Spiculisporic acid
(Synonyms: 4,5-二羧基-γ-十五内酯) 目录号 : GC38675
A biosurfactant
Cas No.:469-77-2
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
Spiculisporic acid is a biosurfactant that has been found in P. spiculisporum.1
1.Ishigami, Y., Zhang, Y., and Goto, M.Molecular and crystal structure of spiculisporic acid and correlation with the surface activityJ. Oleo Sci.62(10)795-802(2013)
| Cas No. | 469-77-2 | SDF | |
| 别名 | 4,5-二羧基-γ-十五内酯 | ||
| Canonical SMILES | CCCCCCCCCC[C@@H]([C@](CCC1=O)(O1)C(O)=O)C(O)=O | ||
| 分子式 | C17H28O6 | 分子量 | 328.4 |
| 溶解度 | DMSO: 250 mg/mL (761.27 mM) | 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 | 3.0451 mL | 15.2253 mL | 30.4507 mL |
| 5 mM | 0.609 mL | 3.0451 mL | 6.0901 mL |
| 10 mM | 0.3045 mL | 1.5225 mL | 3.0451 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。
Spiculisporic acid analogues of the marine-derived fungus, Aspergillus candidus strain HDf2, and their antibacterial activity
Antonie Van Leeuwenhoek 2015 Jul;108(1):215-9.PMID:25912731DOI:10.1007/s10482-015-0462-y.
Two novel antibiotic Spiculisporic acid analogues, named as Spiculisporic acid F (1) and G (2), and two known compounds, (-)-spiculisporic acid (3) and secospiculisporic acid B (4), were isolated by bioactivity-guided fractionation from the fermentation broth of the sea urchin-derived Aspergillus candidus strain HDf2. Their structures were unambiguously established by comprehensive analysis of 1D and 2D NMR, and high-resolution MS spectra, and by comparison with known compounds. Biological experiments demonstrated that compounds 1 and 2 displayed antibacterial activity against Gram-negative Pseudomonas solanacearum and Gram-positive Staphylococcus aureus, but showed no cytotoxicity against SGC-7901 human gastric adenocarcinoma and SPC-A-1 human lung adenocarcinoma tumor cell lines. This is the first critical evidence identifying Spiculisporic acid derivatives as a potential bio-control agent for the soil borne pathogen P. solanacearum (E. F. Smith) Smith. These findings provide further insight into the chemical and biological activity diversity of this class of compounds.
Spiculisporic acid E, a new Spiculisporic acid derivative and ergosterol derivatives from the marine-sponge associated fungus Talaromyces trachyspermus (KUFA 0021)
Nat Prod Commun 2014 Aug;9(8):1147-50.PMID:25233594doi
A new Spiculisporic acid derivative, Spiculisporic acid E (2), and a new natural product 3-acetyl ergosterol 5, 8-endoperoxide (1), were isolated, together with ergosta-4, 6, 8 (14), 22-tetraen-3-one, glaucanic acid and glauconic acid, from the culture of the marine-sponge associated fungus Talaromyces trachyspermus (KUFA 0021). All the compounds were inactive against Gram-positive and Gram-negative bacteria, and Candida albicans, as well as multidrug-resistant isolates from the environment. Spiculisporic acid E (2), glaucanic acid and glauconic acid did not show in vitro growth inhibitory activity against the MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and A375-C5 (melanoma) cell lines by the protein binding dye SRB method.
Molecular and crystal structure of Spiculisporic acid and correlation with the surface activity
J Oleo Sci 2013;62(10):795-802.PMID:24088517DOI:10.5650/jos.62.795.
The crystal of Spiculisporic acid, [4S, 5S-(4,5-dicarboxy-4-pentadecanolide)], is orthorhombic, and the space group is P2₁ 2₁ 2₁ with Z = 4 at 23°C. The cell dimensions are as follows, a = 43.82 (1) Å, b = 7.540 (2) Å, c = 5.579 (2) Å, V = 1843 (1) ų. The molecules form intermolecular networks linked by hydrogen bonds around their polar carboxylic moieties. The hydrophobicity of the lactone ring (γ-butanolide) was evaluated at ca. 4 methylene linkages of n-alkyl chain from both of the molecular alignmental data and the surface active properties of sodium spiculisporates. Then, it was made clear that sodium spiculisporates, anionic polyfunctional biosurfactants, exerted a distinctive characteristic of lower critical micelle concentration (cmc) and γ(cmc) (surface tension at the cmc), simultaneously, through their properties. On the other hand, sodium salts of the lactone-cleaved derivative of Spiculisporic acid (O-acid), showed large dispersing and calcium ion sequestration properties due to their plural polar heads.
Chemotaxonomy of the genus Talaromyces
Antonie Van Leeuwenhoek 1990 Apr;57(3):179-89.PMID:2181929DOI:10.1007/BF00403953.
Species of the ascomycetous genus Talaromyces have been examined for profiles of secondary metabolites on TLC. The greatest number of specific metabolites were produced on oatmeal-, malt extract- and yeast-extract sucrose agars. Profiles of intracellular secondary metabolites produced on oatmeal agar were specific for each species and provided a means of simple differentiation of the taxa. Examination of the most important species using high performence liquid chromatography (HPLC) allowed to solve some taxonomic problems. Known mycotoxins are produced by T. stipitatus (duclauxin, talaromycins, botryodiploidin), T. stipitatus chemotype II (emodin), T. panasenkoi (Spiculisporic acid), T. trachyspermus (Spiculisporic acid), T. macrosporus (duclauxin) and T. wortmannii (rugulosin). Wortmannin is produced by an atypical strain of T. flavus but not T. wortmannii. Several other secondary metabolites were discovered for the first time in the following species: Glauconic acid is produced by T. panasenkoi, T. ohiensis and T. trachyspermus; vermiculine by T. ohiensis; duclauxin by T. flavus var. macrosporus and the mitorubrins by T. flavus and T. udagawae. The profiles of secondary metabolites support the established taxonomy of the species based on morphology, showing the genetic stability of profiles of secondary metabolites in Talaromyces. Two new taxa are proposed: T. macrosporus comb. nov. (stat. anam. Penicillium macrosporum stat. nov.), and Penicillium vonarxii, sp. nov. for the anamorph of T. luteus.
Diversity of Sclerotium rolfsii antagonist fungi isolated from soils of the rhizosphere of tomato crops and identification of some antifungal compounds
Heliyon 2022 Feb 11;8(2):e08943.PMID:35243065DOI:10.1016/j.heliyon.2022.e08943.
Sclerotium rolfsii Sacc. the causative agent of white rot is one of the destructive pathogens of nightshade crops. In Côte d'Ivoire, this fungal pathogen constitutes a major constraint for the cultivation of tomato (Solanum lycopersicum) with 41.01% crop losses in humid forest areas. Controlling this fungus with synthetic chemicals can be effective, but harmful to human health and the environment. The use of biological control agents could be an alternative approach to control S. rolfsii. In this perspective, the objective of this work was to select fungi from the rhizosphere of tomato crops capable of inhibiting the growth of S. rolfsii. To do this, 153 fungi were isolated from the rhizosphere and from direct confrontation tests 10 fungi whose antagonistic power of S. rolfsii varied between 27 and 60% were selected. Molecular identification (ITS) of these antagonist fungi revealed that the isolates belonged to the genera Talaromyces sp. (n = 4), Trichoderma sp. (n = 3), Penicillium sp. (n = 2) and Clonostachys sp. (n = 1). Among these fungi, Talaromyces purpureogenus and Talaromyces assiutensis were able to diffuse compounds in agar capable of inhibiting the growth of S. rolfsii. The chemical study of these 2 fungi made it possible to identify mitorubrin and mitorubrinol produced by T. purpureogenus and Spiculisporic acid produced by T. assiutensis. Mitorubrin and mitorubrinol had inhibitory activities of 100 and 70% at 10 mg/mL, respectively, whereas Spiculisporic acid showed moderate inhibition of 38 at 20 mg/mL of the growth of S. rolfsii; however, its abundant production by the fungus could be an advantage in the control of this phytopathogen. Isolated from the same biotope as S. rolfsii, T. purpureogenus and T. assiutensis represent favorable candidates for the biological control against S. rolfsii.