Volume 3. Issue 9. Pages 1377-1564. 2008 ISSN 1934-578X (printed); ISSN 1555-9475 (online)

www.naturalproduct.us

This Issue is Dedicated to

Professor George R. Waller on the Occasion of his 80th Birthday

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EDITOR-IN-CHIEF

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

PROFESSOR GERALD BLUNDEN The School of Pharmacy & Biomedical Sciences, University of Portsmouth, Portsmouth, PO1 2DT U.K. axuf64@dsl.pipex.com

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 J. ALBERTO MARCO Departamento de Quimica Organica, Universidade de Valencia, E-46100 Burjassot, Valencia, Spain alberto.marco@uv.es

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

ADVISORY BOARD Prof. Viqar Uddin Ahmad Karachi, Pakistan

Prof. Øyvind M. Andersen Bergen, Norway

Prof. Giovanni Appendino Novara, Italy

Prof. Yoshinori Asakawa Tokushima, Japan

Prof. Maurizio Bruno Palermo, Italy

Prof. Carlos Cerda-Garcia-Rojas

Mexico city, Mexico

Prof. Josep Coll Barcelona, Spain

Prof. Geoffrey Cordell Chicago, IL, USA

Prof. Samuel Danishefsky New York, NY, USA

Dr. Biswanath Das Hyderabad, India

Prof. A.A. Leslie Gunatilaka Tucson, AZ, USA

Prof. Stephen Hanessian Montreal, Canada

Prof. Michael Heinrich London, UK

Prof. Kurt Hostettmann Lausanne, Switzerland

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

Prof. Jerzy Jaroszewski Copenhagen, Denmark

Prof. Teodoro Kaufman Rosario, Argentina

Prof. Norbert De Kimpe Gent, Belgium

Prof. Hartmut Laatsch Gottingen, Germany

Prof. Marie Lacaille-Dubois Dijon, France

Prof. Shoei-Sheng Lee Taipei, Taiwan

Prof. Francisco Macias Cadiz, Spain

Prof. Anita Marsaioli Campinas, Brazil

Prof. Imre Mathe Szeged, Hungary

Prof. Joseph Michael Johannesburg, South Africa

Prof. Ermino Murano Trieste, Italy

Prof. Virinder Parmar Delhi, India

Prof. Luc Pieters Antwerp, Belgium

Prof. Om Prakash Manhattan, KS, USA

Prof. Peter Proksch Düsseldorf, Germany

Prof. William Reynolds Toronto, Canada

Prof. Raffaele Riccio Salerno, Italy

Prof. Ricardo Riguera Santiago de Compostela, Spain

Prof. Satyajit Sarker Coleraine, UK

Prof. Monique Simmonds Richmond, UK

Prof. Valentin Stonik Vladivostok, Russia

Prof. Hermann Stuppner Innsbruck, Austria

Prof. Apichart Suksamrarn Bangkock, Thailand

Prof. Hiromitsu Takayama Chiba, Japan

Prof. Karin Valant-Vetschera Vienna, Austria

Prof. Peter G. Waterman Lismore, Australia

Prof. Paul Wender Stanford, USA

Natural Product Communications Vol. 3 (9) 2008 Published online (www.naturalproduct.us)

Editorial

In Honor of the 80th Birthday of Professor George R. Waller It is my privilege and pleasure to introduce this issue, which is dedicated to Professor George R. Waller, Professor Emeritus, Department of Biochemistry and Molecular Biology, Oklahoma State University, Noble Research Center, Stillwater, OK 74078, USA, on the occasion of his 80th birthday. The editors join me in paying tribute to Professor Waller for his outstanding contributions to various aspects of various aspects of biosynthesis and biodegradation of certain alkaloids, flavor of roasted peanuts, allelopathy, saponins, and the biochemical applications of mass spectrometry. He has authored more than 208 original research papers, edited or coedited 12 books, organized several symposia, and contributed to many international journals by reviewing papers, reviewer of NIH and NSF proposals, and taught upper level and graduate courses at OSU. Prof. Waller and Prof. S. S Narwal were the founding leaders of 16 scientists which organized the International Allelopathy Society in Old Delhi, India in 1994. Prof. Waller was elected the President for 1994-96 while it was being established; and the President of the organization between 1996-1999. It has a meeting every three years, and the next meeting will be in Saratoga Springs, NY. He has served as the President of the Phytochemical Society of North America in 1979, President of the Oklahoma State University Affiliate of Sigma Xi in 1967, and Chairman of the Oklahoma Section of the American Chemical Society in 1970. He was the founding editor of Mass Spectrometry Reviews which now is a premier journal of John Wiley & Sons and is now in it's 27th year of publication. It is a great pleasure to honor the scientific achievements of Professor Waller on the occasion of his 80h birthday and to send him warm wishes from all his colleagues and friends. My thanks go to the authors and reviewers who have made this issue of Natural Product Communications possible and to our production department for their efforts in putting this issue in print. We all express our appreciation for his excellent contributions to natural products and wish him all the best for his future.

Pawan K. Agrawal Editor-in-Chief

Natural Product Communications Vol. 3 (9) 2008 Published online (www.naturalproduct.us)

Dedication

This issue of Natural Product Communications is dedicated to Professor emeritus George Waller of the Department of Biochemistry and Molecular Biology at Oklahoma State University in Stillwater, Oklahoma. George is an international giant in alkaloid research, plant biochemistry, and the biochemical applications of mass spectrometry. Following Oklahoma’s pioneering spirit, George is a talented far-sighted researcher who explores, defines, opens, and establishes new research areas. He also makes numerous international connections. He was born in Clinton, NC on July 14, 1927 and received his B.S. degree from North Carolina State University in Raleigh with majors in agriculture and biological chemistry in 1950. From 1950-53 George was an instructor-student at the University of Delaware, Newark where he received a M.S. degree under the direction of Prof. George L. Baker in agriculture and biological chemistry. For the following three years he was a research chemist at the Imperial Paper and Color Company in Glen Falls, NY. In 1956 he joined the biochemistry department at Oklahoma State University as an assistant professor and rapidly rose through the academic ranks. His Ph.D. was completed in 1961 under the direction of Dr. LaVell M. Henderson on ricinine biosynthesis He achieved the rank of full professor in 1967. George had published some 148 papers by 1988 and became a professor emeritus in 1987. Since that time his number of publications has risen to 206 and he hasn’t finished yet. He is editor or coeditor of 12 books and contributed 15 agricultural experiment station bulletins. My colleague Professor George R. Waller was already an established investigator when I arrived at Oklahoma State University in July 1959 and he continues today as an active professor emeritus even attending faculty meetings long after I retired (1998) and moved to Texas. George has an uncanny skill for recognizing and positioning himself at the forefront of significant developing areas of scientific advancements. In 1963 George took a sabbatical leave at the Karolinska Institute with Dr. Ragnar Ryhage having recognized the potential applications of mass spectrometry in biochemistry. In 1965 a prototype of the LKB-9000 Mass Spectrometer was installed in the Waller lab in Stillwater. This mass spectrometer now resides at the Smithsonian Institution. He edited a two volume series on Biochemical Applications of Mass Spectrometry for John Wiley & Sons in 1972 and was the founding editor of Mass Spectrometry Reviews also published by John Wiley & Sons and which has now been published for 27 years. The next research frontier that he recognized was the environment. He founded the Midcontinent Environmental Center Association and edited the “Proceedings of the National Forum on Growth with Environmental Quality?” in 1974. George served as an Assistant Director of the Oklahoma Agricultural Experiment Station (50% time) and was instrumental in my (the author) obtaining an EPA grant that initiated the study of firefly luciferase for some 20 years in my lab. Thanks George. He started research on allelopathy and was instrumental in the foundation of the International Allelopathy Society. He edited an American Chemical Society publication of a symposium “Allelochemicals: Role in Agriculture and Forestry” in 1987. He served as the society’s president from 1996-1999. George supervised the thesis research of 8 Ph. D. and 22 M.S. students. His international acclaim is reflected in the 19 postdoctral fellow and 15 visiting professor who have worked in his laboratory.

Natural Product Communications Vol. 3 (9) 2008 Published online (www.naturalproduct.us) I will let you in on a little secret – there is no way that he could have accomplished all of this without his exceptional wife Hilda. They raised three very independent and talented daughters. What a track record of being at the forefront of three such important developments and then making important contributions to each. George you are truly a gifted scholar and it was my great pleasure to be a colleague of yours. He initiated the Oklahoma Chemist of the Year award given by the Oklahoma Section of the American Chemical Society in 1968; he won the award in 2001. George, congratulations on such a brilliant career that is still in progress.

Franklin R. Leach Professor emeritus

Department of Biochemistry and Molecular Biology Oklahoma State University

Stillwater, Oklahoma 74078 USA

Constituents of ‘Caincin’, a Bioactive Saponin Fraction from the Root-bark of Chiococca alba (L.) Hitch. Jnanabrata Bhattacharyya, S. K. Srivastava, M. F. Agra and George Majetich 1483

A New Biflavanone from Ochna lanceolata Shaik I. Khalivulla, Nimmanapalli P. Reddy, Bandi A.K. Reddy, Ramireddy V.N. Reddy, Duvvuru Gunasekar, Alain Blond and Bernard Bodo 1487

Isoflavonoids from an Egyptian Collection of Colutea istria Mohamed M. Radwan 1491

A Flavonoid Glycoside from the Leaves of Morinda tinctoria Atish K. Sahoo, Nisha Narayanan, S. Rajan and Pulok K. Mukherjee 1495

New Anthocyanins from Stem Bark of Castor, Ricinus communis Robert Byamukama, Monica Jordheim, Bernard Kiremire and Øyvind M. Andersen 1497

Prenylated Xanthones and a Benzophenone from Baphia kirkii Modest C. Kapingu and Joseph J. Magadula 1501

Phytochemical and Antimicrobial Investigation of Latex from Euphorbia abyssinica Gmel. Fathy EL- Fiky, Kaleab Asres, Simon Gibbons, Hala Hammoda, Jihan Badr and Shemsu Umer 1505

Fenugreek Extract Rich in 4-Hydroxyisoleucine and Trigonelline Activates PPARα and Inhibits LDL Oxidation: Key Mechanisms in Controlling the Metabolic Syndrome Alvin Ibarra, Kan He, Naisheng Bai, Antoine Bily, Marc Roller, Aurélie Coussaert, Nicolas Provost

and Christophe Ripoll 1509

Comparison of Different Techniques for Extraction of Biologically Active Compounds from Achillea Millefolium Proa Antoaneta Trendafilova and Milka Todorova 1515

Extraction Methods Play a Critical Role in Chemical Profile and Biological Activities of Black Cohosh Bei Jiang, Kurt A. Reynertson, Amy C. Keller, Linda S. Einbond, Debra L. Bemis, I. Bernard Weinstein, Fredi Kronenberg and Edward J. Kennelly 1519

Antimicrobial Activity and Chemical Composition of Callistemon pinifolius and C. salignus Leaf Essential Oils from the Northern Plains of India Mohit Saxena, Kunal Shrivastava, Santosh K. Srivastava, Suaib Luqman, Ajai Kumar, Mahendra. P. Darokar, Kodakandla V. Syamsundar, Tota Ram and Suman P. S. Khanuja 1533

Analysis of Chemical Constituents of Tithonia rotundifolia Leaf Essential Oil Found in Nigeria Adebayo A. Gbolade, Vânia Tira-Picos and J.M.F. Nogueira 1537

Sedative Effect of Eucalyptus urophylla and E. brassiana in mice Gisele F.D. Teixeira, Roberto C.P. Lima Júnior, Edilberto R. Silveira, Marinalva O. Freitas and Adriana R. Campos 1539

In Vitro Antifungal Activity of Polysulfides-Rich Essential Oil of Ferula latisecta Fruits against Human Pathogenic Dermatophytes Mehrdad Iranshahi, Abdolmajid Fata, Bahareh Emami, Bibi Mohadeseh Jalalzadeh Shahri and Bibi Sedigheh Fazly Bazzaz 1543

Biological Activity and Composition of the Essential Oil of Dracocephalum moldavica L. Grown in Iran Ali Sonboli, Mehran Mojarrad, Abbas Gholipour, Samad Nejad Ebrahimi and Mitra Arman 1547

Antioxidant Activity and Chemical Composition of Essential Oils from Schinus fasciculata (Griseb.) I.M. Johnst and S. praecox (Griseb.) Speg. Ana P. Murray, Silvana A. Rodriguez and María G. Murray 1551

Essential oil Composition of Dendropanax gonatopodus from Monteverde, Costa Rica. An ab initio Examination of Aromadendrane Sesquiterpenoids William N. Setzer 1557

Natural Product Communications 2008

Volume 3, Number 9

Contents

Page

Anti-tuberculosis Compounds from two Bolivian Medicinal Plants, Senecio mathewsii and Usnea florida Qi Hong, David E. Minter, Scott G. Franzblau and Manfred G. Reinecke 1377

Natural Products from Polygonum perfoliatum and their Diverse Biological Activities Chi-I Chang, Fei-Jane Tsai and Chang-Hung Chou 1385

Phytochemical Characterization of the Australian (Aboriginal) Medicinal Plant Dolichandrone heterophylla and Influence of Selected Isolated Compounds on Human Keratinocytes Thomas Dzeha, Kristian Wende, Manuela Harms, Ju Ju (Burriwee) Wilson, Jim Kohen, Subra Vemulpad, Joanne Jamie and Ulrike Lindequist 1387

Analysis of Saponin Mixtures from Alfalfa (Medicago sativa L.) Roots using Mass Spectrometry with MALDI Techniques H. Ewa Witkowska, Zbigniew Bialy, Marian Jurzysta and George R. Waller 1395

Control of Allantoin Accumulation in Comfrey Paulo Mazzafera, Kátia Viviane Gonçalves and Milton Massao Shimizu 1411

Trigonelline (N-methylnicotinic acid) Biosynthesis and its Biological Role in Plants Hiroshi Ashihara 1423

Biosynthesis and Catabolism of Purine Alkaloids in Camellia Plants Misako Kato and Hiroshi Ashihara 1429

A View on the Active Site of Firefly Luciferase Franklin R. Leach 1437

Study on the Chemical Constituents of Premna integrifolia L. Nguyen Thi Bich Hang, Pham Thanh Ky, Chau Van Minh, Nguyen Xuan Cuong, Nguyen Phuong Thao and Phan Van Kiem 1449

Τ-Cadinol Nerolidol Ether from Schisandra chinensis Asmita V. Patel, Gerald Blunden, Peter D. Cary, Lubomír Opletal, Markéta Beránkova, Kersti Karu, David E. Thurston and Milan Pour 1453

Bioactive Semisynthetic Derivatives of (S)-(+)-Curcuphenol Helena Gaspar, Cristina Moiteiro, João Sardinha and Azucena González-Coloma 1457

Eco-contribution to the Chemistry of Perezone, a Comparative Study, Using Different Modes of Activation and Solventless Conditions Joel Martínez, Benjamín Velasco-Bejarano, Francisco Delgado, Rocío Pozas, Héctor M. Torres Domínguez, José G. Trujillo Ferrara, Gabriel A. Arroyo and René Miranda 1465

Chemical Composition of Diterpenes from the Brown Alga Canistrocarpus cervicornis (Dictyotaceae, Phaeophyceae) Aline Santos de Oliveira, Diana Negrão Cavalcanti, Éverson Miguel Bianco, Joel Campos de Paula, Renato Crespo Pereira, Yocie Yoneshigue-Valentin and Valéria Laneuville Teixeira 1469

Cembranoid Diterpenes from the Soft Corals Sarcophyton sp. and Sarcophyton glaucum Daniela Grote, Kamel H. Shaker, Hesham S. M. Soliman, Muhammmad M. Hegazi and Karlheinz Seifert 1473

Dolabellane Diterpenes from Cleome droserifolia Hoda M. Fathy, Mohamed I. Aboushoer, Fathallah M. Harraz, Abdallah A. Omar, Gilles Goetz and Rafael Tabacchi 1479

(Continued inside back cover)