Bikaverin
(Synonyms: 比卡菌素,Lycopersin) 目录号 : GC45391A fungal metabolite with diverse biological activities
Cas No.:33390-21-5
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Bikaverin is a fungal metabolite originally isolated from F. oxysporum f. sp. lycopersici that has diverse biological activities, including antiprotozoal, nematocidal, antiproliferative, and fungicidal properties.1,2,3,4 It is active against L. braziliensis when used at a concentration of 0.15 μg/ml and against B. xylophilus at a concentration of 100 μg/ml.2 It inhibits proliferation of NCI-H460, MIA PaCa-2, MCF-7, and SF-268 cells (IC50s = 0.43, 0.26, 0.42, and 0.38 μM, respectively).3 Bikaverin inhibits the growth of certain plant pathogenic fungi, including R. solani, P. capsici, P. infestans, and M. grisea (IC50s = <1.2, 10, 60, and 70 μg/ml, respectively).4 It inhibits the development and provides disease control of tomato late blight and wheat leaf rust caused by P. infestans and P. recondita, respectively, when applied at a concentration of 300 μg/ml.
References
1. Nord, F.F. Structure of some Fusarium pigments and their action. Intern. Congr. Biochem., Abstrs. of Communs. 1st Congr. Cambridge, Engl. 243-244 (1949).
2. LimÓn, M.C., RodrÍguez-Ortiz, R., and Avalos, J. Bikaverin production and applications. Appl. Microbiol. Biotechnol. 87(1), 21-29 (2010).
3. Zhan, J., Burns, A.M., Liu, M.X., et al. Search for cell motility and angiogenesis inhibitors with potential anticancer activity: Beauvericin and other constituents of two endophytic strains of Fusarium oxysporum. J. Nat. Prod. 70(2), 227-232 (2007).
4. Son, S.W., Kim, H.Y., Choi, G.J., et al. Bikaverin and fusaric acid from Fusarium oxysporum show antioomycete activity against Phytophthora infestans. J. Appl. Microbiol. 104(3), 692-698 (2008).
| Cas No. | 33390-21-5 | SDF | |
| 别名 | 比卡菌素,Lycopersin | ||
| Canonical SMILES | O=C(C=C1OC)C2=C(C(O)=C(OC(C=C(OC)C=C3C)=C3C4=O)C4=C2O)C1=O | ||
| 分子式 | C20H14O8 | 分子量 | 382.3 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.6157 mL | 13.0787 mL | 26.1575 mL |
| 5 mM | 0.5231 mL | 2.6157 mL | 5.2315 mL |
| 10 mM | 0.2616 mL | 1.3079 mL | 2.6157 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Natural blue pigments and Bikaverin
Microbiol Res 2021 Mar;244:126653.PMID:33302226DOI:10.1016/j.micres.2020.126653.
In last years, the main studied microbial sources of natural blue pigments have been the eukaryotic algae, Rhodophytes and Cryptophytes, and the cyanobacterium Arthrospira (Spirulina) platensis, responsible for the production of phycocyanin, one of the most important blue compounds approved for food and cosmetic use. Recent research also includes the indigoidine pigment from the bacteria Erwinia, Streptomyces and Photorhabdus. Despite these advances, there are still few options of microbial blue pigments reported so far, but the interest in these products is high due to the lack of stable natural blue pigments in nature. Filamentous fungi are particularly attractive for their ability to produce pigments with a wide range of colors. Bikaverin is a red metabolite present mainly in species of the genus Fusarium. Although originally red, the biomass containing Bikaverin changes its color to blue after heat treatment, through a mechanism still unknown. In addition to the special behavior of color change by thermal treatment, Bikaverin has beneficial biological properties, such as antimicrobial and antiproliferative activities, which can expand its use for the pharmaceutical and medical sectors. The present review addresses the production natural blue pigments and focuses on the properties of Bikaverin, which can be an important source of blue pigment with potential applications in the food industry and in other industrial sectors.
Bikaverin production and applications
Appl Microbiol Biotechnol 2010 Jun;87(1):21-9.PMID:20376635DOI:10.1007/s00253-010-2551-1.
Bikaverin is a reddish pigment produced by different fungal species, most of them from the genus Fusarium, with antibiotic properties against certain protozoa and fungi. Chemically, Bikaverin is a polyketide with a tetracyclic benzoxanthone structure, resulting from the activity of a specific class I multifunctional polyketide synthase and subsequent group modifications introduced by a monooxygenase and an O-methyltransferase. In some fungi, Bikaverin is found with smaller amounts of a precursor molecule, called norbikaverin. Production of these metabolites by different fungal species depends on culture conditions, but it is mainly affected by nitrogen availability and pH. Regulation of the pathway has been investigated in special detail in the gibberellin-producing fungus Fusarium fujikuroi, whose genes and enzymes responsible for Bikaverin production have been recently characterized. In this fungus, the synthesis is induced by nitrogen starvation and acidic pH, and it is favored by other factors, such as aeration, sulfate and phosphate starvation, or sucrose availability. Some of these inducing agents increase mRNA levels of the enzymatic genes, organized in a coregulated cluster. The biological properties of Bikaverin include antitumoral activity against different cancer cell lines. The diverse biological activities and the increasing information on the biochemical and genetic basis of its production make Bikaverin a metabolite of increasing biotechnological interest.
Recovery and purification of Bikaverin produced by Fusarium oxysporum CCT7620
Food Chem X 2021 Oct 3;12:100136.PMID:34661094DOI:10.1016/j.fochx.2021.100136.
Microbial pigments have a distinguished potential for applications in food and pharmaceutical industries, stimulating the research in this field. The present study evaluated the ideal conditions for extracting Bikaverin (red pigment) from the biomass of Fusarium oxysporum CCT7620. Among the solvents tested, ethyl acetate extraction resulted in the highest Bikaverin concentration and the kinetic study revealed a saturation in Bikaverin concentration from 256 min on. Based on a preliminary economic study, three sequential extractions with ethyl acetate was considered the ideal protocol to recover Bikaverin. After extraction, chromatographic methods were tested to purify Bikaverin. The use of silica gel or Sephadex (open column) could not successfully purify Bikaverin, but the semi-preparative HPLC resulted in a bikaverin-enriched fraction with a purity degree equivalent to the commercial analytical standard. This work provides relevant information regarding the extraction and purification of Bikaverin, which may be useful for other downstraming processes.
Exploring Bikaverin as Metal Ion Biosensor: A Computational Approach
Acta Chim Slov 2019 Jun;66(2):351-359.PMID:33855498doi
A computational exploration of fungi produced pigment Bikaverin as a biosensor towards bioavailable metal ions is presented. Systematic studies of the optimized ground and excited state geometries were attempted for exploring metal ion binding pocket, comparative binding propensity and optical properties of the Bikaverin and its adducts with studied metal ions. The screening of thirteen (13) bioavailable metal ions, revealed a range of binding strength towards Bikaverin receptor with Ca2+, Mg2+ and Al3+as the strongest binders. Besides, upon binding to Bikaverin receptor an enhancement in its fluorescence intensity was observed in the order Ca2+> Al3+> Mg2+. The computationally predicted selectivity of Bikaverin receptor towards Ca2+was experimentally corroborated through the preliminary fluorescence studies. The Bikaverin probe showed an enhancement of fluorescence emission in presence of Ca2+ ions in buffered aqueous medium.
Production of Bikaverin by a Fusarium fujikuroi mutant in submerged cultures
AMB Express 2016 Dec;6(1):34.PMID:27142994DOI:10.1186/s13568-016-0205-0.
A variety of mutants having different colony characteristics, morphology and soluble pigmentation were generated from Fusarium fujikuroi by exposure to UV radiation. Mutants were selected that formed dry, compact, small colonies with reddish-violet pigment on regeneration agar plates. The production of Bikaverin by Mut-4 was examined in shake flasks in media with different nitrogen and carbon sources. The optimal C: N ratio for the maximal Bikaverin production by Mut-4 was 150:1. It produced still higher Bikaverin (6.3 g l(-1)) in a medium containing defatted cottonseed meal as nitrogen source, in combination with glucose. Bikaverin produced was extracted, purified and characterized by UV-visible and NMR spectroscopy. Bikaverin production in the present investigation was substantially higher than that reported by earlier investigators in submerged and solid-state fermentations.