Orfamide A
目录号 : GC44513
A lipopeptide biosurfactant
Cas No.:939960-34-6
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
Orfamide A is a lipopeptide biosurfactant originally isolated from P. protegens. It induces mortality in adult green peach aphids (LC50 = 34.5 μg/ml). Orfamide A (50 μM) blocks appressoria formation in M. oryzae isolates and reduces the number of sporulating blast lesions in M. oryzae-infected plants.
| Cas No. | 939960-34-6 | SDF | |
| Canonical SMILES | CC(C)C[C@@H](C(N[C@@H](CC(C)C)C(N[C@@](CO)([H])C(N[C@@H](C(C)C)C(O[C@H](C)[C@H]1NC([C@H](NC([C@H](CC(C)C)NC(CC(O)CCCCCCCCCCC)=O)=O)CCC(O)=O)=O)=O)=O)=O)=O)NC([C@@H](CO)NC([C@@](CC(C)C)([H])NC([C@]([C@H](CC)C)([H])NC1=O)=O)=O)=O | ||
| 分子式 | C64H114N10O17 | 分子量 | 1295.7 |
| 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 | 0.7718 mL | 3.8589 mL | 7.7178 mL |
| 5 mM | 0.1544 mL | 0.7718 mL | 1.5436 mL |
| 10 mM | 0.0772 mL | 0.3859 mL | 0.7718 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。
Total Synthesis and Structure Correction of the Cyclic Lipodepsipeptide Orfamide A
Chemistry 2022 Apr 6;28(20):e202104417.PMID:35199896DOI:10.1002/chem.202104417.
A total synthesis of the cyclic lipodepsipeptide natural product Orfamide A was achieved. By developing a synthesis format using an aminoacid ester building block and SPPS protocol adaptation, a focused library of target compounds was obtained, in high yield and purity. Spectral and LC-HRMS data of all library members with the isolated natural product identified the 5 Leu residue to be d- and the 3'-OH group to be R-configured. The structural correction of Orfamide A by chemical synthesis and analysis was confirmed by biological activity comparison in Chlamydomonas reinhardtii, which indicated compound configuration to be important for bioactivity. Acute toxicity was also found against Trypanosoma brucei, the parasite causing African sleeping sickness.
Identification of Orfamide A as an insecticidal metabolite produced by Pseudomonas protegens F6
J Agric Food Chem 2013 Jul 17;61(28):6786-91.PMID:23763636DOI:10.1021/jf401218w.
The use of biosurfactants for agricultural crop protection has been gaining interest because they are generally biodegradable and environmentally friendly. In the present study, we identified an insecticidal biosurfactant produced by Pseudomonas protegens F6 (F6) and examined its use for aphid control. The growth of F6 was accompanied by increased aphid mortality and decreased water surface tension. Bioassay-guided chromatography coupled with instrumental analyses, nuclear magnetic resonance (NMR), and time-of-flight mass spectrometer (TOF MS) identified Orfamide A as a major metabolite that showed insecticidal activity against green peach aphid ( Myzus persicae ). Orfamide A revealed a dose-dependent mortality against aphids, producing a LC50 value at 34.5 μg/mL, and caused a considerable decrease in the surface tension value of water, giving about 35.7 mN/m at 10 μg/mL. Laboratory and greenhouse mortality bioassays suggested that Orfamide A may be applicable to control aphids in organic agriculture. This is the first report of Orfamide A as an insecticidal metabolite against Myzus persicae .
Rhizoxin analogs, Orfamide A and chitinase production contribute to the toxicity of Pseudomonas protegens strain Pf-5 to Drosophila melanogaster
Environ Microbiol 2016 Oct;18(10):3509-3521.PMID:27130686DOI:10.1111/1462-2920.13369.
Pseudomonas protegens strain Pf-5 is a soil bacterium that was first described for its capacity to suppress plant diseases and has since been shown to be lethal to certain insects. Among these is the common fruit fly Drosophila melanogaster, a well-established model organism for studies evaluating the molecular and cellular basis of the immune response to bacterial challenge. Pf-5 produces the insect toxin FitD, but a ΔfitD mutant of Pf-5 retained full toxicity against D. melanogaster in a noninvasive feeding assay, indicating that FitD is not a major determinant of Pf-5's oral toxicity against this insect. Pf-5 also produces a broad spectrum of exoenzymes and natural products with antibiotic activity, whereas a mutant with a deletion in the global regulatory gene gacA produces none of these exoproducts and also lacks toxicity to D. melanogaster. In this study, we made use of a panel of Pf-5 mutants having single or multiple mutations in the biosynthetic gene clusters for seven natural products and two exoenzymes that are produced by the bacterium under the control of gacA. Our results demonstrate that the production of rhizoxin analogs, Orfamide A, and chitinase are required for full oral toxicity of Pf-5 against D. melanogaster, with rhizoxins being the primary determinant.
A polyyne toxin produced by an antagonistic bacterium blinds and lyses a Chlamydomonad alga
Proc Natl Acad Sci U S A 2021 Aug 17;118(33):e2107695118.PMID:34389682DOI:10.1073/pnas.2107695118.
Algae are key contributors to global carbon fixation and form the basis of many food webs. In nature, their growth is often supported or suppressed by microorganisms. The bacterium Pseudomonas protegens Pf-5 arrests the growth of the green unicellular alga Chlamydomonas reinhardtii, deflagellates the alga by the cyclic lipopeptide Orfamide A, and alters its morphology [P. Aiyar et al., Nat. Commun. 8, 1756 (2017)]. Using a combination of Raman microspectroscopy, genome mining, and mutational analysis, we discovered a polyyne toxin, protegencin, which is secreted by P. protegens, penetrates the algal cells, and causes destruction of the carotenoids of their primitive visual system, the eyespot. Together with secreted Orfamide A, protegencin thus prevents the phototactic behavior of C. reinhardtii A mutant of P. protegens deficient in protegencin production does not affect growth or eyespot carotenoids of C. reinhardtii Protegencin acts in a direct and destructive way by lysing and killing the algal cells. The toxic effect of protegencin is also observed in an eyeless mutant and with the colony-forming Chlorophyte alga Gonium pectorale These data reveal a two-pronged molecular strategy involving a cyclic lipopeptide and a conjugated tetrayne used by bacteria to attack select Chlamydomonad algae. In conjunction with the bloom-forming activity of several chlorophytes and the presence of the protegencin gene cluster in over 50 different Pseudomonas genomes [A. J. Mullins et al., bioRxiv [Preprint] (2021). https://www.biorxiv.org/content/10.1101/2021.03.05.433886v1 (Accessed 17 April 2021)], these data are highly relevant to ecological interactions between Chlorophyte algae and Pseudomonadales bacteria.
The bacterium Pseudomonas protegens antagonizes the microalga Chlamydomonas reinhardtii using a blend of toxins
Environ Microbiol 2021 Sep;23(9):5525-5540.PMID:34347373DOI:10.1111/1462-2920.15700.
The unicellular alga Chlamydomonas reinhardtii and the bacterium Pseudomonas protegens serve as a model to study the interactions between photosynthetic and heterotrophic microorganisms. P. protegens secretes the cyclic lipopeptide Orfamide A that interferes with cytosolic Ca2+ homeostasis in C. reinhardtii resulting in deflagellation of the algal cells. Here, we studied the roles of additional secondary metabolites secreted by P. protegens using individual compounds and co-cultivation of algae with bacterial mutants. Rhizoxin S2, pyrrolnitrin, pyoluteorin, 2,4-diacetylphloroglucinol (DAPG) and Orfamide A all induce changes in cell morphology and inhibit the growth of C. reinhardtii. Rhizoxin S2 exerts the strongest growth inhibition, and its action depends on the spatial structure of the environment (agar versus liquid culture). Algal motility is unaffected by rhizoxin S2 and is most potently inhibited by Orfamide A (IC50 = 4.1 μM). Pyrrolnitrin and pyoluteorin both interfere with algal cytosolic Ca2+ homeostasis and motility whereas high concentrations of DAPG immobilize C. reinhardtii without deflagellation or disturbance of Ca2+ homeostasis. Co-cultivation with a regulatory mutant of bacterial secondary metabolism (ΔgacA) promotes algal growth under spatially structured conditions. Our results reveal how a single soil bacterium uses an arsenal of secreted antialgal compounds with complementary and partially overlapping activities.