Secondary Metabolites from the Cultures of Medicinal Mushroom Vanderbylia robiniophila and Their Tyrosinase Inhibitory Activities

Vanderbylia robiniophila (Huaier in Chinese) has been used as a traditional herbal medicine in China for over 1600 years. However, the secondary metabolites of V. robiniophila have not been systematically examined. Corresponding chemical investigation in this study led to the discovery of two new compounds, (22E, 24R)-6β, 7α-dimethoxyergosta-8(14), 22-diene-3β, 5α-diol (1) and vanderbyliolide A (8), along with eight known ones (2–7, 9–10). Their structures were determined by extensive spectroscopic analyses and electronic circular dichroism (ECD) calculations. The tyrosinase inhibitory activity of all isolated compounds was evaluated, and compound 10 showed a potential tyrosinase inhibitory effect with an IC50 value of 60.47 ± 2.63 μM. Kinetic studies of the inhibition reactions suggested that 10 provides the inhibitory ability on tyrosinase in an uncompetitive way.

[1]  T. Hirano,et al.  Secoergostane- and ergostane-type steroids from Pleurotus cornucopiae var. citrinopileatus. , 2022, Phytochemistry.

[2]  Ying Wang,et al.  An extraction from Trametes robiniophila Murr. (Huaier) inhibits non-small cell lung cancer proliferation via targeting to epidermal growth factor receptor , 2022, Bioengineered.

[3]  Yu Zhang,et al.  Metabolomic comparison between natural Huaier and artificial cultured Huaier. , 2022, Biomedical chromatography : BMC.

[4]  J. Glamočlija,et al.  Unravelling Anti-Melanogenic Potency of Edible Mushrooms Laetiporus sulphureus and Agaricus silvaticus In Vivo Using the Zebrafish Model , 2021, Journal of fungi.

[5]  J. Shim.  Inhibitory Effects of Cycloheterophyllin on Melanin Synthesis , 2021, Molecules.

[6]  Tim Schäfer,et al.  Mind the mushroom: natural product biosynthetic genes and enzymes of Basidiomycota. , 2021, Natural product reports.

[7]  S. Fogarasi,et al.  Elemental Composition, Antioxidant and Antibacterial Properties of Some Wild Edible Mushrooms from Romania , 2020, Agronomy.

[8]  Zhixiang Wang,et al.  Huaier Suppresses the Hepatocellular Carcinoma Cell Cycle by Regulating Minichromosome Maintenance Proteins , 2020, OncoTargets and therapy.

[9]  K. Chiba.  Discovery of fingolimod based on the chemical modification of a natural product from the fungus, Isaria sinclairii , 2020, The Journal of Antibiotics.

[10]  Qifeng Yang,et al.  Trametes robiniophila Murr in the treatment of breast cancer. , 2020, Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.

[11]  Ding Li,et al.  Phaeosphaones: Tyrosinase Inhibitory Thiodiketopiperazines from an Endophytic Phaeosphaeria fuckelii. , 2020, Journal of natural products.

[12]  Yan Yang,et al.  Three New Butenolides from the Green Alga Caulerpa racemosa var. turbinata , 2020, Chemistry & biodiversity.

[13]  M. Chorilli,et al.  Vitamin c: One compound, several uses. Advances for delivery, efficiency and stability. , 2020, Nanomedicine : nanotechnology, biology, and medicine.

[14]  Jianyun Lu,et al.  The role and mechanism of Asian medicinal plants in treating skin pigmentary disorders. , 2019, Journal of ethnopharmacology.

[15]  Zeyan Li,et al.  HP-1 inhibits the progression of ccRCC and enhances sunitinib therapeutic effects by suppressing EMT. , 2019, Carbohydrate polymers.

[16]  C. Morrow,et al.  Brominated Bisindole Alkaloids from the Celtic Sea Sponge Spongosorites calcicola , 2019, Molecules.

[17]  Shaojiang Song,et al.  Diverse metabolites from corn silk with anti-Aβ1-42 aggregation activity. , 2019, Fitoterapia.

[18]  Jian Huang,et al.  Trametes robiniophila Murr: a traditional Chinese medicine with potent anti-tumor effects , 2019, Cancer management and research.

[19]  S. Socaci,et al.  Bioactive Compounds and Volatile Profiles of Five Transylvanian Wild Edible Mushrooms , 2018, Molecules.

[20]  P. Bie,et al.  Effect of Huaier granule on recurrence after curative resection of HCC: a multicentre, randomised clinical trial , 2018, Gut.

[21]  V. Namasivayam,et al.  Inhibitors of Melanogenesis: An Updated Review. , 2018, Journal of medicinal chemistry.

[22]  Suyu Gao,et al.  New natural inhibitors of hexokinase 2 (HK2): Steroids from Ganoderma sinense. , 2018, Fitoterapia.

[23]  N. Lall,et al.  Isolation of Flavonoids and Flavonoid Glycosides from Myrsine africana and Their Inhibitory Activities against Mushroom Tyrosinase. , 2018, Journal of natural products.

[24]  L. Shan,et al.  Huaier Restrains Proliferative and Migratory Potential of Hepatocellular Carcinoma Cells Partially Through Decreased Yes-Associated Protein 1 , 2017, Journal of Cancer.

[25]  Qifeng Yang,et al.  Huaier aqueous extract protects against dextran sulfate sodium-induced experimental colitis in mice by inhibiting NLRP3 inflammasome activation , 2017, Oncotarget.

[26]  V. Namasivayam,et al.  Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors , 2017, Journal of enzyme inhibition and medicinal chemistry.

[27]  Zhiyong Luo,et al.  A polysaccharide from Huaier induced apoptosis in MCF-7 breast cancer cells via down-regulation of MTDH protein. , 2016, Carbohydrate polymers.

[28]  A. Yang,et al.  Huaier restrains proliferative and invasive potential of human hepatoma SKHEP-1 cells partially through decreased Lamin B1 and elevated NOV , 2016, Scientific Reports.

[29]  Qifeng Yang,et al.  Huaier extract suppresses breast cancer via regulating tumor-associated macrophages , 2016, Scientific Reports.

[30]  T. Nam,et al.  Natural, semisynthetic and synthetic tyrosinase inhibitors , 2016, Journal of enzyme inhibition and medicinal chemistry.

[31]  T. Anke,et al.  Fungal natural products in research and development. , 2014, Natural product reports.

[32]  H. Wang,et al.  A new glucitol from an endophytic fungus Fusarium equiseti Salicorn 8 , 2014, European Food Research and Technology.

[33]  G. Bringmann,et al.  SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. , 2013, Chirality.

[34]  Shuai Li,et al.  Cytotoxic steroids from Monascus purpureus-fermented rice , 2011, Steroids.

[35]  E. Fattorusso,et al.  Zorrimidazolone, a Bioactive Alkaloid from the Non-Indigenous Mediterranean Stolidobranch Polyandrocarpa zorritensis , 2011, Marine drugs.

[36]  M. Roué,et al.  Bioactive Indole Derivatives from the South Pacific Marine Sponges Rhopaloeides odorabile and Hyrtios sp. , 2011, Marine drugs.

[37]  Hui Huang,et al.  Steroids with aromatic A-rings from the Hainan soft coral Dendronephthya studeri Ridley. , 2011, Journal of natural products.

[38]  Makoto Tanaka,et al.  Variation in cytostatic constituents of a sponge-derived Gymnascella dankaliensis by manipulating the carbon source. , 2007, Journal of natural products.

[39]  Jongki Hong,et al.  Monoindole Alkaloids from a Marine Sponge Spongosorites sp. , 2007, Marine drugs.

[40]  M. Kikuchi,et al.  A new ceramide from Ramaria botrytis (Pers.) Ricken , 2007, Journal of Natural Medicines.

[41]  D. Payne,et al.  Selection of Retapamulin, a Novel Pleuromutilin for Topical Use , 2006, Antimicrobial Agents and Chemotherapy.

[42]  X. Yao,et al.  Biphenyl glycosides from the fruit of Pyracantha fortuneana. , 2006, Journal of natural products.

[43]  Jian Huang,et al.  Cytotoxic sterols from marine-derived fungus Pennicillium sp. , 2006, Natural product research.

[44]  E. Sharlow,et al.  Inhibition of melanosome transfer results in skin lightening. , 2000, The Journal of investigative dermatology.

[45]  K. Sakaguchi,et al.  4-Hydroxy-17-methylincisterol, an inhibitor of DNA polymerase-alpha activity and the growth of human cancer cells in vitro. , 1998, Biochemical pharmacology.

[46]  C. Skibola,et al.  Hypothesis: Phenol and hydroquinone derived mainly from diet and gastrointestinal flora activity are causal factors in leukemia , 2001, Leukemia.