Potentilloside A, a New Flavonol-bis-Glucuronide from the Leaves of Potentilla chinensis, Inhibits TNF-α-Induced ROS Generation and MMP-1 Secretion

Lee, So Young; Choi, Yea Jung; Son, So-Ri; Yoon, Youngsook; Lee, Sunhee; Lee, Kyung Tae; Lee, Sullim; Jang, Dae Sik

doi:10.3390/plants11233318

Cited by 4 publications

(4 citation statements)

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“…Similar to our findings, previous studies have demonstrated that flavonoids derived from natural sources exhibit anti-skin aging activity. For instance, potentilloside A has been shown to inhibit ROS generation and MMP-1 secretion in TNF-α-induced HDFs [70]. Additionally, quercetin, myricetin, and kaempferol have been reported to inhibit expression and superoxide anion radicals in UV-induced human dermal fibroblasts [71].…”

Section: Discussionmentioning

confidence: 99%

Laricitrin 3-Rutinoside from Ginkgo biloba Fruits Prevents Damage in TNF-α-Stimulated Normal Human Dermal Fibroblasts

et al. 2023

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Human skin comprises the epidermis and dermis, which perform interactive functional activities with each other in order to maintain the skin’s tensile strength. In particular, the dermal layer is crucial for skin protection. However, skin aging destroys collagen and elastin fibers, causing wrinkles, pigments, and sagging. Skin aging-related factors, such as tumor necrosis factor-α (TNF-α), promote the generation of intercellular reactive oxygen species (ROS). These are known to stimulate the hypersecretion of matrix metalloproteinase-1 (MMP-1), which degrades collagen and inhibits collagen synthesis. In this study, as part of our ongoing discovery of natural products, we investigated potential natural products derived from ginkgo fruit (Ginkgo biloba fruit) with protective effects against TNF-α-induced skin aging. Phytochemical investigation of the MeOH extract of G. biloba fruits, aided by liquid chromatography–mass spectrometry, led to the isolation of 14 compounds (1–14) from the n-butanol-soluble fraction. These were structurally determined to be: (E)-coniferin (1), syringin (2), 4-hydroxybenzoic acid 4-O-β-D-glucopyranoside (3), vanillic acid 4-O-β-D-glucopyranoside (4), glucosyringic acid (5), (E)-ferulic acid 4-O-β-D-glucoside (6), (E)-sinapic acid 4-O-β-D-glucopyranoside (7), ginkgotoxin-5-glucoside (8), ginkgopanoside (9), (Z)-4-coumaric acid 4-O-β-D-glucopyranoside (10), (1′R,2′S,5′R,8′S,2′Z,4′E)-dihydrophaseic acid 3’-O-β-D-glucopyranoside (11), eucomic acid (12), rutin (13), and laricitrin 3-rutinoside (L3R) (14). Biological evaluation of the isolated compounds for their effects on intracellular ROS generation showed that, of these 14 compounds, L3R (14) inhibited TNF-α-stimulated ROS generation (p < 0.001 at 100 μM). Inhibition of ROS generation by L3R led to the suppression of MMP-1 secretion and protection against collagen degradation. The inhibitory effect of L3R was mediated by the inhibition of extracellular signal regulated kinase (ERK) phosphorylation. Furthermore, L3R diminished the secretion of pro-inflammatory cytokines interleukin 6 (IL-6) and interleukin 8 (IL-8). Based on these experimental results, L3R is a potential bioactive natural product that can be used to protect against skin damage, including aging, in cosmetics and pharmaceuticals.

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Section: Discussionmentioning

confidence: 99%

Laricitrin 3-Rutinoside from Ginkgo biloba Fruits Prevents Damage in TNF-α-Stimulated Normal Human Dermal Fibroblasts

et al. 2023

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“…Excessive UV irradiation generates ROS, which is a key cellular factor in physiological photoaging [37]. Excessive oxidative stress generated by UVB irradiation induces the activation of the MAPK signaling pathway, followed by that of AP-1 and NF-kappa B.…”

Section: Discussionmentioning

confidence: 99%

Antiphotoaging Effect of AGEs Blocker™ in UVB-Irradiated Cells and Skh:HR-1 Hairless Mice

Jung

Choi

Yoo

et al. 2023

CIMB

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Chronic exposure to ultraviolet (UV) radiation is a major cause of photoaging. It involves extrinsic aging, wrinkle formation, and skin dehydration, and leads to excessive production of active oxygen that adversely affects the skin. Here, we investigated the antiphotoaging effect of AGEs BlockerTM (AB), which comprises Korean mint aerial part and fig and goji berry fruits. Compared to its individual components, AB was more potent at increasing the expression of collagen and hyaluronic acid and decreasing MMP-1 expression in UVB-irradiated Hs68 fibroblasts and HaCaT keratinocytes. In Skh:HR-1 hairless mice exposed to 60 mJ/cm2 UVB for 12 weeks, oral administration of 20 or 200 mg/kg/day AB restored skin moisture by improving UVB-induced erythema, skin moisture, and transepidermal water loss, and alleviated photoaging by improving UVB-induced elasticity and wrinkles. Moreover, AB upregulated the mRNA levels of hyaluronic acid synthase and collagen-related Col1a1, Col3a1, and Col4a1 genes, increasing hyaluronic acid and collagen expression, respectively. AB inhibited UVB-induced MAPK and AP-1 (c-fos) activation, resulting in significantly downregulated expression of MMP-1 and -9, which are responsible for collagen degradation. AB also stimulated the expression and activity of antioxidative enzymes and reduced lipid peroxidation. Thus, AB is a potential preventive and therapeutic agent for photoaging.

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“…The leaves of P. chinensis were collected in August at Evada Botanical Garden (GPS coordinates: X: 126.926768 and Y: 37.2482236) and dried for extraction. Four flavonol-diglucuronides (1 and 3-5), five flavonol-mono-glucuronides (2 and 8-11), and two flavonemono-glucuronides (6 and 7) were isolated from the 30% ethanol extract of P. chinensis leaves (Figure 1) [13].…”

Section: Sample Preparationmentioning

confidence: 99%

“…All isolates were tested for the inhibition of TNF-α-induced ROS at each concentration, with no effect on cell proliferation or inhibition, and the isolates showed a significant inhibitory effect. Among the isolates, four flavonol-bis-glucuronides, which are rare in nature and whose pharmacological activity is not well known, were tested for their MMP-1 inhibitory effect, and potentilloside A and quercetin-bis-3,7-O-β-D-glucuronide showed significant inhibition [13]. Thus, the possibility of new activities of the two structurally rare compounds was suggested.…”

Section: Introductionmentioning

confidence: 99%

The Effects of Flavonol and Flavone Glucuronides from Potentilla chinensis Leaves on TNF-α-Exposed Normal Human Dermal Fibroblasts

Choi,

Lee,

Son

et al. 2023

Antioxidants

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Skin aging is a complex biological process influenced by a variety of factors, including UV radiation. UV radiation accelerates collagen degradation via the production of reactive oxygen species (ROS) and cytokines, including TNF-α. In a prior investigation, the inhibitory properties of flavonol and flavone glucuronides derived from Potentilla chinensis on TNF-α-induced ROS and MMP-1 production were explored. Consequently, we verified the skin-protective effects of these flavonol and flavone glucuronides, including potentilloside A, from P. chinensis, and conducted a structure–activity relationship analysis as part of our ongoing research. We investigated the protective effects of the extract and its 11 isolates on TNF-α-stimulated normal human dermal fibroblasts (NHDFs). Ten flavonol and flavone glucuronides significantly inhibited ROS generation (except for 7) and suppressed MMP-1 secretion, except for 2. In contrast, six isolates (1, 5, 6, 11, 9, 10, and 11) showed a significant reverse effect on COLIA1 secretion. Comparing the three experimental results of each isolate, potentilloside A (1) showed the most potent skin cell-protective effect among the isolates. Evaluation of the signaling pathway of potentilloside A in TNF-α-stimulated NHDF revealed that potentilloside A inhibits the phosphorylation of ERK, JNK, and c-Jun. Taken together, these results suggest that compounds isolated from P. chinensis, especially potentilloside A, can be used to inhibit skin damage, including aging.

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Potentilloside A, a New Flavonol-bis-Glucuronide from the Leaves of Potentilla chinensis, Inhibits TNF-α-Induced ROS Generation and MMP-1 Secretion

Cited by 4 publications

References 63 publications

Laricitrin 3-Rutinoside from Ginkgo biloba Fruits Prevents Damage in TNF-α-Stimulated Normal Human Dermal Fibroblasts

Laricitrin 3-Rutinoside from Ginkgo biloba Fruits Prevents Damage in TNF-α-Stimulated Normal Human Dermal Fibroblasts

Antiphotoaging Effect of AGEs Blocker™ in UVB-Irradiated Cells and Skh:HR-1 Hairless Mice

The Effects of Flavonol and Flavone Glucuronides from Potentilla chinensis Leaves on TNF-α-Exposed Normal Human Dermal Fibroblasts

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