Chemical properties and inhibitory activities of tyrosinase, α-glucosidase, and urease from chloroform extract of Curcuma aromatica Salisb. rhizomes

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The present study investigated the phytochemical and biological properties of the rhizomes C. aromatica. From the CHCl3 extract of C. aromatic rhizomes, six known compounds, including (-)-hannokinol, (3R,5R)-3,5-diacetoxy-1,7-bis(4- hydroxyphenyl)heptane, naringenin, 2-(4- (hydroxymethyl)phenyl)propan-2-ol, 5-hydroxymethylfurfural, and bisacurone, were isolated. All compounds were tested on the biological inhibitory activities against tyrosinase, αglucosidase, and urease. It was the first time all compounds were isolated from rhizomes of C. aromatica Salisb.

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Nội dung Text: Chemical properties and inhibitory activities of tyrosinase, α-glucosidase, and urease from chloroform extract of Curcuma aromatica Salisb. rhizomes

Cite this paper: Vietnam J. Chem., 2023, 61(S2), 60-65 Research Article DOI: 10.1002/vjch.202300062 Chemical properties and inhibitory activities of tyrosinase, α-glucosidase, and urease from chloroform extract of Curcuma aromatica Salisb. rhizomes Tho Huu Le1,2,3, Thinh Quang Bui1,2, Phu Hoang Dang1,2,3, Hai Xuan Nguyen1,2,3, Truong Nhat Van Do1,2,3, Mai Thanh Thi Nguyen1,2,3, Nhan Trung Nguyen1,2,3* 1 Faculty of Chemistry, University of Science, 227 Nguyen Van Cu Road, District 5, Ho Chi Minh City 70000, Viet Nam 2 Vietnam National University of Ho Chi Minh City, Vo Truong Toan Road, Linh Trung district, Thu Duc City, Ho Chi Minh City 70000, Viet Nam 3 Research Lab for Drug Discovery and Development, University of Science, 227 Nguyen Van Cu Road, District 5, Ho Chi Minh City 70000, Viet Nam Submitted February 18, 2023; Revised April 13, 2023; Accepted April 24, 2023 Abstract "Nghệ trắng" has the scientific name of Curcuma aromatica Salisb., belongs to the Ginger family (Zingiberaceae), and its rhizomes are used to prevent aging, anti-inflammatory, and improve skin. From the chloroform extract of C. aromatica, six known compounds, including (-)-hannokinol (1), (3R,5R)-3,5-diacetoxy-1,7-bis(4-hydroxyphenyl)heptane (2), naringenin (3), 2-(4-(hydroxymethyl)phenyl)propan-2-ol (4), 5-hydroxymethylfurfural (5), and bisacurone (6), were isolated. Structures of all compounds were elucidated by analyzing NMR data together with comparing them to references. All isolated compounds were found for the first time in the C. aromatia rhizomes grown in Vietnam. The results of bioactivity evaluation showed that naringenin (3) has an effect against tyrosinase and α-glucosidase with the IC50 values of 96.4 and 248.2 µM, respectively. (-)-Hannokinol (1) is a moderate bioactivity ingredient capable to inhibiting α-glucosidase and urease with the IC50 value of 216.4 and 244.4 µM, respectively. Consequently, these results suggest that chloroform extract of C. aromatica may be a practical therapeutic approach for diabetes, melanogenesis, and stomach ulcer treatment. Keywords. Curcuma aromatica, tyrosinase, α-glucosidase, urease. 1. INTRODUCTION diarylheptanoids, monoterpenes, sesquiterpenes, diterpenes, alkaloids, and sterols. Previous studies Curcuma aromatica Salisb., belonging to the reported that extracts and compounds isolated from genus Curcuma in the family Zingiberaceae, is this plant had antioxidant, anti-inflammatory, distributed throughout the tropical and subtropical antidiabetic, and anticancer activities.[5-9] regions in the world and widely cultivated in Asian The present study investigated the phytochemical countries, especially in China, India, and Japan.[1] In and biological properties of the rhizomes C. Vietnam, this species, also known as “Nghệ trắng”, is aromatica. From the CHCl3 extract of C. aromatic popularly distributed in Quang Binh Province in the rhizomes, six known compounds, including North and An Giang Province in the South.[2] Its (-)-hannokinol (1), (3R,5R)-3,5-diacetoxy-1,7-bis(4- rhizome is known as an aromatic medicinal herb. hydroxyphenyl)heptane (2), naringenin (3), 2-(4- Rhizomes pasted with milk are used for reducing (hydroxymethyl)phenyl)propan-2-ol (4), stomachache, headache, and acne, improving skin 5-hydroxymethylfurfural (5), and bisacurone (6), tone, while water extract of rhizomes helps treat were isolated. All compounds were tested on the indigestion, rheumatism, and dysentery.[3,4] biological inhibitory activities against tyrosinase, α- C. aromatica is one of Curcuma’s most chemically glucosidase, and urease. It was the first time all investigated species. Phenolic compounds and compounds were isolated from rhizomes of C. terpenoids have been identified, including aromatica Salisb. 60 Wiley Online Library © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH
25728288, 2023, S2, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300062 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry Nhan Trung Nguyen et al. 2. MATERIALS AND METHODS J4 (313.4 mg), J5 (173.0 mg), J6 (1.6 g), J7 (1.1 g), J8 (1.0 g), and J9 (745.7 mg). Sub-fraction J6 was 2.1. Plant material subjected to silica gel, eluted with EtOAc−n-hexane gradient mixtures (v/v, 0:100→100:0) to yield three The rhizomes of Curcuma aromatica were collected sub-fractions, including J6.1 (85.1 mg), J6.2 (831.6 from Tinh Bien district, An Giang province, Viet mg), and J6.3 (29.4 mg). Sub-fraction J6.1 was Nam, in March 2017 and were identified by Mr. Cao subjected to silica gel column chromatography, eluted Ngoc Giang, National Institute of Medical Material. with acetone−n-hexane gradient mixtures (v/v, The voucher sample (DMC-9006) is deposited at the 0:100→60:40), followed by normal-phase Department of Medicinal Chemistry, Faculty of preparative TLC with a CH3OH−EtOAc−n-hexane Chemistry, University of Science, Ho Chi Minh City, mixture (2:18:80), to give 1 (14.5 mg), and 2 (6.9 Viet Nam. mg). Sub-fraction J6.2 was chromatographed over a silica gel column chromatography eluted with 2.2. General experimental procedures chloroform 100% to afford J6.2.1 (508.0 mg), and J6.2.2 (135.2 mg). The fraction J6.2.1 was carried out NMR spectra were taken on a Bruker Avance III 500 by column chromatography, eluted with acetone-n- spectrometer (Brucker BioSpin AG). HRESIMS hexane gradient mixtures (v/v, 0:100→100:0), then measurement was carried out on a Bruker micrOTOF purified by normal-phase preparative TLC with an QII spectrometer (Bruker Singapore Pte., Ltd.). acetone−n-hexane mixture (30:70) to yield 3 (10.5 Analytical and preparative TLCs were carried out on mg) and 6 (3.0 mg). Sub-fraction J6.2.2 was precoated Kieselgel 60F254 or RP-18F254 plates separated by silica gel column chromatography eluted (Merck KGaA). α-glucosidase (EC 3.2.1.20) from with acetone-n-hexane mixtures (v/v, 0:100→80:20), Saccharomyces cerevisiae, p-nitrophenyl-α-D- followed by EtOAc-n-hexane gradient mixtures (v/v, glucopyranoside, tyrosinase (EC 1.14.18.1) from 0:100→100:0) to yield 4 (4.8 mg). Sub-fraction J6.3 mushroom (3933 U/mL), ʟ-3,4- (29.4 mg) was conducted on thin player dihydroxyphenylalanine (ʟ-DOPA), and urease (EC chromatography with an acetone-CHCl3 mixture 3.5.1.5) from Canavalia ensiformis (Jack bean) were (20:80), following a MeOH-CHCl3 mixture (6:94) to purchased from Sigma-Aldrich (Sigma-Aldrich Pte. obtain 5 (6.0 mg). Ltd.). Acarbose, kojic acid, hydroxyurea, urea, and DMSO were purchased from Merck (Merck KGaA). (-)-Hannokinol (1): 1H and 13C-NMR (CD3COCD3, Other chemicals were of the highest grade available. 500 MHz, see table S1), HRESIMS m/z 315.1603 [M-H]-, [𝛼]25 -10.9 (c = 0.10, acetone). 𝐷 2.3. Extraction and isolation (3R,5R)-3,5-Diacetoxy-1,7-bis(4- In this study, the dried rhizomes of C. aromatica (6.5 hydroxyphenyl)heptane (2): 1H and 13C-NMR kg) were subjected to extraction via a Soxhlet (CD3COCD3 and CH3OD, 500 MHz, see Table extractor using methanol as the solvent. The resulting S2), [𝛼]25 +43.6 (c = 0.06, MeOH). 𝐷 extract (834.9 g) was suspended in water and partitioned successively with n-hexane, chloroform, Naringenin (3): 1H and 13C-NMR (DMSO-d6, 500 and ethyl acetate. The resultant solutions were MHz, see Table S3), [𝛼]25 - 23.0 (c = 0.02, MeOH). 𝐷 combined and subsequently evaporated under reduced pressure to yield n-hexane (125.1 g), CHCl3 2-(4-(Hydroxymethyl)phenyl)propan-2-ol (4): 1H (272.2 g), EtOAc (101.9 g), and H2O (300.0 g) and 13C-NMR (CD3COCD3, 500 MHz, see table S4). extracts, respectively. The CHCl3-soluble extract (272.2 g) was subjected to a silica gel column 5-Hydroxymethylfurfural (5): 1H and 13 C-NMR chromatography eluted with acetone–CHCl3 gradient (CD3COCD3, 500 MHz, see Table S5). mixtures (v/v, 0:100→100:0) to afford seventeen fractions, including A (9.2 g), B (2.9 g), C (3.6 g), D Bisacurone (6): 1H and 13C-NMR (CD3COCD3, 500 (4.8 g), E (4.7 g), F (4.3 g), G (5.4 g), H (18.8 g), I MHz, see table S6); HRESIMS m/z 275.1616 (12.5 g), J (5.1 g), K (59.9 g), L (47.9 g), M (16.9 g), [M+Na]+. N (8.7 g), O (10.3 g), P (11.3 g), and Q (44.4 g). The fraction J was passed over silica gel column 2.4. In vitro biological assay chromatography, eluted with acetone–CHCl3 gradient mixtures (v/v, 0:100→100:0) to afford nine fractions, Tyrosinase and α-glucosidase inhibitory activity including J1 (37.9 mg), J2 (18.9 mg), J3 (62.8 mg), assays were performed in our publication.[10,11] © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 61
25728288, 2023, S2, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300062 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry Chemical properties and inhibitory activities… Urease inhibitory activity was described earlier[12] J = 8.4 Hz, H-3'/5' and H-3''/5'') and δH 7.02 (4H, d, J with slight modifications with the concentrations = 8.4 Hz, H-2'/6' and H-2''/6'')]. It also displayed the ranging from 250 to 10 μM. Briefly, 50 μL urease (30 presence of two benzylic methylene groups [δH 2.55 U/mL) was generated in 920 μL sample solution in (2H, ddd, J = 13.8, 9.5, and 7.0 Hz, H-1a and H-7a), phosphate buffer (0.01 M, pH 7.0) to start the and 2.67 (2H, ddd, J = 13.8, 9.6, and 5.8 Hz, H-1b reaction. After incubating at room temperature for 30 and H-7b)], two oxymethine groups [δH 3.88 (2H, m, min, the reaction was initiated by adding 500 μL urea H-3, H-5)] and three methylene groups [δH 1.57 (2H, (60 mM) and the mixtures were incubated for another t, J = 5.8 Hz, H-4), and 1.68 (4H, m, H-2, H-6)]. On 20 min. Then, 30 μL of red phenol reagent (1 mg/mL) the other hand, the 13C NMR spectrum revealed the was added and incubated for the next 10 min to signals of two benzen rings (δC 156.2, 134.2, 130.1, identify the reaction. The anti-urease activity of the and 115.9), seven sp3 carbons comprising three sample was determined by calculating the decrease in methylene groups (δC 31.9, 41.1, and 44.8), and one absorbance measured at 556 nm. Hydroxyurea was a oxymethine group (δC 68.4). The HMBC spectrum positive control in this screening. showed correlations from H-3 to C-1, C-2, C-4, and The activity of samples was determined by C-5; from H-2'/6' to C-1; from H-3'/5' to C-4' (figure enzyme inhibitory percentage in the above assay, 2). According to these spectra, 1 was indicated as a calculated by the following equation: Inhibition (%) diarylheptanoid with a symmetrical structure. = (A0 − A1)/A0 × 100, where A0 and A1 are the Comparison of the spectral data of 1 and those of activities of the enzyme without and with test sample. literature[13] (Table S1) suggested the planar structure The mean values of data from these experiments of compound 1 was 3,5-dihydroxy-1,7-bis(4- determined IC50 values for the tested activities. hydroxyphenyl)heptane. The relative structure was determined by comprising with the 13C NMR 3. RESULTS AND DISCUSSION chemical shifts. Two hydroxyl groups at carbons C-3 and C-5 was suggested anti-configuration based on The phytochemicals of CHCl3 extract of C. aromatic the 13C NMR chemical shifts of both of oxymethine rhizomes yielded six known compounds including carbons which are δC 71.6 ppm for syn-configuration (-)-hannokinol (1), (3R,5R)-3,5-diacetoxy-1,7-bis(4- and δC 62.8 ppm for anti-configuration in the hydroxyphenyl)heptane (2), naringenin (3), 2-(4- literature[13] whereas they illustrated at δC 68.4 ppm in (hydroxymethyl)phenyl)propan-2-ol (4), 5- 1. The absolute configuration of the hydroxyl group hydroxymethylfurfural (5), and bisacurone (6). All at carbons C-3 and C-5 of 1 was determined via isolated compounds are reported for the first time in specific rotation, [𝛼]25 -10.9 (c 0.10, acetone), 𝐷 this species (Figure 1). similar to (-)-hannokinol ([𝛼]25 -19, acetone)[14] while 𝐷 those of (+)-hannokinol was ([𝛼]25 +11.4 (c 0.38, 𝐷 MeOH)).[13] Thus, compound 1 was indicated (-)- hannokinol. Figure 1: The structure of six compounds (1-6) isolated from the C. aromatica rhizomes Compound 1 was isolated as a white powder, dissolved well in acetone, and indicated by spraying with vanillin, a brown circle appeared. Its HRESIMS showed a pseudo-molecular ion peak at m/z 315.1603 [M-H]- (calcd. for C19H23O4, 315.1602) corresponding to the molecular formula C19H24O4. The 1H NMR spectrum of 1 revealed eight protons of Figure 2: Key HMBC correlations (solid arrow) two 1,4–disubstituted aromatic rings [δH 6.73 (4H, d, observed for 1, 2, and 6 © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 62
25728288, 2023, S2, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300062 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry Nhan Trung Nguyen et al. Compound 2 was isolated as a yellowish oil, naringenin[16], showed good similarity. Thus, this which dissolved well in acetone, and indicated by compound was defined as naringenin. spraying with vanillin, a brown circle appeared. The Compound 4 was isolated as a yellowish oil, 1 H NMR and 13C NMR spectrum closely resembled which dissolves in acetone, and indicated by spraying those of 1. However, the 13C NMR spectrum of 2 with vanillin, a light blue circle appeared. The 1H revealed the presence of two acetoxyl groups at δC NMR spectrum of 4 showed the presence of one 1,4- 221.1 and 2170.7. It also was supported by its 1H disubstituted benzene ring [δH 7.28 (2H, d, J = 8.6 Hz, NMR spectrum with two acetoxyl groups were H-3'/5'), 7.47 (2H, d, J = 8.6 Hz, H-2'/6')]. The evidenced at δH 1.96 (6H, s). Thus, 2 was suggested spectrum also displayed the single signal [δH 4.59 as a derivative of 1 with two acetoxyl groups. (2H, s, H-1'')] regarding a hydroxymethyl group Compared with the 1H NMR spectrum of 1, the 1H bonding to a 1,4-disubstituted benzene ring. In NMR chemical shifts of H-3/5 were up-field-shifted addition, another substitution of a benzene ring was to 4.96 ppm indicating that two acetoxyl groups determined by the signal [δH 1.50 (6H, s, H-1, H-3)] attach to both C-3 and C-5 (Table S2). The HMBC of two methyl groups that together attach to a spectrum of 2 is similar to 1 except for adding HMBC quaternary carbon. The 13C NMR spectrum of 4 correlations from H-3/5 to carbonyl carbon at δC showed four signals of the 1,4-disubstituted benzene 170.7 in 2 (figure 2). These data were further ring (δC 125.2, 127.1, 141.1, and 150.0), one methyl confirmed 2 to be 3,5-diacetoxy-1,7-bis(4- signal (δC 32.5), and two oxygenated carbon signals hydroxyphenyl)heptane. Comparison the spectral (δC 64.6 and 71.9) (table S4). A comparison of the data of 2 with those of literature[15] showed that two spectral data of 4 and those of literature values[17] acetoxyl groups at C-3 and C-5 in 2 also existed an suggested the chemical structure of 4 was 2-(4- anti-configuration similar to 1. The absolute (hydroxymethyl)phenyl)propan-2-ol. configuration at C-3 and C-5 of 1 were also concluded Compound 5 was isolated as a yellow oil, by the optical rotation and compared with those of dissolved in acetone. The 1H-NMR spectrum showed reference. The positive specific rotation of 2 was five proton signals, including an aldehydic group [δH measured to be [𝛼]25 + 43.6 (c = 0.06, MeOH), which 𝐷 9.60 (1H, s)], an oxymethylene group [δH 4.65 (2H, is similar to those of (3R,5R)-3,5-diacetoxy-1,7- s)], and a pair of olefin proton signal [δH 7.37 (1H, d, bis(4-hydroxyphenyl)heptane, isolated from the J = 3.5 Hz, H-3), 6.58 (1H, d, J = 3.5 Hz, H-4]. Its 13 rhizomes of Curcuma kwangsiensis ([𝛼]25 +11.8 (c = 𝐷 C-NMR spectrum revealed one aldehydic carbonyl 0.20, MeOH)).[15] The positive specific rotation at C- carbon (δC 178.1), four aromatic carbons of the furan 3 and C-5 of 2 was suggested the 3R and 5R ring comprising two oxygenated carbons (δC 162.9 configurations. Therefore, the structure of compound and 153.5), and two methine olefinic carbons (δC 2 was concluded to be (3R,5R)-3,5-diacetoxy-1,7- 123.6 and 110.2), and one oxymethylene carbon (δC bis(4-hydroxyphenyl)heptane. 57.6) (table S6). According to spectral analysis, Compound 3 was a yellowish powder dissolved compound 5 was indicated as the furan ring with one in DMSO. The 1H-NMR spectrum revealed the hydroxymethyl group and one aldehydic group. signals of a 1,4-disubstituted aromatic ring [δH 6.79 Based on spectroscopic analysis combined with (2H, d, J = 8.5 Hz, H-3'/5')], 7.31 (2H, d, J = 8.5 Hz, literature data,[13] compound 5 was 5-hydroxymethyl- H-2'/6')] and a 1,2,3,5-tetrasubstituted aromatic ring furfural. [δH 5.86 (2H, s, H-6/8)]. Its 1H-NMR also revealed a Compound 6 was isolated as a colorless oil characteristic signal of hydroxyl group [δH 12.14 (1H, dissolved in acetone and indicated by spraying with s, 5-OH)] together with an oxymethine group [δH 5.42 vanillin, appearing as a yellowish circle. Its (1H, dd, J = 12.7, and 2.9 Hz, H-2)], a methylene HRESIMS showed a molecular ion peak at m/z group [δH 2.67 (1H, dd, J = 17.1 and 3.0 Hz, H-3), and 275.1616 [M+Na]+ (calcd. for C15H24O3Na, 3.34 (1H, dd, J = 17.1 and 12.7 Hz, H-3)]. These data 275.1623) corresponding to the molecular formula indicated the characteristic flavanone-type flavonoid. C15H24O3. The 1H-NMR spectrum also revealed the The 13C NMR spectrum showed the resonance signals presence of three olefin protons [δH 5.55 (2H, s, H-2, of a ketone carbon (δC 196.1, C-4), twelve aromatic and H-3), 6.15 (2H, qq, J = 1.2, and 1.2 Hz, H-10)], carbons at δC from 167.1 to 95.1 ppm in the down- four methyl groups [δH 0.86 (3H, d, J = 6.8 Hz, H- field chemical shift and the signals of an oxymethine 14), 1.21 (3H, s, H-15), 1.87 (3H, d, J = 1.2 Hz, H- carbon (δC 78.3), a methylene carbon (δC 41.9) in the 13), 2.09 (3H, d, J = 1.2 Hz, H-12)], three methine up-field region (table S3). Comparison of the NMR groups [δH 2.32 (1H, m, H-1), 2.12 (1H, m, H-7), 3.71 spectral data of 3 with a known flavanone, (1H, m, H-5)], and two methylene groups [δH 1.64 © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 63
25728288, 2023, S2, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300062 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry Chemical properties and inhibitory activities… (1H, m, H-6a), 1.83 (1H, m, H-6b), 2.21 (1H, dd, J = 4. W. Choochote, D. Chaiyasit, D. Kanjanapothi, E. 15.5 and 8.9 Hz, H-8a), 2.50 (1H, dd, J = 15.5 and 4.7 Rattanachanpichai, A. Jitpakdi, B. Tuetun, B. Hz, H-8b)]. The 13C-NMR and HSQC spectra showed Pitasawat. Chemical composition and anti-mosquito resonances of 15 carbons of a sesquiterpene, potential of rhizome extract and volatile oil derived from Curcuma aromatica against Aedes aegypti including a carbonyl carbon (δC 200.6), four olefinic (Diptera: Culicidae), J. Vector Ecol., 2005, 30(2), 302- carbons (δC 125.0, 131.4, 134.3, and 154.5), two 309. oxygenated carbons (δC 73.8 and 70.2) together with 5. M. Kuroyanagi, A. Ueno, K. Ujiie, S. J. C. Sato. signals at δC from 49.4 to 17.2 ppm regarding two Structures of sesquiterpenes from Curcuma aromatica methine, two methylene, and four methyl carbons Salisb, Chem. Pharm. Bull., 1987, 35(1), 53-59. (Table S7). The HMBC spectrum showed the 6. M. Kuroyanagi, A. Ueno, K. Koyama, S. Natori. correlations between H-12(-13)/C-10/C-11, H-10/C- Structures of sesquiterpenes of Curcuma aromatica 9, H-8/C-9/C-10, H-14/C-8/C-7/C-1, H-6/C-7/C-1/C- SALISB. II.: Studies on minor sesquiterpenes, Chem. 5, H-2/C-1, H-3/C-4 and H-15/C-3/C-4/C-5, which Pharm. Bull., 1990, 38(1), 55-58. indicated 6 as bisabolane-type sesquiterpene (figure 7. S. Revathi, N. Malathy. Antibacterial activity of rhizome of Curcuma aromatica and partial 2). A comparison of the spectral data of 6 with those purification of active compounds, Indian J. Pharm. of literature[18,19] revealed the chemical structure of 6 Sci., 2013, 75(6), 732-737. was confirmed as bisacurone. 8. X. D. Qin, Y. Zhao, Y. Gao, F. C. Ren, S. Yang, F. All isolated compounds (1-6) were tested for their Wang. Curcumaromins A, B, and C, Three novel tyrosinase, α-glucosidase, and urease inhibitory curcuminoids from Curcuma aromatica, Helv. Chim. activities. The tyrosinase inhibition assay was carried Acta, 2015, 98(9), 1325-1331. out at concentrations ranging from 100-10 μM while 9. S. Ahmad, M. Ali, S. H. Ansari, F. Ahmed. concentrations ranging from 250-10 μM were Phytoconstituents from the rhizomes of Curcuma observed for α-glucosidase and urease inhibition aromatica Salisb, J. Saudi Chem. Soc., 2011, 15(3), assays. Biological activity research showed that 287-290. 10. N. T. Nguyen, M. H. K. Nguyen, H. X. Nguyen, N. K. compound 3 showed a lightly effect against N. 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