Eupenifeldin
目录号 : GC43643
A cytotoxic fungal metabolite
Cas No.:151803-45-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Eupenifeldin is a pentacyclic bistropolone fungal metabolite originally isolated from E. brefeldianum ATCC 74184. It is cytotoxic against HCT116 and HCTVM46 colon carcinoma cells in vitro (IC50s = 0.005 and 0.002 μg/ml, respectively). In vivo, eupenifeldin (0.3-2 mg/kg per day) increases median survival time in a mouse model of P388 leukemia.
| Cas No. | 151803-45-1 | SDF | |
| Canonical SMILES | OC(C(C=C1C)=O)=CC2=C1C[C@]3([H])[C@@](O2)(C)[C@@H](O)C[C@]4([H])CC5=C(C=C(O)C(C=C5C)=O)O[C@@]4(C)C/C=C/C(C)(C)C3 | ||
| 分子式 | C33H40O7 | 分子量 | 548.7 |
| 溶解度 | DMF: Soluble,DMSO: Soluble,Ethanol: 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 | 1.8225 mL | 9.1124 mL | 18.2249 mL |
| 5 mM | 0.3645 mL | 1.8225 mL | 3.645 mL |
| 10 mM | 0.1822 mL | 0.9112 mL | 1.8225 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。
Delivery of Eupenifeldin via polymer-coated surgical buttresses prevents local lung cancer recurrence
J Control Release 2021 Mar 10;331:260-269.PMID:33484778DOI:10.1016/j.jconrel.2021.01.026.
Lung cancer is the leading cause of cancer deaths worldwide. Unfortunately, high recurrence rates and poor survival remain despite surgical resection and conventional chemotherapy. Local drug delivery systems are a promising intervention for lung cancer treatment with the potential for improved efficacy with reduced systemic toxicity. Here, we describe the development of a chemotherapy-loaded polymer buttress, to be implanted along the surgical margin at the time of tumor resection, for achieving local and prolonged release of a new anticancer agent, Eupenifeldin. We prepared five different formulations of buttresses with varying amounts of Eupenifeldin, and additional external empty polymer coating layers (or thicknesses) to modulate drug release. The in vitro Eupenifeldin release profile depends on the number of external coating layers with the formulation of the greatest thickness demonstrating a prolonged release approaching 90 days. Similarly, the long-term cytotoxicity of eupenifeldin-loaded buttress formulations against murine Lewis lung carcinoma (LLC) and human lung carcinoma (A549) cell lines mirrors the Eupenifeldin release profiles and shows a prolonged cytotoxic effect. Eupenifeldin-loaded buttresses significantly decrease local tumor recurrence in vivo and increase disease-free survival in a lung cancer resection model.
Eupenifeldin, a novel cytotoxic bistropolone from Eupenicillium brefeldianum
J Antibiot (Tokyo) 1993 Jul;46(7):1082-8.PMID:8360103DOI:10.7164/antibiotics.46.1082.
Eupenifeldin was isolated from cultures of Eupenicillium brefeldianum ATCC 74184 by extraction and crystallization. The compound was identified as a pentacyclic bistropolone on the basis of spectral data and its complete structure was established by single-crystal X-ray analysis. The compound is cytotoxic against the HCT-116 cell line and has in vivo antitumor activity in the P388 leukemia model.
Identification of the gene cluster for bistropolone-humulene meroterpenoid biosynthesis in Phoma sp
Fungal Genet Biol 2019 Aug;129:7-15.PMID:30980906DOI:10.1016/j.fgb.2019.04.004.
Eupenifeldin, a bistropolone meroterpenoid, was first discovered as an antitumor agent from the fungus Eupenicillium brefeldianum. We also isolated this compound and a new congener from a strain of Phoma sp. (CGMCC 10481), and evaluated their antitumor effects. Eupenifeldin showed potent in vitro anti-glioma activity. This tropolone-humulene-tropolone meroterpenoid could be originated from two units of tropolone orthoquinone methides and a 10-hydroxyhumulene moiety via hetero-Diels-Alder reactions. To explore the biosynthesis of this class of tropolonic sesquiterpenes, the genome of a eupenifeldin-producing Phoma sp. was sequenced and analyzed. The biosynthetic gene cluster of Eupenifeldin (eup) was identified and partially validated by genomic analysis, gene disruption, and product analysis. A nonreducing polyketide synthase EupA, a FAD-dependent monooxygenase EupB, and a non-heme Fe (II)-dependent dioxygenase EupC, were identified as the enzymes responsible for tropolone formation. While the terpene cyclase EupE of an unknown family was characterized to catalyze humulene formation, and a cytochrome P450 enzyme EupD was responsible for hydroxylation of humulene. This study sheds light on the biosynthesis of Eupenifeldin, and paves the way to further decipher its biosynthetic pathway.
Synthetic Biology Driven Biosynthesis of Unnatural Tropolone Sesquiterpenoids
Angew Chem Int Ed Engl 2020 Dec 21;59(52):23870-23878.PMID:32929811DOI:10.1002/anie.202009914.
Tropolone sesquiterpenoids (TS) are an intriguing family of biologically active fungal meroterpenoids that arise through a unique intermolecular hetero Diels-Alder (hDA) reaction between humulene and tropolones. Here, we report on the combinatorial biosynthesis of a series of unprecedented analogs of the TS pycnidione 1 and xenovulene A 2. In a systematic synthetic biology driven approach, we recombined genes from three TS biosynthetic gene clusters (pycnidione 1, xenovulene A 2 and Eupenifeldin 3) in the fungal host Aspergillus oryzae NSAR1. Rational design of the reconstituted pathways granted control over the number of hDA reactions taking place, the chemical nature of the fused polyketide moiety (tropolono- vs. monobenzo-pyranyl) and the degree of hydroxylation. Formation of unexpected monobenzopyranyl sesquiterpenoids was investigated using isotope-feeding studies to reveal a new and highly unusual oxidative ring contraction rearrangement.
Heat-resistant fungi of importance to the food and beverage industry
Crit Rev Microbiol 1994;20(4):243-63.PMID:7857517DOI:10.3109/10408419409113558.
Spoilage of pasteurized and canned fruit and fruit products caused by heat-resistant molds have been reported repeatedly in recent years. Species most commonly implicated in fruit and fruit product disintegration are Byssochlamys fulva, Byssochlamys nivea, Neosartorya fischeri, Talaromyces flavus, and Eupenicillium brefeldianum. These organisms are saprophytic rather than parasitic and usually contaminate fruits on or near the ground. They can survive heat treatments used for fruit processing and can grow and spoil the products during storage at room temperature, which results in great economic losses. Mold heat resistance is attributed to the formation of sexual spores, ascospores. Ascospores have a wide range of heat resistance, depending on species, strain, age of organism, heating medium, pH, presence of sugars, fats, and acids in heating medium, growth conditions, etc. The mechanism(s) of thermoresistance are not clear; probably some very stable compound(s) critical to germination and outgrowth are present in the heat-resistant ascospores. Besides spoilage, the heat-resistant molds produce a number of toxic secondary metabolites, such as byssotoxin A; byssochlamic acid; the carcinogen, patulin, the tremorgenic substances, fumitremorgin A and C, and verruculogen; fischerin, which caused fatal peritonitis in mice; and Eupenifeldin, a compound possessing cytotoxicity as well as in vivo antitumor activity. Growth of heat-resistant fungi can be controlled by lowering the water activity, adding sulfur dioxide, sorbate, or benzoate; washing of fruits in hypochlorite solution before heat treatment reduces the number of ascospores and makes the heat destruction more successful. More research is needed to elucidate the mechanism(s) of thermoresistance and develop new methods for the complete inactivation of resistant ascospores.