Nanaomycin E
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| Category | Antibiotics |
| Catalog number | BBF-01984 |
| CAS | 72660-52-7 |
| Molecular Weight | 318.28 |
| Molecular Formula | C16H14O7 |
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Description
Nanaomycin E is an antibiotic produced by Str. rosa subsp. notoensis. It has activity against Gram-positive bacteria and fungi.
Specification
| Synonyms | 4a,10a-Epoxy-1H-naphtho(2,3-c)pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, (1S-(1alpha,3beta,4abeta,10abeta))- |
| Storage | Store at -20°C |
| IUPAC Name | 2-[(1R,10S,11S,13R)-7-hydroxy-11-methyl-2,9-dioxo-12,15-dioxatetracyclo[8.4.1.01,10.03,8]pentadeca-3(8),4,6-trien-13-yl]acetic acid |
| Canonical SMILES | CC1C23C(=O)C4=C(C=CC=C4O)C(=O)C2(O3)CC(O1)CC(=O)O |
| InChI | InChI=1S/C16H14O7/c1-7-16-14(21)12-9(3-2-4-10(12)17)13(20)15(16,23-16)6-8(22-7)5-11(18)19/h2-4,7-8,17H,5-6H2,1H3,(H,18,19)/t7-,8-,15-,16+/m0/s1 |
| InChI Key | SVGOJJZXRJJDLY-IUFZWFJJSA-N |
Properties
| Appearance | Orange Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Boiling Point | 660.3°C at 760 mmHg |
| Melting Point | 172-174°C |
| Density | 1.61 g/cm3 |
| Solubility | Soluble in Methanol, Ethyl acetate |
Reference Reading
1. Nanaomycin K, a new epithelial-mesenchymal transition inhibitor produced by the actinomycete "Streptomyces rosa subsp. notoensis" OS-3966
Hirotaka Matsuo, Jun Nakanishi, Yoshihiko Noguchi, Koichi Kitagawa, Katsumi Shigemura, Toshiaki Sunazuka, Yōko Takahashi, Satoshi Ōmura, Takuji Nakashima J Biosci Bioeng. 2020 Mar;129(3):291-295. doi: 10.1016/j.jbiosc.2019.09.007. Epub 2019 Sep 30.
A new nanaomycin analog, nanaomycin K, was isolated from a cultured broth of actinomycete strain "Streptomyces rosa subsp. notoensis" OS-3966. Nuclear magnetic resonance (NMR) analyses revealed that the planar structure of nanaomycin K had an ergothioneine moiety. To determine the absolute configuration, nanaomycin K was semisynthesized using standards of nanaomycin E and l-ergothioneine. The natural and semisynthetic nanaomycin K were identified as the same compounds based on retention time, mass spectrometry, 1H NMR, and optical rotation data. Nanaomycin K showed cytotoxicity against Madin-Darby canine kidney (MDCK) cells undergoing transforming growth factor (TGF) β1-induced epithelial-mesenchymal transition.
2. Nanaomycin E inhibits NLRP3 inflammasome activation by preventing mitochondrial dysfunction
Yudai Matsui, Naoki Takemura, Yoshitaka Shirasaki, Michihiro Takahama, Yoshihiko Noguchi, Kenta Ikoma, Yixi Pan, Shuhei Nishida, Manabu Taura, Akiyoshi Nakayama, Takashi Funatsu, Takuma Misawa, Yoshie Harada, Toshiaki Sunazuka, Tatsuya Saitoh Int Immunol. 2022 Sep 9;34(10):505-518. doi: 10.1093/intimm/dxac028.
Nod-like receptor family pyrin domain-containing 3 (NLRP3) is a cytosolic innate immune receptor that senses organelle dysfunction induced by various stimuli, such as infectious, environmental, metabolic and drug stresses. Upon activation, NLRP3 forms an inflammasome with its adaptor protein apoptosis-associated speck-like protein containing a caspase recruitment domain (ASC) and caspase-1, to trigger the release of inflammatory cytokines. The development of effective anti-inflammatory drugs targeting the NLRP3 inflammasome is in high demand as its aberrant activation often causes inflammatory diseases. Here, we found that nanaomycin A (NNM-A), a quinone-based antibiotic isolated from Streptomyces, effectively inhibited NLRP3 inflammasome-mediated inflammatory responses induced by imidazoquinolines, including imiquimod. Interestingly, its epoxy derivative nanaomycin E (NNM-E) showed a comparable inhibitory effect against the NLRP3 inflammasome-induced release of interleukin (IL)-1β and IL-18 from macrophages, with a much lower toxicity than NNM-A. NNM-E inhibited ASC oligomerization and caspase-1 cleavage, both of which are hallmarks of NLRP3 inflammasome activation. NNM-E reduced mitochondrial damage and the production of reactive oxygen species, thereby preventing the activation of the NLRP3 inflammasome. NNM-E treatment markedly alleviated psoriasis-like skin inflammation induced by imiquimod. Collectively, NNM-E inhibits NLRP3 inflammasome activation by preventing mitochondrial dysfunction with little toxicity and showed an anti-inflammatory effect in vivo. Thus, NNM-E could be a potential lead compound for developing effective and safe anti-inflammatory agents for the treatment of NLRP3 inflammasome-mediated inflammatory diseases.
3. Site of regulation of nanaomycin biosynthesis by inorganic phosphate
R Masuma, D Z Zhen, Y Tanaka, S Omura J Antibiot (Tokyo). 1990 Jan;43(1):83-7. doi: 10.7164/antibiotics.43.83.
The site of regulation of nanaomycin biosynthesis by inorganic phosphate was studied with washed cells previously grown in a chemically defined medium containing a high- or low-phosphate concentration. The former mycelia produced only about one-tenth the amount of nanaomycin A from acetate as did the latter mycelia. On the other hand, the bioconversions of nanaomycin D to A and nanaomycin A to E were only slightly affected. It is suggested that the site of regulation of nanaomycin biosynthesis by inorganic phosphate lies within steps between acetate and nanaomycin D.
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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 ╳
