Isolation of phenylpropanoid sucrose esters from the roots of Persicaria orientalis and their potential as inhibitors of melanogenesis

Masum, Mohammad Nuruzzaman; Choodej, Siwattra; Yamauchi, Kosei; Mitsunaga, Tohru

doi:10.1007/s00044-019-02312-w

Cited by 16 publications

(8 citation statements)

References 40 publications

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“…Based on Masum et al, vanicoside B isolated from ethanolic extracts of Persicaria orientalis roots exhibited a significant high extracellular (71.9% and 72.0%) and intracellular (35.3 and 27.3%) melanin inhibitory activity at 50 and 25 μM, respectively, in the B16 mouse melanoma cells . It showed better inhibitory activity than the positive control, arbutin (58% at 730 μM) . Furthermore, the ethanolic extract also demonstrated the highest tyrosinase inhibition with IC 50 of 22 μg/mL ( l -tyrosine) and 39 μg/mL ( l -DOPA), compared to the ethyl acetate extract ( l -tyrosine = 80 μg/mL; l -DOPA = 311 μg/mL) and n -hexane ( l -tyrosine = >1000 μg/mL; l -DOPA = >1000 μg/mL) .…”

Section: Biological Activitiesmentioning

confidence: 97%

Section: Biological Activitiesmentioning

confidence: 99%

“…Furthermore, the ethanolic extract also demonstrated the highest tyrosinase inhibition with IC 50 of 22 μg/mL ( l -tyrosine) and 39 μg/mL ( l -DOPA), compared to the ethyl acetate extract ( l -tyrosine = 80 μg/mL; l -DOPA = 311 μg/mL) and n -hexane ( l -tyrosine = >1000 μg/mL; l -DOPA = >1000 μg/mL) . The kojic acid was used as the positive control in the mushroom tyrosinase assay, with the IC 50 of 2 μg/mL ( l -tyrosine) and 26 μg/mL ( l -DOPA assay) reported …”

Section: Biological Activitiesmentioning

confidence: 99%

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Searching for Natural Plants with Antimelanogenesis and Antityrosinase Properties for Cosmeceutical or Nutricosmetics Applications: A Systematic Review

Tung,

Yip,

Gew

2023

ACS Omega

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Excessive UV radiation (UVR) exposure has been shown in studies to be a major risk factor for most melanomas, causing premature skin aging as well as immune system suppression due to the increased production of hydrogen peroxide (H2O2) and other reactive oxygen species (ROS) during the melanogenesis process. Although several compounds with antioxidant and antityrosinase activities are widely used in the cosmetic industry, like kojic acid, hydroquinone, ascorbic acid, and arbutin, their use has been limited due to their adverse effects on the skin and cytotoxic issues. Recently, attempts have been made to develop new natural skin-lightening products by using plant extracts that are less toxic and exhibit numerous biological properties with great market demand. In this study, information on the depigmentation effects of various natural plant species was gathered from the SCOPUS database according to the PRISMA guidelines. A total of 414 records were retrieved, and finally, 76 articles were included in the qualitative synthesis by fulfilling all the inclusion criteria. In this review, we discuss the extraction methods and biological assays of 75 highly potential plant species, including the olive, yuzu, longan, and lotus. We concluded that the use of natural plants as skin-whitening agents is highly effective as there is a significant correlation between the content of polyphenolic compounds, antimelanogenesis, antityrosinase, and antioxidant activities. However, it is worth noting that the use of extraction methods or types of solvents is very important in determining the biological activities of plants.

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Section: Biological Activitiesmentioning

confidence: 97%

Section: Biological Activitiesmentioning

confidence: 99%

Section: Biological Activitiesmentioning

confidence: 99%

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Searching for Natural Plants with Antimelanogenesis and Antityrosinase Properties for Cosmeceutical or Nutricosmetics Applications: A Systematic Review

Tung,

Yip,

Gew

2023

ACS Omega

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“…[9] The present study reported the isolation of thirteen phytochemicals from the ethyl acetate fraction of the aerial part of CE and the potential inhibitory effects on platelet aggregation and human blood coagulation of isolated compounds. Two new compounds, caneduloside A (1) and caneduloside B (2), along with tiliroside (5), 3,4dimethoxycinnamic acid (10), dehydrovomifoliol (11), and 4hydroxy-3,5-dimethoxybenzaldehyde (12) exhibited antiplatelet effects, while 1, 10 and 12 also had anticoagulant activities.…”

Section: Introductionmentioning

confidence: 99%

Antiplatelet and Anticoagulant Effects of Two New Phenylpropanoid Sucrose Esters and Other Secondary Metabolites from the Aerial Part of Canna edulis

Nguyen,

et al. 2024

Chemistry & Biodiversity

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This study isolated pure compounds from Canna edulis aerial parts and assessed their antiplatelet and anticoagulant potential. Structural elucidation resulted in the identification of two new compounds: caneduloside A (1) and caneduloside B (2), and eleven known compounds: 6’‐acetyl‐3,6,2’‐tri‐p‐coumaroyl sucrose (3), 6¢‐acetyl‐3,6,2¢‐triferuloyl sucrose (4), tiliroside (5), afzelin (6), quercitrin (7), 2‐hydroxycinnamaldehyde (8), cinnamic acid (9), 3,4‐dimethoxycinnamic acid (10), dehydrovomifoliol (11), 4‐hydroxy‐3,5‐dimethoxybenzaldehyde (12), and (S)‐(‐)‐rosmarinic acid (13). Compounds 3, 4, 6‐9, 13 were previously reported for antithrombotic properties. Hence, antithrombotic tests were conducted for 1, 2, 5, 10‐12. All tested compounds demonstrated a dose‐dependent antiaggregatory effect, and 10 and 12 were the most potent for both ADP and collagen activators. Additionally, 10 and 12 exhibited anticoagulant effects, with prolonged prothrombin time and activated partial thromboplastin time. The new compound 1 displayed antiplatelet and anticoagulant activity, while 2 mildly inhibited platelet aggregation. C. edulis is a potential source for developing antithrombotic agents.

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“…Due to its (mildly) anti-microbial, anti-oxidant, and anti-inflammatory activity, it is also widely used in the cosmetic and healthcare industries worldwide, and is also of relevance in the food industry [1,2,3,4,5,6,7,8,9,10,11,12]. For example, since arbutin inhibits the melanogenesis process by the inhibition of tyrosinase, it is used as a depigmenting agent on skin, preventing and eliminating the growth of dark spots [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15]. A possible mechanism of tyrosinase-inhibition by arbutin has been proposed on the basis of molecular dynamics (MD) computations, leading to the identification of crucial protein-arbutin interactions (Figure 2), which are different from those exhibited by other inhibitors [11].…”

Section: Introductionmentioning

confidence: 99%

Chemical and Biocatalytic Routes to Arbutin †

Zhou

Zhao

et al. 2019

Molecules

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Arbutin (also called β-arbutin) is a natural product occurring in the leaves of a variety of different plants, the bearberries of the Ericaceae and Saxifragaceae families being prominent examples. It is a β-glucoside derived from hydroquinone (HQ; 1,4-dihydroxybenzene). Arbutin has been identified in traditional Chinese folk medicines as having, inter alia, anti-microbial, anti-oxidant, and anti-inflammatory properties that useful in the treatment of different ailments including urinary diseases. Today, it is also used worldwide for the treatment of skin ailments by way of depigmenting, which means that arbutin is a component of many products in the cosmetics and healthcare industries. It is also relevant in the food industry. Hundreds of publications have appeared describing the isolation, structure determination, toxicology, synthesis, and biological properties of arbutin as well as the molecular mechanism of melanogenesis (tyrosinase inhibition). This review covers the most important aspects with special emphasis on the chemical and biocatalytic methods for the production of arbutin.

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Isolation of phenylpropanoid sucrose esters from the roots of Persicaria orientalis and their potential as inhibitors of melanogenesis

Cited by 16 publications

References 40 publications

Searching for Natural Plants with Antimelanogenesis and Antityrosinase Properties for Cosmeceutical or Nutricosmetics Applications: A Systematic Review

Searching for Natural Plants with Antimelanogenesis and Antityrosinase Properties for Cosmeceutical or Nutricosmetics Applications: A Systematic Review

Antiplatelet and Anticoagulant Effects of Two New Phenylpropanoid Sucrose Esters and Other Secondary Metabolites from the Aerial Part of Canna edulis

Chemical and Biocatalytic Routes to Arbutin †

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