scholarly journals Antityrosinase Inhibitory Activity of Phytochemicals from Alpinia aquatica Roscoe

2020 ◽  
Vol 26 (2) ◽  
pp. 209-213
Author(s):  
Nissha Bharrathi Romes ◽  
Wan Mohd Nuzul Hakimi Wan Salleh ◽  
Hasnah Mohd Sirat ◽  
Zaini Assim

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.

2019 ◽  
Vol 25 (4) ◽  
pp. 358-363
Author(s):  
Nur Athirah Hashim ◽  
Farediah Ahmad ◽  
Wan Mohd Nuzul Hakimi Wan Salleh ◽  
Shamsul Khamis

Background: Piper species are aromatic plants used as spices in the kitchen, but their secondary metabolites have also shown biological effects on human health. In traditional medicine, Piper species have been used worldwide to treat several diseases such as urological problems, skin, liver and stomach ailments, for wound healing, and as antipyretic and anti-inflammatory agents. In the present study, we attempted to isolate the phytochemicals from Piper caninum and Piper magnibaccum and evaluate their tyrosinase inhibitory activity. Methods: Phytochemical constituents of the extracts were investigated using various chromatographic and spectroscopic methods. The 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 Piper caninum and Piper magni­baccum afforded nine known compounds which were cepharanone A (1), cepharadione A (2), aristolactam AII (3), 5,7-dimethoxyflavone (4), 24-methylenecycloartan-3-one (5), β-sitosterol (6), piperumbellactam A (7), 24S-ethylcholesta-5,22,25-trien-3β-ol (8) and stigmast-3,6-dione (9). Ethyl acetate extracts from leaves of P. magnibaccum gave the highest inhibition value at 48.35%, while the tested compounds displayed weak tyrosinase activity compared to the positive control, kojic acid. Conclusion: These phytochemical results suggested 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.


2019 ◽  
Vol 57 (2) ◽  
pp. 162
Author(s):  
Quan Minh Pham ◽  
Hoai Van Thi Tran ◽  
Lam Tien Do ◽  
Phuong Lan Doan ◽  
Inh Thi Cam ◽  
...  

Urena lobata L. is used in Vietnamese traditional medicine for the treatment of several diseases. Tree roots are used to treat rheumatism, dysentery, poor digestion, flu, tonsils, malaria, asthma, goiter. Flowers are used to treat chickenpox, fever, and mental disorders. Branches, leaves or whole trees used to treat injuries bruises, rheumatism, mastitis, bites. Phytochemical investigation of the n-hexan and ethyl acetate extract of Urena lobata L. led to the isolation of β-sitosterol (1), β-sitosterol-3-O-β-D-glucopyranoside (2), a-acetylamino-phenylpropyl a-benzoylamino-phenylpropanoate (3), quercetin (4), and trans-tiliroside (5). Their chemical structures were determined by spectroscopic methods including MS, 1D, 2D NMR and comparing with those reported in previous papers. Two compounds 3, 5 were isolated for the first time from Urena lobata plant.


Author(s):  
Cheng-Peng Sun ◽  
Zi-Li Jia ◽  
Xiao-Kui Huo ◽  
Xiang-Ge Tian ◽  
Lei Feng ◽  
...  

As a genus of the Asteraceae, Inula is widely distributed all over the world, and several of them are being used in traditional medicines. A number of metabolites were isolated from Inula species, and some of these have shown to possess ranges of pharmacological activities. The genus Inula contains abundant sesquiterpenoids, such as eudesmanes, xanthanes, and sesquiterpenoid dimers and trimers. In addition, other types of terpenoids, flavonoids, and lignins also exist in the genus Inula. Since 2010, more than 300 new secondary metabolites, including several known natural products that were isolated for the first time from the genus Inula. Most of them exhibited potential bioactivities in various diseases. The review aimed to summarize the advance of recent researches (2010–2020) on phytochemical constituents, biosynthesis, and pharmacological properties of the genus Inula for providing a scientific basis and supporting its application and exploitation for new drug development.


2018 ◽  
Vol 10 (1) ◽  
pp. 384
Author(s):  
Caroline Wijaya ◽  
Berna Elya ◽  
Arry Yanuar

Objective: This study was carried out to evaluate the phytochemical constituents and tyrosinase inhibitory activity of Cassia fistula leaves.Methods: A tyrosinase inhibitory activity assay was performed by measuring the decrease in the intensity of color suggestive of the inhibition ofdopachrome formation resulting from the L-DOPA-tyrosinase reaction.Results: The test results showed that the tyrosinase inhibitory activity of the water fraction of C. fistula leaf extract had the highest IC50 value(152.031 μg/mL) among other fractions (n-hexane, ethyl acetate, and n-butanol). An enzyme kinetic assay showed that the water fraction of C. fistulaleaf extract inhibited tyrosinase with mixed-type inhibition. Phytochemical screening showed that the water fraction of C. fistula leaf extract containedalkaloids, flavonoids, glycosides, phenols, and tannins.Conclusion: The current study indicated that C. fistula leaves possess significant tyrosinase inhibitory activity.


2017 ◽  
Vol 12 (5) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
Hyun Gyu Choi ◽  
In-Gyu Je ◽  
Geum Jin Kim ◽  
Joo-Won Nam ◽  
Sang Hee Shim ◽  
...  

A phthalide, levistolide A (1), and six coumarins, demethylsuberosin (2), fraxetin (3), (-)-marmesinin (4), 3'( S)- O-β-D-glucopyranosyl-3’,4'-dihydroxanthyletin (5), 3'( R)- O-β-D-glucopyranosyl-3’,4'-dihydroxanthyletin (6), and isopraeroside IV (7) were isolated from the methanolic extract of the roots of Angelica tenuissima Nakai. Their chemical structures were confirmed by comparing spectroscopic and reported data. All seven compounds were isolated for the first time from this plant source. The anti-allergic activities of compounds 1-7 were examined using human mast cells, and compounds 1-3 at 10 μM potently suppressed IL-6 expression and inhibited histamine release from human mast cells by more than 30%.


2021 ◽  
Vol 24 (1) ◽  
pp. 1842-1846
Author(s):  
Huynh Bui Linh Chi ◽  
Van Muoi Bui ◽  
Thi Quynh Nhu Phan ◽  
Kim Phi Phung Nguyen

Introduction: The metabolites of lichens concentrated depsidones, depsides, and diphenyl ethers were possessed antibiotic, antifungal, antiviral, antitumor, and anticancer activities. Parmotrema tinctorum (Despr. ex Nyl.) Hale, a species of foliose lichen, is widely distributed in Lam Dong province, Vietnam. Herein, this paper describes the isolation and structure elucidation of seven compounds isolated from this lichen. Methods: Phytochemical investigations of the ethyl acetate extract of the lichen P. tinctorum led to the isolation of seven pure compounds. Their chemical structures were elucidated by extensive HR-ESI-MS and NMR spectroscopic analysis and comparison with previously published data. Results: Seven compounds, namely orcinol (1), orsellinic acid (2), methyl orsellinate (3), methyl heamatomate (4), lecanorin (5), lecanoric acid (6), and gyrophoric acid (7). These compounds were determined the α-glucosidase inhibitory activity. Conclusions: Compound 7 was determined for the first time in P. tinctorum, and this was also the first time these compounds were determined the α-glucosidase inhibitory activity.


2021 ◽  
Vol 22 (11) ◽  
pp. 5616
Author(s):  
Sanggwon Lee ◽  
Heejeong Choi ◽  
Yujin Park ◽  
Hee Jin Jung ◽  
Sultan Ullah ◽  
...  

We previously reported (E)-β-phenyl-α,β-unsaturated carbonyl scaffold ((E)-PUSC) played an important role in showing high tyrosinase inhibitory activity and that derivatives with a 4-substituted resorcinol moiety as the β-phenyl group of the scaffold resulted in the greatest tyrosinase inhibitory activity. To examine whether the 4-substituted resorcinol moiety could impart tyrosinase inhibitory activity in the absence of the α,β-unsaturated carbonyl moiety of the (E)-PUSC scaffold, 10 urolithin derivatives were synthesized. To obtain more candidate samples, the lactone ring in synthesized urolithins was reduced to produce nine reduced urolithins. Compounds 1c (IC50 = 18.09 ± 0.25 μM), 1h (IC50 = 4.14 ± 0.10 μM), and 2a (IC50 = 15.69 ± 0.40 μM) had greater mushroom tyrosinase-inhibitory activities than kojic acid (KA) (IC50 = 48.62 ± 3.38 μM). The SAR results suggest that the 4-substituted resorcinol motif makes an important contribution to tyrosinase inhibition. To investigate whether these compounds bind to human tyrosinase, a human tyrosinase homology model was developed. Docking simulations with mushroom and human tyrosinases showed that 1c, 1h, and 2a bind to the active site of both tyrosinases with higher binding affinities than KA. Pharmacophore analyses showed that two hydroxyl groups of the 4-substituted resorcinol entity act as hydrogen bond donors in both mushroom and human tyrosinases. Kinetic analyses indicated that these compounds were all competitive inhibitors. Compound 2a inhibited cellular tyrosinase activity and melanogenesis in α-MSH plus IBMX-stimulated B16F10 melanoma cells more strongly than KA. These results suggest that 2a is a promising candidate for the treatment of skin pigment disorders, and show the 4-substituted resorcinol entity importantly contributes to tyrosinase inhibition.


2019 ◽  
Vol 2 (6) ◽  
pp. 134-138
Author(s):  
Nguyen Xuan Hai ◽  
Nguyen Trung Nhan ◽  
Nguyen Thi Thanh Mai

Solanum procumbens L. is a medicinal plant belonging to the Solanaceae family. In Vietnam, it is known as "Ca gai leo", and it cultivated in some tropical countries in China, Laos, Cambodia, and Vietnam. From the stem of the ethyl acetate extract of Solanum procumbens, we had isolated one anthraquinone (1), four polyphenols (2-5), and one indole (6). By spectroscopic methods as well as comparing with data in the literature, their chemical structures were elucidated as ziganein (1), benzoic acid (2), salicylic acid (3), 4-hydroxybenzaldehyde (4), vanillic acid (5), and indole-3-carbaldehyde (6). These compounds were isolated for the first time from the genus Solanum.


Author(s):  
Nesma M. Salah ◽  
Ahmed M.A. Souleman ◽  
Kamel H. Shaker ◽  
Seham El Hawary ◽  
Faten K Abd El-Hady

Bioassay guided fractionation led to the isolation of eight compounds from Egyptian Propolis. Hexacosanoic acid; 3,4- dimethoxy-cinnamic acid; 3-methyl-3-butenyl-trans-caffeate ester; together with four flavonoids (Chrysin; Pinostrobin; Tectochrysin and 5-hydroxy-7-methoxy isoflavone). 2,3-dihydroxy-4-methyl-octanoic acid; was isolated for the first time from Egyptian propolis. Their acetylcholinesterase (AChE), alpha-glucosidase and tyrosinase inhibition potential were evaluated. Pinostorbin showed the highest AChE inhibitory activity followed by 3,4-Dimethoxycinnamic acid; 3-methyl- 3-butenyl-trans-caffeate ester. Tectochrysin is the only compound had alpha-glucosidase inhibitory activity higher than that of the drug acarabose. Pinostrobin is the only compound had mild tyrosinase inhibitory activity.


2020 ◽  
Vol 58 (5) ◽  
pp. 533
Author(s):  
Nguyen Phi-Hung

From the whole plant of Isodon ternifolius collected in Vietnam, four triterpens including ursaldehyde (1), ursolic acid (2), b-sitosterol (3) and b-sitosteryl ferulate (4) were purified. Their chemical structures were determined by interpretation of NMR and MS data and comparison with the literatures. Compounds 1-4 were evaluated for their inhibitory activity against PTP1B enzyme activity using in vitro assay. Compounds 1 and 2 displayed potential activities with IC50 values of 16.92 ± 0.12 and 3.42 ± 0.45 μM, respectively. This is the first time that compounds 1 and 4 have been isolated from the Isodon genus and I. ternifolius has been evaluated for the PTP1B inhibitory activity.


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