Citrulluside H and citrulluside T from young watermelon fruit attenuate ultraviolet B radiation‐induced matrix metalloproteinase expression through the scavenging of generated reactive oxygen species in human dermal fibroblasts

Itoh, Tomohiro; Fujita, Singo; Koketsu, Mamoru; Hashizume, Toshiharu

doi:10.1111/phpp.12669

Cited by 4 publications

(4 citation statements)

References 31 publications

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“…In fact, we are not the first to isolate citrulluside T. Itoh et al [27] first isolated citrulluside H and citrulluside T from young watermelon fruits and reported that these two compounds attenuated ultraviolet B radiation-induced matrix metalloproteinase expression by scavenging reactive oxygen species produced by human skin fibroblasts. However, no studies have reported that compounds in the citrulluside family effectively inhibit melanogenesis.…”

Section: Discussionmentioning

confidence: 97%

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Citrulluside T, Isolated from the Citrullus lanatus Stem, Inhibits Melanogenesis in α-MSH-Induced Mouse B16F10 Cells

2023

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With the increasing number of cosmetic consumers emphasizing value consumption and sustainability, upcycling has gained attention as a solution to agricultural by-products, which are the main culprits of environmental problems. In this study, we isolated citrulluside T with whitening activity from discarded Citrullus lanatus stems and investigated the anti-melanogenic effect of citrulluside T and the underlying mechanisms. We found that citrulluside T did not exhibit cytotoxicity up to a concentration of 90 μM and significantly reduced the melanin content and intracellular tyrosinase activity in B16F10 cells. In addition, citrulluside T inhibited the expression of melanogenic enzymes such as tyrosinase, tyrosinase-related protein (TRP)-1, and TRP-2, as well as melanin synthesis via cAMP-dependent protein kinase (PKA)/cAMP response element-binding protein (CREB)-mediated downregulation of microphthalmia-associated transcription factor (MITF), a key transcription factor in melanogenesis. Furthermore, we found that citrulluside T exerted its anti-melanogenic effect by downregulating the β-catenin protein and upregulating phosphorylated β-catenin. Finally, we confirmed that citrulluside T was safe for skin through skin irritation tests on 33 subjects, suggesting its applicability as a protective agent against hyperpigmentation for topical applications such as cosmetics and ointments.

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Section: Discussionmentioning

confidence: 97%

“…The eluate obtained was subjected to compound isolation using 100% methanol on a column packed with Sephadex LH-20 to increase the purity (Figure 1). The isolated compounds were identified via NMR analysis, referring to the literature [26,27].…”

Section: Extraction and Isolation From The Citrullus Lanatus Stemmentioning

confidence: 99%

Citrulluside T, Isolated from the Citrullus lanatus Stem, Inhibits Melanogenesis in α-MSH-Induced Mouse B16F10 Cells

2023

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“…18‐21 We previously isolated phytol from watermelon sprouts and the novel phenolic glycosides citrulluside H (CH) and citrulluside T (CT) from young watermelon fruits, which showed anti-tumor and anti-oxidative activities, respectively. 22‐24…”

Section: Introductionmentioning

confidence: 99%

“…[18][19][20][21] We previously isolated phytol from watermelon sprouts and the novel phenolic glycosides citrulluside H (CH) and citrulluside T (CT) from young watermelon fruits, which showed anti-tumor and anti-oxidative activities, respectively. [22][23][24] In this study, we further investigated the function of these recently isolated phenolic glycosides, including their inhibitory effects on the growth of C. acnes and inflammatory effects. C. acnes releases pro-inflammatory cytokines and chemokines via the innate immune receptors TLR2 and TLR4, and the 2 novel phenol glycosides induced anti-inflammatory effects by reducing the activity of nuclear factor κB (NF-κB), which is activated by TLRs.…”

Section: Introductionmentioning

confidence: 99%

Phenolic Glycosides Citrulluside H and Citrulluside T Isolated From Young Watermelon (Citrullus lanatus) Fruit Have Beneficial Effects Against Cutibacterium acnes-Induced Skin Inflammation

Itoh

Muramatsu

Miyazono

et al. 2022

Natural Product Communications

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Acne vulgaris, typically caused by Cutibacterium acnes ( C. acnes) involves chronic inflammation of the sebaceous follicles and is the most common skin disease, afflicting 85% of adolescents. We previously isolated 2 novel phenolic glycosides, 2-caffeoyl-3-hydroxy-3-methylbutyric 4′-β-D-glucopyranosyloxy-3′-hydroxybenzyl ester (citrulluside H [CH]) and 2-caffeoyl-3-hydroxy-3-methylbutyric 4′-β-d-glucopyranosyloxybenzyl ester (citrulluside T [CT]), from young fruits of watermelon ( Citrullus lanatus). Both compounds suppressed UVB-induced photoaging in human fibroblasts by scavenging intracellular reactive oxygen species (ROS) and thus might be useful as natural skin care ingredients. In this study, we examined the inhibitory effects of these phenolic glycosides on C. acnes growth and C.acnes-induced inflammation. Neither phenolic glycoside inhibited the growth of C. acnes. However, they both significantly suppressed toll-like receptor (TLR) 1/2 or TLR2/6/nuclear factor κB (NF-κB) signaling in heat-killed C. acnes (hk- C. acnes) -stimulated RAW264.7 cells. Additionally, both phenolic glycosides decreased the expression of M1 macrophage biomarkers (cluster of differentiation [ CD] 80, CD86, and inducible NO synthase [ iNOS]), suggesting that they attenuate M1 macrophage activation. These results indicated that both CH and CT are potential therapeutic substances against C. acnes-induced skin inflammation.

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A recent update on the connection between dietary phytochemicals and skin cancer: emerging understanding of the molecular mechanism

Singh,

Mishra,

Mohanto

et al. 2024

Annals of Medicine &Amp; Surgery

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Constant exposure to harmful substances from both inside and outside the body can mess up the body's natural ways of keeping itself in balance. This can cause severe skin damage, including basal cell carcinoma (BCC), squamous cell carcinoma (SCC), and melanoma. However, plant-derived compounds found in fruits and vegetables have been shown to protect against skin cancer-causing free radicals and other harmful substances. It has been determined that these dietary phytochemicals are effective in preventing skin cancer and are widely available, inexpensive, and well-tolerated. Studies have shown that these phytochemicals possess anti-inflammatory, antioxidant, and anti-angiogenic properties that can aid in the prevention of skin cancers. In addition, they influence crucial cellular processes such as angiogenesis and cell cycle control, which can halt the progression of skin cancer. The present paper discusses the benefits of specific dietary phytochemicals found in fruits and vegetables, as well as the signalling pathways they regulate, the molecular mechanisms involved in the prevention of skin cancer and their drawbacks.

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Citrulluside H and citrulluside T from young watermelon fruit attenuate ultraviolet B radiation‐induced matrix metalloproteinase expression through the scavenging of generated reactive oxygen species in human dermal fibroblasts

Cited by 4 publications

References 31 publications

Citrulluside T, Isolated from the Citrullus lanatus Stem, Inhibits Melanogenesis in α-MSH-Induced Mouse B16F10 Cells

Citrulluside T, Isolated from the Citrullus lanatus Stem, Inhibits Melanogenesis in α-MSH-Induced Mouse B16F10 Cells

Phenolic Glycosides Citrulluside H and Citrulluside T Isolated From Young Watermelon (Citrullus lanatus) Fruit Have Beneficial Effects Against Cutibacterium acnes-Induced Skin Inflammation

A recent update on the connection between dietary phytochemicals and skin cancer: emerging understanding of the molecular mechanism

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