Usnic acid (BioDeep_00000007878)

 

Secondary id: BioDeep_00000017243, BioDeep_00000230930

natural product PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


2,6-Diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzofuran-1-one

化学式: C18H16O7 (344.0896)
中文名称: 松萝酸, (-)-松萝酸
谱图信息: 最多检出来源 Viridiplantae(plant) 29.42%

分子结构信息

SMILES: c12c(OC3=CC(=C(C(=O)[C@@]13C)C(=O)C)O)c(c(c(c2O)C)O)C(=O)C
InChI: InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,21-23H,1-4H3

描述信息

A member of the class of dibenzofurans that is dibenzo[b,d]furan-1(9bH)-one substituted by acetyl groups at positions 2 and 6, hydroxy groups at positions 3 and 7 and methyl groups at positions 8 and 9b.
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.457
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.456
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.458
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.459
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.455
(+)-Usnic acid is isolated from isolated from lichens, binds at the ATP-binding pocket of mTOR, and inhibits mTORC1/2 activity. (+)-Usnic acid inhibits the phosphorylation of mTOR downstream effectors: Akt (Ser473), 4EBP1, S6K, induces autophay, with anti-cancer activity[1]. (+)-Usnic acid possesses antimicrobial activity against a number of planktonic gram-positive bacteria, including Staphylococcus aureus, Enterococcus faecalis, and Enterococcus faecium[2].
(+)-Usnic acid is isolated from isolated from lichens, binds at the ATP-binding pocket of mTOR, and inhibits mTORC1/2 activity. (+)-Usnic acid inhibits the phosphorylation of mTOR downstream effectors: Akt (Ser473), 4EBP1, S6K, induces autophay, with anti-cancer activity[1]. (+)-Usnic acid possesses antimicrobial activity against a number of planktonic gram-positive bacteria, including Staphylococcus aureus, Enterococcus faecalis, and Enterococcus faecium[2].
(+)-Usnic acid is isolated from isolated from lichens, binds at the ATP-binding pocket of mTOR, and inhibits mTORC1/2 activity. (+)-Usnic acid inhibits the phosphorylation of mTOR downstream effectors: Akt (Ser473), 4EBP1, S6K, induces autophay, with anti-cancer activity[1]. (+)-Usnic acid possesses antimicrobial activity against a number of planktonic gram-positive bacteria, including Staphylococcus aureus, Enterococcus faecalis, and Enterococcus faecium[2].
(+)-Usnic acid is isolated from isolated from lichens, binds at the ATP-binding pocket of mTOR, and inhibits mTORC1/2 activity. (+)-Usnic acid inhibits the phosphorylation of mTOR downstream effectors: Akt (Ser473), 4EBP1, S6K, induces autophay, with anti-cancer activity[1]. (+)-Usnic acid possesses antimicrobial activity against a number of planktonic gram-positive bacteria, including Staphylococcus aureus, Enterococcus faecalis, and Enterococcus faecium[2].
Usnic acid, a lichen-derived secondary metabolite, has a unique dibenzofuran skeleton. Usnic acid has excellent anticancer and antimicrobial properties. Usnic acid significantly inhibits RANKL-mediated osteoclast formation and function by reducing the transcriptional and translational expression of NFATc1[1].
Usnic acid, a lichen-derived secondary metabolite, has a unique dibenzofuran skeleton. Usnic acid has excellent anticancer and antimicrobial properties. Usnic acid significantly inhibits RANKL-mediated osteoclast formation and function by reducing the transcriptional and translational expression of NFATc1[1].

同义名列表

10 个代谢物同义名

Usnic acid; 2,6-Diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzofuran-1-one; d-Usnic acid; (±)-Usnic acid; (+)-Usnic acid; (-)-TRANS-45-BIS(IODOMETHYL)-2,2-DIMETHYL-13-DIOXOLANE; (S)-Usnic acid; (-)-Usnic acid; (S)-usnate; (-)-Usnic acid



数据库引用编号

63 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

131 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ANXA5, BCL2, CASP7, CASP9, HPD, MAPK8, MTOR, NOS2, VEGFA
Peripheral membrane protein 4 ANXA5, CYP1B1, HPD, MTOR
Endoplasmic reticulum membrane 5 BCL2, CYP1B1, HPD, HSP90B1, MTOR
Nucleus 13 BCL2, CASP7, CASP9, GABPA, HSP90B1, JUN, LIG4, MAPK8, MPO, MTOR, NOS2, PARP1, VEGFA
cytosol 11 ANXA5, BCL2, CASP7, CASP9, GPT, HPD, HSP90B1, MAPK8, MTOR, NOS2, PARP1
dendrite 1 MTOR
nuclear body 1 PARP1
phagocytic vesicle 1 MTOR
nucleoplasm 9 CASP7, GABPA, JUN, LIG4, MAPK8, MPO, MTOR, NOS2, PARP1
RNA polymerase II transcription regulator complex 1 JUN
Cell membrane 1 TNF
Cytoplasmic side 1 MTOR
Golgi apparatus membrane 2 HPD, MTOR
Synapse 1 MAPK8
cell surface 2 TNF, VEGFA
Golgi apparatus 1 VEGFA
Golgi membrane 2 HPD, MTOR
lysosomal membrane 2 GAA, MTOR
neuronal cell body 1 TNF
sarcolemma 1 ANXA5
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 3 CASP7, NOS2, PARP1
Lysosome 3 GAA, MPO, MTOR
plasma membrane 3 GAA, NOS2, TNF
Membrane 8 ANXA5, BCL2, CYP1B1, GAA, HSP90B1, MTOR, PARP1, VEGFA
axon 1 MAPK8
extracellular exosome 6 ANXA5, GAA, GPT, HPD, HSP90B1, MPO
Lysosome membrane 2 GAA, MTOR
endoplasmic reticulum 3 BCL2, HSP90B1, VEGFA
extracellular space 4 CASP7, MPO, TNF, VEGFA
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 2 HSP90B1, NOS2
adherens junction 1 VEGFA
mitochondrion 4 BCL2, CASP9, CYP1B1, PARP1
protein-containing complex 4 BCL2, CASP9, HSP90B1, PARP1
intracellular membrane-bounded organelle 4 CYP1B1, GAA, LIG4, MPO
Microsome membrane 2 CYP1B1, MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 2 GAA, VEGFA
extracellular region 6 ANXA5, GAA, HSP90B1, MPO, TNF, VEGFA
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, MTOR
transcription regulator complex 2 JUN, PARP1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 ANXA5, TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
nucleolus 1 PARP1
midbody 1 HSP90B1
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 NOS2
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 2 ANXA5, HSP90B1
extracellular matrix 1 VEGFA
Peroxisome 1 NOS2
peroxisomal matrix 1 NOS2
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 2 ANXA5, HSP90B1
secretory granule 2 MPO, VEGFA
Zymogen granule membrane 1 ANXA5
chromatin 3 GABPA, JUN, PARP1
phagocytic cup 1 TNF
Chromosome 1 PARP1
Secreted, extracellular space 1 CASP7
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 2 LIG4, PARP1
nuclear chromosome 1 JUN
site of double-strand break 1 PARP1
nuclear envelope 2 MTOR, PARP1
Endomembrane system 1 MTOR
tertiary granule membrane 1 GAA
Melanosome 1 HSP90B1
euchromatin 1 JUN
myelin sheath 1 BCL2
sperm plasma membrane 1 HSP90B1
azurophil granule 1 MPO
endoplasmic reticulum lumen 1 HSP90B1
platelet alpha granule lumen 1 VEGFA
azurophil granule membrane 1 GAA
azurophil granule lumen 1 MPO
apoptosome 1 CASP9
vesicle membrane 1 ANXA5
Sarcoplasmic reticulum lumen 1 HSP90B1
phagocytic vesicle lumen 1 MPO
protein-DNA complex 1 PARP1
ficolin-1-rich granule membrane 1 GAA
basal dendrite 1 MAPK8
condensed chromosome 1 LIG4
Cytoplasmic vesicle, phagosome 1 MTOR
site of DNA damage 1 PARP1
endocytic vesicle lumen 1 HSP90B1
transcription factor AP-1 complex 1 JUN
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cortical cytoskeleton 1 NOS2
endoplasmic reticulum chaperone complex 1 HSP90B1
endothelial microparticle 1 ANXA5
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
autolysosome lumen 1 GAA
BAD-BCL-2 complex 1 BCL2
DNA-dependent protein kinase-DNA ligase 4 complex 1 LIG4
nonhomologous end joining complex 1 LIG4
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
DNA ligase IV complex 1 LIG4
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Theerthu Azhamuthu, Suresh Kathiresan, Ilanchitchenni Senkuttuvan, Nihal Ahamed Abulkalam Asath, Pugazhendhi Ravichandran. Usnic acid attenuates 7,12-dimethylbenz[a] anthracene (DMBA) induced oral carcinogenesis through inhibiting oxidative stress, inflammation, and cell proliferation in male golden Syrian hamster model. Journal of biochemical and molecular toxicology. 2023 Oct; ?(?):e23553. doi: 10.1002/jbt.23553. [PMID: 37840363]
  • Magdalena Kulinowska, Sławomir Dresler, Agnieszka Skalska-Kamińska, Agnieszka Hanaka, Maciej Strzemski. Methodological Aspects of Green Extraction of Usnic Acid Using Natural Deep Eutectic Solvents. Molecules (Basel, Switzerland). 2023 Jul; 28(14):. doi: 10.3390/molecules28145321. [PMID: 37513195]
  • Han Zhang, Xiaojie Li, Xue Liu, Xia Ji, Xuan Ma, Jun Chen, Yanmin Bao, Yingdan Zhang, Liangxiong Xu, Liang Yang, Xiaoyi Wei. The usnic acid derivative peziculone targets cell wall of Gram-positive bacteria revealed by high throughput CRISPRi-seq analysis. International journal of antimicrobial agents. 2023 Jun; ?(?):106876. doi: 10.1016/j.ijantimicag.2023.106876. [PMID: 37276892]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Maulidiyah Maulidiyah, Faradillah Rachman, La Ode Muhammad Zuhdi Mulkiyan, Muhammad Natsir, Nohong Nohong, Akhmad Darmawan, La Ode Agus Salim, Muhammad Nurdin. Antioxidant Activity of Usnic Acid Compound from Methanol Extract of Lichen Usnea sp. Journal of oleo science. 2023 Feb; 72(2):179-188. doi: 10.5650/jos.ess22315. [PMID: 36631103]
  • Serpil Kiliç Yayla, Zekiye Kocakaya, Gökçe Şeker Karatoprak, Selen İlgün, Ahmet Ceylan. Analyzing the Impact of Ramalina digitellata, R. fastigiata, R. fraxinea, and R. polymorpha's Usnic Acid Concentration on Antioxidant, DNA-Protective, Antimicrobial, and Cytotoxic Properties. Chemistry & biodiversity. 2023 Jan; 20(1):e202200816. doi: 10.1002/cbdv.202200816. [PMID: 36482033]
  • Tatyana I Rokitskaya, Alexander M Arutyunyan, Ljudmila S Khailova, Alisa D Kataeva, Alexander M Firsov, Elena A Kotova, Yuri N Antonenko. Usnic Acid-Mediated Exchange of Protons for Divalent Metal Cations across Lipid Membranes: Relevance to Mitochondrial Uncoupling. International journal of molecular sciences. 2022 Dec; 23(24):. doi: 10.3390/ijms232416203. [PMID: 36555847]
  • Hanxue Wang, Min Xuan, Cheng Huang, Changhong Wang. Advances in Research on Bioactivity, Toxicity, Metabolism, and Pharmacokinetics of Usnic Acid In Vitro and In Vivo. Molecules (Basel, Switzerland). 2022 Nov; 27(21):. doi: 10.3390/molecules27217469. [PMID: 36364296]
  • Madhuree Kumari, Siya Kamat, C Jayabaskaran. Usnic acid induced changes in biomolecules and their association with apoptosis in squamous carcinoma (A-431) cells: A flow cytometry, FTIR and DLS spectroscopic study. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2022 Jun; 274(?):121098. doi: 10.1016/j.saa.2022.121098. [PMID: 35257985]
  • Agnieszka Pyrczak-Felczykowska, Tristan A Reekie, Marcin Jąkalski, Aleksandra Hać, Marcelina Malinowska, Anna Pawlik, Kamil Ryś, Beata Guzow-Krzemińska, Anna Herman-Antosiewicz. The Isoxazole Derivative of Usnic Acid Induces an ER Stress Response in Breast Cancer Cells That Leads to Paraptosis-like Cell Death. International journal of molecular sciences. 2022 Feb; 23(3):. doi: 10.3390/ijms23031802. [PMID: 35163724]
  • Tatyana I Rokitskaya, Elena A Kotova, Yuri N Antonenko. Anomalous potentials on bilayer lipid membranes in the presence of usnic acid: Markin-Sokolov versus Nernst-Donnan equilibrium. Bioelectrochemistry (Amsterdam, Netherlands). 2021 Oct; 141(?):107825. doi: 10.1016/j.bioelechem.2021.107825. [PMID: 34030021]
  • Małgorzata Kikowska, Barbara Thiem, Karolina Jafernik, Marta Klimek-Szczykutowicz, Elżbieta Studzińska-Sroka, Halina Ekiert, Agnieszka Szopa. Effect of Elicitation with (+)-Usnic Acid on Accumulation of Phenolic Acids and Flavonoids in Agitated Microshoots of Eryngium alpinum L. Molecules (Basel, Switzerland). 2021 Sep; 26(18):. doi: 10.3390/molecules26185532. [PMID: 34577004]
  • Sreeja Lakshmi, Shamprasad Varija Raghu, Preetham Elumalai, Sureshkumar Sivan. Alkoxy glycerol enhanced activity of Oxyresveratrol in Alzheimer's disease by rescuing Tau protein. Neuroscience letters. 2021 08; 759(?):135981. doi: 10.1016/j.neulet.2021.135981. [PMID: 34023407]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Sukfan P Kwong, Zhenlin Huang, Lili Ji, Changhong Wang. PORIMIN: The key to (+)-Usnic acid-induced liver toxicity and oncotic cell death in normal human L02 liver cells. Journal of ethnopharmacology. 2021 Apr; 270(?):113873. doi: 10.1016/j.jep.2021.113873. [PMID: 33485970]
  • Cristina Avonto, Amar G Chittiboyina, Shabana I Khan, Olivia R Dale, Jon F Parcher, Mei Wang, Ikhlas A Khan. Are atranols the only skin sensitizers in oakmoss? A systematic investigation using non-animal methods. Toxicology in vitro : an international journal published in association with BIBRA. 2021 Feb; 70(?):105053. doi: 10.1016/j.tiv.2020.105053. [PMID: 33212168]
  • Camila Andre Cazarin, Ana Paula Dalmagro, Ana Elisa Gonçalves, Thaise Boeing, Luísa Mota da Silva, Rogério Corrêa, Luiz Carlos Klein-Júnior, Bernardo Carlesso Pinto, Thaís Savoldi Lorenzett, Thales Uchôa da Costa Sobrinho, Ângelo de Fátima, Tiago Coelho de Assis Lage, Sergio Antonio Fernandes, Márcia Maria de Souza. Usnic acid enantiomers restore cognitive deficits and neurochemical alterations induced by Aβ1-42 in mice. Behavioural brain research. 2021 01; 397(?):112945. doi: 10.1016/j.bbr.2020.112945. [PMID: 33022354]
  • Péligris Henrique Dos Santos, Thassio Mesquita, Rodrigo Miguel-Dos-Santos, Grace Kelly Melo de Almeida, Lucas Andrade de Sá, Paula Dos Passos Menezes, Adriano Antunes de Souza Araujo, Sandra Lauton-Santos. Inclusion complex with β-cyclodextrin is a key determining factor for the cardioprotection induced by usnic acid. Chemico-biological interactions. 2020 Dec; 332(?):109297. doi: 10.1016/j.cbi.2020.109297. [PMID: 33096055]
  • Sukfan P Kwong, Changhong Wang. Review: Usnic acid-induced hepatotoxicity and cell death. Environmental toxicology and pharmacology. 2020 Nov; 80(?):103493. doi: 10.1016/j.etap.2020.103493. [PMID: 32961280]
  • Sukfan P Kwong, Hanxue Wang, Liang Shi, Zhenlin Huang, Bin Lu, Xuemei Cheng, Guixin Chou, Lili Ji, Changhong Wang. Identification of photodegraded derivatives of usnic acid with improved toxicity profile and UVA/UVB protection in normal human L02 hepatocytes and epidermal melanocytes. Journal of photochemistry and photobiology. B, Biology. 2020 Apr; 205(?):111814. doi: 10.1016/j.jphotobiol.2020.111814. [PMID: 32092663]
  • Kunal Kumar, Jai P N Mishra, Rana P Singh. Usnic acid induces apoptosis in human gastric cancer cells through ROS generation and DNA damage and causes up-regulation of DNA-PKcs and γ-H2A.X phosphorylation. Chemico-biological interactions. 2020 Jan; 315(?):108898. doi: 10.1016/j.cbi.2019.108898. [PMID: 31715134]
  • Richard Staples, Robert L LaDuca, Ludmila V Roze, Maris Laivenieks, John E Linz, Randolph Beaudry, Alan Fryday, Anthony L Schilmiller, Anna V Koptina, Benjamin Smith, Frances Trail. Structure and Chemical Analysis of Major Specialized Metabolites Produced by the Lichen Evernia prunastri. Chemistry & biodiversity. 2020 Jan; 17(1):e1900465. doi: 10.1002/cbdv.201900465. [PMID: 31701649]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Agnieszka Pyrczak-Felczykowska, Rajeshwar Narlawar, Anna Pawlik, Beata Guzow-Krzemińska, Damian Artymiuk, Aleksandra Hać, Kamil Ryś, Louis M Rendina, Tristan A Reekie, Anna Herman-Antosiewicz, Michael Kassiou. Synthesis of Usnic Acid Derivatives and Evaluation of Their Antiproliferative Activity against Cancer Cells. Journal of natural products. 2019 07; 82(7):1768-1778. doi: 10.1021/acs.jnatprod.8b00980. [PMID: 31282672]
  • Hallysson Douglas A Araújo, José G Silva Júnior, João R Saturnino Oliveira, Maria Helena M L Ribeiro, Mônica C Barroso Martins, Marcos A Cavalcanti Bezerra, André Lima Aires, Mônica C P Azevedo Albuquerque, Mário R Melo-Júnior, Nicodemos T Pontes Filho, Eugênia C Pereira, Diego J Raposo Silva, Janaína V Dos Anjos, Emerson Peter S Falcão, Nicácio H Silva, Vera L Menezes Lima. Usnic Acid Potassium Salt: Evaluation of the Acute Toxicity and Antinociceptive Effect in Murine Model. Molecules (Basel, Switzerland). 2019 May; 24(11):. doi: 10.3390/molecules24112042. [PMID: 31142045]
  • Yuri N Antonenko, Ljudmila S Khailova, Tatyana I Rokitskaya, Ekaterina S Nosikova, Pavel A Nazarov, Ol'ga A Luzina, Nariman F Salakhutdinov, Elena A Kotova. Mechanism of action of an old antibiotic revisited: Role of calcium ions in protonophoric activity of usnic acid. Biochimica et biophysica acta. Bioenergetics. 2019 04; 1860(4):310-316. doi: 10.1016/j.bbabio.2019.01.005. [PMID: 30710552]
  • Ludan Hou, Yiran Jin, Wenjing Sun, Shuai Guan, Huijun Xu, Qiao Wang, Lantong Zhang, Yingfeng Du. Metabolites identification of (+)-usnic acid in vivo by ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. Fitoterapia. 2019 Mar; 133(?):85-95. doi: 10.1016/j.fitote.2018.12.020. [PMID: 30605779]
  • Ilya Prokopiev, Galina Filippova, Eduard Filippov, Ivan Voronov, Igor Sleptsov, Aliy Zhanataev. Genotoxicity of (+)- and (-)-usnic acid in mice. Mutation research. Genetic toxicology and environmental mutagenesis. 2019 Mar; 839(?):36-39. doi: 10.1016/j.mrgentox.2019.01.010. [PMID: 30744810]
  • Ashish Garg, Sweta Garg, Nitendra K Sahu, Sarita Rani, Umesh Gupta, Awesh K Yadav. Heparin appended ADH-anionic polysaccharide nanoparticles for site-specific delivery of usnic acid. International journal of pharmaceutics. 2019 Feb; 557(?):238-253. doi: 10.1016/j.ijpharm.2018.12.049. [PMID: 30594688]
  • Djalma M de Oliveira, Cristiane B Pereira, Graziele Mendes, Jochen Junker, Markus Kolloff, Luiz H Rosa, Carlos A Rosa, Tânia M A Alves, Carlos L Zani, Susana Johann, Betania B Cota. Two new usnic acid derivatives from the endophytic fungus Mycosphaerella sp. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2018 Nov; 73(11-12):449-455. doi: 10.1515/znc-2017-0162. [PMID: 30179857]
  • Yi Yang, Woo Kyun Bae, Ji-Yoon Lee, Yong Jae Choi, Kyung Hwa Lee, Myong-Suk Park, Young Hyun Yu, So-Yeon Park, Rui Zhou, İsa Taş, Chathurika Gamage, Man-Jeong Paik, Jae Hyuk Lee, Ik Joo Chung, Kyung Keun Kim, Jae-Seoun Hur, Sang Kyum Kim, Hyung-Ho Ha, Hangun Kim. Potassium usnate, a water-soluble usnic acid salt, shows enhanced bioavailability and inhibits invasion and metastasis in colorectal cancer. Scientific reports. 2018 11; 8(1):16234. doi: 10.1038/s41598-018-34709-9. [PMID: 30390003]
  • Yazhi Gao, Wei Liu, Xiaoxiong Wang, Lihua Yang, Su Han, Shiguo Chen, Reto Jörg Strasser, Bernal E Valverde, Sheng Qiang. Comparative phytotoxicity of usnic acid, salicylic acid, cinnamic acid and benzoic acid on photosynthetic apparatus of Chlamydomonas reinhardtii. Plant physiology and biochemistry : PPB. 2018 Jul; 128(?):1-12. doi: 10.1016/j.plaphy.2018.04.037. [PMID: 29751250]
  • Kartsev Victor, Lichitsky Boris, Geronikaki Athina, Petrou Anthi, Smiljkovic Marija, Kostic Marina, Radanovic Oliver, Soković Marina. Design, synthesis and antimicrobial activity of usnic acid derivatives. MedChemComm. 2018 May; 9(5):870-882. doi: 10.1039/c8md00076j. [PMID: 30108976]
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