Staplabin
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| Category | Others |
| Catalog number | BBF-03060 |
| CAS | 183006-79-3 |
| Molecular Weight | 485.61 |
| Molecular Formula | C28H39NO6 |
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Description
Staplabin is a substance produced by the fungus Stachybotrys microspora IFO 30018. Staplabin has the effect of stimulating the binding of plasminogen to fibrin and U937 cells.
Specification
| IUPAC Name | 5-[2-[(3E)-4,8-dimethylnona-3,7-dienyl]-3,5-dihydroxy-2-methyl-7-oxo-4,9-dihydro-3H-pyrano[2,3-e]isoindol-8-yl]pentanoic acid |
| Canonical SMILES | CC(=CCCC(=CCCC1(C(CC2=C(C=C3C(=C2O1)CN(C3=O)CCCCC(=O)O)O)O)C)C)C |
| InChI | InChI=1S/C28H39NO6/c1-18(2)9-7-10-19(3)11-8-13-28(4)24(31)16-21-23(30)15-20-22(26(21)35-28)17-29(27(20)34)14-6-5-12-25(32)33/h9,11,15,24,30-31H,5-8,10,12-14,16-17H2,1-4H3,(H,32,33)/b19-11+ |
| InChI Key | PREWWCBUIKRUIM-YBFXNURJSA-N |
Properties
| Appearance | Light Brown Oil |
| Boiling Point | 705.6±60.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Methanol, Butanol |
Reference Reading
1. Progress in Isoindolone Alkaloid Derivatives from Marine Microorganism: Pharmacology, Preparation, and Mechanism
Sijin Hang, Hui Chen, Wenhui Wu, Shiyi Wang, Yiwen Fang, Ruilong Sheng, Qidong Tu, Ruihua Guo Mar Drugs. 2022 Jun 20;20(6):405. doi: 10.3390/md20060405.
Compound 1 (SMTP-7, also FGFC1), an isoindolone alkaloid from marine fungi Starchbotrys longispora FG216 and fungi Stachybotrys microspora IFO 30018, possessed diverse bioactivities such as thrombolysis, anti-inflammatory and anti-oxidative properties, and so on. It may be widely used for the treatment of various diseases, including cerebral infarction, stroke, ischemia/reperfusion damage, acute kidney injury, etc. Especially in cerebral infarction, compound 1 could reduce hemorrhagic transformation along with thrombolytic therapy, as the traditional therapies are accompanied with bleeding risks. In the latest studies, compound 1 selectively inhibited the growth of NSCLC cells with EGFR mutation, thus demonstrating its excellent anti-cancer activity. Herein, we summarized pharmacological activities, preparation of staplabin congeners-especially compound 1-and the mechanism of compound 1, with potential therapeutic applications.
2. SMTP-4D, -5D, -6D, -7D and -8D, a new series of the non-lysine-analog plasminogen modulators with a D-amino acid moiety
Weimin Hu, Yoshikazu Kitano, Keiji Hasumi J Antibiot (Tokyo). 2003 Oct;56(10):832-7. doi: 10.7164/antibiotics.56.832.
Staplabin and SMTPs, triprenyl phenol metabolites of the fungus Stachybotrys microspora, are a family of non-lysine-analog plasminogen modulators that enhance both activation and fibrin binding of plasminogen by modulating plasminogen conformation. These compounds, including SMTP-4, -5, -6, -7 and -8, have an amino acid or an amino alcohol moiety in their structure, and precursor amine feeding greatly increases the biosynthesis of a metabolite of interest. In the present study, we have isolated five novel SMTPs (designated SMTP-4D, -5D, -6D, -7D and -8D) from precursor D-amino acid-fed cultures. Physico-chemical properties as well as chromatographic behavior were distinct from those of the corresponding L-amino acid analogs, which are selectively accumulated in L-amino acid-fed cultures and share common properties with corresponding natural products. The D-series SMTPs enhanced urokinase-catalyzed plasminogen activation by 10-fold at 80 approximately 180 microM.
3. Synergistic interaction in simultaneous exposure to Streptomyces californicus and Stachybotrys chartarum
Kati Huttunen, Jukka Pelkonen, Kristian Fogg Nielsen, Ulla Nuutinen, Juha Jussila, Maija-Riitta Hirvonen Environ Health Perspect. 2004 May;112(6):659-65. doi: 10.1289/ehp.6701.
The microbial exposure associated with health complaints in moldy houses consists of a heterogeneous group of components, including both living and dead bacteria, fungi, and their metabolites and active compounds. However, little is known about the interactions between different microbes and their metabolites, although the cytotoxicity and inflammatory potential of certain individual microbes have been reported. In this study, we investigated the inflammatory responses of mouse RAW264.7 macrophages after exposure to six indoor air microbes (Aspergillus versicolor, Penicillium spinulosum, Stachybotrys chartarum, Bacillus cereus, Mycobacterium terrae, and Pseudomonas fluorescens) alone and together with the actinomycete Streptomyces californicus. The production of nitric oxide, levels of the proinflammatory cytokines tumor necrosis factor alpha (TNF-alpha) and interleukin-6 (IL-6), and cytotoxicity were measured. The coexposure to Sta. chartarum and Str. californicus caused a synergistic increase in the production of IL-6 but not other cytokines. In further experiments, the metabolites from Sta. chartarum or from closely related fungi (atranones B and E, satratoxin G, trichodermin, 7-alpha-hydroxytrichodermol, staplabin, and SMTP-7) and the known fungal toxins sterigmatocystin, citrinin, and ochratoxin A were each tested with Str. californicus. The testing revealed a synergistic response in TNF-alpha and IL-6 production after coexposure to Str. californicus with both trichodermin and 7-alpha-hydroxytrichodermol. Finally, the synergistic inflammatory response caused by Str. californicus and trichodermin together was studied by analyzing for the presence of nuclear factor-kappa-B (NF-kappa-B) in nuclear extracts of the exposed cells. The exposure to Str. californicus induced the binding of NF-kappa-B proteins to the NF-kappa-B consensus sequence as well as to the natural NF-kappa-B site of the IL-6 promoter. Adding trichodermin to the exposure did not increase the DNA binding.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
