Averantin
(Synonyms: 1,3,6,8-四羟基-2-(1-羟基己基)-蒽醌) 目录号 : GC45388A fungal metabolite
Cas No.:5803-62-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Averantin is an anthraquinone fungal metabolite that has been found in Aspergillus.1,2 It is an intermediate in the biosynthesis of aflatoxin B1 .1 Averantin is active against B. subtilis bacteria and the plant pathogenic fungus F. solani in vitro (MICs = 16-32 μg/ml).2
References
1. Bennett, J.W., Lee, L.S., Shoss, S.M., et al. Identification of averantin as an aflatoxin B1 precursor: Placement in the biosynthetic pathway. Appl. Environ. Microbiol. 39(4), 835-839 (1980).
2. Liu, K., Zheng, Y., Miao, C., et al. The antifungal metabolites obtained from the rhizospheric Aspergillus sp. YIM PH30001 against pathogenic fungi of Panax notoginseng. Nat. Prod. Res. 28(24), 2334-2337 (2014).
| Cas No. | 5803-62-3 | SDF | |
| 别名 | 1,3,6,8-四羟基-2-(1-羟基己基)-蒽醌 | ||
| Canonical SMILES | OC1=CC(O)=CC(C(C2=C3C(O)=C([C@@H](O)CCCCC)C(O)=C2)=O)=C1C3=O | ||
| 分子式 | C20H20O7 | 分子量 | 372.4 |
| 溶解度 | DMSO: soluble,Methanol: soluble | 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 | 2.6853 mL | 13.4264 mL | 26.8528 mL |
| 5 mM | 0.5371 mL | 2.6853 mL | 5.3706 mL |
| 10 mM | 0.2685 mL | 1.3426 mL | 2.6853 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。
Identification of Averantin as an aflatoxin B1 precursor: placement in the biosynthetic pathway
Appl Environ Microbiol 1980 Apr;39(4):835-9.PMID:7377778DOI:10.1128/aem.39.4.835-839.1980.
A new blocked mutant of Aspergillus parasiticus produces no detectable aflatoxin B1, but accumulates several polyhydroxyanthraquinones. One of these pigments was identified as Averantin. This is the first report of its formation by A. parasiticus. Radiotracer studies with [14C]Averantin showed that 15.3% of label from Averantin was incorporated into aflatoxin B1. This incorporation was blocked by dichlorvos. With radiotracers and other mutants, Averantin was placed after norsolorinic acid and before averufin in the biosynthetic pathway in which the general steps are norsolorinic acid leads to Averantin leads to averufin leads to versiconal hemiacetal acetate leads to versicolorin A leads to sterigmatocystin leads to aflatoxin B1.
Averufanin is an aflatoxin B1 precursor between Averantin and averufin in the biosynthetic pathway
Appl Environ Microbiol 1987 Jan;53(1):14-6.PMID:3103529DOI:10.1128/aem.53.1.14-16.1987.
Wild-type Aspergillus parasiticus produces, in addition to the colorless aflatoxins, a number of pigmented secondary metabolites. Examination of these pigments demonstrated that a major component was an anthraquinone, averufanin. Radiolabeling studies with [14C]averufanin showed that 23% of the label was incorporated into aflatoxin B1 by the wild type and that 31% of the label was incorporated into O-methylsterigmatocystin by a non-aflatoxin-producing isolate. In similar studies with blocked mutants of A. parasiticus the 14C label from averufanin was accumulated in averufin (72%) and versicolorin A (54%) but not Averantin. The results demonstrate that averufanin is a biosynthetic precursor of aflatoxin B1 between Averantin and averufin.
avnA, a gene encoding a cytochrome P-450 monooxygenase, is involved in the conversion of Averantin to averufin in aflatoxin biosynthesis in Aspergillus parasiticus
Appl Environ Microbiol 1997 Apr;63(4):1349-56.PMID:9097431DOI:10.1128/aem.63.4.1349-1356.1997.
Recent studies have shown that at least 17 genes involved in the aflatoxin biosynthetic pathway are clustered within a 75-kb DNA fragment in the genome of Aspergillus parasiticus. Several additional transcripts have also been mapped to this gene cluster. A gene, avnA (previously named ord-1), corresponding to one of the two transcripts identified earlier between the ver-1 and omtA genes on the gene cluster was sequenced. The nucleotide sequence of the avnA gene contains a coding region for a protein of 495 amino acids with a calculated molecular mass of 56.3 kDa. The gene consists of three exons and two introns. Disruption of the avnA gene in the wild-type aflatoxigenic A. parasiticus strain (SU1-N3) resulted in a nonaflatoxigenic mutant which accumulated a bright yellow pigment. Thin-layer chromatographic studies with six different solvent systems showed that the migration patterns of the accumulated metabolite were identical to those of Averantin, a known aflatoxin precursor. Precursor feeding studies with this mutant showed that norsolorinic acid and Averantin were not converted to aflatoxin whereas 5'-hydroxyaverantin, averufanin, averufin, versicolorin A. sterigmatocystin, and O-methylsterigmatocystin were converted to aflatoxins. Southern blot analysis of the wild-type strain and avnA-disrupted mutant strain indicated that the avnA gene was disrupted in the mutant strain. A search of the GenBank database for similarity indicated that the avnA gene encodes a cytochrome P-450-type monooxygenase, and it has been assigned to a new P-450 gene family named CYP60A1. We have therefore concluded that the avnA gene encodes a fungal cytochrome P-450-type enzyme which is involved in the conversion of Averantin to averufin in the aflatoxin biosynthetic pathway in A. parasiticus.
Structural and spectral assignments of six anthraquinone derivatives from the mangrove fungus (ZSUH-36)
Magn Reson Chem 2008 Sep;46(9):886-9.PMID:18615624DOI:10.1002/mrc.2266.
A new natural product named 6,8,1'-tri-O-methyl Averantin (1) has been isolated together with five known anthraquinones 1'-O-methyl Averantin (2), 6,8-di-O-methyl averufin (3) averufin (4), versicolorin C (5) and 6,8-di-O-methyl averufanin (6) from a mangrove endophytic fungus ZSUH-36 collected from the South China Sea. NMR techniques including COSY, HMQC, and HMBC were used to elucidate the structures of these compounds. We report the unambiguous assignments of the (1)H and (13)C NMR spectra of the new compound 6,8,1'-tri-O-methyl Averantin(1).
Antifungal, phytotoxic and toxic metabolites produced by Penicillium purpurogenum
Nat Prod Res 2014;28(24):2358-61.PMID:25103412DOI:10.1080/14786419.2014.940586.
Nine known metabolites, 6,8,1'-tri-O-methyl Averantin (1), 6,8-di-O-methyl averufnin (2), 6,8-di-O-methyl averufanin (3), aversin (4), 1,3-dihydroxy-6,8-dimethoxy-9,10-anthraquinone (5), 6,8-di-O-methylnidurufin (6), 6,8-di-O-methyl versiconol (7), 5-methyoxysterigmatocystin (8) and (S)-ornidazole (9), were isolated from the extracts of Penicillium purpurogenum, and their structures were elucidated by using spectroscopic methods. The brine shrimp toxicity, anti-phytopathogenic and phytotoxic effects of these compounds were evaluated. Among them, compounds 1 and 8 exhibited the strongest toxicity against brine shrimp (Artemia salina), with lethality rates of 100% at a low concentration of 10 μM, comparable to the positive control toosendanin. Compounds 1, 4 and 7 moderately inhibited the growth of Botrytis cinerea. Moreover, 4 displayed moderate antifungal effects on Gibberella saubinettii. In addition, compounds 6, 7 and 9 produced the phytotoxic effects on radish seedlings at 100 μM. This is the first report on the isolation of these metabolites from this organism.