Desmodianone H and uncinanone B, potential tyrosinase inhibitors obtained from <i>Lespedeza maximowiczii</i> by using bioactivity-guided isolation

Heo, Do Yeon; Kim, Young Mi; Lee, Dong Kun; Park, Sang-Hong; Kim, Jin‐Ki; Park, Hye Min; Lee, Choong Hwan

doi:10.1080/09168451.2014.905180

Cited by 7 publications

(5 citation statements)

References 17 publications

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“…However, the following metabolites were detected in the largest quantities in stems 6 months after germination (Figure 2b): amino acids such as valine (2), isoleucine (3), serine (4), threonine (5), aspartic acid (6), and tyrosine (9); sugars such as xylitol (15), myo-inositol (20), and maltose (22); malonic acid (10); palmitic acid (23); and two nonidentified metabolites (26 and 27). The levels of sugars such as fructose (16), glucose (17), and sucrose (21) were higher in stems harvested in November (at 8 months) than in stems harvested during other months.…”

Section: ■ Resultsmentioning

confidence: 99%

“…In the correlation map (Figure 3c,d), four metabolites, isovitexin (38), daidzein (39), desmodianone H (48), and uncinanone B (49), which were strongly positively correlated with each other, were reported to be regulatory agents of melanogenesis. 9,23,24 As these metabolites were present with the largest quantities in samples harvested 6 months after germination, they may be the most active 6 months after germination. The samples at this time were harvested in September, which is the start of the fall season in Korea.…”

Section: ■ Discussionmentioning

confidence: 99%

“…6 In particular, Lespedeza maximowiczii exhibits inhibitory activity against advanced glycation end products 7 as well as estrogenic activity. 8 Recently, our team studied the tyrosinase inhibitory activity of two compounds, uncinanone B and desmodianone H, isolated from L. maximowiczii, 9 as well that of haginin A (isolated from the Lespedeza crytobotrya), a potent inhibitor of hyperpigmentation induced by ultraviolet radiation. 10 Recently, interest of metabolomics is increasing in plant research fields.…”

Section: ■ Introductionmentioning

confidence: 99%

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Seasonal Variations of Metabolome and Tyrosinase Inhibitory Activity of Lespedeza maximowiczii during Growth Periods

Kim

Park

Lee

et al. 2015

J. Agric. Food Chem.

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Lespedeza species are useful for pasture and energy crops as well as medical plants. We determined the metabolites discriminated from the each growth period (3, 4, 6, 8, 15, and 18 months) after germination in leaves and stems of Lespedeza maximowizii by a metabolomics technique. Specifically, levels of sugars and luteolin-dominated derivatives were significantly elevated in samples harvested in November. This may be related to the cold tolerance mechanism against the low temperatures of the winter season. The concentrations of secondary metabolites, isoflavones and flavanones, as well as tyrosinase inhibitory activity were the highest in the 6 month samples, which were harvested in September, during the fall season. The tyrosinase inhibitory activity in leaves was higher than that in stems irrespective of the growth period. This study suggests that mass spectrometry-based metabolite profiling could be used as a tool to examine quantitative or qualitative metabolite changes related to seasonal variations and to understand the correlation between activity and metabolites.

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Section: ■ Resultsmentioning

confidence: 99%

Section: ■ Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Seasonal Variations of Metabolome and Tyrosinase Inhibitory Activity of Lespedeza maximowiczii during Growth Periods

Kim

Park

Lee

et al. 2015

J. Agric. Food Chem.

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“…In the study reported by Heo et al., two new isoflavones desmodianone H and uncinanone B have been identified as novel tyrosinase inhibitors. However, uncinanone B has higher anti-tyrosinase rate than desmodianone H 264 . Glyasperin C from Glycyrrhiza glabra is another kind of isoflavone identified as tyrosinase inhibitor 265 .…”

Section: Inhibitors From Natural Semisynthetic and Synthetic Sourcesmentioning

confidence: 99%

A comprehensive review on tyrosinase inhibitors

Zolghadri

Bahrami

Khan³

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

740

471

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Tyrosinase is a multi-copper enzyme which is widely distributed in different organisms and plays an important role in the melanogenesis and enzymatic browning. Therefore, its inhibitors can be attractive in cosmetics and medicinal industries as depigmentation agents and also in food and agriculture industries as antibrowning compounds. For this purpose, many natural, semi-synthetic and synthetic inhibitors have been developed by different screening methods to date. This review has focused on the tyrosinase inhibitors discovered from all sources and biochemically characterised in the last four decades.

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“…Isoflavone glabrene is an inhibitor of both monophenolase and diphenolase to tyrosinase [43]. Two isoflavones, uncinanone B and desmodianone H, inhibit tyrosinase activity, with uncinanone B exhibiting stronger inhibition than desmodianone H [44]. The isoflavones daidzein, glyasperin C, formononetin, genistein, mirkoin, texasin, tectorigenin, and odoratin inhibit tyrosinase activity [45].…”

Section: Competitive Inhibitory Typementioning

confidence: 99%

Naturally-Occurring Tyrosinase Inhibitors Classified by Enzyme Kinetics and Copper Chelation

Kim

Choi

Abekura

et al. 2023

IJMS

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Currently, there are three major assaying methods used to validate in vitro whitening activity from natural products: methods using mushroom tyrosinase, human tyrosinase, and dopachrome tautomerase (or tyrosinase-related protein-2, TRP-2). Whitening agent development consists of two ways, melanin synthesis inhibition in melanocytes and downregulation of melanocyte stimulation. For melanin levels, the melanocyte cell line has been used to examine melanin synthesis with the expression levels of TRP-1 and TRP-2. The proliferation of epidermal surfaced cells and melanocytes is stimulated by cellular signaling receptors, factors, or mediators including endothelin-1, α-melanocyte-stimulating hormone, nitric oxide, histamine, paired box 3, microphthalmia-associated transcription factor, pyrimidine dimer, ceramide, stem cell factors, melanocortin-1 receptor, and cAMP. In addition, the promoter region of melanin synthetic genes including tyrosinase is upregulated by melanocyte-specific transcription factors. Thus, the inhibition of growth and melanin synthesis in gene expression levels represents a whitening research method that serves as an alternative to tyrosinase inhibition. Many researchers have recently presented the bioactivity-guided fractionation, discovery, purification, and identification of whitening agents. Melanogenesis inhibition can be obtained using three different methods: tyrosinase inhibition, copper chelation, and melanin-related protein downregulation. There are currently four different types of inhibitors characterized based on their enzyme inhibition mechanisms: competitive, uncompetitive, competitive/uncompetitive mixed-type, and noncompetitive inhibitors. Reversible inhibitor types act as suicide substrates, where traditional inhibitors are classified as inactivators and reversible inhibitors based on the molecule-recognizing properties of the enzyme. In a minor role, transcription factors can also be downregulated by inhibitors. Currently, the active site copper iron-binding inhibitors such as kojic acid and chalcone exhibit tyrosinase inhibitory activity. Because the tyrosinase catalysis site structure is important for the mechanism determination of tyrosinase inhibitors, understanding the enzyme recognition and inhibitory mechanism of inhibitors is essential for the new development of tyrosinase inhibitors. The present review intends to classify current natural products identified by means of enzyme kinetics and copper chelation to exhibit tyrosinase enzyme inhibition.

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Desmodianone H and uncinanone B, potential tyrosinase inhibitors obtained from Lespedeza maximowiczii by using bioactivity-guided isolation

Cited by 7 publications

References 17 publications

Seasonal Variations of Metabolome and Tyrosinase Inhibitory Activity of Lespedeza maximowiczii during Growth Periods

Seasonal Variations of Metabolome and Tyrosinase Inhibitory Activity of Lespedeza maximowiczii during Growth Periods

A comprehensive review on tyrosinase inhibitors

Naturally-Occurring Tyrosinase Inhibitors Classified by Enzyme Kinetics and Copper Chelation

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