Leptosin J
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| Category | Antibiotics |
| Catalog number | BBF-02251 |
| CAS | 160550-15-2 |
| Molecular Weight | 740.89 |
| Molecular Formula | C32H32N6O7S4 |
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Description
It is produced by the strain of J Leptosphaeria sp. OUPS-4. In order to understand its cytotoxic effects, someone tested Leukemia lymphocyte P388 in culture with an ED50 of 1.25 μg/mL.
Specification
| Synonyms | Chaetocin, 2,5:2',5'-dide(epidithio)-19'-deoxy-2',5'-(epitetrathio)-5,6'-epoxy-6-hydroxy-19',19'-dimethyl-, (2alpha,5alpha,6S,6'S,15alpha)-; 22bH-18,22a-(Iminomethano)-10b,23a-methano-10bH,23aH-indolo[2'',3'':2',3'][1,2,3,4,6]tetrathiazocino[6'',5'':1',5']pyrrolo[3',4':6,7]pyrazino[2''',1''':2,3][1,3]oxazepino[4,5-b]indole-1,4,17,25(18H)-tetrone,2,3,5a,6,15,15a-hexahydro-24-hydroxy-3-(hydroxymethyl)-2,26-dimethyl-18-(1-methylethyl)-, (3a,5aa,10bb,10cR*,15aa,18a,22aa,22bb,23ab,24R*)-(+)-; Leptosine J |
| IUPAC Name | (1S,2S,4S,7R,10S,18R,19S,27R,30S,37S)-37-hydroxy-7-(hydroxymethyl)-6,36-dimethyl-30-propan-2-yl-3-oxa-31,32,33,34-tetrathia-6,9,11,26,28,36-hexazadecacyclo[28.4.2.14,18.01,28.02,19.04,9.010,18.012,17.019,27.020,25]heptatriaconta-12,14,16,20,22,24-hexaene-5,8,29,35-tetrone |
| Canonical SMILES | CC(C)C12C(=O)N3C4C5(C(C3(C(=O)N1C)SSSS2)OC67C(C58C(N6C(=O)C(N(C7=O)C)CO)NC9=CC=CC=C89)O)C1=CC=CC=C1N4 |
| InChI | InChI=1S/C32H32N6O7S4/c1-14(2)31-27(44)38-24-29(16-10-6-8-12-18(16)34-24)22(32(38,26(43)36(31)4)47-49-48-46-31)45-30-21(41)28(29)15-9-5-7-11-17(15)33-23(28)37(30)20(40)19(13-39)35(3)25(30)42/h5-12,14,19,21-24,33-34,39,41H,13H2,1-4H3/t19-,21+,22+,23+,24-,28+,29-,30+,31+,32+/m1/s1 |
| InChI Key | PZFMMBJJDMZAIP-DAXBJGKUSA-N |
Properties
| Appearance | Pale Yellow Powder |
| Melting Point | 215-216°C |
| Solubility | Soluble in Chloroform, Ethanol, DMSO |
Reference Reading
1. Leptosins I and J, cytotoxic substances produced by a Leptosphaeria sp. Physico-chemical properties and structures
C Takahashi, A Numata, E Matsumura, K Minoura, H Eto, T Shingu, T Ito, T Hasegawa J Antibiot (Tokyo). 1994 Nov;47(11):1242-9. doi: 10.7164/antibiotics.47.1242.
Leptosins I and J, belonging to a series of epipolythiodioxopiperazines, have been isolated from the mycelium of a strain of Leptosphaeria sp. OUPS-4 attached to the marine alga Sargasssum tortile. Their relative stereostructures have been elucidated by chemical and spectral evidence. These compounds exhibited significant cytotoxic activity against cultured P388 cells.
2. Sea foam as a source of fungal inoculum for the isolation of biologically active natural products
David P Overy, Fabrice Berrue, Hebelin Correa, Novriyandi Hanif, Kathryn Hay, Martin Lanteigne, Kathrine Mquilian, Stephanie Duffy, Patricia Boland, Ramesh Jagannathan, Gavin S Carr, Marieke Vansteeland, Russell G Kerr Mycology. 2014 Jul 3;5(3):130-144. doi: 10.1080/21501203.2014.931893. Epub 2014 Jul 9.
Due to a rate increase in the resistance of microbial pathogens to currently used antibiotics, there is a need in society for the discovery of novel antimicrobials. Historically, fungi are a proven source for antimicrobial compounds. The main goals of this study were to investigate the fungal diversity associated with sea foam collected around the coast of Prince Edward Island and the utility of this resource for the production of antimicrobial natural products. Obtained isolates were identified using ITS and nLSU rDNA sequences, fermented on four media, extracted and fractions enriched in secondary metabolites were screened for antimicrobial activity. The majority of the isolates obtained were ascomycetes, consisting of four recognized marine taxa along with other ubiquitous genera and many 'unknown' isolates that could not be identified to the species level using rDNA gene sequences. Secondary metabolite isolation efforts lead to the purification of the metabolites epolones A and B, pycnidione and coniothyrione from a strain of Neosetophoma samarorum; brefeldin A, leptosin J and the metabolite TMC-264 from an unknown fungus (probably representative of an Edenia sp.); and 1-hydroxy-6-methyl-8-hydroxymethylxanthone, chrysophanol and chrysophanol bianthrone from a Phaeospheria spartinae isolate. The biological activity of each of these metabolites was assessed against a panel of microbial pathogens as well as several cell lines.
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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 ╳
