This article was downloaded by: [Nipissing University] On: 11 October 2014, At: 15:16 Publisher: Taylor & Francis Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK Natural Product Research: Formerly Natural Product Letters Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/gnpl20 Three new eudesmanes from Artemisia japonica a a b Phan Minh Giang , Nguyen Thi Binh , Katsuyoshi Matsunami & Phan Tong Son a a Faculty of Chemistry, VNU University of Science, Vietnam National University, 19 Le Thanh Tong Street, Hanoi, Viet Nam b Graduate School of Biomedical & Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8553, Japan Published online: 05 Mar 2014 To cite this article: Phan Minh Giang, Nguyen Thi Binh, Katsuyoshi Matsunami & Phan Tong Son (2014) Three new eudesmanes from Artemisia japonica, Natural Product Research: Formerly Natural Product Letters, 28:9, 631-635, DOI: 10.1080/14786419.2014.891115 To link to this article: http://dx.doi.org/10.1080/14786419.2014.891115 PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained in the publications on our platform However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content Any opinions and views expressed in this publication are the opinions and views of the authors, and are not the views of or endorsed by Taylor & Francis The accuracy of the Content should not be relied upon and should be independently verified with primary sources of information Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content This article may be used for research, teaching, and private study purposes Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden Terms & Downloaded by [Nipissing University] at 15:16 11 October 2014 Conditions of access and use can be found at http://www.tandfonline.com/page/termsand-conditions Natural Product Research, 2014 Vol 28, No 9, 631–635, http://dx.doi.org/10.1080/14786419.2014.891115 Three new eudesmanes from Artemisia japonica Phan Minh Gianga*, Nguyen Thi Binha, Katsuyoshi Matsunamib and Phan Tong Sona a Faculty of Chemistry, VNU University of Science, Vietnam National University, 19 Le Thanh Tong Street, Hanoi, Viet Nam; bGraduate School of Biomedical & Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8553, Japan Downloaded by [Nipissing University] at 15:16 11 October 2014 (Received December 2013; final version received February 2014) Three new eudesmanes, named artemisidiols A– C, together with eight known compounds, were isolated from the leaves of Artemisia japonica Thunb (Asteraceae) Their structures were determined on the basis of spectroscopic data Although oxygenated eudesmanes frequently occur in Asteraceae plants, the 1a,6a,8aoxygenated pattern of artemisidiols A – C has not been previously reported Keywords: Artemisia japonica; Asteraceae; eudesmane; artemisidiol Introduction The Asteraceae family includes over 20,000 species with a variety of uses, some of which are economically important (Abad et al 2012) More than 500 species form the genus Artemisia growing mainly in Asia, Europe and North America They contain wide-ranging carbon skeletal types including terpenoids, flavonoids, coumarins, caffeoylquinic acids and polyacetylenes with oxidative and stereochemical variations on their carbon skeletons (Kelsey & Shafizadeh 1979; Marco & Barbera 1990; Tan et al 1998; Wu et al 2006; Bora & Sharma 2011; Abad et al 2012) Artemisia japonica Thunb is native to Japan, China, Korea and Viet Nam The Vietnamese people use the plant to treat fever, headache, malaria, hypertension and tuberculosis (Pham 1993; Vo 1997) So far, only a subspecies A japonica ssp littoricola of Korea was investigated in a prior work, which led to the isolation of eudesmanes, acetylenic and phenolic compounds (Kwon & Lee 2001) This study isolated three new eudesmanes with an unusual 1a,6a,8aoxygenated pattern together with eight known compounds from the leaves of the Vietnamese A japonica species (Vietnamese name: Ngải Nhật) Results and discussion The dried and powdered leaves of A japonica were extracted with MeOH at room temperature On concentration under reduced pressure, the MeOH extract was partitioned between H2O and organic solvents of increasing polarity, n-hexane, CH2Cl2 and EtOAc to give corresponding soluble fractions The n-hexane- and CH2Cl2-soluble fractions were subjected to repeated silica gel column chromatography (CC) to afford 11 compounds, of which compounds and 3, and and were isolated as unresolvable mixtures Compounds 1, and are new eudesmanes and are named artemisidiols A –C The structures of the known compounds, 1-pentatriacontanol (4), tricosanoic acid (5), b-sitosterol (6) (Goad & Akihisha 1997), (24R)-cycloart-25-ene-3b,24-diol (7) (Pei et al 2007), (24S)-cycloart-25-ene-3b,24-diol (8) (Pei et al 2007), (23Z)-cycloart-23-ene*Corresponding author Email: phanminhgiang@yahoo.com q 2014 Taylor & Francis Downloaded by [Nipissing University] at 15:16 11 October 2014 632 P.M Giang et al 3b,25-diol (9) (Pei et al 2007), eupatorin (10) (Nagao et al 2002) and 5,40 -dihydroxy-6,7,30 ,50 tetramethoxyflavone (11) (Nagao et al 2002), were determined by comparing their spectroscopic data (MS, 1H and 13C NMR) with reported literature values and those of our authentic samples Compound was isolated as a white amorphous powder, ẵa23 D ỵ 111:3 (c ¼ 0.12, CH3OH) The molecular formula of was determined to be C18H26O6 by positive-ion HR-ESI-MS (m/z 361.1623 [M þ Na]þ) The IR spectrum showed absorption bands for hydroxy group at 3329 cm21, ester carbonyl group at 1733 and 1712 cm21, and double bond at 1627 cm21 In the H and 13C NMR spectra of 1, signals for a 15-carbon skeleton, a methoxy group [dH 3.79 (3H, s); dC 52.1 (q)] and an acetoxy group [dH 1.95 (3H, s); dC 170.4 (s) and 21.1 (q)] were observed The skeletal carbons included a tertiary methyl group [dH 0.93 (3H, s); dC 17.4 (q)], a vinylic methyl group [dH 1.91 (3H, s); 24.6 (q)], three oxygenated methines [dH 3.38 (1H, d, J ¼ 4.0 Hz), dC 73.2 (d); 4.06 (1H, dd, J ¼ 10.5, 9.5 Hz), 71.5 (d); and 5.41 (1H, ddd, J ¼ 12.0, 11.0, 5.0 Hz), 70.2 (d)], trisubstituted double bonds [dH 5.3 (1H, br s); dC 119.9 (d) and 134.5 (s)], an exocyclic double bond [dH 5.74 (1H, s) and 6.34 (1H, s); dC 128.8 (t) and 138.3 (s)] and an ester carbonyl group [dC 167.3 (s)], suggesting an eudesmane-type structure of Thus, on the basis of NMR data, the structure of was established to be of eudesma-3,11(12)-diene type The location of the three oxymethine groups and methoxy group, the proton and carbon-13 assignments, and the determination of the relative stereochemistry were made by detailed analysis of 1H – 1H (NOESY) and 1H – 13C (HSQC and HMBC) correlated 2D spectra (Figure S1) The methoxy group at dH 3.79 was confirmed to be a part of a methyl ester group from the HMBC correlation between this methoxy group and C-13 (dC 167.3) The oxymethine group at dH 3.38 was placed at C-1 since the HMBC long-range couplings between H3-15 (dH 0.93) and C-1 (dC 73.2), and between H-1 (dH 3.38) and C-3 (dC 119.9) and C-5 (dC 45.1) were detected The second oxymethine group at dH 4.06 (dd) was located at C-6 in accordance with its doublet of doublet coupling pattern (Kwon & Lee 2001) and the HMBC cross-peak between H-7 (dH 2.51) and C-6 (dC 71.5) The coupling pattern of the oxymethine signal left at dH 5.41 (ddd) was diagnostic for the location of this oxymethine group at C-8, since this is the only position on the carbon skeleton for the vicinal proton – proton couplings with three other protons The HMBC correlations between this proton (dH 5.41) and the acetoxy group (dC 170.4), between H2-12 (dH 5.74/6.34) and C-7 (dC 57.4), C11 (dC 138.3) and C-13, and between H2-9 (dH 1.65/1.88) and C-7 and C-8 (dC 70.2) confirmed the attachment of the acetoxy group to C-8 Analysis of the coupling constants and NOESY data established the relative stereochemistry of The NOE correlations between H3-15 and H-1, H-6 and H-8 confirmed a-orientation of the hydroxy groups at C-1 and C-6, and the acetoxy group at C-8 The value of JH-1/H-2 (d, J ¼ 4.0 Hz) is typical of an equatorial hydrogen, suggesting the axial orientation of C-1 hydroxy group Trans – diaxial relationships were also evident between H-5 and H-6 (JH-5/H-6 ¼ 10.5 Hz) and between H-8 and H-9a (JH-8/H-9a ¼ 12.0 Hz) The borientation of the C-7 side chain and a-orientation of H-5 were indicated by the NOE correlations between H-5 and H-7 and H-9a Therefore, the structure of was determined as shown in Figure and this compound was named artemisidiol A Compounds and were isolated in an unresolvable mixture as a white amorphous powder, ẵa24 D ỵ 93:0 (c ¼ 0.11, CH3OH) The HR-ESI-MS of the mixture of and showed the presence of two isomers with the same molecular formula, which was determined to be C21H32O6 by positive-ion HR-ESI-MS (m/z 403.2093 [M ỵ Na]ỵ) The IR spectrum showed absorption bands for hydroxy group at 3303 cm21, ester group at 1727 and 1720 cm21 and double bond at 1653 cm21 The 1H and 13C NMR spectra of and were almost superimposable and similar to those of indicating that these compounds shared identical features of the eudesmane-type structures, except for the substituents at C-8 The similarity of the chemical shifts of H-1/C-1 (1: dH 3.38, 2/3: dH 3.37; 1/2/3: dC 73.2), H-6/C-6 (1: dH 4.06, 2/3: dH 4.04; 1: dC 71.5, 2/3: dC 71.6) and H-8/C-8 (1: dH 5.41, 2/3: dH 5.4; 1: dC 70.2, 2: dC 69.87, 3: dC 69.98) confirmed the location of the hydroxy groups at C-1 and C-6 and the ester groups at C-8 Natural Product Research 5´ OH 15 O 10 H 14 2´ 1´ O OH 1´ O OH 1´ 5´ 2´ OH 4´ OCH3 3´ O H3CO O 12 H 11 OH 13 H3CO 2´ 3´ O O 4´ 633 O H OH H3CO O H3CO OH H3CO OH O O 10 OH OH OCH3 OH 24 O H3CO H H Downloaded by [Nipissing University] at 15:16 11 October 2014 HO 24R 24S OCH3 H3CO OH HO O 11 Figure Chemical structures of compounds –3 and – 11 Furthermore, on the basis of 1H NMR intensity (3:2 ¼ 8:7), two distinct sets of NMR data were assigned to identify the C-8 substituents as isovaleroyl group [dH 0.88 (6H, d, J ¼ 6.5 Hz), 1.4 (1H, m), and 2.07 (2H, d, J ¼ 7.0 Hz); dC 22.3 (C-40 ), 22.4 (C-50 ), 25.7 (C-30 ), 43.7 (C-20 ) and 172.4 (C-10 )] in and 2-methylbutyroyl group [dH 0.82 (3H, d, J ¼ 7.5 Hz), 1.04 (3H, d, J ¼ 7.0 Hz), 1.57 (2H, m), and 2.26 (1H, m); dC 11.5 (C-50 ), 16.5 (C-40 ), 26.6 (C-30 ), 41.3 (C-20 ) and 175.9 (C-10 )] in on comparison of the data with those reported for common substituents bonded to natural product skeletons (Budeˇsˇ´ınsky´ & Sˇaman 1995; Ferreira et al 2002) The HMBC spectrum (Figure S2) confirmed the assignments showing the correlations of H3-40 /H3-50 (dH 0.88) to C-20 and C-30 , and H2-20 (dH 2.07) to C-10 in 2; and of H3-40 (dH 0.82) to C-20 and C30 , and H3-50 (dH 1.04) to C-10 , C-20 , and C-30 in The relative stereochemistry of and was assumed to be identical to that of on the basis of their similar NMR data at the chiral centres and proton – proton coupling constants Therefore, the structures of and were determined as shown in Figure and they were named artemisidiols B and C, respectively Oxygenated eudesmanes frequently occur in Asteraceae plants and different functional groups are important in determining their individual biological activities So far, 1,6,8eudesmantriols and their derivatives have not been isolated from Asteraceae species In addition, the stereochemistry of the hydroxy groups of 1– deserves attention since C-1 and C-6 hydroxy groups are often assigned with opposite orientations on the eudesmane skeleton (Wu et al 2006) Experimental 3.1 General experimental procedures Optical rotations were determined using a Jasco P-1030 digital polarimeter (Jasco, Tokyo, Japan) HR-ESI-MS were measured on a Thermo Fischer Scientific LTQ Orbitrap XL mass spectrometer (Thermo Fischer Scientific, Waltham, MA, USA) 1H, 13C NMR, DEPT, 1H – 1H COSY, HSQC, HMBC and NOESY spectra were recorded on a Bruker Avance 500 NMR spectrometer (Bruker, Billerica, MA, USA) Silica gel (Merck, Darmstadt, Germany) was used for CC TLC was performed on precoated silica gel Merck 60 F254 plate 3.2 Plant materials The leaves of the Vietnamese medicinal plant A japonica Thunb were collected in June 2012 in Hoa Binh province, Viet Nam A voucher sample (No AJ-07-12) has been deposited at the 634 P.M Giang et al Laboratory of Chemistry of Natural Products, Faculty of Chemistry, VNU University of Science, Vietnam National University, Hanoi, Viet Nam Downloaded by [Nipissing University] at 15:16 11 October 2014 3.3 Extraction and isolation The dried powdered leaves (4.0 kg) of A japonica were extracted with MeOH at room temperature The combined MeOH extract was concentrated and then successively partitioned between water and organic solvents of increasing polarities to give n-hexane- (87.0 g), CH2Cl2(115.4 g) and EtOAc- (27.0 g) soluble fractions The n-hexane-soluble fraction (40.0 g) was separated by silica gel CC using n-hexane/acetone 49:1, 29:1, 19:1, 12:1, 9:1, 3:1 and 1:1 to give 11 fractions Fraction (2.74 g) was washed with n-hexane to give (52.0 mg) Fraction (4.81 g) on silica gel CC using n-hexane – acetone 90:1, 60:1, 49:1, 29:1, 19:1 and 9:1 yielded (8.8 mg) and (30.0 mg) Fraction (5.06 g) was sequentially separated by Merck RP-18 CC using MeOH –H2O 70%, 80%, 90%, and MeOH and repeated silica gel CC using n-hexane – acetone 19:1, 9:1, 6:1 and 3:1 and n-hexan – EtOAc 29:1, 19:1, 9:1 and 6:1 as solvent systems to give a mixture of and (7.5 mg) and (2.3 mg) Fraction 10 (2.22 g) was treated in a similar manner to that of fraction to give a mixture of and (1.8 mg) The CH2Cl2-soluble fraction (40.0 g) was separated by silica gel CC using n-hexane –acetone 49:1, 29:1, 19:1, 12:1, 9:1, 6:1 and 3:1 to give 11 fractions Fraction (2.29 g) was separated and purified by silica gel CC using n-hexane – acetone 29:1, 19:1, 9:1, 6:1 and 3:1 to give a mixture of and (8.5 mg) Fractions (0.57 g) and (0.68 g) were washed with n-hexane to give (9.0 mg) and 10 (2.8 mg), respectively Fraction (2.42 g) was first separated by Merck RP-18 CC using MeOH – H2O 70%, 80%, 90% and MeOH, and then purified by silica gel CC using n-hexane – acetone 19:1, 9:1, 6:1, 3:1 and 1:1 to give 11 (1.8 mg) Artemisidiol A (1): white amorphous powder; ẵa23 D ỵ 111:3 (c ¼ 0.12, CH3OH); IR nmax (film) cm21: 3329, 1733, 1712, 1627, 1438, 1378, 1247, 1159, 1038; 1H NMR (CDCl3): d 0.93 (3H, s, 15-CH3), 1.65 (1H, m, H-9b), 1.88 (1H, t, J ¼ 12.0 Hz, H-9a), 1.91 (3H, s, 14-CH3), 1.95 (3H, s, 20 -CH3), 2.01 (1H, br d, J ¼ 19.5 Hz, H-2a), 2.27 (1H, br d, J ¼ 10.5 Hz, H-5), 2.49 (1H, br d, J ¼ 19.5 Hz, H-2b), 2.51 (1H, dd, J ¼ 11.0, 9.5 Hz, H-7), 3.38 (1H, d, J ¼ 4.0 Hz, H-1), 3.79 (3H, s, 13-OCH3), 4.06 (1H, dd, J ¼ 10.5, 9.5 Hz, H-6), 5.3 (1H, br s, H-3), 5.41 (1H, ddd, J ¼ 12.0, 11.0, 5.0 Hz, H-8), 5.74 (1H, s, H-12a), 6.34 (1H, s, H-12b); 13C NMR (CDCl3): d 17.4 (C-15), 21.1 (C-20 ), 24.6 (C-14), 32.1 (C-2), 38.6 (C-10), 39.1 (C-9), 45.1 (C-5), 52.1 (13OCH3), 57.4 (C-7), 70.2 (C-8), 71.5 (C-6), 73.2 (C-1), 119.9 (C-3), 128.8 (C-12), 134.5 (C-4), 138.3 (C-11), 167.3 (C-13), 170.4 (C-10 ); HR-ESI-MS (positive-ion mode) m/z 361.1623 [M ỵ Na]ỵ (calcd for C18H26O6Na: 316.1622) Artemisidiol B (2) and Artemisidiol C (3): white amorphous powder; ½a24 D ỵ 93:0 (c ẳ 0.11, CH3OH); IR nmax (film) cm21: 3303, 1727, 1720, 1653, 1456, 1382, 1157, 1062, 1038; HR-ESIMS (positive-ion mode) m/z 403.2093 [M ỵ Na]ỵ (calcd for C21H32O6Na: 403.2091); Artemisidiol B (2): 1H NMR (CDCl3): d 0.88 (6H, d, J ¼ 6.5 Hz, 40 -CH3, 50 -CH3), 0.92 (3H, s, 15-CH3), 1.4 (1H, m, H-30 ), 1.65 (1H, m, H-9b), 1.88 (1H, t, J ¼ 12.0 Hz, H-9a), 1.9 (3H, s, 14CH3), 2.01 (1H, br d, J ¼ 20.0 Hz, H-2a), 2.07 (2H, d, J ¼ 7.0 Hz, 2H-20 ), 2.26 (1H, m, H-5), 2.49 (1H, br d, J ¼ 20.0 Hz, H-2b), 2.53 (1H, t, J ¼ 10.5 Hz, H-7), 3.37 (1H, d, J ¼ 4.0 Hz, H1), 3.77 (3H, s, 13-OCH3), 4.04 (1H, dd, J ¼ 10.5, 10.0 Hz, H-6), 5.29 (1H, br s, H-3), 5.4 (1H, ddd, J ¼ 12.0, 10.5, 5.0 Hz, H-8), 5.74 (1H, s, H-12a), 6.33 (1H, s, H-12b); 13C NMR (CDCl3): d 17.4 (C-15), 22.3 (C-40 ), 22.4 (C-50 ), 24.6 (C-14), 25.7 (C-30 ), 32.1 (C-2), 38.7 (C-10), 39.2 (C9), 43.7 (C-20 ), 45.2 (C-5), 52.0 (13-OCH3), 57.2 (C-7), 69.87 (C-8), 71.6 (C-6), 73.2 (C-1), 119.9 (C-3), 128.9 (C-12), 134.6 (C-4), 138.4 (C-11), 167.3 (C-13), 172.4 (C-10 ); Artemisidiol C (3): 1H NMR (CDCl3): d 0.82 (3H, d, J ¼ 7.5 Hz, 40 -CH3), 0.92 (3H, s, 15-CH3), 1.04 (3H, d, J ¼ 7.0 Hz, 50 -CH3), 1.57 (2H, m, 2H-30 ), 1.65 (1H, m, H-9b), 1.88 (1H, t, J ¼ 12.0 Hz, H-9a), 1.9 (3H, s, 14-CH3), 2.01 (1H, br d, J ¼ 20.0 Hz, H-2a), 2.26 (2H, m, H-20 , H-5), 2.49 (1H, br d, Natural Product Research 635 J ¼ 20.0 Hz, H-2b), 2.56 (1H, t, J ¼ 10.5 Hz, H-7), 3.37 (1H, d, J ¼ 4.0 Hz, H-1), 3.77 (3H, s, 13-OCH3), 4.04 (1H, dd, J ¼ 10.5, 10.0 Hz, H-6), 5.29 (1H, br s, H-3), 5.4 (1H, ddd, J ¼ 12.0, 10.5, 5.0 Hz, H-8), 5.74 (1H, s, H-12a), 6.33 (1H, s, H-12b) 13C NMR (CDCl3): d 11.5 (C-50 ), 16.5 (C-40 ), 17.4 (C-15), 24.6 (C-14), 26.6 (C-30 ), 32.1 (C-2), 38.7 (C-10), 39.1 (C-9), 41.3 (C20 ), 45.2 (C-5), 52.0 (13-OCH3), 57.2 (C-7), 69.98 (C-8), 71.6 (C-6), 73.2 (C-1), 119.9 (C-3), 128.9 (C-12), 134.6 (C-4), 138.4 (C-11), 167.3 (C-13), 175.9 (C-10 ) Supplementary material Supplementary material relating to this article is available online, alongside Figures S1, S2 and spectra of 1, and Downloaded by [Nipissing University] at 15:16 11 October 2014 Acknowledgement This research is funded by Vietnam National Foundation for Science and Technology Development (NAFOSTED) under grant number 104.01-2012.10 References Abad MJ, Bedoya LM, Apaza L, Bermejo P 2012 The Artemisia L genus: a review of bioactive essential oils Molecules 17:2542 –2566 Bora KS, Sharma A 2011 The genus Artemisia: a comprehensive review Pharm Biol 49:101–109 Budeˇsˇ´ınsky´ M, Sˇaman D 1995 Carbon-13 NMR spectra of sesquiterpene lactones Annu Rep NMR Spectrosc 30:231–475 Ferreira MJP, Oliveira FC, Alvarenga SAV, Macari PAT, Rodrigues GV, Emerenciano VP 2002 Automatic identification by 13C NMR of substituent groups bonded to natural products skeletons Comput Chem 26:601–632 Goad LJ, Akihisha T 1997 Analysis of sterols London: Chapmann & Hall Kelsey RG, Shafizadeh F 1979 Sesquiterpene lactones and systematics of the genus Artemisia Phytochemistry 18:1591–1611 Kwon HC, Lee KR 2001 Phytochemical constituents of Artemisia japonica ssp littoricola Arch Pharm Res 24:194–197 Marco J, Barbera O 1990 Natural products from the genus Artemisia In: Atta-ur-Rahman, editor Studies in natural products chemistry Vol Amsterdam: Elsevier; p 261–264 Nagao T, Abe F, Kinjo J, Okabe H 2002 Antiproliferative constituents in plants 10 Flavones from the leaves of Lantana montevidensis Briq and consideration of structure–activity relationship Biol Pharm Bull 25:875–879 Pei YG, Wu QX, Shi YP 2007 Triterpenoids and other constituents from Euphorbia humifusa J Chin Chem Soc 54:1565–1572 Pham HH 1993 An illustrated flora of Vietnam Montreal: Pham Tan RX, Zheng WF, Tang HQ 1998 Biologically active substances from the genus Artemisia Planta Med 64:295–302 Vo VC 1997 Dictionary of Vietnamese medicinal plants Ho Chi Minh City: Medicine Wu QX, Shi YP, Zia ZJ 2006 Eudesmane sesquiterpenoids from the Asteraceae family Nat Prod Rep 23:699– 734 ... http://dx.doi.org/10.1080/14786419.2014.891115 Three new eudesmanes from Artemisia japonica Phan Minh Gianga*, Nguyen Thi Binha, Katsuyoshi Matsunamib and Phan Tong Sona a Faculty of Chemistry, VNU University of Science, Vietnam National... version received February 2014) Three new eudesmanes, named artemisidiols A– C, together with eight known compounds, were isolated from the leaves of Artemisia japonica Thunb (Asteraceae) Their... spectroscopic data Although oxygenated eudesmanes frequently occur in Asteraceae plants, the 1a,6a,8aoxygenated pattern of artemisidiols A – C has not been previously reported Keywords: Artemisia japonica;