 0 = no effect, 5 = no growth or no germination of the seeds Phytotoxic activity of flavonoids from Dicranostyles ampla Natural Product Communications Vol. 5 (8) 2010 1235
axial and equatorial substituent positions. No evidence Standards: Kaempferol-3-O-β-glucopyranoside and for either D or L rhamnose configuration has been myricetin were purchased from Indofine (Hillsborough, found. NJ, USA).
Myricitrin (2) showed high activity against bentgrass Plant material: Dicranostyles ampla Ducke was and moderate activity against lettuce at 1 mg/mL, collected by William H Taylor in an “inundated forest” although the activity decreased at lower concentrations in the Mana Camiri region of Peru in the Fall of 1996. (Table 3). Dihydromyricetin (1) activity was also l A voucher specimen was deposited in the NCNPR ow-moderate for both species, and no effects were (NCNPR-WHT9). observed at the lower concentration. Lemna bioassays displayed no activity below 100 µM for myricetin, Extraction and bioassay-guided fractioning: Ethanol dihydromyricetin (1) and myricitrin (2). Kaempferol-3- extracts of aerial parts from 16 Convolvulaceae O-β-glucopyranoside was tested up to 1 mM and no species (Aniseia martinicensis, Convolvulus arvensis, effect was found. Higher concentrations were not Dicranostyles ampla, D. holostyla, Evolvulus possible due to incompatible solubility with the nummularis, Ipoema acuatica, I. batatoides, I. nil, I. bioassay requirements. The extract’s initial high ophioides, I. pandurata, I. purpurea, I. quamoclit, I. activity, particularly with lettuce, was not reproduced squamosa, I. triloba, I. batatas and Maripa paniculata) by the isolated compounds, maybe because of the were obtained from the Natural Products Repository at presence of highly active compounds in low abundance the National Center for Natural Products Research, and but not constituents in the bioassay solutions containing tested for phytotoxic activity against lettuce (Lactuca single compounds. Further studies about synergistic sativa) and bentgrass (Agrostis stolonifera). For the effects of flavonoids should be considered in the future. preparation of repository extracts for screening purposes, ground plant material was submersed in EtOH Experimental at room temp. for 24 h, followed by Buchner funnel
General experimental procedures: 1H and 13C NMR filtration and concentration by rotary evaporation at spectra were recorded in deuterated DMSO on a Varian <40°C. Aerial parts of Dicranostyles ampla (1 kg) were ANOVA 400 MHz spectrometer (Palo Alto, CA, USA) ground in a Willey-Mill plant grinder and further under standard 1D and 2D conditions and pulse extracted sequentially overnight at room temp. with sequences. Analytical HPLC method development was n-hexane (7 L), dichloromethane (12 L), ethanol (12 L) performed using an Agilent 1100 system equipped with and distilled water (12 L), yielding 15.1, 12.1, 70.3 and a quaternary pump, autosampler, diode-array detector, 89.5 g of extractive, respectively. A 10 g portion of the vacuum degasser and Zorbax C-18, 4.6 x 250 mm, 5 µm ethanol extract was suspended in 90% MeOH-water column. Preparative HPLC purifications were (600 mL) and fractionated by liquid-liquid extraction performed using a Waters Delta-Prep system (Milford, using n-hexane (250 mL, 3 x; 400 mg). Water was MA, USA) equipped with a diode-array detector, a added to ca. 65% methanol (220 mL) and extracted with binary pump and a C-18 Zorbax-SB, 21.2 x 250 mm, chloroform (250 mL, 3 x; 680 mg). Organic solvents 5 µm column. Fractions were collected with a Waters were evaporated under vacuum, obtaining Fraction Collector III (Milford, MA, USA) every 20 approximately 300 mL of aqueous solution, which was seconds. Reversed-phase column chromatography (RP- further extracted with EtOAc (250 mL, 3x, 1.16 g). The CC) was performed using J.T. Baker BAKERBOND phytotoxic EtOAc portion was adsorbed onto 8 g Wide-Pore Butyl Prep LC Packing, 300 Å, 15 µm stationary phase and filtered (2 g, 4x) through a RP-CC (Phillipsburg, NJ, USA). HPLC grade solvents were with 32 g more C-4 RP silica, eluting with water purchased from Fisher Scientific (Pittsburgh, PA, (57 mg), 25 (87 mg), 50 (617 mg), 75 (222 mg) and USA). 100% (27 mg) of MeOH-water mixtures (200 mL each), followed by dichloromethane cleaning fraction High-resolution LC-MS analysis: Both isolated (200 mL, 19 mg). The active fraction (50% MeOH) was compounds were prepared in MeOH and injected further fractionated by prep-HPLC using 20 mL/min directly into a 0.3 mL/min stream of MeOH. Twenty μL flow rate, and water-acetonitrile 0.1% TFA mixtures of sample (approximately 0.1 mg/mL) was injected and the following gradient: 10% acetonitrile for 5 mins, manually at 0.5 min while mass drift compensation followed by a gradient to 30% organic solvent in standards (L-tryptophan (negative ion), PEG (positive 25 mins, then a gradient to 100% acetonitrile in 5 mins, ion)) were injected at 1.5 min over the course of a 2 min held for 5 mins, and then a gradient to initial conditions run. High-resolution ESI MS were obtained using an and column re-equilibration. Similar fractions were Agilent 1100 HPLC coupled to a JEOL AccuTOF combined based on analytical HPLC results, using (JMS-T100LC) (Peabody, MA, USA). 1 mL/min flow rate, room temp. and water-acetonitrile 1236 Natural Product Communications Vol. 5 (8) 2010 Castro et al.
0.1% TFA mixtures and a mobile phase gradient: 10% through a 0.2 μm filter. Each well of nonpyrogenic acetonitrile for 5 mins, followed by a gradient to 20% polystyrene sterile 6-well plates (CoStar 3506, Corning organic solvent in 20 mins, held for 10 mins and Inc., Corning, NY) was filled with 4950 μL of the followed by a gradient to 100% acetonitrile in 0.5 mins, Hoagland media mixed with 50 μL of DDI water, 50 μL held for 5 mins, and then gradient to initial conditions of acetone with the appropriate concentration of test and column re-equilibration. Four pure compounds compound or 50 μL of EtOH with the appropriate were obtained, 2 of them stable and numbered 1 and 2. concentration of test compound. The final concentration of either acetone or EtOH was 1%. Two three-frond Phytotoxicity assay against Lactuca sativa and colonies from 4- to 5-dayold stock cultures were placed Agrostis stolonifera: Screening studies were carried out in each well. Total frond area per well was recorded by with bentgrass (Agrostis stolonifera L.) and lettuce the image analysis system, Scanalyzer (LemnaTec, (Lactuca sativa L.) as model species, representing Würselen, Germany) at days 4 and 7 [26]. Percent monocotyledonous and dicotyledonous plants, increase at days 4-7 was determined relative to baseline respectively. area at day 0. For dose-response results, concentrations greater than 100 μM were considered beyond the range A filter paper (Whatman no. 1) and 5 mg of L. sativa of interest for agronomic purposes [2]. seeds or 10 mg of A. stolonifera seeds were placed in each well of a 24-well multiwell plate (Corning Inc., Dihydromyricetin (ampelopsin) (1)
Corning, NY). Test fractions were dissolved in acetone Yield: 8.4 mg, 0.084% of crude ethanolic extract. 1 13 and mixed with distilled–deionized (DDI) H2O such H NMR and C NMR (DMSO-d6) data matched those that the final concentration of acetone was 3%. To each described previously [24]. - test well, 250 μL of the DDI H2O mixture was added. HR-ESI-MS, m/z (%) = 319.04259 [M - H] calculated Only acetone and DDI H2O were added to each control for C15H12O8, 320.05322. well. When necessary, fractions were dissolved in MeOH, DCM or EtOH, applied over the Whatman filter Myricetin-3-O-α-rhamnoside or myricitrin (2) and once the solvent had evaporated, 250 μL of DDI Yield: 9.4 mg, 0.094 % of crude ethanolic extract. H2O was added. Controls were treated in the same way, 1 H NMR (400 MHz, DMSO-d6): 6.90 (2H, s, H-2’, applying plain organic solvent in the first step. Plates H-6’), 6.39 (1H, s, H-8), 6.21 (1H, s, H-6), 5.20 (1H, s, were covered, sealed with parafilm, and incubated at 2 H-1’’), 3.98 (1H, brs, H-2’’), 3.55 (1H, dd, J = 9.2, 4.0 26°C in a Conviron growth chamber at 173 μmol/m /sec Hz, H-3’’), 3.36 (1H, td, J = 8.8, 4.0 Hz, H-5’’), 3.16 under continuous light intensity. Phytotoxicity was (1H, t, J = 9.6, 9.2 Hz, H-4’’), 0.84 (3H, d, J = 8.0 Hz, qualitatively evaluated by visually comparing the Me). amount of germination of the seeds in each well with 13 C NMR (100 MHz DMSO-d6): 177.8 (C-4), 164.3 the untreated controls after 7-9 days. The qualitative (C-7), 161.4 (C-5), 157.6 (C-2), 156.5 (C-9), 145.7 estimate of phytotoxicity was evaluated by using a (C-3’), 136.5 (C-4’), 134.4 (C-3), 119.8 (C-1’), 108.0 rating scale of 0–5, where 0 meant no effect, and 5 no (CH, C-2’), 104.1 (C-10), 102.0 (CH, C-1’’), 98.7 growth or no germination of the seeds. Each experiment (CH, C-6), 93.6 (CH, C-8), 71.3 (CH, C-4’’), 70.7 was repeated in triplicate. (CH, C-5’’), 70.4 (CH, C-5’’), 70.0 (CH, C-2’’), 17.6
(CH3, C-6’’). Phytotoxicity assay against Lemna paucicostata: HR-ESI-MS, m/z (%) = 463.09456 [M - H]- calculated L. paucicostata stocks were grown from a single colony for C21H20O12, 464.09548. consisting of a mother and two daughter fronds in a beaker on modified Hoagland media containing 1515 Acknowledgments - Short Stay Grant from MCYT mg/L KNO3, 680 mg/L KH2PO4, 492 mg/L MgSO4 (Spanish Government) to A.C. (Beca Predoctoral de •7H2O, 20 mg/L Na2CO3, 1180 mg/L Ca(NO3)2 •4H2O, Formación de Personal Investigador BES-2005-9474) is 0.5 mg/L MnCl2, 0.025 mg/L CoCl2, 0.025 mg/L gratefully acknowledged. We thank Robert Johnson for CuSO4 •5H2O, and 18.355 mg/L Fe-EDTA. The media his technical assistance in the bioassays. was adjusted to pH 5.5 with 1 M NaOH and filtered
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Flavonoids of Enhydra fluctuans Exhibit Anticancer Activity against Ehrlich’s Ascites Carcinoma in Mice Santanu Sannigrahi, Upal Kanti Mazumder, Arijit Mondal, Dilipkumar Pal, Silpi Lipsa Mishra and Souvik Roy 1239
Liquiritigenin Derivatives and Their Hepatotoprotective Activity Rashmi Gaur, Sunil Kumar, Priyanka Trivedi, Rajendra Singh Bhakuni, Dnyaneshwar Umrao Bawankule, Anirban Pal and Karuna Shanker 1243
Podophyllotoxin Derivatives Show Activity Against Brontispa longissima Larvae Jing Zhang, Ying-Qian Liu, Liu Yang and Gang Feng 1247
Anthraquinones from the Roots of Prismatomeris tetrandra Cun-Li Zhang, Hua Guan, Peng-Zhou Xi, Tao Deng and Jin-Ming Gao 1251
Inhibitory Effects of Black Pepper (Piper nigrum) Extracts and Compounds on Human Tumor Cell Proliferation, Cyclooxygenase Enzymes, Lipid Peroxidation and Nuclear Transcription Factor-kappa-B Yunbao Liu, Vivek R. Yadev, Bharat B. Aggarwal and Muraleedharan G. Nair 1253
Cinnamoylphenethylamine 1H-NMR Chemical Shifts: A Concise Reference for Ubiquitous Compounds Hans A. Pedersen, Stine K. Steffensen and Carsten Christophersen 1259
Pro-coagulant Activity of Phenolic Acids Isolated from Blumea riparia Li Huang, Cuiwu Lin, Aiyuan Li, Baoyao Wei, Jianwen Teng and Lue Li 1263
Vascular Effects of a Sulfated Polysaccharide from the Red Marine Alga Solieria filiformis Ana Maria S. Assreuy , Grazielle C. Pontes, Natália V. F. C. Rodrigues, Daniel M. Gomes, Paulo A. Xavier, Glacio S. Araujo, Alexandre H. Sampaio, Benildo S. Cavada, Maria G. Pereira and Wladimir R. L. Farias 1267
Encapsulation and Regeneration of in vitro Derived Zephyranthes grandiflora: an Effective Way for Exchange of Germplasm Moumita Gangopadhyay, Saikat Dewanjee, Dipjyoti Chakraborty and Sabita Bhattacharya 1273
Comparison of Aqueous Plant Extracts Before and After Fermentation with Lactobacillus paracasei LS-2 on Cytokine Induction and Antioxidant Activity Heeson Chon, Gyeomheon Kim and Sungkwon Kim 1277
Volatile Compounds from Tagetes pusilla (Asteraceae) Collected from the Venezuela Andes Diolimar Buitrago, Luis B. Rojas, Janne Rojas and Antonio Morales 1283
Volatile Components of Two Endemic Species from the Apuan Alps (Tuscany, Italy), Centaurea arachnoidea and C. montis-borlae (Asteraceae) Lucia Viegi, Mirko Boracchia, Roberto Cecotti and Aldo Tava 1285
Composition of Essential Oil from Seeds and Cones of Abies alba Anna Wajs, Justyna Urbańska, Ewa Zaleśkiewicz and Radosław Bonikowski 1291
Comparative Analysis of Essential Oil Components of Two Pinus Species from Taibai Mountain in China Yuan Zhang and Zhezhi Wang 1295
Antimicrobial Activity and Volatile Constituents of the Essential Oil of Pulsatilla albana from Iran Ali Shafaghat 1299
Chemical Composition and Antimicrobial Activity of the Essential Oils from Cleome spinosa Megil J. McNeil, Roy B. R. Porter, Lawrence A.D. Williams and Lois Rainford 1301
Virucidal Activity and Chemical Composition of Essential Oils from Aromatic Plants of Central West Argentina Cybele C. García, Eliana G. Acosta, Ana C. Carro, María C. Fernández Belmonte, Renata Bomben, Claudia B. Duschatzky, Marina Perotti, Carola Schuff and Elsa B. Damonte 1307
Neolitsea sericea Essential Oil Attenuates LPS-induced Inflammation in RAW 264.7 Macrophages by Suppressing NF-κB and MAPK Activation Weon-Jong Yoon, Ji-Young Moon, Ji-Yong Kang, Gi-Ok Kim, Nam Ho Lee and Chang-Gu Hyun 1311
Qualitative Analysis of the Smoke-Stream of Different Kinds of Incense by SPME/GC-MS Antonietta Lombardozzi, Morela Strano, Manuela Cortese, Massimo Ricciutelli, Sauro Vittori and Filippo Maggi 1317
Essential Oil Composition and in vivo Volatiles Emission by Different Parts of Coleostephus myconis Capitula Guido Flamini, Pier Luigi Cioni, Simonetta Maccioni and Rosa Baldini 1321
Pesticide and Plasticizer Residues in Citrus Essential Oils from Different Countries Giuseppa Di Bella, Vincenzo Lo Turco, Rossana Rando, Gabriella Arena, Donatella Pollicino, Rosario Rocco Luppino and Giacomo Dugo 1325
Applying New Science for Old Medicines: Targeting Leukocyte-Endothelial Adhesions by Antiinflammatory Herbal Drugs Solomon Habtemariam 1329 Natural Product Communications 2010 Volume 5, Number 8
Contents
Original Paper Page
Phytochemical Investigation of Verbesina turbacensis Kunth: Trypanosome Cysteine Protease Inhibition by (–)-Bornyl Esters Ifedayo V. Ogungbe, Rebecca A. Crouch, William A. Haber and William N. Setzer 1161
Anti-herpetic Activities of Chemical Components from the Brazilian Red Alga Plocamium brasiliense Wilton José Ferreira, Rodrigo Amaro, Diana Negrão Cavalcanti, Claudia Moraes de Rezende, Viveca Antonia Giongo Galvão da Silva, Juliana Eymara Barbosa, Izabel Christina Nunes de Palmer Paixão and Valéria Laneuville Teixeira 1167
Chemical Constituents of the Soft Coral Sarcophyton infundibuliforme from the South China Sea Xue-Ping Sun, Chang-Yun Wang, Chang-Lun Shao, Liang Li, Xiu-Bao Li, Min Chen and Pei-Yuan Qian 1171
Metabolites from the Fungus Phoma sp. 7210, Associated with Aizoon canariense Jingqiu Dai, Hidayat Hussain, Siegfried Dräger, Barbara Schulz, Tibor Kurtán, Gennaro Pescitelli, Ulrich Flörke and Karsten Krohn 1175
Triterpenes from Protium hebetatum Resin Delcio Dias Marques, Ilmar Bernardo Graebner, Telma Leda Gomes de Lemos, Luciana Lucas Machado, Jõao Carlos Costa Assunção and Francisco José Queiroz Monte 1181
Cytotoxicity of 9,11-Dehydroergosterol Peroxide Isolated from Ganoderma lucidum and its Target-related Proteins Ya-Jun Cui, Shu-Hong Guan, Li-Xing Feng, Xiao-Yi Song, Chao Ma, Chun-Ru Cheng, Wen-Bo Wang, Wan-Ying Wu, Qing-Xi Yue, Xuan Liu and De-An Guo 1183
Polar Alkaloids from the Caribbean Marine Sponge Niphates digitalis
Erik L. Regalado, Judith Mendiola, Abilio Laguna, Clara Nogueiras and Olivier P. Thomas 1187
A Short Stereoselective Synthesis of Racemic 2-Epicalvine Basem A. Moosa and Shaikh A. Ali 1191
Cytochrome P450 3A4 Inhibitory Activity Studies within the Lycorine series of Alkaloids James McNulty, Jerald J. Nair, Mohini Singh, Denis J. Crankshaw, Alison C. Holloway and Jaume Bastida 1195
Analysis of Amaryllidaceae Alkaloids from Zephyranthes robusta by GC-MS and Their Cholinesterase Activity Lucie Cahlíková, Andrea Kulhánková, Klára Urbanová, Irena Valterová, Kateřina Macáková and Jiří Kuneš 1201
Stereochemistry and NMR Data Assignment of Cyclopeptide Alkaloids from Zizyphus oxyphylla Muhammad Nisar, Waqar Ahmad Kaleem, Achyut Adhikari, Zulfiqar Ali, Nusrat Hussain, Inamullah Khan, Mughal Qayum and M. Iqbal Choudhary 1205
Geranylated Flavonols from Macaranga rhizinoides Mulyadi Tanjung, Didin Mujahidin, Euis H. Hakim, Ahmad Darmawan and Yana M. Syah 1209
A New Biflavonyloxymethane from Pongamia pinnata Anindita Ghosh, Suvra Mandal, Avijit Banerji and Julie Banerji 1213
Anti-inflammatory and Gastroprotective Properties of Hypericum richeri Oil Extracts Gordana Zdunić, Dejan Gođevac, Marina Milenković, Katarina Šavikin, Nebojša Menković and Silvana Petrović 1215
Production of Flavonoids in Organogenic Cultures of Alpinia zerumbet Cristiane P. Victório, Rosani do Carmo de O. Arruda, Celso Luiz S. Lage and Ricardo M. Kuster 1219
Phenolic Compounds in Leaves of Alchornea triplinervia: Anatomical Localization, Mutagenicity, and Antibacterial Activity Tamara R. Calvo, Diego Demarco, Fabio V. Santos, Helen P. Moraes, Taís M. Bauab, Eliana A. Varanda, Ilce M. S. Cólus and Wagner Vilegas 1225
Continued inside backcover