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Two New Antiinflammatory Elemanolides from Centaurea Chilensis

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.,...... Joumalof <.:.- ETHNO-- PHARMACOLOGY Journa1 of Ethnopharmacology 40 (1993) 149-153 Two new antiinflammatory elemanolides from Centaurea chilensis Rosa E. Negretea, Nadine Backhousea, Ivan Cajigala, CarIa Delportea, Bruce K. Cassels*b, Eberhard Breitmaierc, Gert EckhardtC apharmacognosy Laboratory, Faculty o/ Chemical and Pharmaceutical Sciences, hDepartment o/ Chemistry, Faculty o/ Sciences, University o/ Chile, Casilla 653, Santiago 1, Chile cOrganic Chemistry lnstitute, Bonn University, Bonn, Germany (Received 19 March 1992; revision received 8 Ju1y 1993; accepted 8 Ju1y 1993) Abstraet Two previously undescribed elemanolide esters, the 2-methylpropanoate and 2-methyl-2-propenoate of 11,13• dehydromelitensin, were iso1ated in the course of a bioassay-guided fractionation from the aeria1 parts of Centaurea chilensis Hook, et Am" used traditionally to treat 'gout and rheumatism', The mixture ofboth substances exhibits anti• inflammatory activity in the carrageenan-induced paw edema assay. Key words: Antiinflammatory; E1emanolides; Centaurea chilensis; Asteraceae l. Introduction (Negrete et al., 1988b), and 11{3-H-II,13-dihydro• desacyl-cynaropicrin 8{3-D-glucoside (Negrete et The genus· Centaurea (Asteraceae, tribe al., 1988a). Cynareae) is a well-known source of sesquiterpene No elemanolides have been reported previously lactones. As part of a study of species growing in from C. chilensis Hook. et Am., but other Cen• Chile, we have now obtained two new elemanolide taurea species have afforded melitensin, dehydro• esters from C. chilensis Hook. et Am. Earlier melitensin, and several ester s of these sesquiter• chemical studies on this plant had afforded {3• pene lactones: melitensin was obtained originally sitosterol and stigmasterol (Negrete et al., 1984), from C. melitensis L. (González et al., 1971) and the flavonoids apigenin 7-0-glucoside, chrysoeriol later from C. aspera varo stenophyl/a (Dufour) 7-0-glucoside, chrysoeriol, luteolin, kaempferol, Nyman (Picher et al., 1984); its structure and quercetin, and hispidulin (Negrete et al., 1988a), as stereochemistry have been confirmed by X-ray well as the guaianolides dehydrocostus lactone analysis (Tortajada et al., 1988); this elemanolide and 8a-hydroxydehydrocostus lactone (Negrete has al so been synthesized via Cope rearrangement et al., 1984), 8a-acetoxydehydrocostus lactone of cnicin to 11,13-dehydro-melitensin (González et al., 1974a), which was first isolated from C. pul/ata • Corresponding author. 0378-8741/93/$06.00 © 1993 Elsevier Scientific Pub1ishers Ireland Ltd. AlI rights reserved. SSDl 0378-8741(93)01055-Q 150 R.E. Negrete et al. / J. Ethnopharmacol. 40 (1993) 149-153 L. (González et al., 1974b); C. melitensis afforded ing, respectively 50, 300, and 400 g of residue after melitensin and 11, 13-dehydromelitensin ¡3-hyd• removing the solvents in vacuo. All 3 extracts were roxybutyrates (González et al., 1975); C. arbuti• administered to guinea pigs (see below) to monitor folia Svent. gave 11,13-dehydromelitensin iso• potential antiinflammatory activities. The chloro• valerate (isoarbutifolin) (González et al., 1981), C. form extract proved to be the most active in the phrygia L. yielded the 8a-(5-hydroxy)-angeloyl carageenan-induced paw edema assay, and was ester (Tsankova and Ognyanov, 1985) and C. therefore chromatographed on a silica gel G cineraria L. ssp. umbrosa (Lacaita) Pign. (syn. C. column, eluting with petroleum ether-CH2Cl2 ucriae Lacaita ssp. ucriae) gave the 2-methyl-3,4• mixtures of increasing polarity as shown in dihydroxybutyrate (Bruno and Herz, 1988). Table 1. C. chilensis has been used in folk medicine for 11,13-Dehydromelitensin 2-methylpropanoate 'gout and rheumatism', although the treatment (1) and 2-methyl-2-propenoate (I1) from fractions advocated in recent years only involves external B, C and D (see Table 1) were purified by further use (Muñoz et al., 1981). Several guaianolides are chromatography on silica gel G with petroleum known to possess anti-inflammatory activity, ether-CH2Cl2 (3:2) increasing the CH2CI2 propor• which has been related to the presence of the tion up to 100%. The major constituent obtained a-methylene-')'-Iactone moiety (Hall et al., 1979, in this way (300 mg) seemed to be homogeneous 1980), and this suggested a possible relationship on TLC (silica gel; light petrol-EtOAc 7:3; between the chemistry of this plant and its tradi• RF = 0.35) and had the appearance of a slightly tional use. In this paper we describe the bioassay• greenish lacquer, insoluble 'in petroleum ether, guided isolation, structure elucidation, and anti• somewhat soluble in CHCI3 and in EtOAc, very inflammatory activity of a mixture of two soluble in MeOH, giving a purple Lieber• previously undescribed elemanolide esters: 11,13• mann-Burchard reaction. In CHCI3, the mixture dehydromelitensin 2-methylpropanoate (1) and 2• apparently polymerizes, giving a white precipitate methyl-2-propenoate (I1), from C. chilensis. which cannot be redissolved. EIMS m/z data were: (relative abundance) 264.1366 (0.26%; calculated 2. Materials and methods ClsH2004, 264.1361), 246.1265 (7.65%; calculated ClsHIS03, 246.1256), 228.1149 (8.43%; calculated Aerial parts of Centaurea chilensis were col• C'SH'60b 228.1149). Complete lH_ and l3C_ lected in the flowering season (December) in Las NMR assignments are shown in Table 2. Tacas, La Serena (near sea level, 300S latitude), Anti-inflammatory activity was tested against Chile. A voucher specimen (L. Arancibia 16078) is carrageenan-induced edema in the guinea pig on deposit in the Botany Laboratory of the Facul• hindpaw. A-Carrageenan (1% in saline, 0.1 mI) was ty of Chemical and Pharmaceutical Sciences, Uni• injected into the left plantar aponeurosis of groups versity of Chile, Santiago (SQF). Melting points are uncorrected and were de ter• mined on a Kofler hot stage. IR spectra (KBr Table 1 discs) were recorded utilizing a Leitz IIIG infrared Fraetionation of the ehloroform extraet of Centaurea chilensis spectrometer. NMR spectra in CDCI3 with TMS as internal standard were recorded at 400 MHz Fraetion 25:75Solvent75:2550:50100%1000;',100'10petroleumCH2Cl2petroleumMeOHeompositionether/CH2Cl2ethernone+Anti-+++++ B ('H) and 100.5 MHzCFED (l3C) on a Bruker WM-400 inf1ammatoryaetivity A spectrometer, using commercially available pulse programs for DEPT and 2D spectra ('H_1H and 'H-l3C COSY, COLOC). The HREIMS was recorded on a Kratos MS-30 instrument. The air-dried, ground plant material (4.0 kg), was extracted successively (at room temperature) with petroleum ether, CHCI3, and MeOH, yield- R.E. Negrete et al. / J. Ethnopharmacol. 40 (1993) /49-153 151 of 10-15 guinea pigs of both sexes (Pirbright) by the paw, immersed up to a mark made weighing 200-300 g, fasted for 24 h, with water ad previously just above the ankle, before injecting libitum, and kept at 18-20°C. The volume of the carrageenan, and 3 h later. Drugs or vehicle (pro• injected paw was determined with a plethysmo• pyleneglycol) were administered orally 1 h before meter by measuring the volume of water displaced injection. The percent inhibition of edema· was Table 2 l3c and IH chemical shifts from the 100 MHz 13C and 400 MHz IH NMR spectra - assignments based on the 100/400 MHz FI• decoupled CH correlation CHCCCH147.87113.28112.97145.59613C46.1570.3751.8180.03173.72139.13119.59171.4053.1342.9535.1966.6819.1119.3119.03 C Atoms CH3CH2CH2CHn147.85113.2546.05167.67139.08137.43126.95119.6380.0070.9651.7453.0342.9218.4119.26 61H 3JHH coupling 153a 17a13b13a12IOb19b14a14b18a11b16b18b19a17blOa49b7b3b6b9a8b8a27a5a5blb1a (ppm) b for compound 11. (ppm) (H) a11a6afor compound16al. 6.03; 5.58; 5.54 1.96; 6.14; 5.69 5.83 2.49; 5.00; 4.90; 1.71; 1.16 5.83 2.51; 5.00; 4.90; 1.68; 1.19 a2.49; 4.05; 3.94; 5.40 b 2.51; 4.05; 3.94; 5.40 2.90; 4.46; 6.03 3.05; 4.48; 6.03 6.14; 1.96 6./4; 5.69 1.96 6.03; 5.54 3.05 6.03; 5.58 2.90 5.40; 5.00 4.05; 3.94; 2.49 5.40; 5.00 4.05; 3.94; 2.51 a5.00; 4.90 b5.02; 5.02 4.46 2.90; 2.49 4.48 3.05; 2.51 5.27 3.05; 1.88; 1.68 5.22 2.90; 1.88; 1.71 4.05; 3.94 5.40; 5.00 2.90 5.22; 6.03; 5.58 3.05 4.48; 5.27; 6.03; 5.54 2.49 4.46; 1.16; 1.88; 5.00; 5.40 2.51 4.48; 1.19; 1.88; 5.00; 5.40 1.88; 1.71 1.16 1.88; 1.68 1.19 2.49; 5.00; 4.90; 1.16; 1.88; 1.71 2.51; 5.02; 5.02; 1.19; 1.88; 1.68 2.61 1.16 2.49; -1.71 1.19 2.51; 1.68 1.17 1.19 1.19 1.17 1.96 6.14; 5.69 152 R.E. Negrete et al. /1. Ethnopharmacol. 40 (1993) 149-153 calculated for each group with respect to its made on the basis of DEPT, homo- and hetero• vehicle-treated control group, and analyzed nuclear COSY, and COLOC spectra, and are sum• statistically using Student's t-test. marized in Table 2. 3. Results 4. Discussion and conclusion A 20% infusion of the aerial parts of this plant, The fact that germacradienolides undergo facile similar to that recommended by folk healers, thermal isomerization to elemadienolides has led administered orally to guinea pigs, exhibited weak to the suggestion that some of these latter products (20%) but significant (P < 0.05) anti-inflamma• may be artefacts (Barrero et al., 1989). The drying tory activity at 4 ml!kg in a carrageenan-induced of the plant material, the extraction and all purifi• paw edema assay (Winter et al., 1962).The residue cation steps relating to compounds 1 and n, of the methanol extract of C.
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    SEED SET IN A NON-NATIVE, SELF-COMPATIBLE THISTLE ON SANTA CRUZ ISLAND: IMPLICATIONS FOR THE INVASION OF AN ISLAND ECOSYSTEM JOHN F. BARTHELL1, ROBBIN W. THORP2, ADRIAN M. WENNER3, JOHN M. RANDALL4 AND DEBORAH S. MITCHELL5 1Department of Biology & Joe C. Jackson College of Graduate Studies & Research, University of Central Oklahoma, Edmond, OK 73034; [email protected] 2Department of Entomology, University of California, Davis, CA 95616 3Department of Ecology, Evolution & Marine Biology, University of California, Santa Barbara, CA 93106 4The Nature Conservancy, Invasive Species Program Initiative & Department of Vegetable Crops, University of California, Davis, CA 95616 5Animal Medical Center, Edmond, OK 73034 Abstract—In two previous studies we demonstrated a positive association between honey bee visitation and seed set or seed head weight in the invasive yellow star-thistle, Centaurea solstitialis. However, as reported here, we were unable to find similar evidence for the congeneric tocalote, Centaurea melitensis. Both seed head weights and percent seed set levels obtained from two plots showed no significant differences among four treatments. Indeed, no significant differences occurred between controls (open) and bagged flower heads that excluded honey bees (but allowed native bee visitation). There were also no differences between controls and complete exclusion of bee-pollinators, confirming self-compatibility reported for this species elsewhere. Unlike C. solstitialis, C. melitensis attracts relatively low numbers of honey bees. In addition, C. melitensis is generally more widespread on the Channel Islands than C. solstitialis. We discuss these patterns with reference to the invasiveness of both species on Santa Cruz Island. Keywords: Apis mellifera, Centaurea solstitialis, honey bee, invasive species, pollination, yellow star- thistle INTRODUCTION environments is subject to controversy, increasingly so during the last decade.
  • Sargetia Series Scientia Naturae

    Sargetia Series Scientia Naturae

    www.mcdr.ro / www.cimec.ro A C T A M U S E I D E V E N S I S S A R G E T I A SERIES SCIENTIA NATURAE XXI DEVA - 2008 www.mcdr.ro / www.cimec.ro EDITORIAL BOARD SILVIA BURNAZ MARCELA BALAZS DANIELA MARCU Computer Editing: SILVIA BURNAZ, DORINA DAN Advisory board/ Referenţi ştiinţifici: Prof. univ. dr. Dan Grigorescu – The University of Bucharest Prof. univ. dr. Vlad Codrea – The University Babeş-Bolyai Cluj-Napoca Prof. univ. dr. Lászlo Rákosy – The University Babeş-Bolyai Cluj-Napoca Conf. univ. dr. Marcel Oncu – The University Babeş-Bolyai Cluj-Napoca SARGETIA SARGETIA ACTA MUSEI DEVENSIS ACTA MUSEI DEVENSIS SERIES SCIENTIA NATURAE SERIES SCIENTIA NATURAE L’adresse Address: Le Musée de la Civilisation Dacique et The Museum of Dacian and Roman Romaine Civilization La Section des Sciences Naturelles The Natural Sciences Section Rue 1 Decembrie 39 DEVA 39, 1 Decembrie Street – DEVA ROUMANIE ROMANIA e-mail: [email protected] e-mail: [email protected] Published by the Museum of Dacian and Roman Civilisation Deva All rights reserved Authors bear sole responsibility for the contents of their contributions Printed by qual media Producţie şi Simţire Publicitară & Mediamira Publishing House ISSN 1224-7464 www.mcdr.ro / www.cimec.ro S U M M A R Y – S O M M A I R E Pag. ŞTEFAN VASILE - A new microvertebrate site from the Upper 5 Cretaceous (Maastrichtian) deposits of the Haţeg Basin DIANA PURA - Early Late Cretaceous (Cenomanian) 17 fossiliferous deposits from the Ohaba-Ponor area, SW Romania-preliminary study VLAD A.
  • Germinative Response to Heat Treatments in Relation to Resprouting Ability

    Germinative Response to Heat Treatments in Relation to Resprouting Ability

    Journal of Ecology 2008, 96, 543–552 doi: 10.1111/j.1365-2745.2008.01359.x BurningBlackwell Publishing Ltd seeds: germinative response to heat treatments in relation to resprouting ability S. Paula and J. G. Pausas* Centro de Estudios Ambientales del Mediterráneo (CEAM), Charles R. Darwin 14, Parc Tecnològic, Paterna, València 46980, Spain Summary 1. In Mediterranean fire-prone ecosystems, plant species persist and regenerate after fire by resprouting, by recruiting new individuals from a seed bank (post-fire seeding), or by both resprouting and post-fire seeding. Since species with resprouting ability are already able to persist in fire-prone ecosystems, we hypothesize that they have been subjected to lower evolutionary pressure to acquire traits allowing or enhancing post-fire recruitment. Consequently, we predict that the germination of non-resprouters is more likely to be increased or at least unaffected by heat than the germination of resprouters. 2. To test this hypothesis we compiled published experiments carried out in Mediterranean Basin species where seeds were exposed to different heat treatments. We compared the probability of heat-tolerant germination (i.e. heated seeds had greater or equal germination than the control), the probability of heat-stimulated germination (i.e. heated seeds had greater germination than the control) and the stimulation magnitude (differences in proportion of germination of the heated seeds in relation to the untreated seeds, for heat-stimulated treatments) between resprouters and non-resprouters. 3. Non-resprouters showed higher probability of heat-tolerance, higher probability of heat- stimulation and higher stimulation magnitude even when phylogenetic relatedness was considered. Differences between life-forms and post-fire seeding ability do not explain this pattern.
  • Overview of the Anti-Inflammatory Effects, Pharmacokinetic Properties

    Overview of the Anti-Inflammatory Effects, Pharmacokinetic Properties

    Acta Pharmacologica Sinica (2018) 39: 787–801 © 2018 CPS and SIMM All rights reserved 1671-4083/18 www.nature.com/aps Review Article Overview of the anti-inflammatory effects, pharmacokinetic properties and clinical efficacies of arctigenin and arctiin from Arctium lappa L Qiong GAO, Mengbi YANG, Zhong ZUO* School of Pharmacy, Faculty of Medicine, The Chinese University of Hong Kong, Hong Kong SAR, China Abstract Arctigenin (AR) and its glycoside, arctiin, are two major active ingredients of Arctium lappa L (A lappa), a popular medicinal herb and health supplement frequently used in Asia. In the past several decades, bioactive components from A lappa have attracted the attention of researchers due to their promising therapeutic effects. In the current article, we aimed to provide an overview of the pharmacology of AR and arctiin, focusing on their anti-inflammatory effects, pharmacokinetics properties and clinical efficacies. Compared to acrtiin, AR was reported as the most potent bioactive component of A lappa in the majority of studies. AR exhibits potent anti-inflammatory activities by inhibiting inducible nitric oxide synthase (iNOS) via modulation of several cytokines. Due to its potent anti-inflammatory effects, AR may serve as a potential therapeutic compound against both acute inflammation and various chronic diseases. However, pharmacokinetic studies demonstrated the extensive glucuronidation and hydrolysis of AR in liver, intestine and plasma, which might hinder its in vivo and clinical efficacy after oral administration. Based on the reviewed pharmacological and pharmacokinetic characteristics of AR, further pharmacokinetic and pharmacodynamic studies of AR via alternative administration routes are suggested to promote its ability to serve as a therapeutic agent as well as an ideal bioactive marker for A lappa.