Harzianum A
目录号 : GC45467
A trichothecene fungal metabolite
Cas No.:156250-74-7
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
Harzianum A is a trichothecene fungal metabolite originally isolated from T. harzianum.1 It is cytotoxic to HeLa, MCF-7, and HT-1080 cells (IC50s = 5.07, 10.13, and 0.65 μg/ml, respectively) and exhibits antifungal activity against C. albicans and S. cerevisiae when used at a concentration of 100 μg/ml.1,2
References
1. Corley, D.G., Miller-Wideman, M., and Durley, R.C. Isolation and structure of harzianum A: A new trichothecene from Trichoderma harzianum. J. Nat. Prod. 57(3), 422-425 (1994).
2. Lee, H.B., Kim, Y., Jin, H.Z., et al. A new Hypocrea strain producing harzianum A cytotoxic to tumour cell lines. Lett. Appl. Microbiol. 40(6), 497-503 (2005).
| Cas No. | 156250-74-7 | SDF | |
| Canonical SMILES | CC1=C[C@]2([H])[C@](C3(C)C4(OC4)[C@](C[C@H]3OC(/C=C\C=C\C=C\C(O)=O)=O)([H])O2)(C)CC1 | ||
| 分子式 | C23H28O6 | 分子量 | 400.5 |
| 溶解度 | 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 | 2.4969 mL | 12.4844 mL | 24.9688 mL |
| 5 mM | 0.4994 mL | 2.4969 mL | 4.9938 mL |
| 10 mM | 0.2497 mL | 1.2484 mL | 2.4969 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。
A new Hypocrea strain producing Harzianum A cytotoxic to tumour cell lines
Lett Appl Microbiol 2005;40(6):497-503.PMID:15892749DOI:10.1111/j.1472-765X.2005.01719.x.
Aims: To identify a new fungal strain, Hypocrea sp. F000527 producing a trichothecene metabolite, Harzianum A, and to evaluate its cytotoxicity to tumour cell lines. Methods and results: A fungal strain, F000527, with cytotoxic activity was identified as a new Hypocrea strain based on morphological characteristics and internal transcribed spacers rDNA sequence data. Harzianum A was isolated from wheat bran culture by 50% acetone extraction, silica gel chromatography, Sephadex LH-20 chromatography and HPLC. The chemical structures were determined by ESI- or HRFAB-MS and (1)H and (13)C-NMR analyses. Harzianum A showed cytotoxicity to HT1080 and HeLa cell lines with IC(50) value of 0.65 and 5.07 Łg ml(-1) respectively. Conclusions: Harzianum A with a chemical formula of C(23)H(28)O(6) was isolated from a new Hypocrea strain and showed moderate to strong cytotoxicity to human cancer cell lines. Significance and impact of the study: This is the first report of the production of cytotoxic Harzianum A by a new Hypocrea strain.
Isolation and structure of Harzianum A: a new trichothecene from Trichoderma harzianum
J Nat Prod 1994 Mar;57(3):422-5.PMID:8201317DOI:10.1021/np50105a019.
A new trichothecene, Harzianum A [1], was isolated from the soil-borne fungus Trichoderma harzianum. The structure of 1 was determined by extensive spectral analyses including the nmr techniques of PS-COSY, HMQC, HMBC, and NOESY. Harzianum A [1] contains a (Z,E,E)-2,4,6-octatriendioic acid esterified on the 4 beta hydroxyl group of trichodermol and is structurally related to the trichoverroids. Harzianum A [1] showed no cytotoxicity against baby hamster kidney cells, no activity against Gram-negative and Gram-positive bacteria, but modest antifungal activity at 100 micrograms/ml.
A cytochrome P450 monooxygenase gene required for biosynthesis of the trichothecene toxin Harzianum A in Trichoderma
Appl Microbiol Biotechnol 2019 Oct;103(19):8087-8103.PMID:31384992DOI:10.1007/s00253-019-10047-2.
Trichothecenes are sesquiterpene toxins produced by diverse fungi, including some species of Trichoderma that are potential plant disease biocontrol agents. Trichoderma arundinaceum produces the trichothecene Harzianum A (HA), which consists of the core trichothecene structure (12,13-epoxytrichothec-9-ene, EPT) with a linear polyketide-derived substituent (octa-2,4,6-trienedioyl) esterified to an oxygen at carbon atom 4. The genes required for biosynthesis of EPT and the eight-carbon polyketide precursor of the octa-2,4,6-trienedioyl substituent, as well as for esterification of the substituent to EPT have been described. However, genes required for conversion of the polyketide (octa-2,4,6-trienoic acid) to octa-2,4,6-trienedioyl-CoA, the immediate precursor of the substituent, have not been described. Here, we identified 91 cytochrome P450 monooxygenase genes in the genome sequence of T. arundinaceum, and provided evidence from gene deletion, complementation, cross-culture feeding, and chemical analyses that one of them (tri23) is required for conversion of octa-2,4,6-trienoic acid to octa-2,4,6-trienedioyl-CoA. The gene was detected in other HA-producing Trichoderma species, but not in species of other fungal genera that produce trichothecenes with an octa-2,4,6-trienoic acid-derived substituent. These findings indicate that tri23 is a trichothecene biosynthetic gene unique to Trichoderma species, which in turn suggests that modification of octa-2,4,6-trienoic acid during trichothecene biosynthesis has evolved independently in some fungi.
Requirement of Two Acyltransferases for 4- O-Acylation during Biosynthesis of Harzianum A, an Antifungal Trichothecene Produced by Trichoderma arundinaceum
J Agric Food Chem 2019 Jan 16;67(2):723-734.PMID:30558420DOI:10.1021/acs.jafc.8b05564.
Trichothecenes are sesquiterpenoid toxins produced by multiple fungi, including plant pathogens, entomopathogens, and saprotrophs. Most of these fungi have the acyltransferase-encoding gene tri18. Even though its function has not been determined, tri18 is predicted to be involved in trichothecene biosynthesis because of its pattern of expression and its location near other trichothecene biosynthetic genes. Here, molecular genetic, precursor feeding, and analytical chemistry experiments indicate that in the saprotroph Trichoderma arundinaceum the tri18-encoded acyltransferase (TRI18) and a previously characterized acyltransferase (TRI3) are required for conversion of the trichothecene biosynthetic intermediate trichodermol to Harzianum A, an antifungal trichothecene analog with an octa-2,4,6-trienedioyl acyl group. On the basis of the results, we propose that TRI3 catalyzes trichothecene 4- O-acetylation, and subsequently, TRI18 catalyzes replacement of the resulting acetyl group with octa-2,4,6-trienedioyl to form Harzianum A. Thus, the findings provide evidence for a previously unrecognized two-step acylation process during trichothecene biosynthesis in T. arundinaceum and possibly other fungi.
Trichothecenes in food and feed: Occurrence, impact on human health and their detection and management strategies
Toxicon 2022 Mar;208:62-77.PMID:35104534DOI:10.1016/j.toxicon.2022.01.011.
Trichothecenes (TCNs) are the mycotoxins produced by many fungal species such as Fusarium, Myrothecium, and Stachybotrys and pose a considerable health risk. Based on their characteristic functional moieties, they are divided into four categories: Type A (T-2, HT-2, diacetoxyscirpenol (DAS), Harzianum A, neosolaniol (NEO) and trichodermin), Type B (deoxynivalenol (DON), nivalenol (NIV), trichothecin and fusarenon X), Type C (crotocin) and Type D (satratoxin G & H, roridin A and verrucarin A) with types A and B being the most substantial. TCNs cause growth retardation in eukaryotes, suppress seedling growth or regeneration in plants and could be a reason for animal reproductive failure. Due to the increased frequency of occurrence and widespread distribution of TCNs in food and feed, knowledge of their sources of occurrence is essential to strategise their control and management. Hence, this review provides an overview of various types and sources of TCNs, the associated biosynthetic pathways and genes responsible for production in food and feed. Further, various processing and environmental effects on TCNs production, detection techniques and management strategies are also briefly outlined.