1.5.Vietnamese Plant EO 2013

March 24, 2018 | Author: huynhmtien | Category: Mass Spectrometry, Gas Chromatography, Chemistry, Nature


Comments



Description

Beijing 100083.toyaku. Russia Prof. Andersen Bergen. Japan Prof. PYNE Department of Chemistry University of Wollongong Wollongong. Natural Product Communications. Viqar Uddin Ahmad Karachi. 7963. Pakistan Prof.K. Pedras Saskatoon. Yoshinori Asakawa Tokushima.jp PROFESSOR DAVID E. 2630-Sugitani. Italy Prof. University of Granada. Anderson Park Lane.naturalproduct. Luca Rastrelli Fisciano. Westerville. Duvvuru Gunasekar Tirupati. Monique Simmonds Richmond. Imre Mathe Szeged. University of Portsmouth. China gda5958@163. Valentin Stonik Vladivostok. West Indies Prof. Any unauthorized reproduction. Anna R. Except as allowed under national “fair use” laws. Norway Prof. Germany Prof. Spain Prof. South Africa Prof. Japan tezuka@inm. US$2. US$2.edu. ISSN# 1555-9475). THURSTON Department of Pharmaceutical and Biological Chemistry. Germany Prof. Westerville. Koorbanally Durban. as agent (express or implied) of any third party. Taiwan Prof. Campus de Fuente Nueva. Vladimir I Kalinin Vladivostok. via Bonanno 33. 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. Winston F. Spain Prof. Texas Christian University. Niel A. REINECKE Department of Chemistry. copying is not permitted by any means or for any purpose. Lee Banting Portsmouth.it PROFESSOR DEAN GUO State Key Laboratory of Natural and Biomimetic Drugs.NPC Natural Product Communications EDITOR-IN-CHIEF DR. Karsten Krohn Paderborn. Botswana Prof. London WC1N 1AX. loan. excluding the USA and Canada. M. Australia spyne@uow. transmission or storage may result in either civil or criminal liability. Sorensen Manitoba. USA Prof. s/n. should be addressed to the Natural Product Inc.thurston@pharmacy. F. Australia Prof. TX 76129. ISSN# 1934-578X).jp PROFESSOR STEPHEN G. Portsmouth. UK david. Luc Pieters Antwerp. USA agrawal@naturalproduct. India Prof. Julie Banerji Kolkata. Tokyo 192-0392. Maurizio Bruno [email protected]. Josep Coll Barcelona. Canada Prof. Tinto Barbados. Geoffrey Cordell Chicago. Universita di Pisa. Shoei-Sheng Lee Taipei. Sylvia Urban Melbourne. Italy [email protected] HONORARY EDITOR PROFESSOR GERALD BLUNDEN The School of Pharmacy & Biomedical Sciences. Francisco Macias Cadiz.ac. 56126 Pisa. César A. Italy Prof. for purposes of advertising or promotion. [email protected] PROFESSOR ALESSANDRA BRACA Dipartimento di Chimica Bioorganicae Biofarmacia. .795 (Print + single site online). Canada Prof.au PROFESSOR MANFRED G. 2013 subscription price: US$2. School of Pharmaceutical Sciences. PAWAN K AGRAWAL Natural Product Inc. gift. SETZER Department of Chemistry The University of Alabama in Huntsville Huntsville. Cristina Gracia-Viguera Murcia.edu PROFESSOR WILLIAM N. Italy Prof. Iglesias Arteaga Mexico. Ana Cristina Figueiredo Lisbon. or otherwise). Ohio 43081. The publication of each of the articles contained herein is protected by copyright.395 (Web edition. AL 35809. (NPI). John L. Such permission requests. 2522. Argentina Prof. 29-39 Brunswick Square. Spain Prof. French Polynesia Prof. 7963 Anderson Park Lane. Peking University. Bilia Florence. or to create collective or derivative works. Claims for nonreceipt of issues will be honored if made within three months of publication of the issue. U. Toyama 930-0194. Mexico Prof. Ohio 43081. Martin A.. D. Granada. Phila Raharivelomanana Tahiti. Germany Prof. Berhanu M. Orders should be addressed to Subscription Department. Hachioji. Spain [email protected]. provided that any such republication is accompanied by an acknowledgment (original citation)-Reproduced by permission of Natural Product Communications. USA m. Leopold Jirovetz Vienna. Italy Prof. Peter Proksch Düsseldorf. 18071. Chiaki Kuroda Tokyo. Giovanni Appendino Novara. 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. Authors may reproduce/republish portions of their published contribution without seeking permission from NPC. Forts Worth.com PROFESSOR YOSHIHIRO MIMAKI School of Pharmacy. or other inquiries. Prof.uah.u-toyama.us EDITORS PROFESSOR ALEJANDRO F.edu PROFESSOR YASUHIRO TEZUKA Institute of Natural Medicine Institute of Natural Medicine. IL. UK Dr. Tokyo University of Pharmacy and Life Sciences.com ADVISORY BOARD Prof. USA wsetzer@chemistry. Soledade C. N. To Subscribe: Natural Product Communications is a journal published monthly. Bikram Singh Palampur. India Prof. US$595 (Personal online). BARRERO Department of Organic Chemistry. Catalán Tucumán. Øyvind M. Russia Prof. such as for distribution to any third party (whether by sale. France Prof. Austria Prof. Kurt Hostettmann Lausanne. University of Toyama. Subscriptions are renewed on an annual basis. Abegaz Gaborone. University of London. Italy Prof.ac.395 (Print.unipi.pipex. Horinouchi 1432-1. Ermino Murano Trieste. Natural Product Inc.K. The School of Pharmacy. Portugal Prof. Japan Prof. India Prof. PO1 2DT U. Hungary Prof. Switzerland Prof. Hartmut Laatsch Gottingen. Japan mimakiy@ps. USA. Karen Valant-Vetschera Vienna. New South Wales. Marie Lacaille-Dubois Dijon. All issues are dispatched by airmail throughout the world. Belgium Prof. fruticosum was dominated by sesquiterpenoid compounds (89. maclurei Merr.6%) were the predominant components of the oil of Melodorum fruticosum Lour. The chemical compositions of the oils are summarized in Table 1. [15] identified the main compounds of Artabotrys hexapetalus as β-caryophyllene (11. germacrene D (14.15%.ng Received: November 12th. 0001. terpinen-4-ol (6. Polyalthia longifolia var. Fissistigma rufinerve. Vietnam is blessed with many medicinal plants.1%). In view of this. fruticosum from Thailand [21] were 1-pheny butanone (20. Little is known about the chemistry of this plant.2%). cypernone and 1. but reports on their volatile components are not readily available in the literature. maclurei .15%. light yellow.5%) and spathulenol (4.5%) while Rang and Houng [16] reported an abundance of caryophyllene oxide (36.1%). P.edu. A. Polyalthia longifolia var. α-zingiberene (21. Fissistigma maclurei. were germacrene D (26.5-epoxysavial-4(14)-ene. the oil of this species could be classified into a group whose chemical constituents were dominated by sesquiterpenes.6%). Hanoi. while α-santalene (14.5%).6%).2%). The plant samples yielded low contents of essential oils: 0.*.9%). β-caryophyllene (6. β-caryophyllene (7.1%) in the same oil.3%) were identified in significant quantity from Fissistigma rufinerve (Hook. but a number of biologically active compounds have been characterized from other species in the genus [13. Nigeria thangtd@vinhuni. 18-Hoang Quoc Viet. β-caryophyllene (6.B. rufinerve. β-cubebene (5.242 Tran D. benzyl benzoate (8. Little is known about the chemistry of these plants. vinhensis [17] was found to be rich in α-pinene (16. and F. fruticosum Lour. 0. Vietnam c Natural Products Research Unit.f.3%). while another author [22].3%) and benzyl benzoate (5. -cadinene (6. spathulenol (10. Many Melodorum species are aromatic trees with a characteristic smell. Giang et al. However.edu. light yellow.0%).1%).1%).6%). 2012 The essential oils obtained by hydrodistillation from the leaves of five species of Annonaceace grown in Vietnam were analyzed by gas chromatography (GC) coupled with mass spectrometry (GC/MS).3%). (syn.8%) and β-pinene (7.4%) and caryophyllene oxide (31.3%). Melodorum fruticosum. Faculty of Science.. Both Fissistigma rufinerve (Hook. v/w. v/w. Hoib and Isiaka A. we report herein the essential oil constituents of five species of Annonanaceae from Vietnam [1]. and bicyclogermacrene (6.2%) and β-selinene (9. the oil of A.3%). by using three different fibers in an SPME extraction method. β-caryophyllene (6. identified β-phellandrene . The leaf oil of M. calculated on a dry weight basis. Malaysia and Australia.7%). F. longifolia var. Accepted: December 30th. a shrub that grows up to 8 m tall. M.8]. caryophyllene oxide (5. v/w. pendula.7%) and linalool (9. Thanga. On the other hand.9%). Do N. especially in the evening.14]. M. It gives out a pleasant fragrance. aromadendrene (15.2%).3%) and allo-ocimene (5. light blue. flowers between May and August. & Thomson) Merr. -elemene (6. et Thoms. v/w.NPC Natural Product Communications Essential Oils from Five Species of Annonaceae from Vietnam 2013 Vol. The main components of the flower oil of M. α-terpinene (8. The compositional pattern of this oil differs from previous studies on other species in the genus.1%). Lagos. A. Lasu Post office. Several biologically active compounds have been isolated from this species [7.7%).4%). * a Department of Food Technology. A handsome ornamental is the weeping form of the mast tree.vn.1%).M. isiaka. hongkongensis Hance. β-Caryophyllene (12. limonene (15.ogunwande@lasu. -elemene (6. commonly planted due to its effectiveness in alleviating noise pollution. F. The main constituents of the oil were β-caryophyllene (12. From Table 2.2%) and bicyclogermacrene (11. pendula. is a plant native to South-East Asia. light yellow. Cau Giay. The genus Melodorum comprises about 55 species that are widely distributed through Indo-China. Meiogyne maclurei Sinclair) are climbers that grow up to 6 m tall. alternate leaf. The tree is known to grow over 9 m in height. 0.2%). hongkongensis. compounds such as cyperene. This plant has a cream-colored flower with a single. 2012.6%) and bicycloelemene (11. Keywords: Artabotrys hongkongensis. which were the major components of other Artabotys species [18-20]. Lagos State University. v/w. and 0. The main constituents of Fissistigma maclurei Merr. but other species of the genus are known to contain biologically active compounds [3-5]. 2 239 .) Merr.15%.7%). Tran M. benzyl alcohol (8. Department of Chemistry. α-copaene (10. bicycloelemene (11. 182-Le Duan. pendula Hort was comprised mainly of β-caryophyllene (30.3%) and -cadinene (6. White Cheesewood. Faculty of Chemistry. Other significant components were benzyl benzoate (6. but there is only one literature report on its volatile oil components [12]. trans-α-bergamotene (5. f. The major compounds identified from A. The main constituents of Artabotrys hongkongensis Hance were the sesquiterpenes spathulenol (13. Nghe An Province. It also has medical uses as a tonic and mild cardiac stimulant and hematinic [6]. pendula Hort.4%). were conspicuously absent in this oil sample. 8 No.6%).0%).3%).10%. bicyclogermacrene (11. hongkongensis were spathulenol (13. Ogunwandec.1%).12%. It is a lofty evergreen tree. The genus Artabotrys has about 100 species in the Paleotropics [2]. light yellow. Ojo. P. Vinh University. Vinh City. whereas the oil of Polyalthia longifolia var. Daib. Ojo.8%) and β-asarone (6. Vietnam b Institute of Ecology and Biological Resources. Extracts and compounds isolated from the plant have been reported to possess a number of biological activities [9-11]. Vietnam Academy of Science and Technology. Badagry Expressway.3%). Literature information has shown that the essential oils of these plants have received little chemical analysis. fruticosum.5%). 0. 2 0.0 0.4 0. A. as found in the fruit of P.0 0.7 tr tr 0. .8 3.3 90. 5.0 0.1%) in the oil. A.5-7. a noteworthy observation is the fact that bicyclogermacrene.2 0.8 6.1 21.1 0.8 0. β-caryophyllene (7.2 15.5 1.1 Guaizulene 1781 1779 1.4 0.717.7 0. 8 (2) 2013 Thang et al. hongkongensis Oils rich in both monoterpenes and sesquiterpenes a A. leichhardtii and M.0 0.2 3.2 0.8 0. longifolia var.4%). F.5%) caryophyllene oxide (36.0 1.7 14.0 0. (Wyvuri B. 3. M.8 0. pendula [12].2 0.3 13.1%. co-injection. such as P.1 6.3 0. suaveolens [25] and P. tr.6 0.1 0. longifolia [24].7 3.8 2.1 tr 1.7 55. odoratissimus A. Sankowsky). longifolia var.6 0.8 1. maclurei .5 4.1 0.6 3. P.3%).6%) and elemene (6.6 0.4 0.7 2 3. Compounds * Tricyclene Artemesia triene -Pinene Camphene Sabinene -Pinene -Myrcene -Phellandrene -3-Carene -Terpinene ρ-Cymene -Phellandrene Limonene 1.1 1.2%).1 0.6 0. as seen in P.2 3. hexapetalus b A. βasarone (6.8 Others 5.8 3.49. A. (Claudie River B.0 0.6%) and aromadendrene (19.6 0.7 0.2 0.4 0.7 12. represented by β-caryophyllene (30.9 Valerianol 1675 1656 3. c identified by column RI. while caryophyllene was identified in low quantity in a previous study [12].5 4 0.1 0.9 3. M. nitidissima [26].1 Monoterpene hydrocarbons 8. oils with relative large amounts of hydrocarbon and oxygenated sesquiterpenes.6 10.5 0. trace < 0. germacrene D (14. caryophyllene oxide (31.3 4. four chemical forms of the oils of Polyalthia species may be proposed.) [26].Not present.1 2.2-17.5 2.2 1. 2.6 0.4 - 1.7 0. Chemical forms Oils dominated by sesquiterpenes Species a A.1 0.1 0.6 0. 1. (Topaz G. βcaryophyllene (6. Sankowsky).1 tr tr tr 0. australis and Polyalthia sp. P.8 0. a Retention indices on HP-5MS capillary column.0 0.4 0. rufus. -cadinene (6.8 2. cyperenone (11.5 4.2 2.3%) as prominent compounds.3 0.4 2.8%). uhrii from Australia [23]. co-injection.7 Sesquiterpene hydrocarbons 49.3%).8 0.4 0.8 0. αzingiberene (21.7 14. longifolia var.1 0.1 10.1 0. such as Melodorum sp.6 64.8 0. literature MS pattern and literature retention indices (RIb).1%).5 6. From Table 4.6 Total 94.0 1.5 6.1-10.1 (E.8 3. as exemplified by P.3 0.1 - 3 tr 1. vinhensis Major components α-caryophyllene (14.2 Oxygenated monoterpenes 2. rufinerve Table 2: Chemical forms of the oils of Artabotrys species.2%). α-copaene (6.5 1.1%) cyperene (25. limonene (15.6 1.2 6.5 0.3 1. pierreanus.7 4.6 0.1 2.8 1.6 0.6 0.9%).5 5.2 Tr 0.7 2. b Literature Retention indices (Adams [30]). Sesquiterpenes.3 0.7 0.5 2.1-4.1 0.1 0.7 n-Heneicosane c 2100 0.4%) and -cadinene (4. are the dominant class of compound in P.5 tr tr 0.E)--Farnesene -Cadinene trans--Bisabolene cis-(Z)--Bisabolene epoxide c -Sesquiphellandrene -Cadinene cis-Calamenene -Calacorene Elemol Germacrene B Spathulenol Caryophyllene oxide Globulol Viridiflorol Widdrol Rosifoliol Ledol -Oplopenone RI a 926 930 939 953 976 980 990 1006 1011 1017 1026 1028 1032 1034 1043 1052 1061 1089 1100 1141 1144 1169 1189 1205 1300 1327 1337 1351 1353 1362 1375 1376 1377 1381 1387 1388 1391 1393 1408 1412 1418 1419 1434 1435 1437 1440 1441 1447 1451 1454 1457 1457 1461 1477 1481 1483 1485 1486 1489 1490 1493 1494 1494 1496 1496 1498 1500 1501 1502 1503 1506 1506 1513 1514 1515 RI b 921 923 932 946 969 974 988 1002 1008 1014 1020 1025 1024 1026 1032 1044 1054 1086 1095 1137 1140 1165 1186 1204 1300 1338+ 1335 1345 1350 1359 1373 1374 1374 1381+ 1387 1387 1389 1392 1407 1410 1416 1417 1431 1432 1434 1437 1439 1445 1449 1452 1454 1455 1458 1475 1479 1481 1483 1484 1487 1489 1492 1492 1493 1496 1495 1498 1500 1500 1501 1502 1505 1505 1514 1514 - 1 1.4%).0 11.0 2.6 1.4 1.2%) and β-selinene (9.7 0. Melodorum sp.0 * Compounds identified by RI from column.9 0.4 0. caryophyllene and spathulenol have featured prominently among the volatiles of other species. [12] have reported high quantities of cadinene (24.1 0.0%).7%).4 0.8 4.9 6.5 0. These are oils with an abundance of sesquiterpene hydrocarbons. suaveolens [25] and P.7 0.1 0.8 Oxygenated sesquiterpenes 26.6 0.4 0. except where stated.8 0.7 Benzyl benzoate 1760 1759 5. 4.7%).1 1.2-16.5epoxysavial-4(14)-ene Origin India Ref [18] Vietnam [15] Vietnam [16] Gabon [19] - [20] spathulenol (13.8 99. . pendula.4 11.1 0.Z)-Farnesol 1718 1714 0.4 99. (Z)-β-ocimene (9.8 3.8%) β-caryophyllene (11.7 1. However.8 Eicosane 2000 2000 0. hongkongensis.1 0.7 26.9 16.8 5.0%). A.9 9.5%).2 Phytol 1946 1942 0.7 epoxide α-Muurolol 1644 1644 2.2 0.3 19. -cadinene was conspicuously absent in our result.7 0.6 0.6 5.4 0.2 30.1 2.3 0.6 62. 8-Cineole (Z)-β-Ocimene (E)-β-Ocimene -Terpinene -Terpinolene Linalool cis-Verbenol neo allo-Ocimene Borneol -Terpineol Verbenone n-Tridecane Bicycloelemene -Elemene -Cubebene -Longipinene Neryl acetate -Ylangene Isoledene -Copaene -Elemene -Bourbonene -Cubebene -Elemene (Z)-Jasmone Longifolene -Cedrene -Santalene -Caryophyllene -Gurjunene trans--Bergamotene -Elemene -Guaiene Aromadendrene epi--Santalene -Himachalene -Humulene (E)--Farnesene -Patchuolene allo-Aromadendrene -Gurjunene ar-Curcumene -Curcumene -Amorphene Germacrene D (E)--Ionone -Selinene -Selinene Ledene (Viridiflorene) α -Zingiberene Valencene Cadina-1.P).6 - 4.1 1.6 1.1%) cyperenone .4%).8 1.2 2.6 0.3 3.6 Diterpenes 0.3 0. hexapetalus b A. 1.8 0. nitidissima [26].7 2.0 2.8 5. A.6 1. thomsoni. β-pinene (7.9 0.0 0.5%) Vietnam This study Vietnam [17] Leaf samples.8 6.018. lastoursvillensis A.4-diene -Selinene Bicyclogermacrene -Muurolene Epizonarene trans--Guaiene -Bisabolene (E.4 1.5 4.7 0. α-copaene (10.9 0.6 6.0 1. Melodorum sp.6 3.6 1. + Found in Joulain and Koenig [32].3%) α-pinene (16.1 3. Table 1: Compounds identified in the studied oil samples. Nguyen et al. F.2 0. oils dominated by oxygenated sesquiterpenes.3%).6 - 1523 1525 1530 1546 1550 1561 1576 1583 1585 1593 1599 1605 1608 1608 1521 1522 1528 1544 1548 1559 1577 1582 1590 1592 1599 1600 1602 1607 2.9 0.9%). venustus A. b Flower sample.7%). aromadendrene (15.0 2.5 0. zingiberene (19.1 1.5 4.2 6.3 0. fruticosum. P. insignis. MS pattern and comparison with authentic MS data collection in our library.P.9 0. and oils consisting of monoterpene hydrocarbons. From Table 3.4 1.5 0.4 0. (Font Hills G.5 8.4 0.240 Natural Product Communications Vol.7 0.0 12.0 5 1. linalool (4.2 93. p-methylanisole (7.2 0.2 - allo-Aromadendrene 1641 1639 4. michaelii [26].2 11.3 2.4%).0 0.1 0. .0 2.3 1.9 92.1 3. pendula.7 0. caryophyllene oxide (3.origin unknown (7.5 1.7 1. On the other hand. # Quantitative data not available.2%) and (Z)--ocimene (6.1 kPa. Australia [23] bicyclogermacrene (15-19%) M.and (Font Hills G. sesquiterpenes bicyclogermacrene (1-9%). in September 2011. Sabinene.8%) and allo-aromadendrene/-cadinene (ca.8%) were present in higher amounts in F. aromadendrene. respectively have been deposited at the Botany Museum. (Claudie River B. Fissistigma rubigirosa [28] produced an oil in which the main components were (E)--ocimene (21.1%). and β-caryophyllene (13. F. Agilent Technology). The analytical conditions were: carrier gas H2 (2 mL/min).1%) P. NIST 08 Libraries (on ChemStation HP).7%). australis # β-caryophyllene. longifolia var. The content and composition of essential oils depends on the origin. bicyclogermacrene. β-pinene and limonene Origin Vietnam Ref This study Vietnam [12] Nigeria [24] Nigeria [24] Gabon [25] Australia [26] Australia [26] Australia [26] Australia [26] Gabon [25] a Stem bark sample . with those in the literature. while F.0%). zingiberene (21.4%). oldhamii.3%). fruticosum *. βmonoterpene.75). emission current 40 mA.6%). according to the Vietnamese Pharmacopoeia [29]. The major compounds of the oil of F. germacrene B. trans-α-bergamotene (5. βcaryophyllene (26. caryophyllene oxide (5. column temperature programmed from 60oC (2 min hold) to 220oC (10 min hold) at 4oC/min. benzyl Australia [23] benzenoid Jessup) salicylate (2.0%) P.7%). α-guaiene (7. Australia [23] germacrene D (6-10%). Plant samples were air-dried prior to extraction. National Park. Sankowsky) M. globulol (4. film thickness 0.3%). Chemical forms Oils with large amounts of sesquiterpenes hydrocarbons Species Melodorum sp. -cadinene. β-cubebene (5. On the other hand. thorelii [27] was dominated by -terpinene (22. maclurei were harvested from Vũ Quang. Voucher specimens DND 805.04%). pendula species. (Wyvu -elemene.1%). the volatile constituents of some Fissistigma species from Vietnam have been reported. 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. hydrocarbon and caryophyllene oxide and oxygenated spathulenol sesquiterpenes Polalthia sp.W.7%) bicyclogermacrene (34-50%).25 mm.6%).2%) and β-selinene (9. β-caryophyllene (6. Sankowsky) caryophyllene (10-16%). but there were also significant quantities of bicyclogermacrene (6. bicyclogermacrene.7%) and -cadinene (27. terpinen-4-ol (6. The volume injected was 1. Oils dominated by o P. Inlet pressure was 6. βAustralia [23] Oils containing Melodorum sp. β-caryophyllene (11-16%) Origin Australia Ref [23] Australia [23] bicyclogermacrene (45%). rubigirosa). Therefore. oils rich in monoterpenoid compounds (F. Table 4: Chemical forms of P. phenological stage. longifolia a α-copaene/ α-muurolol (ca. Analysis of the oils: About 15 mg of each oil sample.25 mm. polyanthoides). Each sample was analyzed thrice.2%). maclurei. Samples were injected by splitting and the split ratio was 10:1. D. under the same conditions as those used for GC analysis. oldhamii). fruticosum β-caryophyllene (12. longifolia -cadinene (24.6%).8%) and allo-ocimene (5.4%) P.0%) and α-terpinene (8. rufinerve. the volatile oils of Fissistigma growing in Vietnam are thought to exist in three chemical forms namely. 8 (2) 2013 241 -phellandrene (8. limonene and hydrocarbons ()-β-ocimene #. fruticosum and F.0 scan/s. α-santalene (14. pendula Major components β-caryophyllene (30. in August 2011.8%). and also with . globulol and spathulenol. uhrii M. * contain appreciable amount of monoterpenes and sesquiterpenes. Hà Tĩnh Province. 8. longifolia allo-aromadendrene (19.25%) a Flower sample while others are from the leaves. as such. An Agilent Technologies HP 6890N Plus Chromatograph fitted with a fused silica capillary HP-5 MS column (30 m x 0. caryophyllene oxide (14. -phellandrene (14. spathulenol (10. (Topaz G. hongkongensis. The MS fragmentation patterns were checked with those of other essential oils of known composition with Wiley (Wiley 9th Version). bracteolatum was characterized by a high content of myrcene (83. zingiberene var.3%). large amounts of bicyclogermacrene. DND 808. detector temperature 260oC.4%). michaelii # spathulenol sesquiterpenes # Oils consisting of P.4%). b P. linalool (9. -caryophyllene (23. The authors have found no literature information on the volatile oil content of these species and. α-cadinol (5. Vietnam. germacrene D. thorelii and F. Others are from the leaves. ledol. oils dominated by sesquiterpenoid compounds (F. Vietnam.5 kg of air-dried sample of each species was shredded and their oils obtained by hydrodistillation for 3h at normal pressure. The MS conditions were as follows: ionization voltage 70eV. Thừa Thiên Huế Province Bach. (E)--ocimene (10.7. nitidissima α-pinene.2%) were the major components of F. pendula were obtained from Thanh Hóa Province. Chemical forms Oils with abundant sesquiterpene hydrocarbons Species P. which was dried with anhydrous sodium sulfate. The conditions were the same as described above with He (2 mL/min) as carrier gas.3%). DND 195 and DND 199. this may represent the first of its kind. Vietnam This bicyclogermacrene (11. maclurei were germacrene D (26.5%) α-eudesmol (9-5%).27%). injector temperature (PTV) 250oC.25 m. DND 089.3%). eudesmol (7-11%).0%). The leaves of F.25 m) and interfaced with a mass spectrometer HP 5973 MSD was used for the GC/MS analysis. longifolia var. harvesting time and processing methods [1]. bicyclogermacrene and aromadendrene were the five compounds common to the oil samples. pendula aromadendrene (19.3%). polyanthoides was rich in Natural Product Communications Vol. b Fruit sample. nitidissima β-caryophyllene. Thailand [21] benzyl alchol (8. Vietnam. acquisitions scan mass range of 35-350 amu at a sampling rate of 1. Vietnam. aromadendrene (15.52). rufinerve were collected from Bạch Mã National Park. bicycloelemene.P) Melodorum sp. However.1%).7%). bicyclogermacrene (7.1%) P.2%). αpinene (14-15%) Oils rich in Melodorum sp L. (6. while those of P. leichhardtii Major components bicyclogermacrene (29.1%). in September 2011.7%) compounds M.4%) and -cadinene (13. Gas chromatography (GC) analysis was performed on an Agilent Technologies HP 6890 Plus Gas chromatograph equipped with a FID and fitted with HPWax and HP-5MS columns (both 30 m x 0. β-phellandrene (7. plant parts analyzed. -caryophyllene. a 1-pheny butanone (20. The oil of F. Extraction of the oils: About 0.3%) and (E)--ocimene (43.Essential oils from the leaves of five species of Annonaceace grown in Vietnam Table 3: Chemical forms of Melodorum species. film thickness 0. longifolia var.7%) (8.9%). was dissolved in 1 mL of nhexane (for spectroscopy or chromatography). germacrene D. environmental conditions. benzyl benzoate (20%).5%).2%). suaveolens myrcene. Experimental Plant collection: Leaves of A. and oils with relatively large amounts of monoterpenes and sesquiterpenes (F. Vinh University. while F. β-caryophyllene (6. and spathulenol Oils with relatively P. rufinerve and F.0%). viridiflorene (8.0 L.5%) and -muurolol (5. M. suaveolens β-caryophyllene and humulene (both 34%) # P. study bicycloelemene (11. bracteolatum and F. Leboeuf M. 44. Kessler PJA. 102-105. Puthong S. Goldsack RJ. Santisuk T. Jian-Ping Z. Sichaem J. 1-234. Singh SP. Buchbauer G. (2007) Progress in the study of some Fissistigma species from Vietnam. Hanoi. 58. Schmidt J. (2009) Chemical composition of the stems essential oil of Fissistigma thorelii (Pierre ex Fin. 63. f. Bordoloi PK. Springer-Verlag. Cioni PL. Tetrahedron. 292-294. 82. 1311-1315. Farnsworth NR.4′dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (Z23). 104. Dung NX. 2. (2010) Chemical compositions. 1. Nguyen XD. Flamini G. Thang TD. Chukeatirote E. Milne GWA. 7. Thang TD. König WA. Kinghorn AD. Food Chemistry and Toxicology. Fitoterapia. Fleischhacker W. Worawalai W. and by comparing with MS literature data [30-32]. co-injection with standards (SigmaAldrich. from Hatinh. (1978. Sashidhara KV. (2004) The leaf oils of the Queensland species of Melodorum (Annonaceae). (1991) Chemical composition of the leaf and fruit oil of Polyalthia suaveolens Eng. Mekaroonreung S. Cravo L. Zong-Ping Z. E. Koenig WA. Proceedings of the 3rd National Scientific Conference on Ecology and Biological Resources. antifungal and antioxidant activities of essential oil and various extracts of Melodorum fruticosum flowers. 459-461. Maulik PR. (2012) Flavonoid and megastigmane glycosides from Artabotrys hexapetalus. Rao PG. Hanoi. 419-421. Fang-Rong C. Wei T. 8 (2) 2013 standard substances. 56. Thang TD. (2000) Fissistigmatins A–D: Novel type natural products with flavonoid-sesquiterpene hybrid structure from Fissistigma bracteolatum. Yu. The essential oil of Artabotrys lastourvillensis Pell. 4. Pezzuto JM. 1980. Nguyen XD. KR. Hua-Chien C. (2012) The leaf essential oils of five Vietnamese Desmos species (Annonaceae). .) Merr. Natural Product Communications. Agricultural Publishing House. pendula. (2009) Chemical composition of the leaf essential oil of Polyalthia longifolia var. Vietnamese Pharmacopoeia (1997) Medical Publishing House. 946-950. 30. Nguyen HD. Ishikawa T. Singh SP. (2000) Flora of Vietnam. Giang PM. 94-103. Bhuyan PD. Vietnam. 305-307. 81. Joulain D. 4. Science and Technology Publishing House. Allured Publishing. Har Krishan Bhalla & Sons. Ogunwande IA. Journal of Essential Oil Bearing Plants. Journal of Essential Oil Research. 119-126. Li-Hong H. 16.) Bhandare of Vietnam. 48. Chung-Yi C. 20. Shafi PM. Jirovetz L. 5-7. Huong HH. Journal of Essential Oil Research. 930-932. Ogunbinu AO.01-2010. Hanoi. Washington. India. Boruah P. 4. Nguyen TC. Brophy JJ. Rang DD. 231-234. Deepolngam S. Agricultural Publishing House. 47. Delmas M. 933-937. Vietnam. Berlin/Heidelberg. Thang TD. Yang-Chang W. Thang TD. Phytochemistry. Fournier G. individual components were calculated based on the GC peak area (FID response) without using correction factors. 22-24. Huang-Yi T. 327-330. Vietnam. Tian-Jye H. Varshney VK. Bioorganic and Medicinal Chemistry Letter. 422-425 Somanawat J. Adam G. Carol Stream. Journal of Natural Products. 48. et Diels. Bessiere J. U.) Merr. Wagner C. Dai DN. Adams RP. Natural Product Communications. Hoi TM. MS library search (NIST 08 and Wiley 9th Version). under identical experimental conditions. Sung TV. Xu-Dong H. 19. (2001) Oxidized heptenes from flowers of Melodorum fruticosum. pendula. Yi-Chen C. Hoi TM. Hoi TM. Ruksilp T. Abraham GT. Biochemical Systematics and Ecology. suppresses T cell-mediated immunity in vitro and in vivo. Life Sciences. Jirovetz L. Acknowledgments . Tuchinda P. (2007) Sesquiterpenes-rich essential oils of Polyalthia longifolia Thw. Bessiere JM.27. (Eds). 483-486. Phytochemistry. Kaewamatawong R. (2010) Chemical constituents of essential oil from Artabotrys vinhensis of Vietnam. Ngamrojnavanich N. 1983) EPA/NIH Mass Spectral Data Base. Phytochemistry Letters. Kubitzki K. Puschmann Ch. from Gabon. The identification of constituents was performed on the basis of retention indices (RI) determined with reference to a homologous series of n-alkanes.The authors wish to thank the NAFOSTED (Vietnam) for the financial support of this study through the Project Nr. Goldsack RJ. St. (2010) Cytotoxic cycloartane triterpene and rare isomeric bisclerodane diterpenes from the leaves of Polyalthia longifolia var. 1475–1478. pendula Hort. Germany. References [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] Dai DN. 865-872. Shukla PK. from Nghean. 70-73. Affane-Nguema JP. Talangsri N. MO. Sarkar J. Udchachon J. Hanoi. Dung NX. 1. Menut C. Vietnam. Essien E. Yi-Fu Y. Kant R. Son PT. Journal of Essential Oil Research. Ogunwande IA. Porzel A. Germany. Mve-Mba CE. (2009) A long chain alkylated α-methylene-γ-butyrolactone from Artabotrys odoratissimus fruit. Bordoloi M. Khumkratok S. Shu-Jen C. Ming-Chu H. (Annonaceae) from Nigeria. Yi-Nan Z. Xiang-Gen Z. Journal of Essential Oil Research. Vol. Heller SR. 523-524. Yao-Ching S. Chemistry of Natural Compounds. USA. Forster PI. Z. Hamburg. Vietnam. Drosihn S. (1989) The Atlas of Spectral Data of Sesquiterpene Hydrocarbons. Journal of Essential Oil Research. Pripdeevech P. Rohwerand JG. (2007) Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectrometry. 1-502. 2754-2758. (2009) Antimicrobial evaluation of clerodane diterpenes from Polyalthia longifolia var. pendula. Dehradun. Kanojiya S. 124-127. Journal of Essential Oil Research. In The Families and Genera of Vascular Plants. Lien TP. Merzweiler K. 12. In Aromatic Plants from Asia their Chemistry and Application in Food and Therapy. B. USA) or known essential oil constituents. (1992) Aromatic plants of tropical central Africa. Pripdeevech P. IL. Kumar. (2001) Leaf oils of the Australian species of Polyalthia (Annonaceae). Tip-pyang S. Cave A. (1993) Annonaceae. (2004) The primary study of the chemical composition of the Artabotrys hexapetalus flower in Ninh Binh Province.-M. 11. an effective compound from the Chinese herb medicine Fissistigma oldhamii (Hemsl. Dai DN. Forster PI. Xiang-Hua Z. (2011) A new dimeric aporphine from the roots of Artabotrys spinosus. Bittrich V (Eds). Dai DN. Journal of Science University of Hanoi. Journal of Science and Technology. (1998) Analysis of the essential oils of Artabotrys odoratissimus fruits and leaves from South India. 3. Nguyen TB. Louis. Reutrakul V.S. (1999) Annonaceae essential oils: a review. Vietnam. (2000) Cytotoxic constituents of Polyalthia longifolia var. Verlag.242 Natural Product Communications Vol.VI. Sashidhara KV. Yang Y. (2011) Analysis of the odor constituents of Melodorum fruticosum flower by solid-phase microextraction-gas chromatography-mass spectrometry. (1991) Bioactive butenolides from Melodorum fruticosum. 1-134. Roengsumran S. 1677-1684. Tiyaworanan S. Proceedings of the 3rd National Scientific Conference on Ecology and Biological Resources. The relative amounts of Thang et al. 2685-2689. Siripong P. 5767-5771. 19. Taylor WC. (2007) 7′-(3′. (2007) Chemical composition of the flower essential oil of Artabotrys hexapetalus (L. Journal of Essential Oil Research. 131-142. Thuy LT. Petsom A. Government Printing Office. Chaichantipyuth C. Brophy JJ. & Gagnep. Perineau F. Maja Marasović. Mosquito Larvicidal.us) Essential Oil of Flowers of Anaphalis contorta. Wedge Composition of Cassia fistula Oil and its Antifungal Activity by Disrupting Ergosterol Biosynthesis Md. and Chen-Lung Ho Chemical Constituents and Cytotoxic Evaluation of Essential Oils from Leaves of Porcelia macrocarpa (Annonaceae) Erica Biolcati P. Karol Olejnik. Tran Minh Hoi. Akindele O. Nguyen Anh Tuan. Brett R. Sandra Gray. Carlos R. Elena Stashenko and Raquel Elvira Ocazionez TLC-Bioautographic Evaluation of In Vitro Anti-tyrosinase and Anti-cholinesterase Potentials of Sandalwood Oil Biswapriya B. Guido Flamini. Zvonimir Marijanović. K. Félix Tomi. Lago 225 227 231 235 239 243 249 253 257 261 265 269 273 277 Book Review Medicinal Plants of China. Dai. Ikhlas A. Kelechi. Gagnon and Jean Legault Chemical Composition and Antibacterial Activity of Essential Oils from Myrcia alagoensis (Myrtaceae) Aline do N.naturalproduct. Figueiredo. Joshi Composition of Essential Oils from Seeds of Abies koreana Anna Wajs-Bonikowska. Avoseh. 8 (2) 2013 Published online (www. glabra (‘Carolina Sapphire’) Abbas Ali. Ogunsanwo. PharmD. Thang. Joseph Casanova and Ange Bighelli Essential Oils from Five Species of Annonaceae from Vietnam Tran D. Rizvi Chemical Composition and Biological Activity of the Essential Oil of Amomum biflorum Chakkrapat Singtothong. Atuonwu O.Natural Product Communications Vol. Silva. Patricia Sartorelli and João Henrique G. Ogunmoye. Jane Ellis. Betul Demirci. Ogunwande Essential Oils from the Leaves of Six Medicinal Plants of Nigeria Isiaka A. Biting Deterrent and Antifungal Activity of Essential Oils of Different Plant Parts of Cupressus arizonica var. Kamorudeen O. Zafaryab. Zainab A. Misra and Satyahari Dey Composition. Ophélie Bazzali. Hassan. Farah Ahmad. Aijaz Ahmad. Ogunwande. Tiamiyu and Godgift O. Chaves. Radosław Bonikowski and Piotr Banaszczak Chemical Composition of Hypericum richeri subsp. an Aromatic and Medicinal Plant from India Rajesh K. Tran M. Yusuf. Do N. Irshad. Alimot-Sadiat O. Matsuo. Mariana H. grisebachii Essential Oil from Croatia Igor Jerković. da Silva. Lackey. Lucchese Composition. in-vitro Anticancer. Uetanabaro and Angélica M. Christine Murphy. Nurhayat Tabanca. and Japan: Bioresources for Tomorrow’s Drugs and Cosmetics by Chritophe Wiart. cordifolium Tran Huy Thai. Limonene and Essential Oils from Lippia citriodora and L. Man Singh and M. Khan and David E. Md. glabrum and A. Nudewhenu O. Moshahid A. Nikhat Manzoor. Željan Maleš and Mladen Miloš Chemical Composition of the Essential Oils from Two Vietnamese Asarum Species: A. Husnu Can Baser. Korea. Alisson L. and Antimicrobial Activities of the Leaf Essential Oil of Machilus mushaensis from Taiwan Yu-Chang Su. Michel J. PhD Stephen Pyne 281 . AbdulRazaq O. alba on Yellow Fever Virus Luz Angela Gómez. Tabowei Comparative Study on In Vitro Activities of Citral. Kroata Hazler Pilepić. Hoi and Isiaka A. Ana Paula T. A. Ahmed M. Olivia Márquez.: Leaf. Anju Yadav. Daoud W. Yin Shi-Yu. Hwa Dong Lee. Kai Y. Kuster Protoanemonin Content Variation between Clematis spp. R. Ivana C. Gerardo Cárcamo. Yeon Bok Kim. Bhutani Antifeedant Activity of Spin-Labeled Derivatives of Deoxypodophyllotoxin against Brontispa longissima Larvae Gang Feng. Ying-Qian Liu. Christian Narkowicz and Glenn A Jacobson Methanolic Extract of Nigella sativa Seed Inhibits SiHa Human Cervical Cancer Cell Proliferation Through Apoptosis Tarique N. Patrick Dutartre and Marie-Aleth Lacaille-Dubois Zephgrabetaine: A New Betaine-type Amaryllidaceae Alkaloid from Zephyranthes grandiflora Deepali Katoch. Dharmesh Kumar. Germana Torre. M. de Almeida. Alshatwi Glucosinolate Biosynthesis in Hairy Root Cultures of Broccoli (Brassica oleracea var. Qing-xiang Xiang and Feng-zheng Chen Steroidal Saponins from Dracaena marginata Abdelmalek Rezgui. Gowhar Shafi. Nobutaka Suzuki and Hesham Fahmy Carmichaeline A: A New C20-diterpenoid Alkaloid from Aconitum carmichaeli Shu-hua Li. Ruchi Shekhar and Kamlesh K. Mario Silva. Li Tian-Xian and Qiu Feng Chemopreventive Effect of Sarcophine-diol on NOR-1-Induced TPA-Promoted Skin Carcinogenesis in Female HOS:HR-1 Mice Pawel T. Fernández New Anthraquinone Derivatives from Geosmithia lavendula Lourin G. Md. Robert E. Stem and Root Fangming Jin. Yogendra S. Leticia G. Talita S. Zi-Hua Jiang and Xiaoyi Wei Determination of Bioactive Compounds in the Juice of Pummelo (Citrus grandis Osbeck) Marina Russo. Hosea M. atropurpurea Chuan-Rui Zhang. Periyasamy Latha. Ross Pancreatic Lipase Inhibitory Activity of Cassiamin A. Norman C. Alsaif. Malak. Ruela. Jing Zhang. Mohammed A. Xuan Tian. José M. Stéphanie Delemasure. José Becerra. Sherief Khalifa. Tomofumi Miyamoto. Manju Singh and Chandan S Chanotiya Continued inside backcover 147 149 153 155 157 161 165 169 171 175 177 181 183 187 191 195 199 203 207 211 213 217 221 . Leal. Waters. C. Number 2 Contents Original Paper Page Drimendiol. Neeraj Kumar. Chellakan S Benson and Rajagopalan Rukkumani Antiproliferative Activity of epi-Cercosporin in Human Solid Tumor Cell Lines Ángel Trigos. Moharram. Chiaki Tanaka. Zhang Zhong. Sneha Jagtap.Natural Product Communications 2013 Volume 8. Zhao Qian. MinKyun Na. A Drimane Sesquiterpene with Quorum Sensing Inhibition Activity Cristian Paz. Paola Dugo and Luigi Mondello Antiplasmodial Activity of Compounds from the Surface Exudates of Senecio roseiflorus Leonidah Omosa Kerubo. Hasan. Solomon Derese. Vanessa Domínguez-Villegas. Stephen J. Anjana Munshi. Sang Hyun Kim. Minglei Tian. Naveed A Syed. Langat. Ahmed. Harukuni Tokuda. Sang-Yong Nam. Szymanski. Abdel-Baky. Romij Uddin. Padrón. Eiichiro Ichiishi. Antonella Cotroneo. Upendra Sharma. Anne-Claire Mitaine-Offer. Katia C. Nair Two New Amides from Streptomyces michiganensis Jinghua Xue. italica) Sun-Ju Kim. Aniket Karmase. Padwad. Kwang Hyun Jho and Sang Un Park Characterization of Volatile Components of Zingiber roseum Essential Oil Using Capillary GC on Modified Cyclodextrins VPPalayam S Pragadheesh. Ana M. Liangxiong Xu. Yuan-qin Zhang. a Bianthraquinone from Cassia siamea Dilip Kumar. Ana Calpena. Safwat A. Muhammad A Alfawaz. Michelle R. Woo Tae Park. León. Afaf M. Jun-ruXiong. Brij Lal and Bikram Singh Antioxidant and Anti-inflammatory Compounds in the Popular Landscape Plant Berberis thunbergii var. Ivana Bonaccorsi. Liu Yang. Manuel Norte and José J. Maricela Martínez. Homero Urrutia and Katherine Sossa Microbial Transformation of Curcumol by Aspergillus niger Chen Li-Xia. Martin Peter and Matthias Heydenreich Anti-inflammatory. Moses K. Landeira-Fernandez. Antioxidant and Cytotoxicity Activities of Methanolic Extract and Prenylated Flavanones Isolated from Leaves of Eysehardtia platycarpa Valeri Domínguez-Villegas. Dong Wha Park and Kyung Ho Row Hypoglycemic Effect of Bumelia sartorum Polyphenolic Rich Extracts Halliny S. Schutzki and Muraleedharan G. Pajaniradje Sankar. Sabino. Lei and Ali A. Bishay. Qi-An Jin and Zheng-Qiang Peng Determination of Organic Acids in Salicornia herbacea by Solid-phase Extraction Combined with Liquid Chromatography Dandan Han. Jacob Ogweno Midiwo. Zhang Hui. César Espinoza. Zhi-Wei Zhang. María Luisa García. Akala. Rocha and Ricardo M. David Pertuit. Jeong Ah Kim and Seung Ho Lee Antiproliferative Effects of an Analog of Curcumin in Hep-2 cells: A Comparative Study with Curcumin Mohankumar Kumaravel. Akira Iida. Cutler and Samir A. Beatriz Clares-Naveros and María Luisa Garduño-Ramírez Phenolic Glycosides from Lindera obtusiloba and their Anti-allergic Inflammatory Activities Hyun Gyu Choi.
Copyright © 2024 DOKUMEN.SITE Inc.