| Identification | Back Directory | [Name]
BRYOPOGONIC ACID | [CAS]
571-67-5 | [Synonyms]
NORSTICTIC ACID
BRYOPOGONIC ACID
1,3-Dihydro-1,4,10-trihydroxy-5,8-dimethyl-3,7-dioxo-7H-isobenzofuro[4,5-b][1,4]benzodioxepin-11-carbaldehyde
7H-Isobenzofuro[4,5-b][1,4]benzodioxepin-11-carboxaldehyde, 1,3-dihydro-1,4,10-trihydroxy-5,8-dimethyl-3,7-dioxo- | [Molecular Formula]
C18H12O9 | [MDL Number]
MFCD02113777 | [MOL File]
571-67-5.mol | [Molecular Weight]
372.28 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble | [form ]
A solid | [color ]
White to off-white | [LogP]
2.330 (est) |
| Hazard Information | Back Directory | [Description]
Norstictic acid is a lichen metabolite that has been found in R. farinacea and has antimicrobial and anticancer activities. It is active against A. hydrophilia, B. subtilis, L. monocytogenes, P. vulgaris, S. faecalis, C. albicans, and C. glabrata (MICs = 0.1-6.7 mM). Norstictic acid (1-100 μM) inhibits proliferation, migration, and invasion of MDA-MB-231 cells. In vivo, norstictic acid (15 mg/kg, i.p.) reduces tumor growth in an MDA-MB-231/GFP mouse xenograft model. | [Uses]
Norstictic acid is a potent and selective allossteric transcriptional regulator. Norstictic acid shows anticancer activity. Norstictic acid shows antioxidant activity and antimicrobial activity[1][2][3][4]. | [Anticancer Research]
Norstictic acid (NA) is a depsidone-derived metabolite common in several lichenspecies of the genera Usnea, Ramalina and Parmelia. Various biological activitieshave been reported for NA including antioxidant, antimicrobial and cytotoxic innature (White et al. 2014). Recently, Ebrahim et al. (2016) reported that administrationof NA to MDA-MB-231 cells significantly suppressed the proliferation,migration and invasion. Also, it showed minimal toxicity to non-tumorigenicMCF-10A mammary epithelial cells. They also performed molecular modelling,Z′-LYTE biochemical kinase assay and Western blot analysis, to identify c-Met asa potential macromolecular target. Further, NA treatment significantly suppressedMDA-MB-231/GFP tumour growth of a BC xenograft model in athymic nudemice. At this juncture, they concluded that lichen-derived natural products arepromising resources to discover novel c-Met inhibitors useful to control TNBC(Ebrahim et al. 2016). | [Anticancer Research]
Norstictic acid significantlysuppressed the proliferation,migration and invasion. It alsosignificantly suppressedMDA-MB-231/GFP tumour growthof a breast cancer xenograft modelin athymic nude mice
Ebrahimet al. (2016) | [References]
[1] Garlick JM, et al. Norstictic Acid Is a Selective Allosteric Transcriptional Regulator. J Am Chem Soc. 2021 Jun 30;143(25):9297-9302. DOI:10.1021/jacs.1c03258
[2] Ebrahim HY, et al. Norstictic Acid Inhibits Breast Cancer Cell Proliferation, Migration, Invasion, and In Vivo Invasive Growth Through Targeting C-Met. Phytother Res. 2016 Apr;30(4):557-66. DOI:10.1002/ptr.5551
[3] Rankovi? B, et al. Biological activities of Toninia candida and Usnea barbata together with their norstictic acid and usnic acid constituents. Int J Mol Sci. 2012 Nov 12;13(11):14707-22. DOI:10.3390/ijms131114707
[4] Tay T, et al. Evaluation of the antimicrobial activity of the acetone extract of the lichen Ramalina farinacea and its (+)-usnic acid, norstictic acid, and protocetraric acid constituents. Z Naturforsch C J Biosci. 2004 May-Jun;59(5-6):384-8. DOI:10.1515/znc-2004-5-617 |
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