NPC
Natural Product Communications
EDITOR-IN-CHIEF DR. PAWAN K AGRAWAL Natural Product Inc. 7963, Anderson Park Lane, Westerville, Ohio 43081, USA
[email protected] EDITORS PROFESSOR ALEJANDRO F. BARRERO Department of Organic Chemistry, University of Granada, Campus de Fuente Nueva, s/n, 18071, Granada, Spain
[email protected] PROFESSOR ALESSANDRA BRACA Dipartimento di Chimica Bioorganicae Biofarmacia, Universita di Pisa, via Bonanno 33, 56126 Pisa, Italy
[email protected] PROFESSOR DEAN GUO State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China
[email protected] PROFESSOR YOSHIHIRO MIMAKI School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan
[email protected] PROFESSOR STEPHEN G. PYNE Department of Chemistry University of Wollongong Wollongong, New South Wales, 2522, Australia
[email protected] PROFESSOR MANFRED G. REINECKE Department of Chemistry, Texas Christian University, Forts Worth, TX 76129, USA
[email protected] PROFESSOR WILLIAM N. SETZER Department of Chemistry The University of Alabama in Huntsville Huntsville, AL 35809, USA
[email protected] PROFESSOR YASUHIRO TEZUKA Institute of Natural Medicine Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan
[email protected] 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
[email protected]
HONORARY EDITOR PROFESSOR GERALD BLUNDEN The School of Pharmacy & Biomedical Sciences, University of Portsmouth, Portsmouth, PO1 2DT U.K.
[email protected]
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. Vladimir I Kalinin Vladivostok, Russia Prof. Niel A. Koorbanally Durban, South Africa
Prof. Karsten Krohn Paderborn, Germany Prof. Chiaki Kuroda Tokyo, Japan 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. 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 Dr. Bikram Singh Palampur, India 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
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. 2013 subscription price: US$2,395 (Print, ISSN# 1934-578X); US$2,395 (Web edition, ISSN# 1555-9475); US$2,795 (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
Composition of Essential Oil from Aerial and Underground Parts of Geum rivale and G. urbanum Growing in Poland
2013 Vol. 8 No. 4 505 - 508
Aleksandra Owczarek*, Jan Gudej and Agnieszka Kicel Department of Pharmacognosy, Medical University of Lodz, 90-151 Lodz, Poland
[email protected] Received: December 6th, 2012; Accepted: February 26th, 2013
A study of the composition of essential oils from aerial and underground parts of Geum rivale L. and Geum urbanum L. growing in Poland led to the identification of 130 compounds. The main compound of the essential oil from underground parts of G. urbanum was eugenol (69.2%), whereas cis-myrtanal (53.3%) was the major constituent of the essential oil from roots of G. rivale. The essential oils from aerial parts of the plants contained large amounts of aliphatic compounds with (Z)-3-hexenol (38.4%) being the dominant constituent of the essential oil from aerial parts of G. urbanum and 1-octen-3-ol (33.9%) from G. rivale. Keywords: Geum rivale, Geum urbanum, Essential oil, Eugenol, Myrtanal, (Z)-3-Hexenol, 1-Octen-3-ol.
The genus Geum L. (Rosaceae) comprises about 60 species widespread all over the world except in tropical and arctic regions. G. rivale L. and G. urbanum L. are perennial herbs commonly distributed in Poland in deciduous forest, parks and meadows. Both species are used in traditional medicine. The roots of G. urbanum (Gei urbani rhizoma et radix) are used as astringent agents in treating diarrhea, indigestion, gingivitis and haemorrhoids. The aerial parts of G. urbanum (Gei urbani herba) and rhizome of G. rivale (Gei rivali rhizoma) are used in a similar way, but less frequently [1,2]. Previous research shows the presence of tannins and phenolic acids in aerial and underground parts of the investigated plants [3,4]. Aerial parts of G. rivale were also reported to contain flavonoids, triterpenes and sterols [4]. Essential oil is known for the roots of Geum species, and recently the presence of volatiles in aerial parts of G. iranicum was reported [5]. The essential oil composition of G. urbanum and G. rivale roots growing in Germany has been published so far [6], but, to the best of our knowledge, no studies have been carried out on the volatile constituents of aerial parts of the plants. The aim of this study was to investigate the chemical composition of essential oils of roots and aerial parts of G. rivale and G. urbanum growing in Poland. The content of essential oil in the plant material was small, as has been reported before in the case of G. iranicum [5]. In total, 130 compounds were identified in the studied material, most of them in the aerial parts of the plants. The identified compounds accounted for 92.9-99.6% of the investigated oils. The results of the analysis are shown in Table 1. The components are listed in order of their elution time from an Rtx-1 column. In the essential oils from the underground parts of G. rivale and G. urbanum, 31 and 32 compounds were identified, respectively, comprising 97.5% and 99.6% of the oils. The composition of the oil from G. urbanum root was dominated by eugenol (69.2%), followed by cis-myrtanal (15.3%), and related compounds with a pinane skeleton: trans-myrtanol (3.2%), myrtenal (3.0%), trans-myrtanal (2.9%) and myrtenol (2.1%). These six compounds accounted for 95.7% of the oil. Some other monoterpenes were detected, but only in small amounts (0.9%), with phellandral (0.5%) being the most abundant one. Besides these, the oil contained also 1.6% of the
bicyclic ketone – nopinone. Pinane derivatives were the dominant group in G. rivale root oil with the main compound being cis-myrtanal (53.3%), followed by trans-myrtanal (7.1%), trans-myrtanol (6.8%), myrtenal (6.1%), myrtenol (5.5%) and cis-myrtanol (4.5%). Other monoterpenes accounted for 6.1% of the oil, with linalool (2.4%) being the most abundant one. The content of eugenol (2.9%) was very low in comparison with G. urbanum root oil. The qualitative composition of the essential oils from the roots of G. urbanum and G. rivale were largely in agreement with a previous study [6]. Most compounds identified in that study were also detected in our samples, among them all the major compounds. However, we managed to identify 12 compounds that have not been reported so far in the essential oil from G. urbanum root, and 12 that have not been reported for G. rivale root. Some quantitative differences were also found, especially in the essential oil from underground parts of G. rivale. The content of cis-myrtanal in our sample was almost 15% higher, while the content of trans-myrtanal, myrtenal and myrtenol was about 5% lower in comparison with the essential oil from underground parts of G. rivale growing in Germany [6]. These differences could probably be explained by different place of collection, collection time or distillation duration. Essential oils from aerial parts of G. rivale and G. urbanum contained 83 and 100 compounds, respectively, representing 95.5% and 92.9% of the oils. The compositions of the two oils were similar, but very different from those of the root oils. Aliphatic alcohols were the major group of compounds. (Z)-3-hexenol (38.4%) and 1-octen-3-ol (14.6%) dominated the oil from G. urbanum. The same compounds, but in the opposite order, were predominant in the oil from G. rivale; 3-octen-1-ol comprised 33.9% and (Z)-3-hexenol 16.2% of the oil. The oils contained also a variety of sesquiterpenes (32 different compounds), with (E,E)-αfarnesen being the most abundant in this group in both samples. Some monoterpenes and (Z)-3-hexenyl esters were also detected. The compounds, that dominated in the root essential oils, i.e. eugenol and monoterpenes, with a pinane skeleton, were present only in small amounts.
506 Natural Product Communications Vol. 8 (4) 2013
Owczarek et al.
Table 1: Composition of essential oil from aerial and underground parts of G. rivale and G. urbanum. Peak No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75
Constituent (E)-2-Hexenal (Z)-3-Hexen-1-ol (E)-3-Hexen-1-ol Hexanol Heptanal 1-Isopropylcyclohex-1-ene Camphene Heptanol 1-Octen-3-ol 6-Methyl-5-hepten-2-ol Octanal 3-Octanol (Z)-3-Hexenyl acetate α-Phellandrene p-Cymene Benzacetaldehyde 2-Ethyl-1-hexanol β-Phellandrene 1,8-Cineole Limonene (E)-β-Ocimene (E)-2-Octen-1-ol Octanol trans-Linalool oxide (furanoid) cis-Linalool oxide (furanoid) Terpinolene Nonanal Linalool Undecane Nopinone Camphor trans-Pinocarveol (Z)-3-Nonen-1-ol Pinocarvone 1-(1,4-Dimethyl-3-cyclohexen-1-yl)cis-Myrtanal Nonanol Terpinen-4-ol trans-Myrtanal (Z)-3-Hexenyl butyrate Myrtenal Methyl salicylate α-Terpineol Myrtenol Decanal β-Cyclocitral Dodecane Citronellol (Z)-3-Hexenyl-2-methylbutanoate (Z)-3-Hexenyl isovalerate cis-Myrtanol Geraniol trans-Myrtanol Geranial Perilla aldehyde Phellandral Decanol Nonanoic acid Cuminyl alcohol Dihydroedulane II Dihydroedulane I Perilla alcohol Undecanal Theaspirane A Tridecane (Z)-3-Hexenyl tiglate Eugenol δ-Elemene Dehydro-ar-ionene α-Cubebene β-Damascenone (Z)-3-Hexenyl hexanoate Cyclosativene α-Ylangene α-Copaene
RI Rtx-1
RI Lit
RI TGWax
838 835 846 847 872 921 934 954 965 977 981 981 989 995 1012 1014 1018 1019 1019 1021 1040 1053 1058 1059 1073 1079 1083 1085 1099 1107 1119 1123 1139 1139 1154 1158 1158 1162 1166 1168 1170 1171 1173 1180 1186 1197 1199 1212 1217 1220 1234 1238 1241 1245 1247 1253 1258 1268 1274 1280 1283 1283 1289 1290 1299 1306 1331 1331 1338 1347 1362 1366 1367 1371 1374
831 838 844 845 878 923 941 953 962 978 981 981 987 1002 1015 1012
1237 1396 1371 1360 1201 1067 1077 1461 1458 1461 1304 1399 1328 1177 1284 1657 1491 1221 1219 1209 1262 1624 1564 1453 1474 1294 1407 1555 1105 1597 1533 1665 1691
1023 1024 1025 1041 1052 1063 1058 1072 1082 1076 1086 1100 1110 1123 1126 1134 1137 1156 1149 1164 1173 1172 1171 1176 1178 1180 1192 1200 1213 1217 1218 1238 1235 1240 1244 1260 1249 1264 1263 1273 1284 1288 1280 1290 1299 1300 1297 1331 1340 1329 1355 1363 1363
1570 1573 1662 1613 1586 1474 1647 1798 1707 1803 1513 1637 1205 1772 1498 1871 1854 1882 1743 1802 1742 1763 2173 2106 1531 2017
1305 1674 2194
1835 1495
1376 1379
1502
Aerial parts G. rivale G. urbanum tr tr 16.2 38.4 0.1 0.2 1.2 1.4 0.2 0.4 tr 0.3 0.4 33.9 14.6 0.3 0.2 0.1 5.0 0.6 0.2 0.7 0.3 0.2 tr 0.1 0.1 0.1 tr tr 0.1 tr 3.7 3.3 0.5 0.6 0.1 tr tr 0.1 2.9 5.0 2.6 2.6 tr 0.1 0.1 0.1 tr 0.4 0.1 0.1 0.2** 0.5** 1.2 0.2 tr 0.4 0.2 0.2 1.0 1.4 tr 0.1 0.5 0.6 tr 0.1 tr 0.1 tr 0.2 0.2 0.1 tr tr 2.1 0.2 0.5 0.1 tr 0.2 0.4 tr tr 0.3 0.2 tr tr tr tr 0.1 0.5 0.1 tr 0.2 0.2 0.6 0.2 tr 0.1 0.2 3.9 0.1
Underground parts G. rivale G. urbanum 0.1* tr* tr* tr* 1.2 tr 0.1* 0.1* tr* tr* 0.1* 0.1* 2.4 0.2 2.0 1.6 tr* 1.3 0.4 tr* tr* 53.3 15.3 7.1 2.9 6.1 3.0 tr 0.6 0.1 5.5 2.1 0.2 tr 4.5 0.7 6.8 3.2 0.8 0.1 1.4 0.5 0.2 0.1 2.9 69.2 0.1
tr* tr
Essential oil of Geum rivale and G. urbanum
76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130
β-Bourbonene β-Cubebene Tetradecane β-Caryophyllene β-Copaene Geranylacetone α-Humulene Alloaromadendrene Dehydro-β-ionone β-Ionone γ-Muurolene Germacrene D (Z,E)-α-Farnesene Tridecanal α-Muurolene (E,E)-α-Farnesene γ-Cadinene δ-Cadinene α-Calacorene trans-Nerolidol (Z)-3-Hexenyl benzoate Spathulenol Caryophyllene oxide Fokienol Viridiflorol Guaiol Humulene epoxide II Farnesene epoxide Cubenol γ-Eudesmol T-Muurolol β-Eudesmol α-Cadinol α-Eudesmol (Z)-3-Hexenyl salicylate Bulnesol Pentadecanal Heptadecane Benzyl benzoate Octadecane Hexadecanol Nonadecane Heptadecanal Isophytol Hexadecanoic acid Eicosane Octadecanal Geranyllinalool Octadecanol Phytol Docosane Tricosane Tetracosane Pentacosane Hexacosane
Natural Product Communications Vol. 8 (4) 2013 507
1382 1385 1398 1416 1425 1431 1449 1457 1459 1465 1469 1475 1483 1491 1493 1496 1506 1514 1529 1549 1549 1565 1570 1576 1582 1586 1594 1599 1616 1619 1627 1637 1640 1642 1647 1654 1696 1696 1741 1799 1867 1898 1899 1939 1947 1998 2002 2012 2070 2100 2197 2297 2397 2498 2610
1386 1390 1400 1421 1424 1430 1455 1462 1460 1468 1474 1479 1480 1493 1496 1498 1507 1520 1527 1553 1545 1563 1578 1582 1592 1593 1602 1630 1618 1633 1641 1643 1653 1648 1651 1702 1700 1730 1800 1866 1900 1908 1949 1951 2000 2012 2008 2070 2114 2200 2300 2400 2500 2600
1533 1549 1609
1682 1659 1880 1948 1699 1723 1728 1828 1734 1762 1769 1932 2047 2141 2145 2002 2096 2058 2078 2198 2234 2242 2226 2276 2216 2037 1697 2649 2350 1900 2242 2291 2657 2345 2539 2586 2601 2192 2300 2408 2498 2606
Eugenol: Pinane skeleton monoterpenes: Other monoterpenes: Sesquiterpenes hydrocarbonate: Oxygenated sesquiterpenes: Aliphatic compounds: Others: Total identified:
0.1 0.2 0.6 tr 0.7 0.4 0.2 0.2 0.5 0.1 0.2 6.2 0.1 0.8 0.1 0.3** 0.7** 0.2 0.8 0.2 0.5 0.2 0.3 0.3 0.2** 0.1** tr tr tr tr tr 4.4 0.1 0.1 tr 0.0 0.5 4.8 14.5 2.8 67.5 5.4 95.5
0.5 0.3 tr 0.1 tr 0.1 0.1 0.1 0.1 0.3 4.3 0.1 tr 1.6 0.5 tr tr tr tr 0.1 0.1 0.1 0.1 0.1 0.1 0.4 tr tr 0.1 tr 0.1 0.1 0.1 0.1 tr tr 0.1 tr 4.1 tr 0.1 tr 0.1 0.1 0.5 0.6 6.9 5.2 2.2 72.0 5.5 92.9
-
tr* 0.1* tr tr* tr -
0.3* tr* tr tr 2.9 84.5 6.1 0.1 0.0 1.8 2.1 97.5
tr* 0.1* 0.1* tr* tr* 69.2 27.6 0.9 0.1 0.2 0.0 1.6 99.6
tr - < 0.05%; * volatiles new for the organ; **percentages determined on TGWax column
Eugenol is an important natural compound with many biological properties [7], including antioxidant [8], antimicrobial [9], antifungal [10], analgesic [11], anti-stress [12], anticancer [13] and gastroprotective [14] activities. Myrtanal is a less common compound. It is present in reasonable quantities in underground parts of some Geum species [6], as well as in roots of some Paeonia species [15]. Its activity has not been much studied so far. However, there are some reports about its antimicrobial activity [16]. (Z)-3hexen-1-ol, called “leaf alcohol”, and 1-octen-3-ol are frequently present in green parts of plants and are believed to be associated with their stress-response [17].
Experimental Plant material: Aerial and underground parts of G. rivale and G. urbanum were collected during flowering at locations in Lodz (Poland) in May and June, respectively. The species were identified by Prof. Jan Gudej from the Faculty of Pharmacognosy, Medical University of Lodz, where voucher specimens were deposited. Isolation of essential oil: Essential oils from fresh aerial and underground parts of the plants were obtained by hydrodistillation for 3 h in a Clevenger-type apparatus with diethyl ether/n-pentane
508 Natural Product Communications Vol. 8 (4) 2013
Owczarek et al.
(1:1) as collecting solvent. The collected oils were dried over anhydrous sodium sulfate and stored at 4°C until analysis.
temperature 260°C, split ratio 1:20, carrier gas helium at a flow rate of 0.8 mL/min.
Chromatographic analysis: The analyses of the essential oils were carried out on a Trace GC Ultra apparatus (Thermo Electron) with FID and MS DSQ II detectors and FID-MS splitter (SGE Analytical Science). Mass range was 30-400 amu, ion source-temperature: 200°C, ionization energy: 70eV. Operating conditions: apolar capillary column Rtx-1 MS (Restek, 60 m × 0.25 mm i.d., film thickness 0.25 µm), temperature program: 50-300°C at 4°C/min, SSL injector temperature 280°C, FID temperature 300°C, split ratio 1:20, carrier gas helium at a regular pressure 200 kPa; polar capillary column TraceGold TGWax-MS A (Thermo Scientific, 30 m × 0.25 mm, film thickness 0.25 µm), temperature program: 50245°C (30 min) at 4°C/min, SSL injector temperature 250°C, FID
Identification of compounds: Identification of compounds was based on the comparison of their MS with commercial libraries (NIST 98.1, Wiley Registry of Mass Spectral Data 8th edn, and MassFinder 4.1) along with relative retention indices (RI, non-polar column and polar column). Identification of myrtanal isomers was based on comparison of their retention indices with literature data, but only on a polar column [6]. Acknowledgments - This work is supported by the Medical University of Lodz, grant No. 502-34-011. Authors would like to thank Danuta Kalemba from the Institute of General Food Chemistry, Lodz University of Technology for carrying out the GCMS analyses and consultations.
References [1] [2] [3] [4] [5] [6] [7] [8] [9] [10] [11] [12] [13] [14] [15] [16] [17]
Strzelecka H, Kowalski J. (2000) Encyklopedia zielarstwa i ziołolecznictwa. PWN, Warsaw, 261-262. Macků J, Krejča J. (1989) Atlas roślin leczniczych. Zakład Narodowy imienia Ossolinskich – Wydawnictwo, Wroclaw, 108-110. Gstirner F, Widenmann H. (1964) Contents of the rhizoma of Geum urbanum. Scientia Pharmaceutica, 32, 98-104. Panizzi L, Catalano S, Miarelli C. (2000) In vitro antimicrobial activity of extracts and isolated constituents of Geum rivale. Phytotherapy Research, 14, 561-563. Shahani S, Monsef-Esfahani HR. (2011) Chemical composition of essential oil and hydrolate of Geum iranicum Khatamaz. Journal of Essential Oil Research, 23, 29-33. Vollman C, Schultze W. (1995) Composition of the root essential oils of several Geum species and related members of the subtribe Geinae (Rosaceae). Flavour and Fragrance Journal, 10, 173-178. Pramod K, Ansari, SH, Ali J. (2010) Eugenol: a natural compound with versatile pharmacological actions. Natural Product Communications, 5, 1999-2006. Nagababu E, Rifkind JM, Boindala S, Nakka L. (2010) Assessment of antioxidant activity of eugenol in vitro and in vivo. Methods in Molecular Biology, 610, 165-180. Shapiro S, Meier A, Guggenheim B. (1994) The antimicrobial activity of essential oils and essential oil components towards oral bacteria. Oral Microbiology and Immunology, 9, 202-208. Campaniello D, Corbo MR, Sinigaglia M. (2010) Antifungal activity of eugenol against Penicillium, Aspergillus, and Fusarium species. Journal of Food Protection, 73, 1124-1128. Park SH, Sim YB, Lee JK, Kim SM, Kang YJ, Jung JS, Suh HW. (2011) The analgesic effects and mechanisms of orally administered eugenol. Archives of Pharmacal Research, 34, 501-507. Garabadu D, Shah A, Ahmad A, Joshi VB, Saxena B, Palit G, Krishnamurthy S. (2011) Eugenol as an anti-stress agent: modulation of hypothalamic-pituitary-adrenal axis and brain monoaminergic systems in a rat model of stress. Stress, 14, 145-155. Vidhya N, Devaraj SN. (2011) Induction of apoptosis by eugenol in human breas cancer cells. Indian Journal of Experimental Biology, 49, 871-878. Santin JR, Lemos M, Klein-Júnor LC, Machado ID, Costa P, de Oliveira AP, Tilia C, de Souza JP, de Sousa JP, Bastos Jk, de Andrade SF. (2011) Gastroprotective activity of essential oil of the Syzygium aromaticum and its major component eugenol in different animal models. NaunynSchmiedeberg’s Archives of Pharmacology, 383, 871-878. Orhan I, Demirci B, Omar I, Siddiqui H, Kaya E, Choudhary MI, Ecevit-Gen G, Özhatay N, Şener B, Başer K, Hüsnü C. (2010) Essential oil compositions and antioxidant properties of the roots of twelve Anatolian Paeonia taxa with special reference to chromosome counts. Pharmaceutical Biology, 48, 10-16. Gupta N, Saxena G, Kalra SS. (2011) Antimicrobial activity pattern of certain terpenoids. International Journal of Pharma and Bio Sciences, 2, 87-91. Radulović N, Blagojević P, Palić R. (2010) Comparative study of leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae). Molecules, 15, 6168-6185.
Natural Product Communications Vol. 8 (4) 2013 Published online (www.naturalproduct.us)
Volatile Composition of Six Horsetails: Prospects and Perspectives Françoise Fons, Didier Froissard, Jean-Marie Bessière, Alain Fruchier, Bruno Buatois and Sylvie Rapior Chemical Compositions of the Rhizome, Leaf and Stem Oils from Malaysian Hornstedtia leonurus Nor Akmalazura Jani, Hasnah Mohd. Sirat, NorAzah Mohamad Ali and Azrina Aziz Effect on Emotional Behavior and Stress by Inhalation of the Essential oil from Chamaecyparis obtusa Hikaru Kasuya, Erika Hata, Tadaaki Satou, Masaki Yoshikawa, Shinichiro Hayashi, Yoshinori Masuo and Kazuo Koike Chemical Composition and Antibacterial Activity of Rhizome Oils from Five Hedychium Species Ratchuporn Suksathan, Siriwoot Sookkhee, Somboon Anuntalabhochai and Sunee Chansakaow Chemical Composition and Antimicrobial Activity of Three Essential Oils from Curcuma wenyujin Jingjing Zhu, Agnieszka D. Lower-Nedza, Meng Hong, Song Jiec, Zhimin Wang, Dong Yingmao, Christine Tschiggerl, Franz Bucar and Adelheid H. Brantner Essential Oil Composition and Antimicrobial Activity of Aerial Parts and Ripe Fruits of Echinophora spinosa (Apiaceae) from Italy Daniele Fraternale, Salvatore Genovese and Donata Ricci Composition and in vitro Anticancer Activities of the Leaf Essential Oil of Neolitsea variabillima from Taiwan Yu-Chang Su, Kuan-Ping Hsu, Eugene I-Chen Wang and Chen-Lung Ho
509 513 515 519
523
527 531
Review/Account Natural Products from Marine Algae of the Genus Osmundaria (Rhodophyceae, Ceramiales) Kelvin Osako and Valéria Laneuville Teixeira Phenols, Alkaloids and Terpenes from Medicinal Plants with Antihypertensive and Vasorelaxant Activities. A Review of Natural Products as Leads to Potential Therapeutic Agents Francesco Maione, Carla Cicala, Giulia Musciacco, Vincenzo De Feo, Anibal G. Amat, Armando Ialenti and Nicola Mascolo Diosmin – Isolation Techniques, Determination in Plant Material and Pharmaceutical Formulations, and Clinical Use Anna Bogucka – Kocka, Michał Woźniak, Marcin Feldo, Janusz Kocki and Katarzyna Szewczyk
533
539 545
Natural Product Communications 2013 Volume 8, Number 4 Contents Original Paper Anti-melanogenesis Constituents from the Seaweed Dictyota coriacea Ryeo Kyeong Ko, Min-Chul Kang, Sang Suk Kim, Tae Heon Oh, Gi-Ok Kim, Chang-Gu Hyun, Jin Won Hyun and Nam Ho Lee Methyl Carnosate, an Antibacterial Diterpene Isolated from Salvia officinalis Leaves Elisa Climati, Fabio Mastrogiovanni, Maria Valeri, Laura Salvini, Claudia Bonechi, Nilufar Zokirzhonovna Mamadalieva, Dilfuza Egamberdieva, Anna Rita Taddei and Antonio Tiezzi Cytotoxicity of Meroterpenoids from Sargassum siliquastrum against Human Cancer Cells Jung Im Lee, Myoung K. Kwak, Hee Y. Park and Youngwan Seo Isolation of Methyl 27-caffeoyloxyoleanolate – A New Oleanane Triterpenoid from the Roots of Hibiscus vitifolius Duraisamy Ramasamy and Ariamuthu Saraswathy Synthesis and Cytotoxic Activity of New Betulin and Betulinic Acid Esters with Conjugated Linoleic Acid (CLA) Barbara Tubek, Paweł Mituła, Natalia Niezgoda, Katarzyna Kempińska, Joanna Wietrzyk and Czesław Wawrzeńczyk Analysis of Pyrrolizidine Alkaloids and Evaluation of Some Biological Activities of Algerian Senecio delphinifolius (Asteraceae) Soukaina Tidjani, Philippe N. Okusa, Amar Zellagui, Laetitia Moreno Y Banuls, Caroline Stévigny, Pierre Duez and Salah Rhouati Berbanine: a New Isoquinoline-isoquinolone Alkaloid from Berberis vulgaris (Berberidaceae) Anna Hošťálková, Zdeněk Novák, Milan Pour, Anna Jirošová, Lubomír Opletal, Jiří Kuneš and Lucie Cahlíková Dicentrine Production in Callus and Cell Suspension Cultures of Stephania venosa Tharita Kitisripanya, Jukrapun Komaikul, Nirachara Tawinkan, Chuennapha Atsawinkowit and Waraporn Putalun New Flavan and Alkyl α,β-Lactones from the Stem Bark of Horsfieldia superba Nabil Ali Al-Mekhlafi, Khozirah Shaari, Faridah Abas, Ethyl Jeyaseela Jeyaraj, Johnson Stanslas, Shaik Ibrahim Khalivulla and Nordin H. Lajis New Flavonol Triglycosides from the Leaves of Soybean Cultivars Yoshinori Murai, Ryoji Takahashi, Felipe Rojas Rodas, Junichi Kitajima and Tsukasa Iwashina Melitidin: A Flavanone Glycoside from Citrus grandis ‘Tomentosa’ Wei Zou, Yonggang Wang, Haibin Liu, Yulong Luo, Si Chen and Weiwei Su Two New Chalcones from the Flowers of Clerodendrum inerme Shaik Khadar Shahabuddin, Rachakunta Munikishore, Golakoti Trimurtulu, Duvvuru Gunasekar, Alexandre Deville and Bernard Bodo A Novel Phenolic Compound from Phyllanthus emblica Gaimei She, Ruiyang Cheng, Lei Sha, Yixia Xu, Renbin Shi, Lanzhen Zhang and Yajian Guo Anti-austeric Activity of Phenolic Constituents of Seeds of Arctium lappa Yasuhiro Tezuka, Keiichi Yamamoto, Suresh Awale, Feng Li, Satoshi Yomoda and Shigetoshi Kadota Bioactive Lignans from the Leaves and Stems of Schisandra wilsoniana Guang-Yu Yang, Rui-Rui Wang, Zhong-Hua Gao, Yin-Ke Li, Liu-Meng Yang, Xiao-Nian Li, Shan-Zhai Shang, Yong-Tang Zheng, Wei-Lie Xiao and Han-Dong Sun Antioxidative / Acetylcholinesterase Inhibitory Activity of Some Asteraceae Plants Ivana Generalić Mekinić, Franko Burčul, Ivica Blažević, Danijela Skroza, Daniela Kerum and Višnja Katalinić Antioxidant and Antimicrobial Activities, and Phenolic Compounds of Selected Inula species from Turkey Alper Gökbulut, Onural Özhan, Basri Satılmış, Kadir Batçıoğlu, Selami Günal and Engin Şarer Two New Dihydrostilbenoid Glycosides Isolated from the Leaves of Litsea coreana and their Anti-inflammatory Activity Wenjian Tang, Weili Lu, Xiaoqing Cao, Yilong Zhang, Hong Zhang, Xiongwen Lv and Jun Li Inhibitory Activity of Benzophenones from Anemarrhena asphodeloides on Pancreatic Lipase Yang Hee Jo, Seon Beom Kim, Jong Hoon Ahn, Qing Liu, Bang Yeon Hwang and Mi Kyeong Lee Identification and Quantification of Furanocoumarins in Stem Bark and Wood of Eight Algerian Varieties of Ficus carica by RP-HPLC-DAD and RP-HPLC-DAD-MS Samia Rouaiguia-Bouakkaz, Habiba Amira-Guebailia, Céline Rivière, Jean-Claude Delaunay, Pierre Waffo-Téguo and Jean-Michel Mérillon UPLC-Q-TOF/MS Coupled with Multivariate Statistical Analysis as a Powerful Technique for Rapidly Exploring Potential Chemical Markers to Differentiate Between Radix Paeoniae Alba and Radix Paeoniae Rubra Nian-cui Luo, Wen Ding, Jing Wu, Da-wei Qian, Zhen-hao Li, Ye-fei Qian, Jian-ming Guo and Jin-ao Duan Antimicrobial Activity of Crude Methanolic Extract from Phyllanthus niruri Darah Ibrahim, Lim Sheh Hong and Ninthianantham Kuppan Cellulose Contents of Some Abundant Indian Seaweed Species Arup K. Siddhanta, Sanjay Kumar, Gaurav K. Mehta, Mahesh U. Chhatbar, Mihir D. Oza, Naresh D. Sanandiya, Dharmesh R. Chejara, Chirag B. Godiya and Stalin Kondaveeti Anti-inflammatory Potential of Silk Sericin Pornanong Aramwit, Pasarapa Towiwat and Teerapol Srichana Composition of Essential Oil from Aerial and Underground Parts of Geum rivale and G. urbanum Growing in Poland Aleksandra Owczarek, Jan Gudej and Agnieszka Kice Continued Inside backcover
Page 427
429 431 433 435 439 441 443
447 453 457 459 461 463
467 471 475 479 481
485
487 493
497 501 505
