Justicidin C

Design, synthesis, and evaluation of cytotoxic activities of arylnaphthalene lignans and aza-analogs.[Pubmed:33586249]

Arch Pharm (Weinheim). 2021 Jun;354(6):e2000479.

A concise and versatile synthetic strategy for the total synthesis of arylnaphthalene lignans and aza-analogs was developed. The main objective was to develop synthetic tactics for the creation of the lactone and lactam unit that would give access to an array of synthetic, natural, and/or bioactive compounds through rather simple chemical manipulation. The flexibility and potentiality of these new processes were further illustrated by the total synthesis of retrojusticidin B (13b), Justicidin C (14b), and methoxy-vitedoamine A (22a). In this study, a series of novel aryl-naphthalene lignans and aza-analogs were synthesized, and the cytotoxic activities of all compounds on cancer cell growth were evaluated. The target compounds were structurally characterized by (1) H NMR (nuclear magnetic resonance), (13) C NMR, infrared, high-resolution mass spectrometry, and X-ray crystallography. The IC(50) values of these compounds on five tumor cell lines (A549, HS683, MCF-7, SK-MEL-28, and B16-F1) were obtained by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) colorimetric assay. Five of the compounds exhibited excellent activity compared to 5-fluorouracil and etoposide against the five cell lines tested, with IC(50) values ranging from 1 to 10 muM.

Development of a mesoporous silica based solid-phase extraction and ultra-performance liquid chromatography-MS/MS method for quantifying lignans in Justicia procumbens.[Pubmed:32040861]

Electrophoresis. 2020 Mar;41(5-6):379-385.

Justicia procumbens is a food and medicine homologous variety, popularly used for making vegetable soups. In this study, a novel mesoporous silica was synthesized and used as the sorbent of SPE for the purification of lignans from J. procumbens. A laboratory-made SPE cartridge was packed with 100 mg of mesoporous silica, which was washed with 10% methanol and eluted using 0.8 mL acetonitrile after sample loading. Afterward, the extract was analyzed by ultra-performance liquid chromatography (UPLC) and MS/MS. All the lignans were efficiently separated in 6 min with the noise level in the range of 50-150 cps. 6'-Hydroxy justicidin B, 6'-hydroxy justicidin A, justicidin B, chinensinaphthol methyl ether, Justicidin C, and neojusticdin A were identified to be the dominant molecular species in J. procumbens with contents of 0.065-0.37 mg/g in three tested sample batches from different geographic origins. In conclusion, the proposed mesoporous silica based SPE UPLC-MS/MS method is efficient in linearity (R(2) = 0.9989-0.9996), sensitivity (LOD

Ultra high performance liquid chromatography-electrospray ionization-tandem mass spectrometry and pharmacokinetic analysis of justicidin B and 6'-hydroxy justicidin C in rats.[Pubmed:27874243]

J Sep Sci. 2017 Feb;40(3):604-611.

Arylnaphthalene lignans have attracted considerable interest with the discovery of their antineoplastic activities. Two such compounds are justicidin B and 6'-hydroxy Justicidin C, both of which have been isolated from the herb Justicia procumbens. We sought to develop and validate a sensitive and accurate, ultra high performance liquid chromatography with electrospray ionization tandem mass spectrometry method for the structural determination and pharmacokinetics of justicidin B and 6'-hydroxy Justicidin C. Chromatographic separation was achieved on an Agilent 300SB-C(18) column using water (0.5% formic acid, 10 mM NH(4) COOH) methanol as the mobile phase. The plasma samples obtained after oral administration of the active extract of Justicia procumbens were successfully analyzed with our novel method, thereby demonstrating its sound applicability and reliability. The lower limit of quantification for justicidin B and 6'-hydroxy Justicidin C was 0.50 and 1.00 ng/mL in 50 muL rat plasma, respectively. The elimination half-life and clearance of justicidin B was estimated to be 1.27 +/- 0.61 h and 5.40 +/- 0.22 L/h/kg while that of 6'-hydroxy Justicidin C was 2.07 +/- 0.70 h and 11.84 +/- 1.06 L/h/kg. This newly developed and validated method was successfully applied to the quantification and pharmacokinetic study of justicidin B and 6'-hydroxy Justicidin C in rats.