Volume 5. Issue 2. Pages 175-350. 2010 ISSN 1934-578X (printed); ISSN 1555-9475 (online)

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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 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

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

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Prof. Peter G. Waterman Lismore, Australia

HONORARY EDITOR

PROFESSOR GERALD BLUNDEN The School of Pharmacy & Biomedical Sciences,

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

axuf64@dsl.pipex.com

Compositional Variability in Essential Oil from Different Parts of Alpinia speciosa from India Rajendra C. Padaliaa*, Chandan S. Chanotiyab and V. Sundaresana

aCentral Institute of Medicinal and Aromatic Plants (CIMAP, CSIR), Resource Center, Pantnagar- 263 149, Uttarakhand, India bCentral Institute of Medicinal and Aromatic Plants (CIMAP, CSIR), Lucknow-226 015,UP, India padaliarc@rediffmail.com Received: September 3rd, 2009; Accepted: December 1st, 2009

The essential oils from the leaves, flowers and roots of cultivated Alpinia speciosa K. Schum. were examined by capillary GC and GC-MS. Monoterpenoids composed 89.6% of the total identified constituents of the leaf oil, out of which 59.3% were oxygenated, represented mainly by terpinen-4-ol (28.4%) and 1,8-cineole (19.2%). The flower and leaf oils had a uniform qualitative, but different quantitative composition. However, the flowers oil was also dominated by oxygenated monoterpenoids (68.9%) viz., terpinen-4-ol (26.0%), 1,8-cineole (24.4%) and linalool (6.1%), along with the monoterpene hydrocarbon, sabinene (11.3%). On the contrary, the root oil had an entirely different composition and was characterized by endo-fenchyl acetate (40.1%), 1,8-cineole (11.8%), camphene (7.8%), bornyl acetate (6.9%) and borneol (5.8%). Moreover, endo-fenchyl acetate, exo-fenchyl acetate and endo-fenchol were characteristic of only the A. speciosa root oil. Keywords: Alpinia speciosa, Zingiberaceae, essential oil composition, endo-fenchyl acetate, 1,8-cineole, terpinen-4-ol, exo-fenchyl acetate. The genus Alpinia, comprising more than 230 species, belongs to the family Zingiberaceae. Alpinia species are used as spices, food additives and in the indigenous system of medicine [1a-1c]. Besides being used as a digestive, spleen and liver tonic, in dyspepsia, gastralgia, sea-sickness and for abdominal colic pains, various Alpinia species have been shown to possess several pharmacological properties, for example antiulcer, anticancer, myorelaxant, antispasmodic, anti-inflammatory, cytoprotective and spasmolytic activities [2a-2d]. Alpinia speciosa (syn. A. nutans Rosc.) is a robust herb, originating from the East Indies, with a leafy stem 2-3.5 m tall. The plant is commonly known as shell ginger or shellflower because of its individual pink flowers, particularly when in bud, which resemble sea shells [3, 4]. In addition, A. speciosa is well known for its wide use during World War I, when its leaves were used to make paper, which was more transparent and more rasping in nature [5a-5b]. A. speciosa is appreciated for its medicinal properties, including anti-ulcer, antioxidant, anti-hemorrhoidal, spasmolytic and diuretic activities, as well as being used, as a remedy for meteorims, catarrh and gastric disorders [6a-6f].

The chemical composition of the essential oils of various Alpinia species have been investigated [7-19]. Monoterpenoids [1,8-cineole, terpinen-4-ol, camphor, camphene, pinenes (α-, β-), and cinnamic acid] were the major constituents of A. speciosa [6b,6c, 16-19]. The present investigation deals with the comparative oil composition of different parts of A. speciosa cultivated in the Tarai region at the CIMAP resource center at Pantnagar, Uttarakhand, India. GC and GC-MS analysis of the essential oils of the leaves, flowers and roots of A. speciosa led to the identification of 35 constituents forming 86.2% to 92.2% of the total oil composition. The identified constituents with their respective percentages are given in Table I in order of their elution from a DB-5 column. Monoterpenoids contributed 89.6% of the leaf oil, out of which 59.3% were oxygenated, these being represented by terpinen-4-ol (28.4%), and 1,8- cineole (19.2%). Other constituents in significant amounts were sabinene (8.2%), p-cymene (8.0%), and γ-terpinene (5.7%). The flower essential oil was also rich in monoterpenoids (84.6%), with terpinen-4-ol (26.0%), 1,8-cineole (24.4%), sabinene (11.2%) and linalool

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280 Natural Product Communications Vol. 5 (2) 2010 Padalia et al.

Table 1: Comparative compositions of A. speciosa leaf, flower and root oils.

*Mode of detection: Retention Index (RI), Based on homologous series of n-alkanes; C9-C25; coinjection with standards, MS (GC-MS); t = trace (<0.1%); nd : not detected. (6.1%) being the major constituents. Although the flower and leaf oils had a uniform qualitative composition, the constituents differed quantitatively. On the contrary, the root essential oil possessed an entirely different composition, with fenchyl derivatives forming 42% of the total identified constituents, the major ones of which were endo-fenchyl acetate (40.1%), 1,8-cineole (11.8%), camphene (7.8%), bornyl acetate (6.9%) and borneol (5.8%). In all the investigated oils, monoterpenoids were the dominant class of constituents (84.6%-90.1%), with oxygenated monoterpenes (59.3%-71.8%) as the most abundant representatives. It was interesting to note that the distribution profile of components of the essential oils of leaf and flower were quite similar. On the other hand, there was considerable variation in the terpenoid profile of the roots. The

presence of endo-fenchyl acetate, exo-fenchyl acetate, and endo-fenchol is a unique feature of the root oil. These constituents were completely absent in the leaf and flower oils. Moreover, other constituents like cis-sabinene hydrate, α-thujene, cis-p-menth-2-en-1-ol and trans-p-menth-2-en-1-ol present in the leaf and flower oils were not detected in the root oil. The composition of the leaf and flower oils was very close to that reported earlier showing terpinen-4-ol and 1,8-cineole as the major constituents responsible for the characteristic sweet smell [19]. Hence, the aerial parts may be utilized as a substitute for culinary and perfumery materials. Furthermore, our analysis revealed only a limited amount of sesquiterpenoids (1.0%-2.1%) in the essential oils of A. speciosa, as compared with earlier reports in which these compounds constituted the most significant part of the oil [17-19]. This is the first time that the comparative oil composition of different parts of A. speciosa from India has been reported, as well as the unique presence of endo-fenchyl acetate, exo-fenchyl acetate, and endo-fenchol as the major constituents of the root essential oil. Experimental

Plant materials: The fresh leaves, flowers and roots of A. speciosa were collected from CIMAP Resource Center, Pantnagar at the blooming stage. Plant herbarium and voucher specimens have been deposited in CIMAP Resource Center, Pantnagar. Isolation of the oil: The fresh leaves, flowers and roots (1 kg each) were subjected to hydro-distillation using a Clevenger-type apparatus for 3 h. The oil yields in leaves, flowers and roots were 0.2%, 0.3% and 0.4%, respectively. The oils were dried over anhydrous Na2SO4 and were stored in sealed vials under refrigeration prior to analysis. GC and GC-MS analysis: The oils were analyzed on a Varian CP-3800 GC apparatus using a DB-5 non-polar fused silica capillary column (30 m x 0.25 mm i.d., film thickness 0.25 µm) equipped with a flame-ionization detector (FID). The column temperature (60-240 °C) was programmed at 3°C/min with final hold time of 10 min., using H2 as carrier gas at 1mL/min constant flow. The injector and detector temperatures were 300°C and 310°C, respectively. Samples were injected using a split ratio 1:40; injection volume 0.5μL neat. GC/MS utilized a PerkinElmer AutoSystem XL GC interfaced with a Turbomass Quadrupole mass spectrometer fitted with an Equity-5 fused silica capillary column (60 m x 0.32 mm i.d., film thickness 0.25 µm; Supelco Bellefonte, PA, USA). The oven column temperature ranged from 70–250°C, programmed at 3°C/min, with initial and final hold time of 2 min, using He as carrier gas at 10

Composition ( FID %) Constituents* RI Leaf Flower Root

α-Thujene 927 2.1 0.4 nd α-Pinene 934 1.1 0.6 3.1 Camphene 949 0.2 0.4 7.8 Sabinene 973 8.2 11.3 0.3 β-Pinene 977 2.5 0.4 0.4 β-Myrcene 989 0.6 0.2 1.1 α-Phellandrene 1009 nd nd 0.2 α-Terpinene 1016 0.7 0.1 0.1 p-Cymene 1023 8.0 1.5 0.4 Limonene 1028 1.2 0.3 3.4 1,8-Cineole 1031 19.2 24.4 11.8 (Z)-β-Ocimene 1038 nd nd 0.3 (E)-β-Ocimene 1048 nd nd 1.0 γ-Terpinene 1057 5.7 0.5 0.2 cis-Sabinene hydrate 1066 2.0 2.4 nd Terpinolene 1087 t t t Fenchone 1088 0.7 0.1 0.4 Linalool 1098 3.9 6.1 0.7 endo-Fenchol 1113 nd nd 1.3 cis-p-Menth-2-en-1-ol 1120 1.3 1.9 nd trans-p-Menth-2-en-1-ol 1137 1.0 1.4 nd Camphor 1143 0.1 0.7 0.7 Camphene hydrate 1147 nd 0.2 0.3 Borneol 1164 0.3 0.6 5.8 Terpinen-4-ol 1177 28.4 26.0 1.0 p-Cymen-8-ol 1182 0.4 0.3 1.1 α-Terpineol 1188 1.8 4.0 1.5 endo-Fenchyl acetate 1220 nd nd 40.1 exo-Fenchyl acetate 1232 nd nd 0.2 Bornyl acetate 1285 0.2 0.8 6.9 β-Caryophyllene 1419 0.6 1.1 0.2 (E)-β-Farnesene 1456 nd nd 0.3 Germacrene D 1481 t t 0.5 δ-Cadinene 1523 nd nd 0.8 Caryophyllene oxide 1584 0.4 0.5 0.3

Monoterpene hydrocarbons 30.3 15.7 18.3 Oxygenated monoterpenes 59.3 68.9 71.8 Sesquiterpene hydrocarbons 0.6 1.1 1.8 Oxygenated sesquiterpenes 0.4 0.5 0.3 Total identified 90.6 86.2 92.2

Essential oil of Alpinia speciosa Natural Product Communications Vol. 5 (2) 2010 281

psi constant pressure, a split ratio of 1:30, and an injection size of 0.03 µL neat; injector, transfer line and source temperatures were 250°C; ionization energy 70 eV; mass scan range 40-450 amu. Characterization was achieved on the basis of retention time, Kovats Index, relative retention index using a homologous series of n-alkanes (C9-C25 hydrocarbons, Polyscience Corp. Niles IL), coinjection with standards in GC (Aldrich and Fluka), MS library search

(NIST/EPA/NIH version 2.1 and Wiley registry of MS data 7th edition) and by comparing with the MS literature data [20a-20b]. The retention times of standards were also used to confirm the identities. The relative amounts of individual components were calculated based on GC peak areas without using correction factors. Acknowledgements -The authors are grateful to the Director, CIMAP for the facilities and encouragement.

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Natural Product Communications 2010

Volume 5, Number 2

Contents

Original Paper Page

Antimosquito and Antimicrobial Clerodanoids and a Chlorobenzenoid from Tessmannia species Charles Kihampa, Mayunga H.H. Nkunya, Cosam C. Joseph, Stephen M. Magesa, Ahmed Hassanali, Matthias Heydenreich and Erich Kleinpeter 175

Two New Terpenoids from Trichilia quadrijuga (Meliaceae) Virginia F. Rodrigues, Hadria M. Carmo, Raimundo Braz Filho, Leda Mathias and Ivo J. Curcino Vieira 179

Effect of Miconazole and Terbinafine on Artemisinin Content of Shooty Teratoma of Artemisia annua Rinki Jain and Vinod Kumar Dixit 185

A New Triterpenoid Saponin from the Stem Bark of Pometia pinnata Faryal Vali Mohammad, Viqar Uddin Ahmad, Mushtaq Noorwala and Nordin HJ.Lajis 191

27-Hydroxyoleanolic Acid Type Triterpenoid Saponins from Anemone raddeana rhizome Li Fan, Jin-Cai Lu, Jiao Xue, Song Gao, Bei-Bei Xu, Bai-Yi Cao and Jing-Jing Zhang 197

Steroids from the South China Sea Gorgonian Subergorgia suberosa Shu-Hua Qi, Cheng-Hai Gao, Pei-Yuan Qian and Si Zhang 201

Auroside, a Xylosyl-sterol, and Patusterol A and B, two Hydroxylated Sterols, from two Soft Corals Eleutherobia aurea and Lobophytum patulum Dina Yeffet, Amira Rudi, Sharon Ketzinel, Yehuda Benayahu and Yoel Kashman 205

Anti-tuberculosis Compounds from Mallotus philippinensis Qi Hong, David E. Minter, Scott G. Franzblau, Mohammad Arfan, Hazrat Amin and Manfred G. Reinecke 211

Phenolic Derivatives with an Irregular Sesquiterpenyl Side Chain from Macaranga pruinosa Yana M. Syah and Emilio L. Ghisalberti 219

Hexaoxygenated Flavonoids from Pteroxygonum giraldii Yanhong Gao, Yanfang Su, Shilun Yan, Zhenhai Wu, Xiao Zhang, Tianqi Wang and Xiumei Gao 223

Comparative Study of the Antioxidant Activities of Eleven Salvia Species Gábor Janicsák, István Zupkó, Imre Máthé and Judit Hohmann 227

Dibenzocyclooctadiene Lignans from Fructus Schisandrae Chinensis Improve Glucose Uptake in vitro Jing Zhang, Lei Ling Shi and Yi Nan Zheng 231

Honokiol and Magnolol Production by in vitro Micropropagated Plants of Magnolia dealbata, an Endangered Endemic Mexican Species Fabiola Domínguez, Marco Chávez, María Luisa Garduño-Ramírez, Víctor M. Chávez-Ávila, Martín Mata and Francisco Cruz-Sosa 235

Design, Synthesis and Biological Evaluation of Novel Spin-Labeled Derivatives of Podophyllotoxin Jia-qiang Zhang, Zhi-wei Zhang, Ling Hui and Xuan Tian 241

Secondary Metabolites of the Phytopathogen Peronophythora litchii Haihui Xie, Yaoguang Liang, Jinghua Xue, Qiaolin Xu, Yueming Jiang and Xiaoyi Wei 245

Bioassay-guided Isolation of Antibacterial and Cytotoxic Compounds from the Mesophilic Actinomycete M-33-5 Mustafa Urgen, Fatma Kocabaş, Ayşe Nalbantsoy, Esin Hameş Kocabas, Ataç Uzel and Erdal Bedir 249

Aristolactams, 1-(2-C-Methyl-β-D-ribofuranosyl)-uracil and Other Bioactive Constituents of Toussaintia orientalis Josiah O. Odalo, Cosam C. Joseph, Mayunga H.H. Nkunya, Isabel Sattler, Corinna Lange, Gollmick Friedrich, Hans-Martin Dahse and Ute Möllman 253

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