%0 Journal Article %1 ISI:000304791900017 %A Dastan, Dara %A Salehi, Peyman %A Gohari, Ahmad Reza %A Zimmermann, Stefanie %A Kaiser, Marcel %A Hamburger, Matthias %A Khavasi, Hamid Reza %A Ebrahimi, Samad Nejad %C THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND %D 2012 %I PERGAMON-ELSEVIER SCIENCE LTD %J PHYTOCHEMISTRY %K Apiaceae; ECD; Plasmodium Sesquiterpene TDDFT; X-ray analysis; coumarin; falciparum} pseudalliacea; {Ferula %P 170-178 %R 10.1016/j.phytochem.2012.02.016 %T Disesquiterpene and sesquiterpene coumarins from Ferula pseudalliacea, and determination of their absolute configurations %V 78 %X The first disesquiterpene coumarin, sanandajin, five sesquiterpene coumarins, kamolonol acetate, fekrynol acetate, ethyl galbanate, methyl galbanate, farnesiferol B, and a sesquiterpene, aristolone, were isolated from a n-hexane extract of Ferula pseudalliacea roots. The structures were elucidated by 1D and 2D NMR, HR-ESIMS data, and kamolonol acetate was confirmed by single-crystal X-ray analysis. The absolute configuration of compounds was established by comparison of experimental and simulated ECD spectra using time dependence density function theory (TDDFT). In vitro antiplasmodial activity against Plasmodium falciparum K1 strain was determined. sanandajin, kamolonol acetate and methyl galbanate showed moderate antiplasmodial activity, with IC50 values of 2.6, 16.1 and 7.1 AM, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

@article{ISI:000304791900017, abstract = {{The first disesquiterpene coumarin, sanandajin, five sesquiterpene coumarins, kamolonol acetate, fekrynol acetate, ethyl galbanate, methyl galbanate, farnesiferol B, and a sesquiterpene, aristolone, were isolated from a n-hexane extract of Ferula pseudalliacea roots. The structures were elucidated by 1D and 2D NMR, HR-ESIMS data, and kamolonol acetate was confirmed by single-crystal X-ray analysis. The absolute configuration of compounds was established by comparison of experimental and simulated ECD spectra using time dependence density function theory (TDDFT). In vitro antiplasmodial activity against Plasmodium falciparum K1 strain was determined. sanandajin, kamolonol acetate and methyl galbanate showed moderate antiplasmodial activity, with IC50 values of 2.6, 16.1 and 7.1 AM, respectively. (C) 2012 Elsevier Ltd. All rights reserved.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}}, affiliation = {{Salehi, P (Reprint Author), Shahid Beheshti Univ, Med Plants \& Drugs Res Inst, Dept Phytochem, Tehran, Iran. Dastan, Dara; Salehi, Peyman; Ebrahimi, Samad Nejad, Shahid Beheshti Univ, Med Plants \& Drugs Res Inst, Dept Phytochem, Tehran, Iran. Gohari, Ahmad Reza, Univ Tehran Med Sci, Fac Pharm, Med Plants Res Ctr, Tehran, Iran. Zimmermann, Stefanie; Hamburger, Matthias; Ebrahimi, Samad Nejad, Univ Basel, Div Pharmaceut Biol, CH-4056 Basel, Switzerland. Zimmermann, Stefanie; Kaiser, Marcel, Swiss Trop \& Publ Hlth Inst, Dept Med Parasitol \& Infect Biol, CH-4002 Basel, Switzerland. Kaiser, Marcel, Univ Basel, CH-4003 Basel, Switzerland. Khavasi, Hamid Reza, Shahid Beheshti Univ, Dept Chem, Tehran, Iran.}}, author = {Dastan, Dara and Salehi, Peyman and Gohari, Ahmad Reza and Zimmermann, Stefanie and Kaiser, Marcel and Hamburger, Matthias and Khavasi, Hamid Reza and Ebrahimi, Samad Nejad}, author-email = {{p-salehi@sbu.ac.ir goharii\_a@sina.tums.ac.ir}}, biburl = {https://www.bibsonomy.org/bibtex/23d97b5c006d90fd39973c421a6fcfc7f/hkhavasi}, cited-references = {{Abd El-Razek Mohamed H., 2001, Phytochemistry (Oxford), V58, P1289, DOI 10.1016/S0031-9422(01)00324-7. Adams M, 2009, PHYTOCHEM LETT, V2, P159, DOI 10.1016/j.phytol.2009.05.006. Adams M, 2009, NAT PROD COMMUN, V4, P1377. Ahmed AA, 1999, PHYTOCHEMISTRY, V50, P109, DOI 10.1016/S0031-9422(98)00489-0. Argotte-Ramos R, 2006, J NAT PROD, V69, P1442, DOI 10.1021/np060233p. Bednyak A.E., 1962, MAT I GO PERVOGO VSE, P182. Eigner D, 1999, J ETHNOPHARMACOL, V67, P1, DOI 10.1016/S0378-8741(98)00234-7. Fraga BM, 2005, NAT PROD REP, V22, P465, DOI 10.1039/b501837b. Frisch MJ, 2009, GAUSSIAN 09 REVISION. HOFER O, 1984, MONATSH CHEM, V115, P477, DOI 10.1007/BF00810009. HOFER O, 1983, MONATSH CHEM, V114, P1399. Iranshahi M, 2004, PHARM BIOL, V42, P440, DOI 10.1080/13880200490886102. Iranshahi M, 2009, PHARM BIOL, V47, P344, DOI 10.1080/13880200902752884. Iranshahi M, 2008, PHYTOCHEMISTRY, V69, P2753, DOI 10.1016/j.phytochem.2008.08.009. Iranshahi M, 2007, PHYTOCHEMISTRY, V68, P554, DOI 10.1016/j.phytochem.2006.11.002. Kanani MR, 2011, CHEM BIODIVERS, V8, P503, DOI 10.1002/cbdv.201000148. Lee KH, 2003, PHYTOCHEMISTRY, V64, P535, DOI 10.1016/S0031-9422(03)00243-7. Ma CY, 2006, J NAT PROD, V69, P346, DOI 10.1021/np050313d. MISEEVA G P, 1978, Chemistry of Natural Compounds (English Translation of Khimiya Prirodnykh Soedinenii), V14, P110, DOI 10.1007/BF00565894. Murray R.D.H., 1982, NATURAL COUMARINS, P555. Muthaura CN, 2011, EXP PARASITOL, V127, P609, DOI 10.1016/j.exppara.2010.11.004. Nazari ZE, 2011, PHYTOTHER RES, V25, P315, DOI 10.1002/ptr.3311. O'Boyle NM, 2008, J COMPUT CHEM, V29, P839, DOI 10.1002/jcc.20823. Oketch-Rabah HA, 2000, FITOTERAPIA, V71, P636, DOI 10.1016/S0367-326X(00)00222-7. Pimenov M. G., 2004, Turkish Journal of Botany, V28, P139. Ross SA, 2008, NAT PROD COMMUN, V3, P791. RUCKER G, 1984, PHYTOCHEMISTRY, V23, P1647, DOI 10.1016/S0031-9422(00)83460-3. Sheldrick G.M., 1997, SHELX97 PROGRAM CRYS. Slusarczyk S, 2011, PLANTA MED, V77, P1594, DOI 10.1055/s-0030-1270933. Stoe Cie, 2000, XSTEP32 STOE CIE GMB. Stoe Cie, 2009, X AREA VERS 1 31 PRO. Subeki Subeki, 2005, J Nat Prod, V68, P537. Tamemoto K, 2001, PHYTOCHEMISTRY, V58, P763, DOI 10.1016/S0031-9422(01)00307-7. Veselovskaya N.V., 1981, KHIM PRIR SOEDIN, V17, P798. Yenjai C, 2000, PLANTA MED, V66, P277, DOI 10.1055/s-2000-8558. Zargari A., 1997, MED PLANTS, V2. Zaugg J, 2011, PHYTOCHEMISTRY, V72, P2385, DOI 10.1016/j.phytochem.2011.08.014. Zhou P, 2000, PHYTOCHEMISTRY, V53, P689, DOI 10.1016/S0031-9422(99)00554-3.}}, doc-delivery-number = {{952KR}}, doi = {{10.1016/j.phytochem.2012.02.016}}, funding-acknowledgement = {{Shahid Beheshti University Research Council}}, funding-text = {{We are grateful to Shahid Beheshti University Research Council for partial support of this work.}}, interhash = {de115c1608d4a2a765ba635a726dd7b6}, intrahash = {3d97b5c006d90fd39973c421a6fcfc7f}, issn = {{0031-9422}}, journal = {{PHYTOCHEMISTRY}}, journal-iso = {{Phytochemistry}}, keywords = {Apiaceae; ECD; Plasmodium Sesquiterpene TDDFT; X-ray analysis; coumarin; falciparum} pseudalliacea; {Ferula}, keywords-plus = {{CONSTITUENTS; FRUITS; ETHERS; ROOTS}}, language = {{English}}, month = {{JUN}}, number-of-cited-references = {{38}}, orcid-numbers = {{Ebrahimi, samad/0000-0003-2167-8032 Kaiser, Marcel/0000-0003-1785-7302}}, pages = {{170-178}}, publisher = {{PERGAMON-ELSEVIER SCIENCE LTD}}, research-areas = {{Biochemistry \& Molecular Biology; Plant Sciences}}, researcherid-numbers = {{Ebrahimi, samad/F-2477-2017 }}, times-cited = {{13}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Disesquiterpene and sesquiterpene coumarins from Ferula pseudalliacea, and determination of their absolute configurations}}, type = {{Article}}, unique-id = {{ISI:000304791900017}}, usage-count-last-180-days = {{2}}, usage-count-since-2013 = {{28}}, volume = {{78}}, web-of-science-categories = {{Biochemistry \& Molecular Biology; Plant Sciences}}, year = {{2012}} }