Бострикоидин

Description

Bostricoidine is a naphthoquinone pigment produced by fungi of the genus Fusarium, a component of the fusarubin/bostricoidine biosynthetic pathway. CAS 4589-33-7, chemical formula C15H11NO5.

Basic Attributes

• Chemical formula: C15H11NO5
• Molecular weight: 285.255; exact weight: 285.064
• UNII: RNE518Z6ZA
• NSC Number: 103645
• PSA Specifications: 92.7
• XLogP3: 0.9

According to primary source data: 285.255; 285.064; 92.7; 0.9.

Physico-chemical characteristics

• Melting point: 243–244 °C

Chemical structure

According to the IUPAC nomenclature, 6,9-dihydroxy-7-methoxy-3-methylbenz[g]isoquinoline-5,10-dione, a nitrogen-containing representative of the naphthoquinone class, structurally related to fusarubine. The presence of a nitrogen-containing isoquinoline fragment distinguishes bostricoidin from most other fusarubine group pigments, in which the oxygen-containing naphthoquinone core does not include a nitrogen atom in the ring.

Synonyms

The databases also contain the entry UNII-RNE518Z6ZA, as well as the alternative systematic name benzo(g)isoquinoline-5,10-dione, 6,9-dihydroxy-7-methoxy-3-methyl-, a variant spelling of the same compound.

Biological role and activity

One of the pigments produced by fungi of the genus Fusarium serves as a marker of the presence of Fusarium infection on grain crops, fruits and in the soil. It has antibiotic activity, including an antibacterial effect; suppression of the growth of tuberculosis bacillus (strain H37) in vitro has been recorded. Compounds from the fusarubine-bostricoidin biosynthetic pathway generally exhibit a wide range of biological activities—antibiotic, fungicidal, insecticidal, and herbicidal. The pigment is also involved in the formation of black perithecial pigmentation in some Fusarium species, together with the related compound 5-deoxybostricoidin, which is part of the melanin coating of the fruiting bodies of the fungus.

Scope of application

It is used as a research reagent in mycology and analytical chemistry - a marker for identification and quantitative assessment of contamination of plant materials by fungi of the genus Fusarium, as well as an object for studying the antibiotic activity of naphthoquinone pigments and their possible use as prototypes of new antimicrobial compounds.

Significance as a biomarker

The presence of bostricoidin and related pigments in grain, flour and other cereal processing products is used by analytical laboratories as an indirect indicator of contamination of raw materials by fungi of the genus Fusarium, along with the direct determination of mycotoxins, since the synthesis of pigments and toxins in the fungus is often regulated by common pathways of secondary metabolism.

Storage and transportation

Store in a dry, cool place, protected from light, in an airtight original container - the pigment is sensitive to oxidation and photodegradation, characteristic of hydroxylated naphthoquinones.

Related pigments

It is included in the same biosynthetic series with fusarubin, noryavanicin, isofusarubine and 5-deoxybostricoidine - a group of naphthoquinone pigments formed in various Fusarium species from a common polyketide precursor and differing in the degree of oxidation and hydroxylation of the ring system.

Identification

Key reference characteristics: CAS 4589-33-7, UNII RNE518Z6ZA, NSC number 103645, molecular weight 285.255, exact weight 285.064, melting point 243-244 °C. The coincidence of these parameters with independent databases confirms the correctness of pigment identification.