Structure, molecular modification and anti-tumor activity of melanin from Lachnum singerianum

[Display omitted] •A non-water-soluble natural melanin (LIM-a) was separated and purified from Lachnum YM296.•Molecular formula (C28H20N2O7S2) and possible structural formula of component LIM-a were proposed.•The structural formula of LIM-a was concluded.•HLIM-a possesses higher anti-tumor activity...

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Bibliographic Details
Published in:Process biochemistry (1991) 2019-01, Vol.76, p.203-212
Main Authors: Ye, Ziyang, Lu, Ying, Zong, Shuai, Yang, Liuqing, Shaikh, Farnaz, Li, Jinglei, Ye, Ming
Format: Article
Language:English
Subjects:
Anti-tumor activity
Anticancer properties
Antitumor agents
Arginine
Biocompatibility
Biomedical materials
Column chromatography
Cytokines
Distilled water
Histidine
Histidine modification
Homogeneous melanin
Immune response
Immune system
Immunohistochemistry
In vivo methods and tests
Infrared analysis
Infrared spectroscopy
Lachnum singerianum
Lysine
Mass spectrometry
Mass spectroscopy
Melanin
Molecular structure
Molecular weight
NMR
Nuclear magnetic resonance
Solubility
Spectroscopic analysis
Spectroscopy
Tumors
Water solubility
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Summary:[Display omitted] •A non-water-soluble natural melanin (LIM-a) was separated and purified from Lachnum YM296.•Molecular formula (C28H20N2O7S2) and possible structural formula of component LIM-a were proposed.•The structural formula of LIM-a was concluded.•HLIM-a possesses higher anti-tumor activity than LIM-a. Intracellular melanin (LIM) was extracted from Lachnum singerianum YM296 mycelium. LIM-a, LIM-b and LIM-c were resolved from LIM by Sephadex G-15 column chromatography, in which LIM-a was the main homogeneous component with a molecular weight of 530 Da. Based on the elemental analysis, mass spectrometry, infrared spectroscopy and NMR analysis, the molecular formula (C28H20N2O7S2) and possible structural formula of LIM-a were proposed. In order to increase its water solubility, non-water-soluble LIM-a was modified by histidine, lysine and arginine, and histidine-melanin (HLIM-a) had the highest water solubility, being 47.7 mg mL−1 in distilled water at room temperature. Infrared spectroscopy, mass spectroscopy and 1H NMR analysis of HLIM-a indicated that histidine-melanin was formed by conjugating LIM-a molecule with histidine molecule. In vivo test showed that both LIM-a and HLIM-a had significant anti-tumor activity, in which HLIM-a showed better efficacy. Immunohistochemistry analysis and cytokines detection suggested that LIM-a and HLIM-a may repress tumor growth through activating the immune response.
ISSN:1359-5113
1873-3298
DOI:10.1016/j.procbio.2018.09.007