INFORMATION FOR AUTHORS Full details of how to submit a manuscript for publication in Natural Product Communications are given in Information for Authors on our Web site http://www.naturalproduct.us. Authors may reproduce/republish portions of their published contribution without seeking permission from NPC, provided that any such republication is accompanied by an acknowledgment (original citation)-Reproduced by permission of Natural Product Communications. Any unauthorized reproduction, transmission or storage may result in either civil or criminal liability. The publication of each of the articles contained herein is protected by copyright. Except as allowed under national “fair use” laws, copying is not permitted by any means or for any purpose, such as for distribution to any third party (whether by sale, loan, gift, or otherwise); as agent (express or implied) of any third party; for purposes of advertising or promotion; or to create collective or derivative works. Such permission requests, or other inquiries, should be addressed to the Natural Product Inc. (NPI). A photocopy license is available from the NPI for institutional subscribers that need to make multiple copies of single articles for internal study or research purposes. To Subscribe: Natural Product Communications is a journal published monthly. 2012 subscription price: US$1,995 (Print, ISSN# 1934-578X); US$1,995 (Web edition, ISSN# 1555-9475); US$2,495 (Print + single site online); US$595 (Personal online). Orders should be addressed to Subscription Department, Natural Product Communications, Natural Product Inc., 7963 Anderson Park Lane, Westerville, Ohio 43081, USA. Subscriptions are renewed on an annual basis. Claims for nonreceipt of issues will be honored if made within three months of publication of the issue. All issues are dispatched by airmail throughout the world, excluding the USA and Canada.

NPC Natural Product Communications

EDITOR-IN-CHIEF

DR. PAWAN K AGRAWAL Natural Product Inc. 7963, Anderson Park Lane, Westerville, Ohio 43081, USA agrawal@naturalproduct.us

EDITORS

PROFESSOR ALEJANDRO F. BARRERO Department of Organic Chemistry, University of Granada, Campus de Fuente Nueva, s/n, 18071, Granada, Spain afbarre@ugr.es

PROFESSOR ALESSANDRA BRACA Dipartimento di Chimica Bioorganicae Biofarmacia, Universita di Pisa, via Bonanno 33, 56126 Pisa, Italy braca@farm.unipi.it

PROFESSOR DEAN GUO State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China gda5958@163.com

PROFESSOR YOSHIHIRO MIMAKI School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan mimakiy@ps.toyaku.ac.jp

PROFESSOR STEPHEN G. PYNE Department of Chemistry University of Wollongong Wollongong, New South Wales, 2522, Australia spyne@uow.edu.au

PROFESSOR MANFRED G. REINECKE Department of Chemistry, Texas Christian University, Forts Worth, TX 76129, USA m.reinecke@tcu.edu

PROFESSOR WILLIAM N. SETZER Department of Chemistry The University of Alabama in Huntsville Huntsville, AL 35809, USA wsetzer@chemistry.uah.edu

PROFESSOR YASUHIRO TEZUKA Institute of Natural Medicine Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan tezuka@inm.u-toyama.ac.jp

PROFESSOR DAVID E. THURSTON Department of Pharmaceutical and Biological Chemistry, The School of Pharmacy, University of London, 29-39 Brunswick Square, London WC1N 1AX, UK david.thurston@pharmacy.ac.uk

ADVISORY BOARD Prof. Berhanu M. Abegaz Gaborone, Botswana

Prof. Viqar Uddin Ahmad Karachi, Pakistan

Prof. Øyvind M. Andersen Bergen, Norway

Prof. Giovanni Appendino Novara, Italy

Prof. Yoshinori Asakawa Tokushima, Japan

Prof. Lee Banting Portsmouth, U.K.

Prof. Julie Banerji Kolkata, India

Prof. Anna R. Bilia Florence, Italy

Prof. Maurizio Bruno Palermo, Italy

Prof. César A. N. Catalán Tucumán, Argentina

Prof. Josep Coll Barcelona, Spain

Prof. Geoffrey Cordell Chicago, IL, USA

Prof. Ana Cristina Figueiredo Lisbon, Portugal

Prof. Cristina Gracia-Viguera Murcia, Spain

Prof. Duvvuru Gunasekar Tirupati, India

Prof. Kurt Hostettmann Lausanne, Switzerland

Prof. Martin A. Iglesias Arteaga Mexico, D. F, Mexico

Prof. Leopold Jirovetz Vienna, Austria

Prof. Karsten Krohn Paderborn, Germany

Prof. Hartmut Laatsch Gottingen, Germany

Prof. Marie Lacaille-Dubois Dijon, France

Prof. Shoei-Sheng Lee Taipei, Taiwan

Prof. Francisco Macias Cadiz, Spain

Prof. Imre Mathe Szeged, Hungary

Prof. Joseph Michael Johannesburg, South Africa

Prof. Ermino Murano Trieste, Italy

Prof. M. Soledade C. Pedras Saskatoon, Canada

Prof. Luc Pieters Antwerp, Belgium

Prof. Peter Proksch Düsseldorf, Germany

Prof. Phila Raharivelomanana Tahiti, French Polynesia

Prof. Luca Rastrelli Fisciano, Italy

Prof. Monique Simmonds Richmond, UK

Prof. John L. Sorensen Manitoba, Canada

Prof. Valentin Stonik Vladivostok, Russia

Prof. Winston F. Tinto Barbados, West Indies

Prof. Sylvia Urban Melbourne, Australia

Prof. Karen Valant-Vetschera Vienna, Austria

HONORARY EDITOR

PROFESSOR GERALD BLUNDEN The School of Pharmacy & Biomedical Sciences,

University of Portsmouth, Portsmouth, PO1 2DT U.K.

axuf64@dsl.pipex.com

Comparative Study of the Chemical Composition of Essential Oils of Five Tagetes Species Collected in Venezuela Kaylin Armas, Janne Rojas*, Luis Rojas and Antonio Morales Organic Biomolecular Research Group, Research Institute, Faculty of Pharmacy and Bioanalysis, University of Los Andes, Mérida, Venezuela janner@ula.ve

Received: June 11th, 2012; Accepted: July 12th, 2012

The leaves and inflorescences of five species of Tagetes, family Asteraceae, were collected from different locations in Mérida state, Venezuela, and their essential oils analyzed by GC and GC/MS. Several differences were observed in the composition of these oils, mainly regarding the major components, which for T. caracasana were trans-ocimenone (64.3%) and cis-tagetone (13.7%), and for T. erecta, piperitone (35.9%) and terpinolene (22.2%). High amounts of trans-anethole (87.5%) and estragole (10.7%) were observed in T. filifolia, while T. subulata essential oil contained terpinolene (26.0%), piperitenone (13.1%) and limonene (10.8%). For T. patula, two different oil samples were analyzed, leaves (TPL) and inflorescences (TPI). The TPL oil showed terpinolene (20.9%) and piperitenone (14.0%) as main components, while the TPI sample was composed mainly of β-caryophyllene (23.7%), terpinolene (15.6%) and cis-β-ocimene (15.5%).

Keywords: Tagetes, Asteraceae, Essential oil, trans-Anethole, trans-Ocimenone.

Asteraceae is the largest family of vascular plants with more than 23,000 species [1, 2]. The Tagetes genus, which belongs to this large family, is native to Mexico and Central America, but is now spread worldwide. Some species, such as T. erecta, T. patula and T. tenuifolia are cultivated as ornamental plants, while T. minuta can also be found in the wild [3]. Many of these are traditionally exploited for human use as beverages [4] and condiments [5]. In traditional medicine, Tagetes species have been used for their diuretic, antispasmodic anti-inflammatory, anti-hemorrhagic, diaphoretic, anthelmintic and carminative properties [6]. Furthermore, antioxidant, antiviral and insecticidal activities have also been reported [7-10]. Recently, this genus has been the subject of renewed interest in most developed countries as a source of numerous multifunctional secondary metabolites, which have found application as natural substances instead of chemical synthetic compounds [11]. Terpenoids, flavonoids, thiophenes, polythiophenes and pyrethroids are among the components reported for different Tagetes species [12]. On the other hand, the essential oil composition has also been studied reporting a variety of mono and sesquiterpenes such as limonene, ocimene, tagetone, terpinolene, carvacrol, carvone, β-caryophyllene, germacrene D and γ-elemene [13,14]. The purpose of the present study was to investigate and compare the chemical composition of the essential oil of five Tagetes species collected in the Venezuelan Andes. Essential oils from fresh leaves of TC (2.8 mL, 0.24%, w/v), TE (1.0 mL, 0.05%, w/v), TF (2.5 mL, 0.26%, w/v), TS (1.0 mL, 0.08%, w/v), TPL (2.5 mL, 0.09%, w/v) and TPI (0.5 mL, 0.09%, w/v) were analysed by GC and GC/MS techniques. A list of identified components, along with their percentages of the total oil is given in Table 1. Several differences might be observed in the composition of the essential oils analyzed. TC showed trans-ocimenone (64.3%) and cis-tagetone (13.7%) as main components. For TE, piperitone (35.9%) and terpinolene (22.2%) were observed in major proportions, while TF is mainly composed of trans-anethole (87.5%) and estragole (10.7%). TPL, TPI and TS showed terpinolene (20.9% TPL; 15.6% TPI; 26.0% TS) and piperitone

Table 1: Chemical composition of five Tagetes species collected from Mérida-Venezuela.

Compounds* RI TC TE TF TPL TPI TS Sabinene 976 --- 0.6 --- 0.7 --- 0.9 Limonene 1031 --- 8.8 --- 8.4 6.8 10.8 Z-β-Ocimene 1040 3.5 1.8 --- 8.1 15.5 9.5 E-β-Ocimene 1050 --- 7.0 --- 0.7 1.7 1.0 Dihydrotagetone 1061 7.4 --- --- --- --- --- Terpinolene 1088 --- 22.2 --- 20.9 15.6 26.0 1,3,8-p-Menthatriene 1097 --- 0.6 --- --- --- --- Z-Epoxy-ocimene 1128 --- 1.9 --- 1.9 --- 2.4 E-Epoxy-ocimene 1137 --- --- --- 0.9 --- 0.9 E-Tagetone 1146 --- --- --- 3.0 --- 1.9 Z-Tagetone 1153 13.7 --- --- 3.9 2.6 2.8 1,8-Menthadien-4-ol 1183 --- --- --- --- --- 1.4 Estragole 1205 --- --- 10.7 --- --- --- Z-Ocimenone 1231 6.7 --- --- 7.3 8.7 5.5 E-Ocimenone 1239 64.3 --- --- 9.5 5.1 9.5 Piperitone 1252 --- 35.9 --- 7.8 3.7 5.4 Safrole 1285 --- 1.3 --- 2.0 --- --- E-Anethole 1305 --- --- 87.5 --- --- --- Piperitenone 1340 --- 3.2 --- 14.0 8.4 13.1 β-Caryophyllene 1418 1.3 4.8 --- 5.8 23.7 6.0 E-β-Farnesene 1467 --- --- --- 0.9 --- --- Germacrene D 1480 --- 2.8 --- 1.7 4.8 1.5 Bicyclogermacrene 1494 --- 2.3 1.0 1.1 1.6 1.5 E,E-α-Farnesene 1519 --- --- 0.8 --- --- --- Nerolidol 1570 --- 0.8 --- --- --- --- 2,2':5'2''-Terthiophene 2222 --- --- --- --- 1.9 ---

* The composition of the essential oil was determined by comparison of the MS of each component with Wiley GC/MS library data and also from its retention index (RI). TC: Tagetescaracasana, TE: T.erecta, TF: T.filifolia, TPL: T.patula leaves, TPI: T.patula inflorescences, TS: T.subulata.

(14.0% TPL; 13.1% TS) among the major components, along with β-caryophyllene (23.7% TPI), cis-β-ocimene (15.5% TPI) and limonene (10.8% TS). Compounds such as dihydrotagetone (7.4 %) and 1,8-menthadien-4-ol (1.4 %) were only observed in TC and TS, respectively. 1,3,8-p-Menthatriene (0.6%) and nerolidol (0.8%) were present only in TE, andestragole (10.7%), trans-anethole (87.5%) and e.e-α-farnesene (0.8%) in TF. Trans-β-farnesene (0.9%) was detected in TPL and 2,2':5'2''-terthiophene (1.9%) was present only in the TPI sample. Several Tagetes species have been previously investigated and the composition of their essential oils reported. T. minuta is mainly composed oftagetone, tagetenone, dihydrotagetone,ocimene, ocimenone and terpineol [2,17,18]. A very similar composition shows T. bipinata, T. maxima and T. multiflora characterized by β-ocimene, dihydrotagetone,

NPC Natural Product Communications 2012 Vol. 7 No. 9

1225 - 1226

1226 Natural Product Communications Vol. 7 (9) 2012 Armas et al.

tagetoneand tagetenone [12,19]. T. patula showed piperitone, trans-β-ocimene, terpinolene and β-caryophyllene [20,21]. However, another investigation revealed that the root oil of the same species was mainly composed of terthiophene and other sulfur-thiophene structures [22].On the other hand, the essential oil from flowers of T. erecta was composed of β-caryophyllene, limonene, methyleugenol, (E)-ocimene, piperetone, piperitenone and terpinolene [21,23]. T. pusilla from Venezuela showed the presence of only trans-anethole and 4-allylanisole [14], while the oil of the same species collected from Bolivia showed trans-anethole and α-pinene as the only two components observed [24]. T. terniflora from Argentina yielded cis-tagetone and cis-ocimene, while T. laxa from the same location contained trans-tagetenone, cis-tagetenone, cis-β-ocimene and trans-β-ocimene [25]. Experimental

Plant material: Tagetes patula (TPL and TPI), T. caracasana (TC), T. subulata (TS) and T erecta (TE) were collected in Mérida, Municipio Libertador, Mérida State, located at 1600 m above sea level, while T. filifolia (TF) was collected in La Culata, Mérida state at 2800 m above sea level. Voucher specimens (TPL and TPI 001, TC 002, TS 003, TE 004), TF 005) have been deposited in the

Herbarium of the Faculty of Pharmacy and Bioanalysis, University of Los Andes. Fresh leaves (TPL: 2800g; TPI: 560 g; TC: 1180 g; TS: 1255 g, TE 2152 g; TF: 950 g) were cut into small pieces and subjected to hydrodistillation for 4 h, using a Clevenger-type apparatus. The oils were dried over anhydrous sodium sulfate and stored at 4ºC for further analysis. Gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS): The experimental conditions for GC and GC-MS analyses were quite similar to those reported earlier [14]. Retention indices were calculated relative to C8-C24n-alkanes, and compared with values reported in the literature [15,16]. Identification of the oil components was based on the Wiley MS Data Library (6th ed.), followed by comparisons of MS data with published literature [15]. Acknowledgements - The authors wish to thank Juan Carmona, Faculty of Pharmacy Herbarium for the identification of the plant material and Dr Rosa Aparicio, Faculty of Pharmacy, Research Institute for recording the GC-MS.

References

[1] Kadereit J, Jeffrey C. (2007) Families and Genera of Vascular Plants, Springer-Verlag, Berlín, Germany. [2] Vázquez A, Demmel G, Criado S, Aimar M, Cantero J, Rossi L, Velasco M. (2011) Phytochemistry of Tagetes minuta L. (Asteraceae) from

Córdoba, Argentina: Comparative study between essential oil and HS-SPME analyses. Blacpma, 10, 351-362. [3] Lawrence B. (1985) Essential oils of the Tagetes genus, Perfume and Flavorist, 10, 73-82. [4] Laferriere J, Weber C, Kohlhepp E. (1991) Mineral composition of some traditional Mexican teas. Plant Foods for Human Nutrition, 41, 277-282. [5] Giron L, Freire V, Alonzo A, Caceres A. (1995) Ethnobotanical survey of the medicinal flora used by Caribs of Guatemala. Journal of

Ethnopharmacology, 34, 173-187. [6] Figueroa S, Estevez M, Gimenez T. (1995) Propiedades antibacterianas, antimicoticas e insecticida de aceites esenciales de especies vegetales

aromáticas nativas. Biofarbo, 4, 51-62. [7] Abad M, Bermejo P, Sánchez S, Chiriboga X, Carrasco L. (1999) Antiviral activity of some South American medicinal plants. Phytotherapy

Research, 13, 142-146. [8] Gillij Y, Gleiser R, Zygadlo J. (2008) Mosquito repellent activity of essential oils of aromatic plants growing in Argentina. Bioresource

Technology, 9, 2507-2515. [9] Gutiérrez M, Stefanazzi N, González J, Benzi V, Ferrero A. (2009) Actividad fumigante de aceites esenciales de Schinus molle (Anacardiaceae) y

Tagetes terniflora (Asteraceae) sobre adultos de Pediculus humanus capitis (Insecta; Anoplura; Pediculidae). Blacpma, 8, 176-179. [10] Hincapié C, Monsalve Z, Seigler D, Alarcón J, Cespedes C. (2011) Antioxidant activity of Blechnum chilense (Kaulf.) Mett., Curcuma domestica

Valeton and Tagetes verticillata Lag. & Rodriguez. Blacpma, 10, 315 -324. [11] Marotti M, Piccaglia R, Biavati B, Marotti I. (2004) Characterization and yield evaluation of essential oils from different Tagetes species, Journal

of Essential Oil Research, 16, 440-444. [12] Cavalli J, Tomi F, Casanova J. (2007) Combined analysis of the essential oil from Tagetes bipinata by GC, GC/MS and 13C-NMR spectroscopy.

Journal of Essential Oil Research, 19, 330–332. [13] Gil A, Ghersa G, Leicach S. (2000) Essential oil yield and composition of Tagetes minuta accessions from Argentina. Biochemical Systematics and

Ecology, 28, 261–274. [14] Buitrago D, Rojas L, Rojas J, Morales A. (2010) Volatile compounds from Tagetes pusilla (Asteraceae) collected from the Venezuela Andes.

Natural Product Communications, 5, 1283-1284. [15] Adams R. (2007) Identification of essential oil components by GC/MS. Allured Publishing Corporation, Carol Stream, IL, USA. [16] Davies N. (1990) Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicone and carbowax 20 M. phases.

Journal of Chromatography A, 503, 1-24. [17] Moghaddam M, Omidbiagi R. (2007) Chemical composition of the essential oil of Tagetes minuta L. Journal of Essential Oil Research, 19, 1-4 [18] Moghaddam M, Omidbiagi R. (2006) Chemical composition of the essential oil of Tagetes minuta L. Journal of Essential Oil Research, 18,

572-573. [19] Pichette A, Garneau F, Collin G, Jean F. (2005) Essential oils from Bolivia. IV. Compositae: Tagetes aff. maxima Kuntze and Tagetes multiflora

H.B.K. Journal of Essential Oil Research, 17, 27-28. [20] Rondón M, Velasco J, Hernández J, Pecheneda M, Rojas J, Morales A, Carmona J, Díaz T. (2006) Chemical composition and antibacterial activity

of the essential oil of Tagetes patula L. (Asteraceae) collected from the Venezuela Andes. Revista Latinoamericana de Química, 34, 32-36. [21] Martínez R, Diaz B, Vásquez L, Compazgnone R, Tillett S, Canelón D, Torrico F, Suárez A. (2009) Chemical composition of essential oils and

toxicological evaluation of Tagetes erecta and Tagetes patula from Venezuela. Journal of Essential Oil Bearing Plants, 12, 476-481. [22] Szarka S, Héthelyi E, Lemberkovics É, Bálványos I, Szöke É. (2007) Essential oil constituents of intact plants and in vitro cultures of Tagetes

patula L. Journal of Essential Oil Research, 19, 85-88. [23] Pérez R, Hernández H, Hernández S. (2006) Antioxidant activity of Tagetes erecta essential oil. Journal of the Chilean Chemical Society, 51,

883-886. [24] Figueroa S, Estevez M, Gimenez T. (1995) Propiedades antibacterianas, antimicoticas e insecticida de aceites esenciales de especies vegetales

aromáticas nativas. Biofarbo, 4, 51-62. [25] Zygadlo J, Abburra D, Maestri D, Guzman C. (1993) Essential oil composition of Tagetes terniflora H.B.K. and Tagetes laxa Cabrera. Journal of

Flavour Fragrance, 8, 273-275.

Natural Product Communications Vol. 7 (9) 2012 Published online (www.naturalproduct.us)

Plant Growth Inhibitor from the Malaysian Medicinal Plant Goniothalamus andersonii and Related Species Tomoko Takemura, Tsunashi Kamo, Raihan Ismil, Baki Bakar, Naoya Wasano, Syuntaro Hiradate and Yoshiharu Fujii 1197

Furanone Derivatives from Terrestrial Streptomyces spp. Muhammad Arfan, Khaled A. Shaaban, Anja Schüffler and Hartmut Laatsch 1199

Cytotoxicity Analysis of Active Components in Bitter Melon (Momordica charantia) Seed Extracts Using Human Embryonic Kidney and Colon Tumor Cells Elizabeth S. Chipps, Renuka Jayini, Shoko Ando, April D. Protzman, M. Zubayed Muhi, M. Abdul Mottaleb, Ahmed Malkawi and M. Rafiq Islam 1203

Phytochemical and Biological Studies on Some Egyptian Seaweeds Khaled N. M. Elsayed, Mohamed M. Radwan, Sherif H. M. Hassan, Mohamed S. Abdelhameed, Ibraheem B. Ibraheem, and Samir A. Ross 1209

Electrochemical Characterization of the Marine Antioxidant Gadusol Ernesto Maximiliano Arbeloa, Cristina Luján Ramírez, Raúl Ariel Procaccini and María Sandra Churio 1211

Insecticidal Properties of Annonaceous Acetogenins and Their Analogues. Interaction with Lipid Membranes Lilian Di Toto Blessing, Juan Ramos, Sonia Diaz, Aída Ben Altabef, Alicia Bardón, Margarita Brovetto, Gustavo Seoane and Adriana Neske 1215

Activity of Alkanediol Alkanoates against Pathogenic Plant Fungi Rhizoctonia solani and Sclerotium rolfsii Paraj Shukla, Suresh Walia, Vivek Ahluwalia, Balraj S. Parmar and Muraleedharan G. Nair 1219

A Somaclonal Variant of Rose-Scented Geranium (Pelargonium spp.) with Moderately High Content of Isomenthone in its Essential Oil Swaroop S Kulkarni, Nagawara S Ravindra, Kalavagunta V N S Srinivas and Raghavendra N Kulkarni 1223

Comparative Study of the Chemical Composition of Essential Oils of Five Tagetes Species Collected in Venezuela Kaylin Armas, Janne Roja, Luis Rojas and Antonio Morales 1225

Chemical Composition and Antiphytoviral Activity of Essential Oil of Micromeria graeca Elma Vuko, Valerija Dunkić, Nada Bezić, Mirko Ruščić and Dario Kremer 1227

Chemical Composition and Biological Activity of the Essential Oil from Jamaican Cleome serrata Megil J. McNeil, Roy B. R. Porter and Lawrence A. D. Williams 1231

Chemical Compositions and Biological Activities of Amomum subulatum Essential Oils from Nepal Prabodh Satyal, Noura S. Dosoky, Brittany L. Kincer and William N. Setzer 1233

Chemical Composition and Antimicrobial Activity of Salvia x jamensis Essential Oil Daniele Fraternale, Guido Flamini, Angela Bisio, Maria Cristina Albertini and Donata Ricci 1237

Antimicrobial and Antioxidant Activities of Stachys lavandulifolia subsp. lavandulifolia Essential Oil and its Infusion Gökalp İşcan, Betül Demirci, Fatih Demirci, Fatih Göger, Neşe Kırımer, Yavuz B. Köse and Kemal Hüsnü Can Başer 1241

Composition, Anticancer, and Antimicrobial Activities in vitro of the Heartwood Essential Oil of Cunninghamia lanceolata var. konishii from Taiwan Yu-Chang Su, Kuan-Ping Hsu, Eugene I-Chen Wang and Chen-Lung Ho 1245

Review/Account Secondary Metabolites of Eichhornia crassipes (Waterhyacinth): A Review (1949 to 2011) Pottail Lalitha, Shubashini.K.Sripathi and Ponnusamy Jayanthi 1249

Natural Product Communications 2012

Volume 7, Number 9

Contents

Original Paper Page

Catalytic and Molecular Properties of Rabbit Liver Carboxylesterase Acting on 1,8-Cineole Derivatives María del H. Loandos, Ana C. Muro, Margarita B. Villecco, Marcelo F. Masman, Paul G.M. Luiten, Sebastian A. Andujar, Fernando D. Suvire and Ricardo D. Enriz 1117

Antiparasitic and Anticancer Carvotacetone Derivatives of Sphaeranthus bullatus Francis Machumi, Abiy Yenesew, Jacob O. Midiwo, Matthias Heydenreich, Erich Kleinpeter, Babu L. Tekwani, Shabana I. Khan, Larry A. Walker and Ilias Muhammad 1123

Naturally Occurring Limonene to Cinnamyl-type γ-Butyrolactone Substituted Aldol Condensation Derivatives as Antioxidant Compounds Pushpinder Kaur, Pralay Das, Abha Chaudhary and Bikram Singh 1127

Sesquiterpenes from Onopordum illyricum and their Antifeedant Activity Sergio Rosselli, Antonella Maria Maggio, Marisa Canzoneri, Monique S. J. Simmonds and Maurizio Bruno 1131

Three New Lactarane Sesquiterpenoids from the Mushroom Russula sanguinea Yasunori Yaoita, Moe Hirao, Masao Kikuchi and Koichi Machida 1133

Royleanumin, a New Phytotoxic neo-Clarodane Diterpenoid from Teucrium royleanum Shabir Ahmad, Muhammad Arfan, Naheed Riaz, Riaz Ullah, Ziarat Shah and Azhar Ul-Haq Ali Shah 1137

Bioactive-guided Identification of Labdane Diterpenoids from Aerial Parts of Aristeguietia glutinosa as anti-Trypanosoma cruzi agents Javier Varela, María L. Lavaggi, Mauricio Cabrera, Alejandra Rodríguez, Patricio Miño, Ximena Chiriboga, Hugo Cerecetto and Mercedes González 1139

Characterization of Yew Tree (Taxus) Varieties by Fingerprint and Principal Component Analyses Kalle Truus, Merike Vaher, Maria Borissova, Marju Robal, Tuuli Levandi, Rando Tuvikene, Peeter Toomik and Mihkel Kaljurand 1143

Identification of Triterpenes from Milkweed (Asclepias syriaca) Erzsébet Háznagy-Radnai, Edit Wéber, Szilvia Czigle and Imre Máthé 1147

Evaluation of the Anti-angiogenic Activity of Saponins from Maesa lanceolata by Different Assays Kenn Foubert, Annelies Breynaert, Mart Theunis, Rita Van Den Bossche, Guido R. Y De Meyer, André Van Daele, Ahmad Faizal, Alain Goossens, Danny Geelen, Edward M. Conway, Arnold Vlietinck, Luc Pieters and Sandra Apers 1149

Conversion of Protopanaxadiol Type Saponins to Ginsenoside Rg3 by Lemon Cheng-Peng Sun, Wei-Ping Gao, Bao-Zhong Zhao and Le-Qin Cheng 1155

Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Biological Activity of Cucumariosides B1 and B2,Two New Minor Non-Sulfated Unprecedented Triosides Alexandra S. Silchenko, Anatoly I. Kalinovsky, Sergey A. Avilov, Pelageya V. Andryjaschenko, Pavel S. Dmitrenok, Ekaterina A. Martyyas and Vladimir I. Kalinin 1157

Osteoclastogenesis Inhibitory Effect of Ergosterol Peroxide Isolated from Pleurotus eryngii Satoru Yokoyama, Tran Hai Bang, Kuniyoshi Shimizu and Ryuichiro Kondo 1163

A Novel Sterol Sulfate and New Oligosaccharide Polyester from the Aerial Parts of Polygala sibirica Yue Lin Song, Si Xiang Zhou, He Lin Wei, Yong Jiang and Peng Fei Tu 1165

Angustinine – A New Benzopyridoquinolizine Alkaloid from Alangium lamarckii Mumu Chakraborty and Sibabrata Mukhopadhyay 1169

Antifungal Activity of Hydrochloride Salts of Tylophorinidine and Tylophorinine Mini Dhiman, Rajashri R. Parab, Sreedharannair L. Manju, Dattatraya C. Desai and Girish B. Mahajan 1171

Evaluation of Antibacterial and Anti-biofilm Activities of Cinchona Alkaloid Derivatives against Staphylococcus aureus Malena E. Skogman, Janni Kujala, Igor Busygin, Reko Leino, Pia M. Vuorela and Adyary Fallarero 1173

Simultaneous Determination of Alkaloids and Flavonoids from Aerial Parts of Passiflora Species and Dietary Supplements using UPLC-UV-MS and HPTLC Bharathi Avula, Yan-Hong Wang, Chidananda Swamy Rumalla, Troy J. Smillie and Ikhlas A. Khan 1177

Chemical Fingerprinting by RP-RRLC-DAD and Principal Component Analysis of Ziziphora clinopodioides from Different Locations Shuge Tian, Qian Yu, Lude Xin, Zhaohui Sunny Zhou and Halmuart·Upur 1181

Simultaneous Determination of Four Major Constituents of Semen Vaccariae Using HPLC-DAD Haijiang Zhang, Wei Yao, Yunyun Chen, Peipei He, Yao Chen, Peipei Chen, Jia Han and Xiaoyu Li 1185

Biological Activity of Isoflavonoids from Azorella madreporica Luisa Quesada, Carlos Areche, Luis Astudillo, Margarita Gutiérrez, Beatriz Sepúlveda and Aurelio San-Martín 1187

Analysis of Homoisoflavonoids in Caesalpinia digyna by HPLC-ESI-MS, HPLC and Method Validation Somendu K. Roy, Amit Srivastava and Sanjay M. Jachak 1189

Oligonol-induced Degradation of Perilipin 1 is Regulated through Lysosomal Degradation Machinery Junetsu Ogasawara, Kentaro Kitadate, Hiroshi Nishioka, Hajime Fujii, Takuya Sakurai, Takako Kizaki, Tetsuya Izawa, Hitoshi Ishida and Hideki Ohno 1193

Continued inside backcover