Stictic acid

• CAS: 549-06-4
• Catalog Number: ACM549064
• Category: Main Products
• Molecular Weight: 386.3
• Molecular Formula: C19H14O9
• Synonyms: Scopularic acid
• Appearance: Light tan solid

Case Study

Stictic Acid: in vitro Growth Inhibition of Human Colon Adenocarcinoma (HT-29) Cells

Pejin, Boris, et al. Arabian Journal of Chemistry 10 (2017): S1240-S1242.

Stictic acid, a depsidone isolated from the lichen Lobaria pulmonaria, was profiled in vitro against two human cancer cell lines (HT-29 colon adenocarcinoma and MCF-7 breast adenocarcinoma) and one non-malignant human cell line (MRC-5). The biological activity was measured using an MTT cell-viability assay performed on human HT-29 and MCF-7 cancer cell lines and on MRC-5 nonmalignant fibroblasts to determine IC50 values and relative sensitivity.
Biological testing revealed a notable growth-inhibitory effect against HT-29 colon adenocarcinoma with an IC50 of 29.29 µg/mL, whereas growth inhibition toward the MRC-5 nonmalignant line was minimal (IC50 = 2478.40 µg/mL); the compound was reported to be substantially more active against HT-29 than against MCF-7 (a 689-fold difference in sensitivity was observed in the dataset).
When placed alongside previously studied lichen metabolites, stictic acid showed greater potency against HT-29 than several other natural products from lichens cited in the literature (for example, atranorin and gyrophoric acid with IC50 values >200 µg/mL and usnic acid reported at ≈99.7 µg/mL in related studies), suggesting stictic acid merits prioritized consideration for colorectal-cancer lead development.

Evaluation of Stictic Acid as a Bioactive Compound from Usnea Species: Antioxidant and Antimicrobial Potential

Oran, Seyhan, et al. Iranian journal of pharmaceutical research: IJPR 15.2 (2016): 527.

This study quantified stictic acid in three Usnea lichens ( U. intermedia, U. filipendula, U. fulvoreagens) and evaluated their extracts for antioxidant and antimicrobial activity. Using HPLC, the highest stictic acid level reported was 9.85 ± 0.49 mg stictic acid per g dried lichen in the acetone extract of U. filipendula, while the lowest stictic level measured was 2.98 ± 0.28 mg/g in the methanol extract of U. intermedia.
Antioxidant & Antimicrobial Activity
Antioxidant (ABTS) and total-phenolic assays varied by species and solvent: the highest ABTS antioxidant value reported was 181.0 ± 4.4 mg TE/100 g dried lichen for the methanol extract of U. fulvoreagens, and the highest total phenolic content was 329.7 ± 18.5 mg GAE/100 g dried lichen for the acetone extract of U. filipendula. Overall, methanol tended to yield higher antioxidant activity (ABTS) while solvent effects on total phenolics varied among species; the data indicate that solvent polarity materially affects which functional constituents (and activities) are recovered.
Broth microdilution testing of the methanol extracts showed MIC values ranging from 64 µg/mL to 512 µg/mL across the bacterial strains tested. Notably, most fluoroquinolone-resistant Escherichia coli isolates (with the exception of isolate E101) were sensitive to the methanol extracts of these Usnea species, demonstrating antibacterial potential of the extracts in clinically relevant resistant isolates.

Custom Q&A

What is the molecular formula of stictic acid?

The molecular formula of stictic acid is C19H14O9.

What is the molecular weight of stictic acid?

The molecular weight of stictic acid is 386.3 g/mol.

What are the synonyms for stictic acid?

The synonyms for stictic acid include NSC-87511, NSC87511, NZR6AX77LP, and more.

Where is stictic acid found?

Stictic acid is found in Cetraria aculeata, Dimelaena oreina, and other organisms.

What is the IUPAC name of stictic acid?

The IUPAC name of stictic acid is 13,17-dihydroxy-5-methoxy-7,12-dimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.03,8.014,18]octadeca-1(11),3(8),4,6,12,14(18)-hexaene-4-carbaldehyde.

What is the InChI of stictic acid?

The InChI of stictic acid is InChI=1S/C19H14O9/c1-6-4-9(25-3)8(5-20)15-10(6)17(22)27-14-7(2)13(21)11-12(16(14)26-15)19(24)28-18(11)23/h4-5,19,21,24H,1-3H3.

What is the InChIKey of stictic acid?

The InChIKey of stictic acid is SKCUFZLDTAYNBZ-UHFFFAOYSA-N.

What is the canonical SMILES of stictic acid?

The canonical SMILES of stictic acid is CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C4=C(C(=C3C)O)C(=O)OC4O)C=O)OC.

What is the CAS number of stictic acid?

The CAS number of stictic acid is 549-06-4.

What is the hydrogen bond donor count of stictic acid?

The hydrogen bond donor count of stictic acid is 2.