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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

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Prof. Giovanni Appendino Novara, Italy

Prof. Yoshinori Asakawa Tokushima, Japan

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Prof. Julie Banerji Kolkata, India

Prof. Anna R. Bilia Florence, Italy

Prof. Maurizio Bruno Palermo, Italy

Prof. César A. N. Catalán Tucumán, Argentina

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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. Jerzy Jaroszewski Copenhagen, Denmark

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

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Prof. Luc Pieters Antwerp, Belgium

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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

The Leaf Essential Oils of Five Vietnamese Desmos Species (Annonaceae) Do Ngoc Daia,b, Tran Minh Hoib, Tran Dinh Thangc,* and Isiaka A. Ogunwanded,*

aInstitute Ecology and Biological Resources, Viet Nam Academy of Science and Technology, Vietnam

bFaculty of Biology, Vinh University, 182-Le Duan Vihn, Vietnam

cFaculty of Chemistry, Vihn University, 182-Le Duan vihn, Vietnam

dDepartment of Chemistry, Faculty of Science, Lagos State University, Badagry Expressway Ojo, P.M.B. 0001, Lasu Post Office, Ojo, Lagos, Nigeria thangtd@vinhuni.edu.vn; isiaka.ogunwande@lasunigeria.org

Received: November 2nd, 2011; Accepted: December 15th, 2011

The leaf essential oils of five Desmos species from Vietnam have been extracted by steam distillation and subjected to GC and GC-MS analyses. The plant samples were Desmos cochinchinensis Lour., D. penduculosus (A. DC.) Ban, D. penducolosus var. tonkinensis Ban, D. chinensis Lour., and D. dumosus (Roxb.) Saff. The oils were rich in sesquiterpene hydrocarbons (65.9%-88.9%) and monoterpene hydrocarbons (6.3%-30.9%). The oxygenated counterparts were less common. The quantitatively significant constituents of the oils were α-pinene (2.4%-12.1%), β-elemene (2.2-39.5%), β-caryophyllene (13.9-26.3%), germacrene D (9.9-15.5%), bicyclogermacrene (2.0-11.4%) and α-humulene (3.8-7.5%). The studied oils could be classified into two chemical forms: oils with abundance of β-caryophyllene, germacrene D and α-pinene (D. cochinchinensis, D. penducolosus var. tonkinensis, D. chinensis and D. Dumosus) and oil with high amounts of β-elemene, β-caryophyllene and germacrene D (D. penduculosus). Keywords: Desmos cochinchinensis, Desmos penduculosus, Desmos penducolosus var. tonkinensis, Desmos chienensis, Desmos dumosus, Monoterpenes, Sesquiterpenes.

Desmos Lour., a small genus in the family Annonaceae, comprises 25-30 species, which are endemic to tropical and subtropical Asia. They are usually erect or scandent shrubs, rarely trees with indumenta of simple hairs [1,2]. Studies have shown that the genus is a source of biologically active compounds such as flavonoids [3,4], alkaloids [5,6], chalcone [7,8], triterpenoids [9,10] and fatty acids [11]. Several other classes of medicinally useful compounds have been characterized from this genus [12-15]. There are relatively few studies on the analyses of the content and composition of essential oil from Desmos species. β-Caryophyllene (56.2%) and spathulenol (61.5%) respectively were the main compounds identified in the young and ripened flowers of D. cochinchinensis [16]. Linalool (46.19%) and methyl geranate (26.64%) were the most abundant components of D. chinensis extracted by head space-solid phase microextraction (HS-SPME), while caryophyllene (31.7%) and caryophyllene oxide (12.9%) dominated the oil extracted by steam distillation (SD) [17]. The volatile oil composition of some other species, such as D. goezeanus, D. wardianus and Desmos sp. (Mossman River L.W.Jessup) from Australia [18], and D. cochinchinensis var. fulvescens [19] and D. chinensis [20] from Vietnam have been reported. In this paper, we report on the chemical constituents identified from D. cochinchinensis Lour., D. penduculosus (A. DC.) Ban., D. penducolosus var. tonkinensis Ban., D. chinensis Lour. and D. dumosus (Roxb.) Saff. growing in Vietnam. The leaves of the five studied species gave low yields of essential oils: 0.55% (v/w; D. cochinchinensis ; intense yellow); 0.20% (v/w; D. penduculosus; greenish-yellow); 0.35% (v/w; D. penduculosus var. tonkinensis; yellow); 0.30% (v/w; D. chinensis; yellow) and

0.25% (v/w; D. dumosus; light yellow), calculated on a dry weight basis. The chemical composition of the oils is summarized in Table 1. Eleven of the identified constituents were common to all the oil samples. The oil of D. cochinchinensis was characterized by the abundance of α-pinene (11.5%), β-caryophyllene (26.3%), germacrene D (14.6%) and bicyclogermacrene (11.4%). However, β-elemene, cadinene and spathulenol, which were the major compounds of the previously reported flower oils of D. cochinchinensis [16,19], occurred in lesser amounts in the present oil sample. A total of thirty-five constituents could be identified in the oil of D. penduculosus, the major ones being the sesquiterpene hydrocarbons β-elemene (39.5%), β-caryophyllene (13.9%) and germacrene D (9.9%). Other significant constituents of the oil were -elemene (5.6%), -elemene (4.8%) and α-humulene (3.8%). On the other hand, β-caryophyllene (15.6%) and germacrene D (16.1%) were the most abundant compounds of D. penduculosus var. tonkinensis, which was also characterized by significant amounts of β-elemene (5.3%), α-pinene (7.5%), α-humulene (7.6%), bicycloelemene (7.8%) and bicycolgermacrene (7.7%). The main compounds identified in the oil of D. chinensis were α-pinene (12.1%), β-caryophyllene (20.2%) and germacrene D (15.5%). Other quantitatively significant constituents were limonene (8.9%), bicycloelemene (5.6%), α-humulene (6.5%), β-pinene (4.7%) and bicyclogermacrene (4.4%). The compositional pattern revealed a variation from previous report from China [17]. Linalool, methyl geranate and caryophyllene oxide, which constituted the bulk of the oil of Chinese origin were conspicuously absent in the Vietnamese oil.

NPC Natural Product Communications 2012 Vol. 7 No. 2

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232 Natural Product Communications Vol. 7 (2) 2012 Dai et al.

Table 1: Essential oil composition of Desmos species from Vietnam.

Percentage (%) Compounds # RIa RIb

1 2 3 4 5 (E,E) 2,4-Hexadienal 910 910 1.2 - - - - -Thujene 931 930 tr - tr 0.2 - -Pinene 939 939 11.5 2.4 7.5 12.1 9.5 Camphene 953 954 - 0.5 0.1 - 0.1 Sabinene 976 975 0,2 - 0.3 0.2 0.3 -Pinene 982 979 3.8 0.7 3.7 4.7 3.7 -Myrcene 990 991 1.2 0.3 1.3 1.3 1.1 -Phellandrene 1006 1005 0.1 0.2 0.2 - 0.1 -3-Carene 1013 1011 0.2 0.5 0.5 0.3 0.3 -Terpinene 1016 1017 0.2 0.4 0.3 0.3 0.1 p-Cymene 1027 1025 0.2 0.2 0.2 0.2 0.1 Limonene 1032 1029 4.2 0.2 2.6 8.9 1.8 1,8-Cineole 1034 1031 tr - 0.3 - 0.2 (Z)--Ocimene 1043 1037 0.1 - - - - (E)--Ocimene 1052 1050 1.6 - 2.9 0.8 2.7 -Terpinene 1061 1060 1.0 0.9 1.6 1.5 0.6 Acetophenone 1065 1065 tr - tr - - 2,4(8)- p-Menthadiene 1088 1088 tr - - - - -Terpinolene 1090 1088 tr - 0.1 - 0.1 Methyl benzoate 1090 1091 tr - 0.1 - - Linalool 1100 1098 2.4 0.1 0.3 0.4 1.0 Nonanal 1106 1101 - - 0.2 - 0.1 allo-Ocimene 1128 1132 - - tr - - Camphor 1145 1146 - - 0.5 - 2.1 Ethyl benzoate 1175 1173 tr - tr - - -Terpineol 1189 1189 tr - - - - Geraniol 1253 1253 tr - - - - Benzoic acid * 1310 - - tr - tr Bicycloelemene 1336 tr 0.2 7.8 5.6 8.9 -Elemene 1340 1338 - 4.8 - - - -Cubebene 1351 1351 0.2 0.1 0.5 0.3 0.6 -Ylangene 1375 1375 - - tr - - Isoledene 1376 1376 tr - - - - -Copaene 1377 1377 0.9 0.7 2.4 1.5 1.8 -Cubebene 1388 1388 1.0 0.7 - 2.7 2.3 -Elemene 1391 1391 2.2 39.5 5.3 4.8 5.0 -Cedrene 1411 1412 - 0.1 - - - -Caryophyllene 1419 1419 26.3 13.9 15.6 20.2 20.4 -Bergamotene 1435 1435 - 0.1 - - - -Elemene 1437 1437 0.3 5.6 - 0.7 0.3 Aromadendrene 1441 1441 - - 0.3 0.2 0.2 -Humulene 1454 1454 7.1 3.8 7.6 6.5 7.5 -Pachoulene 1457 1457 - 0.1 - - - -Gurjunene 1477 1477 0.3 - - - - epi-Bicyclosesqui-phellandrene * 1478 0.3 0.2 0.3 - 0.3 -Amorphene 1485 1485 - - 0.3 0.9 0.3 Germacrene D 1485 1485 14.6 9.9 16.1 15.5 15.1 -Selinene 1486 1490 - 2.2 0.2 0.5 0.2 -Selinene 1494 1490 - 1.5 - - - Cadina-1,4-diene 1496 1496 0.1 - 0.2 0.1 0.2 Bicyclo-germacrene 1500 1495 11.4 2.0 7.7 4.4 7.0 -Muurolene 1500 1499 - - - - 0.1 -Bisabolene 1506 1506 - - 0.1 0.2 - -Cadinene 1514 1514 tr - - - - Z--Bisabolene 1515 1515 - - 0.1 - 0.1 -Cadinene 1525 1523 3.2 3.4 3.1 1.8 1.7 -Cadinene 1539 1539 - - 0.1 - - cis-Calamenene 1540 1540 - 0.1 - - - Elemol 1550 1550 0.3 - 0.4 - 0.1 Germacrene B 1561 1561 0.3 0.7 - - - (E)-Nerolidol 1563 1563 0.3 - 0.4 - 0.3 Germacrene D -4-ol 1574 1576 tr - 0.1 - 0.1 Spathulenol 1579 1578 0.2 - 0.2 0.1 - Caryophyllene oxide 1583 1583 - - - - 0.4 Viridiflorol 1593 1593 0.4 - 0.1 - 0.1 Salvial-4(14)-en-1-one 1595 1595 - - 0.1 - - Longiborneol 1599 1599 tr - - - - Guaiol 1601 1601 - 0.7 - - - -Muurolol 1646 1646 0.4 0.2 0.3 0.2 0.2 -Cadinol 1654 1654 0.5 - 0.3 0.3 0.1

Bulnesol 1672 1672 - 0.3 - - - 10-nor-Calamenene-10-one 1702 1702 - - 0.1 - - Benzyl benzoate 1760 1760 0.3 0.4 0.9 0.5 0.4 Phytol 2125 1943 - - 0.1 - - Total 98.5 97.6 93.4 97.9 96.6 Monoterpene hydrocarbons 24.3 6.3 21.3 30.5 20.5 Oxygenated monoterpenes 2.4 0.1 1.1 0.4 3.3 Sesquiterpene hydrocarbons 68.2 88.9 67.7 65.9 71.1 Oxygenated sesquiterpenes 2.1 1.9 2.0 0.6 1.2 Others 1.5 0.4 1.3 0.5 0.5

- Not present; tr, trace < 0.1%; *identified by MS pattern and comparison with authentic MS data collection in our library; #Compounds identified by RI and MS pattern and comparison with authentic MS data collection in our library except where stated. aExperimental retention indices relative to series of n-alkanes (see experimental); b Literature retention indices [23]; 1. D. cochinchinensis 2. D. penduculosus; 3. D. penducolosus var. tonkinensis; 4. D. chinensis; 5. D. dumosus. Table 2: Major compounds identified from the oils of Desmos species.

Species Origin Major compounds Ref D. cochinchinensis var. fulvescens (l)

Vietnam β-elemene (16.1%), -cadinene (13.8%), β-caryophyllene (13.7%)

19

D. cochinchinensis (f) Vietnam trans-caryophyllene (56.2%)*, spathulenol (61.7%)#

16

D. chinensis (f) Vietnam β -caryophyllene (28.9%), bicyclogermacrene (11.5%), a-humulene (7.2%), D-germacrene (7.2%), and β -elemene (6.4%).

20

D. chinensis (l) a China linalool (46.2%), methyl geranate (26.6%)

17

D. chinensis (l) b China caryophyllene (31.8%), caryophyllene oxide (12.9%)

17

D. goezeanus PIF 25001 (l)

Australia bicyclogermacrene (10.0%), benzyl benzoate (40.1%), benzyl salicylate (15.3%)

18

D. goezeanus PIF 25085 (l)

Australia benzyl benzoate (18.6%), benzyl salicylate (45.0%)

18

Desmos species (Mosman River) (l)

Australia benzyl benzoate (59.1%), bicyclogermacrene (8.4%)

18

D. wardianus (l) Australia α-pinene (36.9%), (E,E)-farnesol (6.3%), limonene (4.8%), (E)-β-ocimene (4.7%)

18

l= leaves; f= flowers; a = HSPE extraction; b = SD extraction;* young flower; # ripened flower Forty-four compounds were identified in D. dumosus oil, with sesquiterpenes (72.3%) the dominant class. β-Caryophyllene (20.4%), germacrene D (15.1%), α-pinene (9.5%), bicycloelemene (8.9%), α- humulene (7.5%) and β-elemene (5.0%) were the major compounds. Monoterpenoids (28.5%) were also identified in significant quantities. No literature report on the oil compositions of D. penduculosus and D. dumosus were found and so the present investigation may represent the first of its kind. The chemical profiles of the studied oils revealed some quantitative and qualitative variations from previous reports on oils of Desmos species from other part of the world (Table 2). Benzyl benzoate and benzyl salicylate, which are the main constituents of the oils of Australian origin [18], were conspicuously absent in the present study. Also, methyl geranate and caryophyllene oxide, which featured prominently in the oils of Chinese origin [17], were also not identified in the Vietnamese sample. The studied oil samples could be classified into two chemical forms namely: oils with abundance of β-caryophyllene, germacrene D and α-pinene (D. cochinchinensis, D. penducolosus var. tonkinensis, D. chinensis, and D. dumosus), and oil with high amount of β-elemene, β-caryophyllene and germacrene D

Leaf essential oils of five Desmos species from Vietnam Natural Product Communications Vol. 7 (2) 2012 233

(D. penduculosus). The content and composition of essential oils depends on the origin, environmental conditions, phonological stage, plant parts analyzed, harvesting time and processing methods [21].Some of these factors may have been responsible for the observed variations in the oil contents when compared with other species from other parts of the world. Experimental

Plant materials: Leaves were collected from Vu Quang National Park, Hatinh Province, Vietnam, in October 2007. Voucher specimens namely: D. cochinchinensis (DND 213), D. penduculosus (DND 214), D. penduculosus var. tonkinensis (DND 215), D. chinensis (DND 216) and D. dumosus (DND 217) were deposited at the Herbarium of Vinh University. Extraction of the essential oils: Air-dried leaves were shredded and pulverized, and the oils obtained by steam distillation for 3 h at normal pressure, according to the Vietnamese Pharmacopoeia [22]. Gas chromatography analysis: About 15 mg of each oil sample, which was dried with anhydrous sodium sulfate, was dissolved in 1mL of n-hexane (for spectroscopy or chromatography). GC analysis was performed on an Agilent Technologies HP 6890 Plus Gas chromatograph equipped with a FID and fitted with HP-Wax and HP-5MS columns (both 30 m x 0.25 mm, film thickness 0.25 m, Agilent Technology). The analytical conditions were: carrier gas H2 (10 mL/min), injector temperature (PTV) 250oC, detector temperature 260oC, column temperature programmed from 60oC

(2 min hold) to 220oC (10 min hold) at 4oC/min. Samples were injected by splitting, and the split ratio was 10:1. The volume injected was 1.0 L. Inlet pressure was 6.1 kPa. Gas chromatography-mass spectrometry analysis: An Agilent Technologies HP 6890N Plus Chromatograph fitted with a fused silica capillary HP-5 MS column (30 m x 0.25 mm, film thickness 0.25 m) and interface with a mass spectrometer HP 5973 MSD was used for the GC/MS analysis, under the same conditions used for GC analysis, with He (10 mL/min) as carrier gas. The MS conditions were as follows: ionization voltage 70 eV; emission current 40 mA; acquisitions scan mass range of 35-350 amu at a sampling rate of 1.0 scan/s. Identification of constituents: The identification of constituents was performed on the basis of retention indices (RI) determined with reference to a homologous series of n-alkanes, under identical experimental conditions, co-injection with either standards (Sigma-Aldrich, St. Louis, MO, USA) or known essential oil constituents, MS library search (NIST 08 and Wiley 9th Version), and by comparing with MS literature data [23,24]. The relative amounts of individual components were calculated based on the GC peak area (FID response) without using correction factors.\ Acknowledgements - The authors thank Prof. J.J. Brophy, for useful literature information. The authors from Vietnam wish to thank the NAFOSTED (Vietnam) for the financial support of this study through the Project Nr. 104.01-2010.27.

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Volatiles from Magnolia grandiflora Flowers: Comparative Analysis by Simultaneous Distillation-Extraction and Solid Phase Microextraction Disnelys Báez, Jorge A. Pino and Diego Morales 237

Essential Oil Composition, Cytotoxic and Antibacterial Activities of Five Etlingera Species from Borneo Charles Santhanaraju Vairappan, Thilahgavani Nagappan and Kishneth Palaniveloo 239

Essential Oil Composition and Antibacterial Activity of Monticalia greenmaniana (Asteraceae) José Cárdenas, Janne Rojas, Luís Rojas-Fermin, María Lucena and Alexis Buitrago 243

Bioactivity of the Essential Oil of an Argentine Collection of Acanthospermum hispidum (Asteraceae) Mariana Alva, Susana Popich, Susana Borkosky, Elena Cartagena and Alicia Bardón 245

Antibacterial Activity and Comparison of the Volatile Constituents Obtained by Several Extraction Methods from the Flowers, Stems and Leaves of Astrodaucus orientalis Marzieh Torabbeigi, Parviz Abroomand Azar, Anousheh Sharifan and Zahra Aghaei Meibodi 249

In vitro Inhibitory Activity of Essential Oil Vapors against Ascosphaera apis Pavel Kloucek, Jakub Smid, Jaroslav Flesar, Jaroslav Havlik, Dalibor Titera, Vojtech Rada, Ondrej Drabek and Ladislav Kokoska 253

Chemical Composition and Biological Activity of Essential Oil from Pulicaria undulata from Yemen Nasser A. Awadh Ali, Farukh S. Sharopov, Mehdi Alhaj, Gabrielle M. Hill, Andrea Porzel, Norbert Arnold, William N. Setzer, Jürgen Schmidt and Ludger Wessjohann 257

Composition, Antioxidant, Antimicrobial and Anti-wood-decay Fungal Activities of the Twig Essential Oil of Taiwania cryptomerioides from Taiwan Chen-Lung Ho, Su- Sing Yang, Tsong-Min Chang and Yu-Chang Su 261

Essential Oil from the Leaves of Annona vepretorum: Chemical Composition and Bioactivity Emmanoel Vilaça Costa, Lívia Macedo Dutra, Paulo Cesar de Lima Nogueira, Valéria Regina de Souza Moraes, Marcos José Salvador, Luis Henrique Gonzaga Ribeiro and Fernanda Ramos Gadelha 265

Chemical Composition and Insecticidal Activity of the Essential Oil of Artemisia eriopoda Against Maize Weevil, Sitophilus zeamais Guo Hua Jiang, Quan Ru Liu, Sha Sha Chu and Zhi Long Liu 267

The Chemical Composition of the Essential Oils of Cirsium palustre and C. rivulare and their Antiproliferative Effect Jolanta Nazaruk, Ewa Karna and Danuta Kalemba 269

Review/Account Phytotherapy of Alcoholism Michał Tomczyk, Marijana Zovko-Končić and Lech Chrostek 273

Natural Product Communications 2012

Volume 7, Number 2

Contents

Original Paper Page

Antiviral Furanosesquiterpenes from Commiphora erythraea Elio Cenci, Federica Messina, Elisabetta Rossi, Francesco Epifano and Maria Carla Marcotullio 143

Sesquiterpenes from the Inner Bark of the Silver Birch and the Paper Birch Roderick J. Weston and Gerald J. Smith 145

Two New Ballonigrin-type Diterpenoids from the Roots of Ballota limbata Umar Farooq, Afsar Khan, Ather Farooq Khan, Saleha Suleman Khan, Rizwana Sarwar, Viqar Uddin Ahmad and Amir Waseem 149

A Novel Anticancer Diterpenoid from Jatropha gossypifolia Abiodun Falodun, Udo Kragl, Serge-Mitherand Tengho Touem, Alexander Villinger, Thomas Fahrenwaldt and Peter Langer 151

Antihepatitis B Virus Constituents of Solanum erianthum Shen-Chieh Chou, Tsurng-Juhn Huang, En-Hung Lin, Chun-Huei Huang and Chang-Hung Chou 153

Physical Properties and Molecular Conformations of Indole Alkaloids and Model Protein Interactions – Theoretical vs. Experimental Study Bojidarka Ivanova and Michael Spiteller 157

Antiparasitic and Anticancer Constituents of the Endophytic Fungus Aspergillus sp. strain F1544 Sergio Martínez-Luis, Lilia Cherigo, Elizabeth Arnold, Carmenza Spadafora, William H. Gerwick and Luis Cubilla-Rios 165

Chemical and Bioactivity Evaluation of the Bark of Neonauclea purpurea Netiya Karaket, Kanyaratt Supaibulwatana, Supatsara Ounsuk, Valérie Bultel-Poncé, Van Cuong Pham and Bernard Bodo 169

Antifeedants from Chinese Medicinal Herb, Erythrina variegata var. orientalis, Against Maize Weevil Sitophilus zeamais Zhi Long Liu, Sha Sha Chu, Guo Hua Jiang and Shao Liang Liu 171

Kaempferol Tri- and Tetraglycosides from the Flowers of Clematis Cultivar Keisuke Sakaguchi, Junichi Kitajima and Tsukasa Iwashina 173

Flowers from Kalanchoe pinnata are a Rich Source of T Cell-Suppressive Flavonoids Marcela A. S. Coutinho, Michelle F. Muzitano, Elaine A. Cruz, Maria C. Bergonzi, Carlos R. Kaiser, Luzineide W. Tinoco, Anna R. Bilia, Franco F. Vincieri, Bartira Rossi-Bergmann and Sônia S. Costa 175

Novel Flavanes from Livistona halongensis Tran Van Loc, Pham Duc Thang, Nguyen The Anh, Pham Thi Ninh, Trinh Thi Thuy and Tran Van Sung 179

Chemical Profiling of Constituents of Smilacis glabrae Using Ultra-high Pressure Liquid Chromatography Coupled with LTQ Orbitrap Mass Spectrometry Xiong Li, Yu Feng Zhang, Liu Yang, Yi Feng, Yuan Hui Deng, Yi Ming Liu and Xing Zeng 181

Phenolic Constituents from the Heartwood of Artocapus altilis and their Tyrosinase Inhibitory Activity Mai Ha Khoa Nguyen, Hai Xuan Nguyen, Mai Thanh Thi Nguyen and Nhan Trung Nguyen 185

Chemical Constituents of two Sages with Free Radical Scavenging Activity Omur L. Demirezer, Perihan Gurbuz, Ayşe Kuruuzum-Uz, Zuhal Guvenalp Cavit Kazaz and Ali A. Donmez 187

Synthesis of Uliginosins A and B George A. Kraus and Feng Liu 191

Eucleanal: A New Napthalene Derivative from Euclea divinorum Margaret Mwihaki Ng’ang’a, Hidayat Hussain, Sumesh Chhabra, Caroline Langat-Thoruwa, Karsten Krohn, Javid Hussain, Ahmed Al-Harrasi and Ivan Robert Green 193

A Double-blind, Randomized, Clinical Trial on the Antileishmanial Activity of a Morinda citrifolia (Noni) Stem Extract and its Major Constituents Fouzia A. Sattar, Fayaz Ahmed, Nadeem Ahmed, Samina A. Sattar, Muhammad A. K. Malghani and Muhammad I. Choudhary 195

Biotransformation of Gambogenic Acid by Chaetomium globosum CICC 2445 Si-Jia Tao, Yang Wang, Xing Zhang, Shu-Hong Guan and De-An Guo 197

Between Species Diversity of Hypericum perforatum and H. maculatum by the Content of Bioactive Compounds Edita Bagdonaite, Valdimaras Janulis, Liudas Ivanauskas and Juozas Labokas 199

Total Phenolic Content and Antioxidant Activity of Salvia spp. Exudates Laura Giamperi, Anahi Bucchini, Angela Bisio, Emanuela Giacomelli, Giovanni Romussi and Donata Ricci 201

An Efficient Microwave Assisted Extraction of Phenolic Compounds and Antioxidant Potential of Ginkgo biloba Pushpinder Kaur, Abha Chaudhary, Bikram Singh and Gopichand 203

Synthesis and Anti-tumor Activity Evaluation of Rhein-Aloe Emodin Hybrid Molecule Ye-fei Yuan, Xiang-yu Hu, Ying He and Jia-gang Deng 207

A New Peptide Isolated from a Marine Derived Streptomyces bacillaris Youcai Hu and John B. MacMillan 211

Biological Activity and Tissue Specific Accumulation of Fluorescently Labeled Methyl Jasmonate Naoki Kitaoka, Yuzou Sano, Seizo Fujikawa, Kensuke Nabeta and Hideyuki Matsuura 215

Continued inside backcover