Initial research on chemical constituents of curcuma singularis rhizomes - Nguyen Manh Cuong

Journal of Science and Technology 54 (2C) 2016 402-408 INITIAL RESEARCH ON CHEMICAL CONSTITUENTS OF CURCUMA SINGULARIS RHIZOMES Nguyen Manh Cuong1, *, Doan Thi Van1, Ninh The Son1, To Dao Cuong1, Pham Ngoc Khanh1, Vu Thi Ha1, Tran Thu Huong1, Nguyen Phuong Hanh2, Nguyen Quoc Binh3 1Institute of Natural Products Chemistry, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi 2Institute of Ecology and Biological Resources, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi 3Vietnam National Museum of Nature, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi *Email: nmcuong_inpc@yahoo.com.vn Received: 20 May 2016; Accepted for publication: 28 October 2016 ABSTRACT From the rhizomes of Curcuma singularis Gagnep (Zingiberaceae family), six compounds, including three terpenoids, p-menthane-1,2,4-triol (1), amoxantin A (2), rugosic acid B (3); two diols, 2,3-butanediol (4) [2R,3R-butanediol (4a) and 2S,3S-butanediol (4b)], and meso-2,3- butanediol (5), along with 3-hydroxy-4-methoxy benzoic acid (6) were isolated. All of six compounds were obtained for the first time from the Curcuma genus. The structures of those compounds were determined by 1D and 2D-NMR spectroscopic data. Keywords: Curcuma singularis Gagnep., Zingiberaceae, rhizomes, terpenoid, labdadien, butanediol, benzoic acid. 1. INTRODUCTION Curcuma is a large genus belonging to Zingiberaceae family, comprise of 147 species over the world [1] and 15 species in Vietnam [2]. Several Curcuma species were used in traditional medicine for the treatment of gastrointestinal disorders, abdominal pain, jaundice, and hepatitis [3]. Curcuma singularis Gagnep., local name “cây khỏe” were used by ethnic people in Tay Nguyen provinces as medicinal remedy for increasing vitality, boosting health, treating rheumatism and fortifying kidney. Around the world, so far there have been many publications on the chemical compositions and biological activity of the Curcuma species such as Curcuma longa L. [4, 5], C. wenyujin [6], and C. comosa [7]. Compounds mainly found in this genus were tecpenoids and diaryl phenyls [4 - 7]. However, to the best of our knowledge, there are not any studies announced on the chemical compositions and biological activity of C. singularis. In this paper, we present some our initial findings on the chemical compositions of the rhizomes of Curcuma singularis Gagnep. Initial research on chemical constituents of Curcuma singularis rhizomes 403 2. MATERIALS AND METHODS 2.1. Plant material The rhizomes of C. singularis were collected in Kon Pne commune, K’bang distrist, Gialai province, Vietnam in April 2015. The plant was identified by botanist Dr. Nguyen Quoc Binh, Institute of Ecology and Biological Resources (VAST), Vietnam. A voucher specimen (C-557) is deposited in the Herbarium of the Institute of Natural Products Chemistry (VAST), Hanoi, Vietnam. 2.2. General experimental procedures 1H-NMR (500 MHz) and 13C-NMR (125 MHz) were measured on a Bruker Avance 500 MHz spectrometer, Institute of Chemistry. ESI-MS were obtained from an Agilent 1100 Series LC/MSD Trap SL, Institute of Chemistry. Chromatographic separation was carried out on silica gel (Si 60 F254, 40-63 mesh, Merck) and RP-C18 column. All solvents were redistilled before use. Pre-coated TLC plates (Si 60 F254) were used for analytical purposes. 2.3. Extraction and isolation Dried powdered rhizomes of C. singularis (3.2 kg) were extracted with ethanol 80o (3 × 7L) at room temperature and concentrated under reduced pressure to yield a black crude ethanol extract (300 g). The crude ethanol extract was suspended in hot ethanol-water (1:1, v/v) and successively partitioned with chloroform, ethyl acetate and water. The resulting fractions were concentrated under reduced pressure to give the corresponding solvent-soluble fractions chloroform (198 g, CS-C), ethyl acetate (6.0 g, CS-E) and water (96 g, CS-W). The chloroform fraction (CS-C, 198 g) was chromatographed on a silica gel column, using solvent gradient of n-hexan : ethyl acetate (6:1, v/v) to afford 8 fractions (C1-C8). The fraction C1 (15 g) was chromatographed on a silica gel column, eluting with n-hexane : ethyl acetate (100:1, v/v) to afford 4 subfractions (C1A-C1D). Precipitate from C1C subfraction (3.5 g) was filtered and washed to yield compound 2 (100 mg). The fraction C5 (1.59 g) was chromatographed on a silica gel column, eluting with dichloromethane : acetone (20/1, v/v) to afford 7 subfractions (C5A-C5G). The subfraction C5E (243 mg) was eluted with isocratic solvent system of n-hexane : acetone (5:1, v/v) on a silica gel column to yield compound 1 (4 mg). The ethyl acetate fraction (CS-E, 6.0 g) was subjected for chromatography column (CC) on a flash silica gel column (400-630 mesh), eluting with chloroform-acetone (10:1, v/v) to afford 11 fractions (E1-E11). The fraction E2 (110 mg) was chromatographed on a silica gel column, eluting with chloroform : ethyl acetate (10:1, v/v) to afford 2 subfractions (E2A-E2B). Precipitate from E2A (80 mg) was filtered and washed with chloroform to yield compound 6 (10.0 mg). The fraction E10 (220 mg) was chromatographed on a silica gel column, eluting with ethyl acetate : methanol (5:1, v/v) to afford 5 subfractions (E10A-E10E). The subfraction E10B (25 mg) was rechromatographed over a RP-18 column eluting with methanol : water (1:1, v/v) to yield compound 3 (6 mg). The water fraction (CS-W, 96 g) was subjected to a Diaion CC, eluting with gradient solvent mixture of water-methanol (1:0→0:1) to produce 5 fractions (W1-W5). The fraction W1 (70 g) was purified on a silica gel CC using chloroform : methanol : water (6:1:0.1, v/v) to Nguyen Manh Cuong, et al 404 afford 11 fractions (W1A-W1J). The subfraction W1A (1.6 g) was chromatographed on a silica gel column, eluting with chloroform : acetone (6:1, v/v) to afford 5 subfractions and yield compound 4 (100 mg) and compound 5 (80 mg). p-menthane-1,2,4-triol (1): White needle crystals (C10H20O3). 1H-NMR (500 MHz, MeOD), δH (ppm): 0.93 (3H, d, J = 7.0 Hz, H-9), 0.94 (3H, d, J = 7.0 Hz, H-8), 1.26 (3H, s, 1- CH3), 1.44 (2H, m, H-6), 1.60 (1H, dd, J = 13.0, 6.5 Hz, H-7), 1.63 (1H, dt, J = 14.0, 3.0 Hz, Ha- 3), 1.85 (1H, dd, J = 13.5, 4.0 Hz, Ha-5), 1.93 (1H, dd, J = 13.5, 3.5 Hz, Hb-5), 1.96 (1H, dt, J = 14.0, 3.5 Hz, Hb-3), 3.53 (1H, brs, H-2). 13C-NMR (125 MHz, MeOD), δC (ppm): 17.1 (q, C-9), 17.2 (q, C-8), 27.1 (q, 1-CH3), 30.3 (t, C-6), 30.4 (t, C-5), 34.9 (t, C-3), 39.0 (d, C-7), 72.1 (s, C- 1), 75.7 (s, C-4), 75.7 (d, C-2). Amoxantin A (2): Yellowish needle crystals (C18H28O). 1H-NMR (500 MHz, CDCl3), δH (ppm): 0.85 (3H, s, H-19), 0.89 (6H, s, H-18, H-20), 1.02 (1H, ddd, J = 3.0, 13.0, 13.0 Hz, Ha-1), 1.10 (1H, dd, J = 2.5, 12.5 Hz, H-5), 1.19 (1H, ddd, J = 4.5, 13.5, 14.0 Hz, Ha-3), 1.37 (1H, m, Hb-1), 1.39 (1H, m, Ha-6), 1.41 (1H, m, Ha-2), 1.44 (1H, m, Hb-3), 1.54 (1H, m, Hb-2), 1.72 (1H, m, Hb-6), 2.09 (1H, ddd, J = 5.0, 12.5, 13.5 Hz, Ha-7), 2.27 (3H, s, H-14), 2.44 (1H, m, Hb-7), 2.47 (1H, m, H-9), 4.41 (1H, d, J = 1.0 Hz, Ha-17), 4.79 (1H, d, J = 1.0 Hz, Hb-17), 6.07 (1H, d, J = 16.0 Hz, H-12), 6.87 (1H, dd, J = 6.0, 16.0 Hz, H-11). 13C-NMR (125 MHz, CDCl3), δC (ppm): 15.1 (q, C-20), 19.0 (t, C-2), 21.9 (q, C-19), 23.3 (t, C-6), 27.2 (q, C-14), 33.5 (s, C-4), 33.6 (q, C-18), 36.6 (t, C-7), 39.3 (s, C-10), 40.9 (t, C-1), 42.1 (t, C-3), 54.5 (d, C-5), 60.8 (d, C- 9), 108.6 (t, C-17), 133.6 (d, C-12), 146.6 (d, C-11), 148.6 (s, C-8), 198.1 (s, C-13). Rugosic acid B (3): Colorless crystals (C15H22O5). 1H-NMR (500 MHz, MeOD), δH (ppm): 0.94 (3H, d, J = 7.0 Hz, H-13), 1.02 (3H, d, J = 6.5 Hz, H-12), 1.15 (3H, s, 7-CH3), 1.68 (1H, m, Ha-8), 1.71 (1H, m, Ha-9), 1.78 (1H, m, Hb-8), 1.92 (1H, d, J = 12.0 Hz, Ha-6), 2.02 (1H, d, J = 12.0 Hz, Hb-6), 2.06 (1H, m, Hb-9), 2.14 (1H, dd, J = 7.5, 3.0 Hz, H-10), 2.41 (1H, m, H-11), 4.02 (1H, d, J = 5.0 Hz, H-2), 6.63 (1H, d, J = 5.0 Hz, H-3). 13C-NMR (125 MHz, MeOD), δC (ppm): 20.7 (q, C-13), 24.4 (t, C-9), 24.8 (q, 7-CH3), 25.8 (q, C-12), 26.1 (d, C-11), 45.3 (t, C-8), 49.7 (s, C-7), 54.0 (d, C-10), 57.1 (t, C-6), 66.4 (d, C-2), 97.8 (s, C-1), 103.2 (s, C-5), 134.2 (d, C-3), 141.4 (s, C-4), 173.5 (s, CO). 2,3-butanediol (4): Yellowish oil (C4H10O2). 1H-NMR (500 MHz, MeOD), δH (ppm): 1.16 (6H, d, 6.0 Hz, H-1, H-4), 3.56 (2H, m, H-2, H-3). 13C-NMR (125 MHz, MeOD), δC (ppm): 18.6 (q, C-1), 18.7 (q, C-4), 72.6 (d, C-2), 72.7 (d, C-3). meso-2,3-butanediol (5): Yellowish oil (C4H10O2). 1H-NMR (500 MHz, MeOD), δH (ppm): 1.14 (6H, d, 6.5 Hz, H-1, H-4), 3.53 (2H, m, H-2, H-3). 13C-NMR (125 MHz, MeOD), δC (ppm): 18.7 (q, C-1, C-4), 72.7 (d, C-2, C-3). 3-Hydroxy-4-methoxybenzoic acid (6): White needle crystals (C8H8O4). 1H-NMR (500 MHz, MeOD), δH (ppm): 3.91 (3H, s, H-8), 6.86 (1H, d, J = 8.5 Hz, H-5), 7.57 (1H, d, J = 2.5 Hz, H-2), 7.58 (1H, d, J = 2.5, 8.5 Hz, H-6). 13C-NMR (125 MHz, MeOD), δC (ppm): 56.4 (q, 4- OCH3), 113.8 (d, C-5), 115.8 (d, C-2), 123.1 (s, C-1), 125.3 (d, C-6), 148.7 (s, C-3), 152.7 (s, C- 4), 170.0 (s, CO). Initial research on chemical constituents of Curcuma singularis rhizomes 405 OH OH OH 1 4 8 9 7 OH COOH HO O 1 3 4 7 9 10 11 12 13 COOH OH OCH3 1 4 6 6 2 3 6 2 3 2 3 54a OHH HHO HHO OHH OHH OHH 4b4 O 18 19 4 2 1 10 5 9 7 11 13 14 1 2 3 17 20 Figure 1. Compounds (1-6) from rhizomes of Curcuma singularis species. 3. RESULT AND DISCUSSION Compound 1 was obtained as white needle crystals. The 1H-NMR of 1 showed characteristic signals for a monoterpene, including two methyl protons of isopropyl group at [δH 0.93 (J = 7.0 Hz, H-9), δH 0.94 (J = 7.0 Hz, H-8)], one methyl group at δH 1.26 (1-CH3), three methylene groups at [δH 1.44 (m, H-6), δH 1.85 (dd, J = 13.5, 4.0 Hz, Ha-5), δH 1.93 (dd, J = 13.5, 3.5 Hz, Hb-5), δH 1.63 (dt, J = 14.0, 3.0 Hz, Ha-3) and δH 1.96 (dt, J = 14.0, 3.5 Hz, Hb-3)], and two methine protons at [δH 1.60 (dd, J = 13.0, 6.5 Hz, H-7), δH 3.53 (brs, H-2)]. In agreement with those, 13C-NMR/DEP of 1 showed 10 carbon signals, assignable to three methyl carbons at [δC 17.1 (q, C-9), δC 17.2 (q, C-8), δC 27.1 (q, 1-CH3)], three methylene carbons at [δC 30.3 (t, C-6), δC 30.4 (t, C-5), δC 34.9 (t, C-3)], two methine carbons at [δC 39.0 (d, C-7), δC 75.7 (d, C-2)], and two quaternary carbons at [δC 72.1 (s, C-1), δC 75.7 (s, C-4)]. Analysis of HMBC spectra, methyl proton 1-CH3 correlated to C-1, C-2 and C-6, which confirmed the position of methyl group at C-1. Similarly, isopropyl side chain at C-4 was confirmed by the HMBC correlations between H-8/H-9 and C-4/C-7. From 1D, 2D-NMR data, together with a comparison with spectral data in published literature, the chemical structure of 1 was elucidated as a polyoxygen-monoterpene with trivial name p-menthane-1,2,4-triol [8]. Compound 2 was isolated as yellowish needle crystals. The 1H-NMR spectrum of 2 displayed patterns of diterpenoid, bicyclic skeleton of bisnorlabdane, with characteristic signals of three methyl groups at δH 0.85 (s, H-19), δH 0.89 (s, H-18, H-20), one exomethylene group at [δH 4.41 (d, J = 1.0 Hz, Ha-17), δH 4.79 (d, J = 1.0 Hz, Hb-17), one α, β-unsaturated ketone side chain at [δH 6.80 (dd, J = 10.0, 16.0 Hz, H-11), δH 6.07 (J = 16.0 Hz, H-12), δH 2.27 (s, H-14)]. 13C-NMR/DEPT spectra of 2 contained 18 carbon signals, composed of four methyl groups at [δC 27.2 (q, C-14), δC 33.6 (q, C-18), δC 21.9 (q, C-19), δC 15.1 (q, C-20)], six methylene carbons at [δC 40.9 (t, C-1), δC 19.0 (t, C-2), δC 42.1 (t, C-3), δC 23.3 (t, C-6), δC 36.6 (t, C-7), δC 108.6 (t, C-17)], four methine carbons at [δC 54.5 (d, C-5), δC 60.8 (d, C-9), δC 146.6 (d, C-11), δC 133.6 (d, C-12)], three quaternary carbons at [δC 33.5 (s, C-4), δC 148.6 (s, C-8), δC 39.3 (s, C-10)], and Nguyen Manh Cuong, et al 406 carbonyl group at δC 198.1 (s, C-13). The chemical structure of 2 was also confirmed by COSY and HMBC spectroscopies. In the COSY spectra, the presence of a skeletal bisnorlabdane was determined, due to cross peaks of three consecutive methylene protons H-1/H-2/H-3, two methylene protons H-6/H-7, two olefinic protons H-11/H-12. In the HMBC spectra, selective key correlations between of H-18 and H-19/C-4, H-20/C-10, and H-14/C-13, have assigned the positions of methyl groups (Figure 1). In addition, the connectivity of exomethylene group and ring at C-8, which was observed by correlations of H-17/C-7, C-8 and C-9. In the same manner, the linkage between the α, β-unsaturated ketone side chain and the ring at C-9 was improved by correlations of H-11/C-8, C-9, and C-10. By comparison of the spectroscopic data with those in published literature, compound 2 was identified as amoxantin A [9]. Compound 3 was isolated as colourless crystals. The 1H-NMR of 3 showed the presence of a sesquiterpene of carotane skeleton, including, one methyl group at δH 1,15 (s, 7-CH3), and two methyl protons of isopropyl group at [δH 0.94 (d, J = 7.0 Hz, H-13), δH 1.02 (d, J = 6.5 Hz, H- 12)], three methylene protons at [δH 1.68 (m, Ha-8), δH 1.71 (m, Ha-9), δH 1.78 (m, Hb-8), δH 1.92 (d, J = 12.0 Hz, Ha-6), δH 2.02 (d, J = 12.0 Hz, Hb-6), δH 2.06 (m, Hb-9)], three methine protons at [δH 2.14 (dd, J = 7.5, 3.0 Hz, H-10), δH 2.41 (m, H-11), δH 4.02 (d, J = 5.0 Hz, H-2)], and olefinic proton at δH 6.63 (d, J = 5.0 Hz, H-3). The 13C-NMR/DEPT data indicated a total number of 15 carbons, comprising characteristic signals of a sesquiterpene, due to three methyl carbons at [δC 20.7 (q, C-13), δC 24.8 (q, 7-CH3), δC 25.8 (q, C-12)], three methylene carbons at [δC 24.4 (t, C- 9), δC 45.3 (t, C-8), δC 57.1 (t, C-6)], four methine carbons at [δC 26.1 (d, C-11), δC 54.0 (d, C- 10), δC 66.4 (d, C-2), δC 134.2 (d, C-3)], and five quaternary carbons at [δC 49.7 (s, C-7), δC 97.8 (s, C-1), δC 103.2 (s, C-5), δC 141.4 (s, C-4), δC 173.5 (s, CO)]. The observed correlations of methyl proton 7-CH3/C-1, C-6, C-7, and C-8 in the HMBC spectra have determined the position of 7-CH3 group at C-7, whereas the lingkage position of isopropyl group at C-10 was determined by correlations between H-12 and H-13/C-10 and C-11. Furthermore, the linkage of carboxyl group and olefinic carbon C-4 was determined from the correlations of H-3/C-1, C-2, and C-5. From 1D, 2D-NMR and literature data, compound 3 was identified to be rugosic acid B [10]. Compound 4 (the mixture of 4a and 4b) was isolated as a yellowish oil. Based on the 1H- NMR and 13C-NMR/DEPT spectral data, compound 4 was identified as a vicinal-diols. In the 1H-NMR spectrum, superimpose doublet signal at δH 1.16 (J = 6.0 Hz) was due to two methyl groups H-1 and H-4, whereas superimpose multiple signal at δH 3.56 was of two hydroxygenated-methine protons H-2 and H-3. Furthermore, the 13C-NMR spectrum clearly showed the appearances of four carbon signals at [δC 18.6 (q, C-1), δC 18.7 (q, C-4), δC 72.6 (d, C-2), and δC 72.7 (d, C-3)]. By comparison of the NMR data with those reported in the publication, compound 4 was determined as a mixture of enatiomers [(2R, 3R)-2,3-butanediol (4a) and (2S, 3S)-2,3-butanediol (4b)] [11]. Compound 5 was isolated as a yellowish oil. The 1H-NMR data of 5 was similar to those of 4, showing the existence of a symmetric polyalcohol. Two symmetric methyl groups H-1 and H- 4 was founded at δH 1.14 (J = 6.5 Hz, d), while two hydroxygenated-methine protons H-2 and H- 3 were characterized with multiple signals, at δH 3.53. Unlike compounds 4a and 4b, only two signals with strong intensity were observed in the 13C-NMR/DEPT spectra of 5, at δC 18.7 (q, C- 1, C-4), and δC 72.7 (d, C-2, C-3)]. Those data suggest compound 5 having an internal plane of symmetry. Therefore, from above mention and literature research, the chemical structure of 5 was confirmed as meso-2,3-butanediol [12]. Compound 6 was obtained as white needle crystals. The 1H-NMR spectrum data clearly indicated that this compound displayed as a pattern of 3,4-disubstituted benzoic acid, including ABX aromatic protons at [δH 6.86 (d, J = 8.5 Hz, H-5), δH 7.58 (d, J = 2.5, 8.5 Hz, H-6) and δH Initial research on chemical constituents of Curcuma singularis rhizomes 407 7.57 (d, J = 2.5 Hz, H-2)], one methoxy group at δH 3.91 (4-OCH3, s). In accordance with 1H- NMR spectrum data, 13C-NMR/DEPT spectrum data of 6 exhibited eight carbons, comprising one methoxy carbon at δC 56.4 (4-OCH3), three aromatic carbons at [δC 113.8 (d, C-5), δC 125.3 (d, C-6) and δC 115.8 (d, C-2)], three quaternary carbons at [δC 123.1 (s, C-1), δC 148.7 (s, C-3) and δC 152.7 (s, C-4)], and a carbonyl group in the downfield, at δC 170.0 ppm. From above mentions and a comparison with literature data, compound 6 was determined as a derivative of benzoic acid, named 3-hydroxy-4-methoxybenzoic acid [13]. 4. CONCLUSION From the rhizomes of Curcuma singularis Gagnep. (Zingiberaceae), six compounds, including 3 terpenoids, p-menthane-1,2,4-triol (1), amoxantin A (2), rugosic acid B (3), 2 diols, 2,3-butanediol (4) [2R,3R-butanediol (4a) and 2S,3S-butanediol (4b)], meso-2,3-butanediol (5), along with 3-hydroxy-4-methoxybenzoic acid (6) were obtained. All of six compounds were isolated for the first time from the Curcuma genus. The structures of those compounds were determined by 1D and 2D-NMR spectroscopic data. Acknowledgement. This research was financially supported by the Vietnam Academy of Science and Technology, Vietnam (Project No: 04.10/15-16). REFERENCES 1. 18/05/2016. 2. Pham Hoang Ho, ed. – An Illustrated Flora of Vietnam, Vol III, Youth Publisher, Hanoi, 2000, p. 454-457. 3. La Dinh Moi, ed. – Essential - Oil plant resources in Viet Nam, Vol II, Agricultural Publisher, Hanoi, 2002, p. 229-260. 4. Li S. Y., Yuan W., Deng G. R., Wang P., Yang P. Y. and Aggarwal Br. B. - Chemical composition and product quality control of turmeric (Curcuma longa L.), Pharm. Crops 2 (2011) 28-54. 5. Zeng Y. C., Qiu F., Takahashi K. K., Liang J. M., Qu G. X. and Yao X. S. - New sesquiterpenes and calebin derivatives from Curcuma longa - Chem. Pharm. Bull. 55 (6) (2007) 940-943. 6. Dong Y. O., Ma X. Y., Cai X. Q., Yan P. C., Yue L., Lin C., Shao W. W. - Sesquiterpenoids from Curcuma wenyujin with anti-influenza viral activities - Phytochemistry 85 (2013) 122-128. 7. Jitsanong T. C., Khanobdee K. N., Piyachaturawat P., Wongprasert K. - Diarylheptanoid 7-(3,4 dihydroxyphenyl)-5-hydroxy-1-phenyl-(1E)-1-heptene from Curcuma comosa Roxb. protects retinal pigment epithelial cells against oxidative stress-induced cell death - Toxicol. in Vitro 25 (2011) 167-176. 8. Todorova M., Voglerb B. H. and Tsankova E. - Terpenoids from Achillea setacea. Z. Naturforsch. 55c (2000) 840-842. 9. Kim K. H., Choi J. W., Choi S. U., Seo E. K., Lee K. R. - Amoxantin A: A new bisnorlabdane diterpenoid from Amomum xanthioides - Bull. Korean Chem. Soc. 31 (2010) 1035-1037. Nguyen Manh Cuong, et al 408 10. Hashidoko Y. S., Tahara S. & Mizutani J. N. - Isolation of Four Novel Carotanoids as Possible Metabolites of Rugosic Acid a in Rosarugosa Leaves - Agric. Biol. Chem. 55 (4) (1991) 1049-1053. 11. Consolacion Y. R., Agnes B. A. and Shen C. C. - Chemical constituents of Ficus nota - Der. Pharma. Chemica 6 (4) (2014) 98-101. 12. Baek J., Kim T. Y., Kim W., Lee H. J., Yi J. - Selective production of 1,3-butadiene using glucose fermentation liquor - Green Chemistry (supporting information) 16 (2014) 3051- 3057. 13. Ding H. Y., Lin H. C., Teng C. M. and Wu Y. C. - Phytochemical and Pharmacological Studies on Chinese Paeonia Species - Journal of the Chinese Chemical Society 47 (2000) 381-388. TÓM TẮT BƯỚC ĐẦU NGHIÊN CỨU THÀNH PHẦN HÓA HỌC THÂN RỄ CÂY CURCUMA SINGULARIS Nguyễn Mạnh Cường1, *, Đoàn Thị Vân1, Ninh Thế Sơn1, Tô Đạo Cường1, Phạm Ngọc Khanh1, Vũ Thị Hà1, Trần Thu Hường1, Nguyễn Phương Hạnh2, Nguyễn Quốc Bình3 1Viện Hóa học các Hợp chất TN, Viện HLKHCNVN, 18 Hoàng Quốc Việt, Cầu Giấy, Hà Nội 2Viện Sinh thái và TN sinh vật, Viện HLKHCNVN, 18 Hoàng Quốc Việt, Cầu Giấy, Hà Nội 3Bảo tàng thiên nhiên Việt Nam, Viện KLKHCNVN, 18 Hoàng Quốc Việt, Cầu Giấy, Hà Nội *Email: nmcuong_inpc@yahoo.com.vn Từ thân rễ loài Curcuma singularis Gagnep. (Zingiberaceae), sáu hợp chất bao gồm ba hợp chất terpenoit, p-menthane-1,2,4-triol (1), amoxantin A (2), axit rugosic B (3), hỗn hợp hai diol, 2,3-butanediol (4) [2R,3R-butanediol (4a) và 2S,3S-butanediol (4b)], meso-2,3-butanediol (5) và một dẫn xuất của axit benzoic 3-hydroxy-4-methoxybenzoic acid (6) đã được phân lập. Sáu hợp chất trên được phát hiện lần đầu tiên từ chi Curcuma. Cấu trúc hóa học của các hợp chất 1-6 được xác định dựa trên các dữ kiện phổ 1D và 2D-NMR. Từ khóa: Curcuma singularis Gagnep., Zingiberaceae, thân rễ, tecpenoit, labdadien, butanediol, axit benzoic.