Flavonoids from Alpinia vietnamica, and their cytotoxic, antioxidative, and α-glucosidase inhibitory activities

Chia sẻ: _ _ | Ngày: | Loại File: PDF | Số trang:5

Thêm vào BST

Báo xấu

12
lượt xem 2
download

Download Vui lòng tải xuống để xem tài liệu đầy đủ

Alpinia vietnamica H.Ð. Tran, Luu & Skornick was identified as a new species in 2019, which is widely distributed in Thua Thien Hue, Quang Nam, and Kon Tum provinces, Vietnam. The current study wishes to report phytochemical investigation, and the biological activities (cytotoxic, antioxidative, and α-glucosidase inhibitory) of isolated compounds.

Chủ đề:

Bình luận(0) Đăng nhập để gửi bình luận!

Lưu

Nội dung Text: Flavonoids from Alpinia vietnamica, and their cytotoxic, antioxidative, and α-glucosidase inhibitory activities

Received: 25 May 2023 Revised: 7 August 2023 Accepted: 14 August 2023 DOI: 10.1002/vjch.202300182 RESEARCH ARTICLE Flavonoids from Alpinia vietnamica, and their cytotoxic, antioxidative, and α-glucosidase inhibitory activities Nguyen Thanh Tra1,2 Nguyen Thi Thuy Hoa2 Nguyen Thi Thuy Linh1 Nguyen Thi Thu Ha1,2 Ba Thi Cham1 Le Thi Tu Anh1 Ninh The Son1,2 1 Institute of Chemistry, Vietnam Academy Science and Technology (VAST), Cau Giay, Hanoi, Abstract Vietnam Phytochemical research of the 80% EtOH whole plant extract of Alpinia 2 Graduate University of Science and Technology, vietnamica H.Ð. Tran, Luu & Skornick resulted in the isolation and structural Vietnam Academy Science and Technology elucidation of seven compounds 1–7, including two flavones quercetin-3-O- (VAST), Cau Giay, Hanoi, Vietnam α-L-rhamnosyl (1→2)-α-L-rhamnoside (1) and diosmetin (2), three flavanones Correspondence pinocembrin (3), alpinetin (4) and 5-O-methylnaringenin (5), and two chalcones Ninh The Son, Institute of Chemistry, Vietnam cardamonin (6) and helichrysetin (7). The isolated compounds have shown bio- Academy Science and Technology (VAST), 18 logical effects at different levels. Two chalcones 6–7 showed cytotoxicity toward Hoang Quoc Viet, Cau Giay, Hanoi 10000, Vietnam. four cancer cell lines KB, MCF7, A549, and HepG2, especially compound 7 strongly Email: ntson@ich.vast.vn inhibited the growth of A549 cancerous cells with the IC50 of 6.81 μM. Flavone 1 strongly exhibited antioxidative activity to scavenge DPPH radicals with the IC50 of Funding information 51.68 μM. Flavone 2 and flavanone 4 moderately inhibited enzyme α-glucosidase Vietnam Academy Science and Technology, with the IC50 values of 296.34–324.64 μM. Grant/Award Number: VAST04.04/22-23 KEYWORDS Alpinia vietnamica, antioxidant, cytotoxicity, flavonoids, rhizome, α-glucosidase inhibitory 1 INTRODUCTION Vietnam.6 The current study wishes to report phytochem- ical investigation, and the biological activities (cytotoxic, Alpinia is a genus of 230 flowering plants in the ginger antioxidative, and α-glucosidase inhibitory) of isolated family Zingiberaceae.1 Species are native to tropical and compounds. subtropical climates.1 Plants of this genus were exten- sively utilized for various aims for years. For instance, Alpinia purpurata is often used as an ornamental plant.2 2 MATERIALS AND METHODS Alpinia galanga is one of the crucial ingredients for cur- ries, and has been utilized as a flavoring in meat and soup 2.1 Plant materials preparations.1,3 Almost Alpinia species are also extensively used as traditional medicines for various diseases such as A. vietnamica fresh whole plant was collected from Thuong indigestion, vomiting, gastralgia, etc.1 Quang, Nam Dong, Hue province, Vietnam in August 2021. Regarding the phytochemical investigation, in 2017, Ma The plant material was identified by taxonomist Vu Tien et al. summarized that more than 500 compounds were Chinh, Vietnam National Museum of Nature. The voucher isolated from 35 species, in which flavonoids, terpenoids, specimen AV-2021 has been deposited at Institute of Chem- and diarylheptanoids are the principal compounds.1 In the istry, Vietnam Academy of Science and Technology. pharmacological aspect, Alpinia plants have a wide range of bioactivities such as anticancer, antioxidant, antiviral, and cardiovascular activities.1,4,5 2.2 General experimental procedures Alpinia vietnamica H.Ð. Tran, Luu & Skornick was identi- fied as a new species in 2019, which is widely distributed The equipment for the current study are described in in Thua Thien Hue, Quang Nam, and Kon Tum provinces, Supporting Information. © 2024 Vietnam Academy of Science and Technology and Wiley-VCH GmbH. 98 wileyonlinelibrary.com/journal/vjch Vietnam J. Chem. 2024;62:98–102.
25728288, 2024, 1, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300182 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 TRA ET AL. 99 2.3 Extractions and purification 157.3 (C-8a), 151.1 (C-4′), 146.8 (C-3′), 123.0 (C-6′), 118.6 (C- 1′), 112.9 (C-2′), 112.1 (C-5′), 103.7 (C-4a), 103.5 (C-3), 98.8 The dried powders of A. vietnamica whole plant (2.5 kg) (C-6), 93.9 (C-8), 55.7 (4′-OMe). were immersed with 80% EtOH (3 L × 3 times, 48 h). After concentration under reduced pressure, the obtained EtOH extract (19.4 g) was suspended in H2 O, and then partitioned 2.3.3 Pinocembrin (3) with n-hexane and EtOAc. These soluble fractions (frs) were then evaporated, to afford the corresponding frs, including Yellowish amorphous powder; HR-ESIMS (+): m/z 257.0800 n-hexane (2.6 g), EtOAc (8.6 g), and H2 O residue (8.2 g). [M+H]+ (calcd. for C15 H13 O4 : 257.0803); 1 H NMR (CDCl3 , The fr EtOAc was fractionated into nine frs E1-E9 by sil- 600 MHz): 7.37-7.45 (5H, m, H-2′ to H-6′), 6.00 (2H, s, H- ica gel column chromatography (CC) eluting with a gradient 6, H-8), 5.43 (1H, dd, 3.0, 13.2 Hz, H-2), 3.09 (1H, dd, 13.2, of CH2 Cl2 -MeOH (1:0 to 0:1, v/v). The fr E3 (0.8 g) was 17.4 Hz, H-3a), 2.84 (1H, dd, 3.0, 17.4 Hz, H-3b); 13 C NMR chromatographed over silica gel, eluting with a stepwise (CDCl3 , 150 MHz): 195.7 (C-4), 164.7 (C-7), 164.3 (C-5), 163.1 gradient of CH2 Cl2 -CH3 COCH3 (10:1 to 1:10, v/v), to give (C-8a), 138.3 (C-1′), 128.9 (C-3′, C-4′, C-5′), 126.1 (C-2′, C-6′), four frs E31-E34. Compounds 1 (6.7 mg) and 4 (12.1 mg) 103.2 (C-4a), 96.7 (C-6), 95.5 (C-8), 79.2 (C-2), 43.3 (C-3). were separated from the fr E34 by using a Sephadex LH-20 CC [MeOH/CH2 Cl2 (9:1, v/v)]. The fr E4 (1.2 g) was fraction- ated by normal silica gel CC [CH2 Cl2 -EtOAc (9:1, v/v)], to 2.3.4 Alpinetin (4) afford compound 6 (15.3 mg), and three frs E41-E43. The fr E42 (0.3 g) was chromatographed over RP-18 column Yellowish amorphous powder; HR-ESIMS (+): m/z 271.0960 [MeOH-H2 O (2:1, v/v)], to yield compound 5 (2.9 mg). The [M+H]+ (calcd. for C16 H15 O4 : 271.0967); 1 H NMR (CD3 OD, fr E5 (0.7 g) was subjected to a Sephadex LH-20 CC [MeOH- 600 MHz): 7.50 (2H, m, H-2′, H-6′), 7.43 (2H, m, H-3′, H-5′), CH2 Cl2 (9:1, v/v)], to afford three frs E51-E53. Compounds 7.37 (1H, m, H-4′), 6.11 (1H, d, 1.8 Hz, H-6), 6.06 (1H, d, 1.8 Hz, 7 (3.5 mg) and 2 (4.2 mg) were isolated from the corre- H-8), 5.44 (1H, dd, 3.0, 13.2 Hz, H-2), 3.84 (3H, s, 5-OMe), 2.99 sponding frs E51 and E52 by the preparative TLC (thin layer (1H, dd, 13.2, 16.8 Hz, H-3a), 2.77 (1H, dd, 3.0, 16.8 Hz, H-3b); 13 C NMR (CD OD, 150 MHz): 191.6 (C-4), 167.4 (C-7), 164.5 chromatography) [CH2 Cl2 -MeOH (95:5, v/v)]. 3 (C-5), 164.3 (C-8a), 140.6 (C-1′), 129.6 (C-3′, C-5′), 129.4 (C- 4′), 127.2 (C-2′, C-6′), 105.7 (C-4a), 97.2 (C-8), 94.4 (C-6), 80.1 2.3.1 Quercetin-3-O-α-L-rhamnosyl (C-2), 56.1 (5-OMe), 46.4 (C-3). (1→2)-α-L-rhamnoside (1) Yellowish amorphous powder; HR-ESIMS (+): m/z 595.1648 2.3.5 5-O-Methylnaringenin (5) [M+H]+ (calcd. for C27 H31 O15 : 595.1649); 1 H NMR (CD3 OD, 600 MHz): 7.36 (1H, d, 2.0 Hz, H-2′), 7.34 (1H, dd, 2.0, 7.0 Hz, Yellowish amorphous powder; HR-ESIMS (+): m/z 287.0906 H-6′), 6.40 (1H, d, 1.5 Hz, H-8), 6.94 (1H, d, 7.0 Hz, H-5′), 6.22 [M+H]+ (calcd. for C16 H15 O5 : 287.0913); 1 H NMR (CD3 OD, (1H, d, 1.5 Hz, H-6), 5.51 (1H, d, 1.0, H-1″), 5.01 (1H, d, 1.5 Hz, 600 MHz): 7.32 (2H, d, 8.4 Hz, H-2′, H-6′), 6.83 (2H, d, 8.4 Hz, H-1″’), 4.30 (1H, dd. 1.5, 3.0 Hz, H-2″), 3.89 (1H, dd, 2.5, 8.0 Hz, H-3′, H-5′), 6.10 (1H, d, 2.4 Hz, H-6), 6.03 (1H, d, 2.4 Hz, H- H-3″), 3.96 (1H, dd, 1.5, 3.0 Hz, H-2″’), 3.63-3.60 (2H, m, H- 8), 5.33 (1H, dd, 3.0, 13.2 Hz, H-2), 3.84 (3H, s, 5-OMe), 3.04 5″, H-3″’), 3.45 (1H, dd, 5.0, 8.5 Hz, H-5″’), 3.39-3.34 (2H, m, (1H, dd, 13.2, 16.2 Hz, H-3a), 2.68 (1H, dd, 3.0, 16.2 Hz, H-3b); 13 C NMR (CD OD, 150 MHz): 192.2 (C-4), 167.2 (C-7), 166.7 H-4″, H-4″’), 1.23 (3H, d, 5.0 Hz, 5″-Me), 0.97 (3H, d, 5.0 Hz, 3 5″’-Me); 13 C NMR (CD3 OD, 150 MHz): 179.5 (C-4), 165.9 (C-7), (C-5), 164.3 (C-8a), 158.9 (C-4′), 131.3 (C-1′), 128.9 (C-2′, C- 163.2 (C-5), 159.2 (C-2), 158.5 (C-8a), 149.8 (C-4′), 146.4 (C- 6′), 116.3 (C-3′, C-5′), 105.7 (C-4a), 97.1 (C-8), 94.2 (C-6), 80.1 3′), 136.3 (C-3), 122.9 (C-6′), 122.8 (C-1′), 116.9 (C-2′), 116.4 (C-2), 56.1 (5-OMe), 46.3 (C-3). (C-5′), 105.9 (C-4a), 103.7 (C-1″’), 102.4 (C-1″), 99.8 (C-6), 94.7 (C-8), 79.0 (C-2″), 73.9 (C-4″), 73.5 (C-4″’), 72.2 (C-5″), 72.0 (C- 3″), 71.9 (C-2″’, C-5″’), 70.3 (C-2″’), 17.8 (5″-Me), 17.7 (5″’-Me). 2.3.6 Cardamonin (6) Yellowish amorphous powder; HR-ESIMS (+): m/z 271.0962 2.3.2 Diosmetin (2) [M+H]+ (calcd. for C16 H15 O4 : 271.0970); 1 H NMR (DMSO, 600 MHz): 7.72 (2H, m, H-2, H-6), 7.83 (1H, d, 15.6 Hz, H- Yellowish amorphous powder; HR-ESIMS (+): m/z 301.0705 8), 7.66 (1H, d, 15.6 Hz, H-7), 7.44 (3H, m, H-3 to H-5), 6.02 [M+H]+ (calcd. for C16 H13 O6 : 301.0712); 1 H NMR (DMSO, (1H, d, 1.8 Hz, H-3′), 5.93 (1H, d, 1.8 Hz, H-5′), 3.87 (3H, s, 2′- 600 MHz): 7.51 (1H, dd, 2.4, 8.4 Hz, H-6′), 7.40 (1H, d, 2.4 Hz, OMe); 13 C NMR (DMSO, 150 MHz): 191.7 (C-9), 166.2 (C-4′), H-2′), 7.06 (1H, d, 8.4 Hz, H-5′), 6.70 (1H, s, H-3), 6.45 (1H, d, 165.0 (C-6′), 162.7 (C-2′), 141.7 (C-7), 134.9 (C-1), 130.3 (C- 1.8 Hz, H-8), 6.19 (1H, d, 1.8 Hz, H-6), 3.85 (3H, s, 4′-OMe); 13 C 4), 129.0 (C-3, C-5), 128.3 (C-2, C-6), 127.5 (C-8), 105.1 (C-1′), NMR (DMSO, 150 MHz): 181.6 (C-4), 164.1 (C-7), 163.5 (C-2), 95.8 (C-5′), 91.7 (C-3′), 56.0 (2′-OMe).
25728288, 2024, 1, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300182 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 100 TRA ET AL. FIGURE 1 Isolated compounds from A. vietnamica. 2.3.7 Helichrysetin (7) 1″’ (δC 103.7), and two methyl groups 5″-Me (δH 1.23, 3H, d, 5.0 Hz)/(δC 17.8) and 5″’-Me (δH 0.97, 3H, d, 5.0 Hz)/δC Yellowish amorphous powder; HR-ESIMS (+): m/z 287.0906 17.7.9 The HMBC correlation H-1″’/C-2″ revealed that the [M+H]+ (calcd. for C16 H15 O5 : 287.0913); 1 H NMR (CD3 OD, connection between two sugar units was typical (1→2) link- 600 MHz): 7.80 (1H, d, 15.6 Hz, H-8), 7.70 (1H, d, 15.6 Hz, H- age, whereas the key HMBC correlation H-1″/C-3 argued 7), 7.53 (2H, d, 8.4 Hz, H-2, H-6), 6.85 (2H, d, 8.4 Hz, H-3, H-5), that glycone linked to carbon C-3 of aglycone. From these 6.03 (1H, d, 2.4 Hz, H-3′), 5.95 (1H, d, 2.4 Hz, H-5′), 3.94 (3H, s, findings, compound 1 was confirmed as quercetin-3-O-α- 2′-OMe); 13 C NMR (CD3 OD, 150 MHz): 194.0 (C-9), 168.6 (C- L-rhamnosyl (1→2)-α-L-rhamnoside. To date, this substance 4′), 166.4 (C-6′), 164.6 (C-2′), 161.1 (C-4), 143.7 (C-7), 131.3 was only found in the stem of A. densespicata with moderate (C-2, C-6), 128.4 (C-1), 125.5 (C-8), 116.9 (C-3, C-5), 104.0 (C- anti-inflammatory inhibitory activity.10 1′), 97.1 (C-5′), 92.5 (C-3′), 56.3 (2′-OMe). Compound 2 was also obtained as a yellowish amor- phous powder. The molecular formula of compound 2 was established as C16 H12 O6, which is deduced from the quasi- 2.4 Biological assays molecular ion peak at m/z 301.0705 [M+H]+ (calcd. for C16 H13 O6 : 301.0712) in the HR-ESIMS (+) spectrum. The 1 H Experimental protocols for cytotoxicity, antioxidant, and NMR data of compound 2 included the signals of ring AC [H- α-glucosidase inhibition are provided in Supporting Infor- 3 (1H, δH 6.70, s), H-6 (1H, δH 6.19, d, 1.8 Hz), and H-8 (1H, δH mation.7,8 6.45, d, 1.8 Hz)], and the signals of ring B [ABX spin system H-2′ (δH 7.40, 1H, d, 2.4 Hz), H-6′ (δH 7.51, 1H, dd, 2.4, 8.4 Hz), and H-5′ (δH 7.06, 1H, d, 8.4 Hz), and 4′-OMe (δH 3.85, 3H, s)]. 3 RESULTS AND DISCUSSION The 13 C NMR data of 2 matched well with the 1 H NMR data, including the signals of six CH, nine C4 , and one OMe. The Compound 1 was separated as a yellowish amorphous HMBC correlation 4′-OMe/C-4′ indicated that the methoxy powder. The molecular formula of this compound was group located at C-4′. Based on this analysis, compound 2 C27 H30 O15 , which is deduced from the quasi-molecular was identified to be a flavone, which is named diosmetin.11 ion peak at m/z 595.1648 [M+H]+ (calcd. for C27 H31 O15 : This substance was also found in several Alpinia plants, such 595.1649) in its HR-ESIMS (+) spectrum. The 1D, 2D-NMR as A. zerumbet leaf.12 data indicated that compound 1 was a quercetin glycoside Compound 3 was purified as a yellowish amorphous (Figure 1). The 1 H NMR of quercetin nucleus was character- powder. In the HR-ESIMS (+) spectrum, the quasi-molecular ized by the signals of ring AC [H-6 (1H, δH 6.22, d, 1.5 Hz) and ion peak at m/z 257.0800 [M+H]+ (calcd. for C15 H13 O4 : H-8 (1H, δH 6.40, d, 1.5 Hz)], and the signals of ring B [ABX 257.0803), indicating the chemical formula of this com- spin system H-2′ (δH 7.36, 1H, d, 2.0 Hz), H-6′ (δH 7.34, 1H, dd, pound was C15 H12 O4 . The 1 H NMR data of compound 3 2.0, 7.0 Hz), and H-5′ (δH 6.94, 1H, d, 7.0 Hz)]. Glycone was displayed a pattern of flavanone. A broad singlet signal at structurally formulated by two α-L-rhamnosyl units with δH 6.00 was assigned H-6 and H-8. Methine and methylene two characteristic anomeric protons H-1″ (δH 5.51, 1H, d, protons of ring C resonated at 2.84–5.43 ppm. Chemical 1.0 Hz)/C-1″ (δC 102.4) and H-1″’ (δH 5.01, 1H, d, 1.5 Hz)/C- shifts at δH 7.37–7.45 belong to ring B. The 13 C NMR data
25728288, 2024, 1, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300182 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 TRA ET AL. 101 TA B L E 1 Cytotoxic, antioxidative, and antidiabetic results of flavonoids 1–7 (IC50 μM). Cytotoxic DPPH radical α-Glucosidase No. KB MCF7 A549 HepG2 scavenging inhibition 1 – 138.37 ± 13.65 43.48 ± 6.35 – 51.68 ± 2.16 – 2 – – 293.07 ± 26.60 – 250.97 ± 4.43 324.64 ± 14.52 3 – 315.71 ± 28.30 177.59 ± 14.0 – – – 4 390.74 ± 33.40 – – – – 296.34 ± 3.74 5 – – – – – – 6 223.62 ± 18.50 236.79 ± 21.40 409.02 ± 36.10 306.42 ± 28.30 – – 7 69.86 ± 6.62 23.02 ± 2.73 6.81 ± 0.60 89.98 ± 9.38 – – Ellipticine 1.66 ± 0.08 1.58 ± 0.16 1.62 ± 0.12 1.66 ± 0.16 Quercetin 32.99 ± 0.83 Acarbose 208.43 ± 4.68 – denotes inactive. is in agreement with the 1 H NMR data, including the sig- C-2′. Based on these findings, compound 6 was elucidated nals of eight CH, one CH2 , and six C4 . Based on these as cardamonin.15 data, compound 3 was identified to be (2S)-pinocembrin.13 Compound 7 was purified as a yellowish amorphous This flavanone was one of the principal compounds in A. powder. The NMR data of compound 7 was similar to those katsumadai seed.14 of 6, except for the replacement of proton H-4′ in com- Compound 4 was isolated as a yellowish amorphous pound 6 by OH in compound 7. This was further confirmed powder with the quasi-molecular ion peak at m/z 271.0960 by the quasi-molecular ion peak at m/z 287.0906 [M+H]+ [M+H]+ (calcd. for C16 H15 O4 : 271.0967) in the HR-ESIMS (+) (calcd. for C16 H15 O5 : 287.0913) in its HR-ESIMS (+) spec- spectrum. Its 1 H and 13 C NMR data are very similar to those trum. The NMR data of 7 were in accordance with those of compound 3 (Figure 1). However, 5-OH group in com- of helichrysetin.17 Similar to compound 3, compounds 4– pound 3 was replaced by 5-OMe [δH 3.84 (3H, s) and δC 56.1] 7 were also characteristic metabolites of A. katsumadai in compound 4. This was further confirmed by the HMBC seed.18 correlation 5-OMe/C-5. Based on these findings, compound All isolated compounds 1–7 have been further submitted 4 was elucidated as alpinetin.15 to cytotoxic, DPPH radical scavenging, and α-glucosidase Compound 5 was separated as a yellowish amorphous inhibitory activities (Table 1). Significantly, two chalcones 6, powder. Its structure is a derivative of compounds 3–4 7 showed cytotoxic activity against four cancer cell lines KB, (Figure 1). As compared with compound 4, the ring B of MCF7, A549, and HepG2. Especially, compound 6 strongly compound 5 was substituted by 4′-OH group [δH 7.32 (2H, controlled A549 cancer cells with the IC50 of 6.81 μM, when d, 8.4 Hz, H-2′, H-6′), δH 6.83 (2H, d, 8.4 Hz, H-3′, H-5′), ellipticine was used as a positive control (IC50 1.62 μM). Both δC 128.9 (C-2′, C-6′), and δC 116.3 (C-3′, C-5′)]. In agree- flavone 1 and flavanone 3 exhibited cytotoxicity toward ment with NMR data, the quasi-molecular ion peak at m/z MCF7 and A549 cancer cells, whereas flavone 2 and fla- 287.0906 [M+H]+ (calcd. for C16 H15 O5 : 287.0913) in the HR- vanone 4 were only active against A549 and KB cancer cells, ESIMS (+) spectrum indicated that the chemical formula respectively. of this compound was C16 H14 O5 . Based on these findings, Regarding antioxidative assay, flavone 1 strongly cap- compound 5 was elucidated as 5-O-methylnaringenin.16 tured DPPH radicals with the IC50 value of 51.68 μM. While Compound 6 was purified as a yellowish amorphous flavone 2 has a moderate effect with the IC50 value of powder. In the HR-ESIMS (+) spectrum, the quasi-molecular 250.97 μM, the remaining compounds 3–7 were inactive. ion peak at m/z 271.0962 [M+H]+ (calcd. for C16 H15 O4 : Taking α-glucosidase inhibitory assay into consideration, 271.0970) showed that the chemical formula of compound flavone 2 and flavanone 4 possessed the IC50 values of 6 was C16 H14 O4 . The 1 H-NMR data of compound 6 showed a 324.64 and 296.34 μM, respectively, but the remaining com- pattern of a chalcone, consisting an one-substituted phenyl pounds failed to do so. Acarbose was used as a reference ring [δH 7.72 (2H, m, H-2, H-6) and δH 7.44 (3H, m, H-3 compound with the IC50 value of 208.43 μM. to H-5)], a four-substituted phenyl ring [δH 6.02 (1H, d, 1.8 Hz, H-3′) and δH 5.93 (1H, d, 1.8 Hz, H-5′)], one trans- double bond [δH 7.66 (1H, d, 15.6 Hz, H-7) and δH 7.83 4 CONCLUSION (1H, d, 15.6 Hz, H-8)], and one methoxy [δH 3.87 (3H, s, 2′- OMe)]. The 13 C NMR spectrum was reported to contain nine This is the first time we reported phytochemical and CH, five C4 , and one OCH3 . With the HMBC correlation 2′- biological studies of an endemic Vietnamese Alpinia OMe/C-2′, the OCH3 group was identified to be located at species A. vietnamica. Flavonoids are likely to be the main
25728288, 2024, 1, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300182 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 102 TRA ET AL. chemical class in this plant. The isolated compounds 9. K. V. Rao, A. G. Damu, B. Jayaprakasam, D. Gunasekar. Flavonol showed biological activities at different levels. Chalcone glycosides from Casia hirsuta, J. Nat. Prod. 1999, 62, 305. 10. Y. J. Kuo, P. C. Hsiao, L. J. Zhang, M. D. Wu, Y. H. Liang, H. O. Ho, Y. H. Kuo. 7 strongly inhibited the growth of A549 cancer cells with Labdane diterpenoid glycosides from Alpinia densespicata and their the IC50 value of 6.81 μM. Flavone 1 was strong to capture nitric oxide inhibitory activities in macrophages, J. Nat. Prod. 2009, 72, DPPH radicals with the IC50 value of 51.68 μM. Flavone 2 and 1097. flavanone 4 moderately inhibited enzyme α-glucosidase 11. M. M. Victor, J. M. David, M. V. M. Cortez, J. L. Leite, G. S. B. D. Silva. with the IC50 values of 296.34–324.64 μM. A highyield process for extraction of hesperidin from orange (Citrus sinensis L. osbeck) peels waste, and its transformation to diosmetin, a valuable and bioactive flavonoid, Waste Biomass Valorization 2021, ACKNOWLEDGMENTS 12, 313. This research was financially supported by a grant from the 12. M. A. Ghareeb, M. Sobeh, S. Rezq, A. M. El-Shazly, M. F. Mahmoud, Vietnam Academy Science and Technology (VAST04.04/22- M. Wink. HPLC-ESI-MS/MS profiling of polyphenolics of a leaf extract 23). from Alpinia zerumbet (Zingiberaceae) and Its Anti-inflammatory, anti-nociceptive, and antipyretic activities in vivo, Molecules 2018, 23, C O N F L I C T O F I N T E R E S T S TAT E M E N T 3238. 13. K. H. Yen, N. Nyokat, C. J. Kutoi, A. S. Hamzah, I. F. Lim. Chemical con- The authors declare no conflict of interest. stituents of Artocarpus odoratissimus from Sarawak, J. Appl. Pharm. Sci. 2017, 7, 137. D ATA AVA I L A B I L I T Y S TAT E M E N T 14. B. Groblacher, O. Kunert, F. Bucar. Compounds of Alpinia katsumadai The data that support the findings of this study are available as potential efflux inhibitors in Mycobacterium smegmatis, Bioorg. from the corresponding author upon reasonable request. Med. Chem. 2012, 20, 2701. 15. H. T. Lu, Y. L. Zou, R. Deng, H. Shan. Extraction, purification and antirad- RERERENCES ical activities of alpinetin and cardamomin from Alpinia katsumadai 1. X. N. Ma, C. L. Xie, Z. Miao, Q. Yang, X. W. Yang. An overview of chemi- Hayata, Asian J. Chem. 2013, 25, 9503. cal constituents from Alpinia species in the last six decades, RCS Adv. 16. J. G. Kim, T. P. L. Le, H. R. Hong, J. S. Han, J. H. Ko, S. H. Lee, M. K. 2017, 7, 14114. Lee, B. Y. Hwang. Nitric oxide inhibitory constituents from the fruits 2. E. W. C. Chan, S. K. Wong. Phytochemistry and pharmacology of of Amomum tsao-ko, Nat. Prod. Sci. 2019, 25, 76. ornamental gingers, Hedychium coronarium and Alpinia purpurata: 17. F. A. E. Malolo, A. B. Nouga, A. Kakam, K. Franke, L. Ngah, O. Flausino, a review, J. Integr. Med. 2015, 13, 368. E. M. Mpondo, F. Ntie-Kang, J. C. Ndom, V. D. S. Bolzani, L. Wessjohann. 3. A. K. Ramanunny, S. Wadhwa, M. Gulati, S. Vishwas, R. Khursheed, Protease-inhibiting, molecular modeling and antimicrobial activi- K. R. Paudel, S. Gupta, O. Porwal, S. M. Alshahrani, N. K. Jha, D. K. ties of extracts and constituents from Helichrysum foetidum and Chellappan, P. Prasher, G. Gupta, J. Adams, K. Dua, D. Tewari, S. K. Helichrysum mechowianum (Compositae), Chem. Cent. J. 2015, 9, 32. Singh. Journey of Alpinia galanga from kitchen spice to nutraceuti- 18. Q. C. Feng, H. Q. Bin, S. J. Zheng, W. Z. Tao, X. L. Shan, X. H. Xi. Analysis cal to folk medicine to nanomedicine, J. Ethnopharmacol. 2022, 291, of eight bioactive compounds in Alpinia species by HPLC-DAD, Nat. 115144. Prod. Res. Dev. 2008, 20, 422. 4. S. Dash, M. K. Panda, M. C. Singh, B. P. Jit, Y. D. Singh, J. K. Patra. Bioac- tive molecules from the Alpinia genus: A comprehensive review, Curr. S U P P O R T I N G I N F O R M AT I O N Pharm. Biotechnol. 2020, 21, 1412. Additional supporting information can be found online in 5. A. Chouni, S. Paul. A review on phytochemical and pharmacological the Supporting Information section at the end of this article. potential of Alpinia galanga, Pharmacogn. J. 2018, 10, 9. 6. H. T. Luu, H. D. Tran, T. L. Nguyen, Q. B. Nguyen, J. L. Skornickova. Alpinia vietnamica (Zingiberaceae), a new species from central Viet- nam, Ann. Bot. Fenn. 2018, 56, 221. 7. N. T. T. Ha, N. V. Tuyen, N. T. Tra, L. T. T. Anh, N. T. Son, M. Litaudon, P. V. How to cite this article: N. T. Tra, N. T. T. Hoa, N. T. T. Cuong, B. H. Tai, P. V. Kiem. Garcimckeans A-C, three new xanthones Linh, N. T. T. Ha, B. T. Cham, L. T. T. Anh, N. T. Son. from the stems of Garcinia mckeaniana, and their cytotoxic activity, Flavonoids from Alpinia vietnamica, and their Nat. Prod. Res. 2023, 37, 77. 8. L. T. T. Anh, N. T. Son, N. V. Tuyen, P. T. Thuy, P. M. Quan, N. T. T. cytotoxic, antioxidative, and α-glucosidase Ha, N. T. Tra. Antioxidative and α-glucosidase inhibitory constituents inhibitory activities, Vietnam J. Chem. 2024, 62, 98. of Polyscias guilfoylei: Experimental and computational assessments, https://doi.org/10.1002/vjch.202300182 Mol. Diversity 2022, 26, 229.