Justicidin B: A Promising Bioactive Lignan

Abstract

Adverse effects and drug resistance to the current onchopharmacologicals have increased the demand for alternative novel therapeutics. We herein introduce justicidin B, an arylnaphthalen lignan isolated from different plant origins, especially Justicia, Phyllanthus, Haplophyllum and Linum species. This cyclolignan exhibits a wide array of biological properties ranges from piscicidal to antifungal, antiviral and antibacterial activities. Activity against Trypanosoma brucei makes justicidin B a potential antiprotozoal agent for the treatment of neglected tropical diseases. Pharmacological properties like antiplatelet, anti-inflammatory and bone resorption inhibition have been also attributed to justicidin B. This compound is a potent cytotoxic substance on several cell lines, especially chronic myeloid and chronic lymphoid leukemia. Pharmacological values, natural variation, as well as biotechnological production of justicidin B by plant cell, tissue and organ culture are also described in this review. Chemical characteristics and chromatographic methods to identify justicidin B and its biosynthetic pathway have been discussed. Different approaches to the total synthesis of justicidin B are compared. This review would shed light on the role of justicidin B as an intriguing natural compound and provides a chance to optimize conditions for industrial applications.

Flavonoids and Ellagitannins Characterization, Antioxidant and Cytotoxic Activities of Phyllanthus acuminatus Vahl

“…As described in the Methods and Materials section, fractioning with Sephadex LH-20 of the non-polar extract of P. acuminatus , allowed the isolation of a compound characterized by 1 H-NMR, 13 C-NMR and 2D-(HMBC, HSQC, COSY)-NMR data coincident with reports from the literature [ 37 , 38 , 39 ] on aryl naphthalene lignan Justicidin B ( 20 ) C 21 H 16 O 6 ( Figure 13 ), a metabolite previously reported in P. acuminatus [ 7 ] and extensively studied because of its high antitumoral potential against different cancer cell lines [ 40 ], thus enabling a comparison of bioactivities among this metabolite and the phenolic extract, as described in the following sections.…”

“…When evaluating the selectivity index (SI), defined as the ratio of IC 50 values of normal cells to cancer cells (AGS or SW620), P. acuminatus extract showed the highest selectivity result for SW620 colon cancer cells (SI = 21.5), followed closely for AGS gastric cancer cells (SI = 20.1), while Justicidin B results showed SI of 5.4 and 4.2 respectively, thus, lower selectivity values than P. acuminatus extract for both AGS and SW620 cancer cell lines. When comparing these selectivity results with reports using similar MTT assay conditions, Justicidin B displayed non-specific cytotoxicity in normal peripheral blood mononuclear cells (PMBC), HepG2 hepatoma, and PC3 prostrate tumor cell lines [ 40 ], while P. niruri phenolic extract showed selectivity values of 2.2 and 2.8, respectively, for AGS gastric and SW colon cancer cells [ 44 ]. Although selectivity (SI ≥ 3) and cytotoxicity (IC 50 ≤ 20) results for P. acuminatus extract on AGS gastric and SW620 colon cancer cells fall within the parameters of the National Cancer Institute (NCI) [ 49 , 50 ] for plant extracts to be considered promising in the preliminary assay, further studies on mechanisms of action are needed.…”

Development of a mesoporous silica based solid‐phase extraction and ultra‐performance liquid chromatography–MS/MS method for quantifying lignans in Justicia procumbens

“…Biological assays indicated that chinensinaphthol methyl ether exhibited antiplatelet, antitumor, and antiviral activities [28]. Justicidin B, an arylnaphthalen lignan, was calculated to be a large quantity (0.30 mg/g), which was famous for its wide array of biological properties ranges from cytotoxic to antifungal, antiviral, and antibacterial activities [29]. Justicidin C revealed a concentration‐dependent antiplatelet activity on rabbit platelet aggregation induced by arachidonic acid [5], and its content was 0.17 mg/g.…”

6′-Hydroxy Justicidin B Triggers a Critical Imbalance in Ca2+ Homeostasis and Mitochondrion-Dependent Cell Death in Human Leukemia K562 Cells

“…Studies have shown that justicidins have a variety of biological activities, such as neuroprotection ( Gu et al, 2016 ), cytotoxicity ( Hemmati and Seradj, 2016 ), antiviral activity ( Asano et al, 1996 ), and a wide range of anti-tumor effects. As a potential bioactive substance, its cytotoxicity to numerous cells lines has been systematically studied ( He et al, 2012 ; Ilieva et al, 2014 ; Jin et al, 2014 ; Momekov et al, 2014 ; Won et al, 2015 ).…”