Niphimycin
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| Category | Bioactive by-products |
| Catalog number | BBF-04144 |
| CAS | 11056-18-1 |
| Molecular Weight | 1142.45 |
| Molecular Formula | C59H103N3O18 |
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Description
Niphimycin is an antimicrobial metabolized from Streptomyces.
Specification
| Related CAS | 12676-71-0 |
| Synonyms | Scopafungin |
| IUPAC Name | 3-oxo-3-[[(10E,12E,15R,20E)-5,7,9,19,23,25,27,31,33,34,35-undecahydroxy-8,14,18,22,26,30-hexamethyl-15-[(E,2S,4S)-4-methyl-12-[(N'-methylcarbamimidoyl)amino]dodec-8-en-2-yl]-17-oxo-16,37-dioxabicyclo[31.3.1]heptatriaconta-10,12,20-trien-3-yl]oxy]propanoic acid |
| Canonical SMILES | CC1CCC(C(C(CC(C(C=CC(C(C(=O)OC(C(C=CC=CC(C(C(CC(CC(CC2CC(C(C(O2)(CC1O)O)O)O)OC(=O)CC(=O)O)O)O)C)O)C)C(C)CC(C)CCCC=CCCCNC(=NC)N)C)O)C)O)O)C)O |
| InChI | InChI=1S/C59H103N3O18/c1-34(18-14-12-10-11-13-17-25-62-58(60)61-9)26-38(5)55-37(4)19-15-16-20-45(64)39(6)49(68)28-42(63)27-43(78-54(74)32-53(72)73)29-44-30-51(70)56(75)59(77,80-44)33-52(71)36(3)22-23-46(65)40(7)50(69)31-48(67)35(2)21-24-47(66)41(8)57(76)79-55/h10-11,15-16,19-21,24,34-52,55-56,63-71,75,77H,12-14,17-18,22-23,25-33H2,1-9H3,(H,72,73)(H3,60,61,62)/b11-10+,19-15+,20-16+,24-21+/t34-,35?,36?,37?,38-,39?,40?,41?,42?,43?,44?,45?,46?,47?,48?,49?,50?,51?,52?,55-,56?,59?/m0/s1 |
| InChI Key | VAYOSPAPALLOIO-WBWCZIISSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 1184.6°C at 760 mmHg |
| Density | 1.26 g/cm3 |
Reference Reading
1. Structure-activity relationship studies on niphimycin, a guanidylpolyol macrolide antibiotic. Part 1: The role of the N-methyl-N''-alkylguanidinium moiety
Takatsugu Inoue, Toshio Tanaka, Keiji Matsumoto, Hideo Iio, Yoshinosuke Usuki, Koichi Yoshioka Bioorg Med Chem Lett . 2006 Mar 15;16(6):1553-6. doi: 10.1016/j.bmcl.2005.12.024.
Several N-methyl-N''-alkylguanidinium derivatives were synthesized and used as simplified analogues of niphimycin (NM), a guanidylpolyol macrolide, in structure-activity relationship studies. The C16-alkylated derivative exerted fungicidal activity by directly damaging the fungal plasma membrane and inducing oxidative stress in a manner similar to niphimycin. These results indicate that the N-methyl-N''-alkylguanidinium moiety is required for antifungal activity by NM.
2. Discovery of Niphimycin C from Streptomyces yongxingensis sp. nov. as a Promising Agrochemical Fungicide for Controlling Banana Fusarium Wilt by Destroying the Mitochondrial Structure and Function
Miaoyi Zhang, Bingyu Cai, Yankun Zhao, Kai Li, David E Wedge, Wei Wang, Yufeng Chen, Jianghui Xie, Yongzan Wei, Zhiqiang Pan, Dengbo Zhou, Dengfeng Qi J Agric Food Chem . 2022 Oct 12;70(40):12784-12795. doi: 10.1021/acs.jafc.2c02810.
BananaFusariumwilt caused byFusarium oxysporumf. sp.cubense(Foc) is the most destructive soil-borne fungal disease. Tropical race 4 (FocTR4), one of the strains ofFoc, can infect many commercial cultivars, which represents a threat to global banana production. Currently, there are hardly any effective chemical fungicides to control the disease. To search for natural product-based fungicides for controlling bananaFusariumwilt, we identified a novel strainStreptomyces yongxingensissp. nov. (JCM 34965) from a marine soft coral, from which a bioactive compound, niphimycin C, was isolated using an activity-guided method. Niphimycin C exhibited a strong antifungal activity againstFocTR4 with a value of 1.20 μg/mL for EC50and obviously inhibited the mycelial growth and spore germination ofFocTR4. It caused the functional loss of mitochondria and the disorder of metabolism ofFocTR4 cells. Further study showed that niphimycin C reduced key enzyme activities of the tricarboxylic acid (TCA) cycle and the electron transport chain (ETC). It displayed broad-spectrum antifungal activities against the selected 12 phytopathogenic fungi. In pot experiments, niphimycin C reduced the disease indexes in banana plantlets and inhibited the infection ofFocTR4 in roots. Hence, niphimycin C could be a promising agrochemical fungicide for the management of fungal diseases.
3. Identification of antifungal niphimycin from Streptomyces sp. KP6107 by screening based on adenylate kinase assay
Jin Sung Hong, Beom Seok Kim, Hye Yoon Kim, Jeong Do Kim, Jong Hyun Ham J Basic Microbiol . 2013 Jul;53(7):581-9. doi: 10.1002/jobm.201200045.
Microbial culture extracts are used for natural product screening to find antifungal lead compounds. A microbial culture extract library was constructed using 343 actinomycete isolates to examine the value of the adenylate kinase (AK) assay for screening to identify antifungal metabolites that disrupt cell integrity in plant pathogenic fungi. A culture extract of Streptomyces sp. strain KP6107 lysed cells of Fusarium oxysporum f.sp. lycopersici which resulted in high AK activity. The active ingredient N-1 was purified from the culture extract using various chromatographic procedures and identified to be the guanidyl-polyol macrolide antibiotic, niphimycin, which is a potent fungal cell membrane disruptor. Niphimycin showed broad-spectrum antifungal activity against Alternaria mali, Aspergillus oryzae, Colletotrichum coccodes, Colletotrichum gloeosporioides, Cercospora canescens, Cylindrocarpon destructans, F. oxysporum f.sp. cucumerinum, F. oxysporum f.sp. lycopersici, and Rhizoctonia solani at concentrations of 8-64 µg ml(-1). Anthracnose development in pepper plants was completely inhibited by treatment with 50 µg ml(-1) niphimycin, which was as effective as chlorothalonil. These results show that the AK assay is an efficient and selective tool in screening for cell membrane/wall disruptors of plant pathogenic fungi.
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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 ╳
