Extracellular melanogenesis inhibitory activity and the structure-activity relationships of ugonins from Helminthostachys zeylanica roots

Yamauchi, Kosei; Mitsunaga, Tohru; Itakura, Yuki; Batubara, Irmanida

doi:10.1016/j.fitote.2015.05.006

Cited by 25 publications

(17 citation statements)

References 26 publications

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“…This study has established that the MeOH extract of S. androgynus leaves contains nucleosides, terpenoids, flavonoid glycosides, along with other compounds including steroids as active principles which exhibited cytotoxic activity against HL60, AZ521, SKBR3, and A549 four human cell lines, as well as have been demonstrated to be the relevant active principles of the extract. Moreover, the results also revealed that the flavonoid glycosides exhibited superior capacities to melanogenesis‐inhibitory, because of the structure activity relationship investigation revealed that the flavone skeleton and/or phenolic hydroxy groups, which had been reported in recent literature . This study has thus demonstrated that the MeOH extract of S. androgynus leaves and its constituents may also be valuable as potential anticancer agents and skin‐whitening agents.…”

Section: Resultssupporting

confidence: 67%

Melanogenesis‐Inhibitory and Cytotoxic Activities of Chemical Constituents from the Leaves of Sauropus androgynus L. Merr. (Euphorbiaceae)

Zhang

Zhu

et al. 2018

Chemistry & Biodiversity

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A new steroid, 20-hydroxyisofucosterol (stigmasta-5,24(28)-diene-3β,20β-diol) (7), along with six known compounds 1 - 6 were isolated from the MeOH extract of the leaves of Sauropus androgynus L. Merr. (Euphorbiaceae). The structure of new steroid was determined by HR-APCI-MS and various NMR techniques in combination with literature data. Subsequently, their anti-inflammatory, cytotoxic activities against five human cell lines, as well as inhibitory activities against the α-MSH induced melanogenesis on the B16 cell line were evaluated. As the results, steroid compounds, 6 and 7 exhibited moderate cytotoxic to HL60, AZ521, SKBR3, and A549 tumor cell lines (IC 26.9 - 45.1 μm) with high tumor selectivity for A549 relative to WI38 cell lines (SI 2.6 and 3.0, resp.). And, flavonoid compounds, 4 and 5 exhibited superior inhibitory activities against melanogenesis (67.0 - 94.7% melanin content), even with no or low toxicity to the cells (90.1 - 99.6% cell viability) at the concentrations from 10 to 100 μm. Furthermore, Western blot analysis suggested that compound 5 could inhibit melanogenesis by suppressing the protein expressions of MITF, TRP-1, TRP-2, and tyrosinase.

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Section: Resultssupporting

confidence: 67%

Melanogenesis‐Inhibitory and Cytotoxic Activities of Chemical Constituents from the Leaves of Sauropus androgynus L. Merr. (Euphorbiaceae)

Zhang

Zhu

et al. 2018

Chemistry & Biodiversity

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“…Levels of phospho-AMPK (pAMPK) at Thr-172 were assessed to evaluate AMPK activation. Ugonins J and K are structurally related to natural flavonoid luteolin [23], which has been demonstrated to attenuate hepatic steatosis [24]. Therefore, the agent luteolin was used as a positive control drug in the subsequent experiment.…”

Section: Resultsmentioning

confidence: 99%

Helminthostachys zeylanica alleviates hepatic steatosis and insulin resistance in diet-induced obese mice

Chang

Chiang²,

Lai

et al. 2019

BMC Complement Altern Med

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BackgroundObesity and its associated health conditions, type 2 diabetes mellitus (T2DM) and nonalcoholic fatty liver disease (NAFLD), are worldwide health problems. It has been shown that insulin resistance is associated with increased hepatic lipid and causes hepatic steatosis through a myriad of mechanisms, including inflammatory signaling.MethodsHelminthostachys zeylanica (HZ) is used widely as a common herbal medicine to relieve fever symptoms and inflammatory diseases in Asia. In the present study, we evaluated whether HZ has therapeutic effects on obesity, NAFLD and insulin resistance. The protective effects of HZ extract were examined using free fatty acid-induced steatosis in human HuS-E/2 cells and a high-fat diet-induced NAFLD in mice.ResultsThe major components of the HZ extract are ugonins J and K, confirmed by HPLC. Incubation of human hepatocytes, HuS-E/2 cells, with palmitate markedly increased lipid accumulation and treatment with the HZ extract significantly decreased lipid deposition and facilitated AMPK and ACC activation. After 12 weeks of a high-fat diet with HZ extract treatment, the HFD mice were protected from hyperlipidemia and hyperglycemia. HZ extract prevented body weight gain, adipose tissue expansion and adipocyte hypertrophy in the HFD mice. In addition, fat accumulation was reduced in mice livers. Moreover, the insulin sensitivity-associated index, which evaluates insulin function, was also significantly restored.ConclusionsThese results suggest that HZ has a promising pharmacological effect on high-fat diet-induced obesity, hepatic steatosis and insulin resistance, which may have the potential for clinical application.

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“…Current studies used the crude extracts of HZ to evaluate the anti-inflammatory effects through in vivo hepatotoxicity [ 14 , 15 ] and acute lung injury models [ 16 ]. Several unique flavonoids isolated from HZ were reported to possess a variety of biological activities including antioxidant activities [ 17 , 18 ], anti-inflammatory activities [ 17 , 19 , 20 , 21 , 22 , 23 , 24 ], melanogenesis inhibitory activities [ 25 , 26 ]; neuroprotection [ 27 ], antiosteoporosis [ 23 , 28 , 29 ], anti-cancer [ 30 , 31 ], and immunomodulatory effects [ 32 ]; and prevention of neointimal hyperplasia and migration [ 33 ].…”

Section: Introductionmentioning

confidence: 99%

Hepatoprotective Effect of Ugonin M, A Helminthostachys zeylanica Constituent, on Acetaminophen-Induced Acute Liver Injury in Mice

Kuo

et al. 2018

Molecules

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The present study aimed to discover the possible effectiveness of Ugonin M, a unique flavonoid isolated from Helminthostachys zeylanica—a traditional Chinese medicine used as anti-inflammatory medicine—and to elucidate the potential mechanisms of Ugonin M in the acute liver injury induced by acetaminophen (APAP). In this study, Ugonin M significantly ameliorated APAP-induced histopathological changes and the typical liver function biomarkers (i.e., alanine aminotransferase (ALT), aspartate aminotransferase (AST), and total bilirubin (T-Bil)). It also affected APAP-induced abnormal lipid metabolism including total cholesterol (TC) and triglyceride (TG) in the serum. In inflammatory pharmacological action, Ugonin M suppressed the pro-inflammatory mediators such as nitric oxide (NO) and the lipid peroxidation indicator malondialdehyde (MDA). In addition, Ugonin M reinforced hemeoxygenase-1 (HO-1) protein expression and the production of antioxidant enzymes viz superoxide dismutase (SOD), glutathione peroxidase (GPx), and catalase (CAT). Furthermore, inflammation-associated cytokines including tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and IL-1β as well as proteins such as inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) were decreased by the pretreatment of Ugonin M. Moreover, this study found that pretreatment of Ugonin M apparently decreased nuclear factor-kappa B (NF-κB) and mitogen-activated protein kinases (MAPKs) activation via inhibition of the degradation of NF-κB, inhibitory κB-α (IκB-α), extracellular regulated kinase (ERK), c-Jun-N-terminal (JNK), and p38 active phosphorylation. In conclusion, Ugonin M significantly showed a protective effect against APAP-induced liver injury by reducing oxidative stress and inflammation. Thus, Ugonin M could be one of the effective components of H. zeylanica that plays a major role in the treatment of inflammatory disorders.

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Extracellular melanogenesis inhibitory activity and the structure-activity relationships of ugonins from Helminthostachys zeylanica roots

Cited by 25 publications

References 26 publications

Melanogenesis‐Inhibitory and Cytotoxic Activities of Chemical Constituents from the Leaves of Sauropus androgynus L. Merr. (Euphorbiaceae)

Melanogenesis‐Inhibitory and Cytotoxic Activities of Chemical Constituents from the Leaves of Sauropus androgynus L. Merr. (Euphorbiaceae)

Helminthostachys zeylanica alleviates hepatic steatosis and insulin resistance in diet-induced obese mice

Hepatoprotective Effect of Ugonin M, A Helminthostachys zeylanica Constituent, on Acetaminophen-Induced Acute Liver Injury in Mice

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