Isolation of two novel purple naphthoquinone pigments concomitant with the bioactive red bikaverin and derivates thereof produced by Fusarium oxysporum

Abstract

Filamentous fungi have gained growing interest as sources of diverse pigmented secondary metabolites. Some specific polyketides from Ascomycetous species have demonstrated a wide range of industrial applications in food, cosmetic, textile, and in the design of pharmaceutical products. The formulation of recipes containing fungal polyketides has increased over recent years. Fusarium strains were proven useful to mankind in a variety of technologies. Nevertheless, there is still need of new isolates of Fusarium for use in emerging and already existing fields. In this article, we report the concomitant production of the bioactive red bikaverin along with two novel purple pigments by the phytopathogenic Fusarium oxysporum LCP531 strain isolated from soil. In literature, the production of purple pigment had only been described in cultures of Fusarium Fujikuroi, Fusarium verticillioides, and Fusarium graminearum. The production of these naphthoquinonic pigments, their distribution (either produced in mycelia or excreted in liquid medium) and their chemical profiles were investigated with respect to nutrient composition. The pigments were extracted by using a pressurized liquid extraction method, monitored by colorimetric analysis and characterized by HPLC‐DAD chromatography. To our knowledge, this is the first report of these two novel wild‐type purple naphtoquinones pigments along with bikaverin, where additionally, the culture conditions were put into perspective to optimize fermentation cultures and extraction process accordingly to the pigment/biomolecule desired. These colored naphthoquinones should be promising fungal functional compounds which could be expected to have a place of choice, along with other antibacterial, antifungal, antiviral, anticancer, and antineoplastic derivatives. © 2018 American Institute of Chemical Engineers Biotechnol. Prog., 35: e2738, 2019

Fungal Pigments and Their Prospects in Different Industries

“…Studies have reported pigments such as bikaverin, nor-bikaverin, fusarubins, some naphthoquinone(8-O-methybostrycoidin, 8-O-methylfusarubin, 8-O-methylnectriafurone, 8-O-methyl-13-hydroxynorjavanicin, 8-O-methylanhydrofusarubinlactol, and 13-hydroxynorjavanicin), and a novel isoquinoline-type, pigment 2-(4-((3E,5E)-14-aminotetradeca-3,5-dienyloxy)butyl)-1,2,3,4tetrahydroisoquinolin-4-ol (ATDBTHIQN), from Fusarium fujikuroi (formerly known as Fusarium moniliforme) (Figure 2) [25,63,65]. Similarly, differently colored naphthoquinones [bostrycoidin, 9-O-methylfusarubin, 5-O-methyljavanicin, 8-O-methylbostrycoidin, 1,4-naphthalenedione-3,8dihydroxy-5,7-dimethoxy-2-(2-oxopropyl), 5-O-methylsolaniol, and 9-O-methylanhydrofusarubin], two anthraquinones compounds [2-acetyl-3,8-dihydroxy-6-methoxy anthraquinone and 2-(1-hydroxyethyl)-3,8-dihydroxy-6-methoxy anthraquinone], and polyketide pigment (bikaverin) were reported from Fusarium oxysporum(Figure 2)[25,47,64,67]. Another species of Fusarium, Fusarium graminearum, has been found to produce a variety of pigments such as 5-deoxybostrycoidin anthrone, 6-O-dimethyl-5deoxybostrycoidin anthrone, purpurfusarin, 6-O-demethyl-5-deoxybostrycoidin, 5-deoxybostrycoidin, and aurofusarin (Figure 2)[25,64,66,121].…”

Malagasy Dye Plant Species: A Promising Source of Novel Natural Colorants with Potential Applications – A Review

“…Red carotenoids from plants are quite frequent. Natural carotenoids exhibit different health benefits confirmed by recent studies: strong antioxidant property, anti‐inflammatory effects, anti‐obesity, anticancer, prevention of cardiovascular diseases, of night blindness, and of liver fibrosis, etc …”

“…These biomolecules which are derived from isoprenoids, represent a diverse class of phenolic compounds . The three main groups of naturally occurring quinones are benzoquinones, naphthoquinone, and anthraquinones . These natural dyes produce yellow, orange, red, or reddish‐brown to purple colors.…”

“…Around the world, several other naphthoquinones are used as cosmetics or hair dyes, such as the colorants of henna (e. g., the lawsone, CI Natural orange 6, CI 75480) and of walnut shell extracts (e. g., the naphthoquinone juglone, CI Natural brown 7, CI 75520). Interestingly, some of these naturally‐occurring naphthoquinone dyes from Boraginaceae exhibit similar biological activities to those of natural anthraquinone dyes: the known spectrum of activity of naphthoquinones includes antibiotic, antiviral, anti‐inflammatory, antiproliferative, and antitumoral effects . The induction of cell death by juglone is related to the p53 oxidation, DNA damage by phosphorylation of the histone variant H2AX, and consequent inhibition of transcription and of mRNA .…”

“…Other less common groups of natural colorants, include the curcuminoid dyes present in the rhizome of turmeric Curcuma longa , the main one being the yellow‐colored curcumin (E‐100; US.CFR 73.600, 73.615). Other examples are xanthonoid dyes such as mangiferin present in Aphloia theiformis , pyrrole derivatives such as chlorophyll, alkaloid dyes such as berberine present in the roots of Thalictrum flavum , and betalain dyes .…”