Phytoconstituents from Alpinia purpurata and their in vitro inhibitory activity against Mycobacterium tuberculosis

Villaflores, Oliver B.; Macabeo, Allan Patrick G.; Gehle, Dietmar; Krohn, Karsten; Franzblau, Scott G.; Aguinaldo, Alicia M.

doi:10.4103/0973-1296.71785

Cited by 28 publications

(5 citation statements)

References 18 publications

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“…Compound (1) has been isolated previously from A. flabellata, 9 while compound (2) from Alpinia purpurata. 10 Besides, compounds (3) and ( 4) have been isolated previously from Zingiber cassumunar, 11 while compound (5) from A. flabellata. 12 In addition, compounds (6) and ( 7) have been reported previously from A. globosa.…”

Section: Resultsmentioning

confidence: 99%

Antityrosinase Inhibitory Activity of Phytochemicals from Alpinia aquatica Roscoe

et al. 2020

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Background: Genus Alpinia are commonly used as spices and ingredients in traditional medicines. In the present study, we attempted to isolate the phytochemicals from Alpinia aquatica and evaluate their tyrosinase inhibitory activity. Methods: Phytochemical constituents of the extract were investigated using various chromatographic and spectroscopic methods. The chemical structures of the isolated phytochemicals were established by analysis of their spectroscopic data, as compared to that of reported data. Tyrosinase inhibitory activity was also tested on the extracts and selected compounds using mushroom tyrosinase as the enzyme. Results: Fractionation and purification of the extracts of Alpinia aquatica afforded seven known compounds which are 5-hydroxy-3,7,4’-trimethoxyflavone (1), 4’,5-dihydroxy-3,7-dimethoxyflavone (2), 2-methoxy-8-(2’,4’,5’-trimethoxyphenyl)-1,4-naphthaquinone (3), cis-3S-(2’,4’,5’-trimethoxyphenyl)-4S-[(E)-2’’’,4’’’,5’’’-trimethoxystyryl]cyclohexene (4), 2,4,5-trimethoxybenzaldehyde (5), stigmasterol (6) and β-sitosterol (7). The ethyl acetate extract of pseudostems possessed the highest tyrosinase inhibition of 31.0% among the extracts, while compound (1) gave tyrosinase inhibition of 48.0%. Conclusion: Compounds (3) and (4) were isolated for the first time from A. aquatica and Alpinia genus. These phytochemical results suggest that the extracts could assist as a potential source of bioactive compounds. Further research is needed in which the extract could possibly be exploited for pharmaceutical use.

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Section: Resultsmentioning

confidence: 99%

Antityrosinase Inhibitory Activity of Phytochemicals from Alpinia aquatica Roscoe

et al. 2020

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“…Inhibition of ferroptosis proved to be an attractive approach for treatment of IBD. Kumatakenin is a polymethoxylated flavonoid isolated from traditional Chinese medicinal cloves and Alpinia purpurata (Villaflores et al, 2010;Woo et al, 2017). Previous work has Frontiers in Pharmacology frontiersin.org confirmed that kumatakenin exerts significant anti-inflammatory effects, and induced cell death of cancer cell lines.…”

Section: Discussionmentioning

confidence: 99%

“…Kumatakenin also inhibits SARS-CoV-2 replication in Vero E6 and Calu-3 cells (Leal et al, 2021). Finally, kumatakenin has been shown to suppress cytokine production (Villaflores et al, 2010). However, the influence of kumatakenin on IBD remains unclear.…”

Section: Open Access Edited Bymentioning

confidence: 99%

Kumatakenin inhibited iron-ferroptosis in epithelial cells from colitis mice by regulating the Eno3-IRP1-axis

et al. 2023

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Inhibition of epithelial ferroptosis in colonic tissues relieved clinical symptoms and improved endoscopic presentations in inflammatory bowel disease (IBD). Kumatakenin, the main ingredient of traditional Chinese medicinal cloves and Alpinia purpurata, is reported to possess therapeutic benefits. However, whether kumatakenin could inhibit ferroptosis and further alleviate colitis remains unclear. Here, we measured the effects of kumatakenin on ferroptosis of colonic epithelial cells from colitis mice. The colitis model was induced in mice by oral intake of 2.5% dextran sulfate sodium in drinking water. RNA sequencing was performed to investigate the mechanism underlying kumatakenin-mediated effects on colitis. The results showed that different doses of kumatakenin significantly alleviated symptoms and suppressed intestinal inflammation in the colitis mouse model. Kumatakenin supplementation decreased cellular iron levels and suppressed ferroptosis in epithelial cells from colitis mice. RNA sequencing, qPCR, and pharmacological inhibition assays showed that kumatakenin reduced cellular iron levels and suppressed ferroptosis in epithelial cells from colitis mice at least partially by upregulating expression of enolase (Eno-3). Furthermore, kumatakenin decreased iron levels in epithelial cells by modulating the Eno3-iron regulatory protein (IRP1) axis. Molecular docking results revealed that kumatakenin could bind Eno3 via hydrogen bonding with the amino acid residues Thr208, Val206, and Pro203. This work will provide a scientific basis for the clinical use of kumatakenin in the treatment of colitis.

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“…The column chromatrography of the ethyl acetate extract of M. glabra resulted in the isolation of quercetin 3, 5, 3'-trimethyl ether (1) [20] and kumatakenin (2) [21]. The isolation of the methanol extract of M. glabra afforded scoparone (3) [22], 6, 7, 8-trimethoxycoumarin (4) [23], marmesin (5) [24], glabranin (6) [13], umbelliferone (7) [25], scopoletin (8) [26] and sesamin ( 9) [27].…”

Section: Isolation Of Compounds From M Glabra Extractsmentioning

confidence: 99%

Oxygen radical antioxidant capacity (ORAC) and antibacterial properties of Melicope glabra bark extracts and isolated compounds

et al. 2021

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Melicope glabra (Blume) T. G. Hartley from the Rutaceae family is one of the richest sources of plant secondary metabolites, including coumarins and flavanoids. This study investigates the free radical scavenging and antibacterial activities of M. glabra and its isolated compounds. M. glabra ethyl acetate and methanol extracts were prepared using the cold maceration technique. The isolation of compounds was performed with column chromatography. The free radical scavenging activity of the extracts and isolated compounds were evaluated based on their oxygen radical absorbance capacity (ORAC) activities. The extracts and compounds were also subjected to antibacterial evaluation using bio-autographic and minimal inhibitory concentration (MIC) techniques against two oral pathogens, Enterococcus faecalis and Streptococcus mutans. Isolation of phytoconstituents from ethyl acetate extract successfully yielded quercetin 3, 5, 3’-trimethyl ether (1) and kumatakenin (2), while the isolation of the methanol extract resulted in scoparone (3), 6, 7, 8-trimethoxycoumarin (4), marmesin (5), glabranin (6), umbelliferone (7), scopoletin (8), and sesamin (9). The study is the first to isolate compound (1) from Rutaceae plants, and also the first to report the isolation of compounds (2–5) from M. glabra. The ORAC evaluation showed that the methanol extract is stronger than the ethyl acetate extract, while umbelliferone (7) exhibited the highest ORAC value of 24 965 μmolTE/g followed by glabranin (6), sesamin (9) and scopoletin (8). Ethyl acetate extract showed stronger antibacterial activity towards E. faecalis and S. mutans than the methanol extract with MIC values of 4166.7 ± 1443.4 μg/ml and 8303.3 ± 360.8 μg/ml respectively. Ethyl acetate extract inhibited E. faecalis growth, as shown by the lowest optical density value of 0.046 at a concentration of 5.0 mg/mL with a percentage inhibition of 95%. Among the isolated compounds tested, umbelliferone (7) and sesamin (9) exhibited promising antibacterial activity against S. mutans with both exhibiting MIC values of 208.3 ± 90.6 μg/ml. Findings from this study suggests M. glabra as a natural source of potent antioxidant and antibacterial agents.

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Phytoconstituents from Alpinia purpurata and their in vitro inhibitory activity against Mycobacterium tuberculosis

Cited by 28 publications

References 18 publications

Antityrosinase Inhibitory Activity of Phytochemicals from Alpinia aquatica Roscoe

Antityrosinase Inhibitory Activity of Phytochemicals from Alpinia aquatica Roscoe

Kumatakenin inhibited iron-ferroptosis in epithelial cells from colitis mice by regulating the Eno3-IRP1-axis

Oxygen radical antioxidant capacity (ORAC) and antibacterial properties of Melicope glabra bark extracts and isolated compounds

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