Clonostachin
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| Category | Others |
| Catalog number | BBF-03722 |
| CAS | |
| Molecular Weight | 1667.97 |
| Molecular Formula | C78H134N14O25 |
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Description
Clonostachin is a peptide amino alcohol produced by Clonostachys sp. F5898. It has the effect of inhibiting platelet aggregation.
Specification
| IUPAC Name | [(2R,3R,4R,5R)-1,2,4,5,6-pentahydroxyhexan-3-yl] (2R,3S)-2-[[(2R)-2-[[(2S,4R)-1-[2-[[(2R)-2-[[2-[[(2S,4R)-1-[(2R)-2-[[(2S)-2-[[(2S,4R)-1-[(2S)-2-[[(2S)-2-[[(2S,4R)-1-(2-acetamido-2-methylpropanoyl)-4-hydroxypyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-2-methylbutanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-2-methylbutanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-2-methylpropanoyl]amino]-2-methylbutanoyl]amino]-2-methylpropanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-2-methylbutanoyl]amino]-3-methylpentanoate |
| Canonical SMILES | CCC(C)C(C(=O)OC(C(CO)O)C(C(CO)O)O)NC(=O)C(C)(CC)NC(=O)C1CC(CN1C(=O)C(C)(C)NC(=O)C(C)(CC)NC(=O)C(C)(C)NC(=O)C2CC(CN2C(=O)C(C)(CC)NC(=O)C(CC(C)C)NC(=O)C3CC(CN3C(=O)C(C)(CC)NC(=O)C(CC(C)C)NC(=O)C4CC(CN4C(=O)C(C)(C)NC(=O)C)O)O)O)O |
| InChI | InChI=1S/C78H134N14O25/c1-22-41(10)55(64(109)117-57(54(101)38-94)56(102)53(100)37-93)81-66(111)75(18,23-2)86-63(108)52-32-45(98)34-90(52)69(114)74(16,17)87-67(112)76(19,24-3)88-65(110)72(12,13)83-62(107)51-31-46(99)36-92(51)71(116)78(21,26-5)85-59(104)48(28-40(8)9)80-61(106)50-30-44(97)35-91(50)70(115)77(20,25-4)84-58(103)47(27-39(6)7)79-60(105)49-29-43(96)33-89(49)68(113)73(14,15)82-42(11)95/h39-41,43-57,93-94,96-102H,22-38H2,1-21H3,(H,79,105)(H,80,106)(H,81,111)(H,82,95)(H,83,107)(H,84,103)(H,85,104)(H,86,108)(H,87,112)(H,88,110)/t41-,43+,44+,45+,46+,47-,48-,49-,50-,51-,52-,53+,54+,55+,56+,57+,75+,76+,77-,78+/m0/s1 |
| InChI Key | FXTKDCWUFZIDPM-QPEYCMPISA-N |
Reference Reading
1. Peptaibols, tetramic acid derivatives, isocoumarins, and sesquiterpenes from a Bionectria sp. (MSX 47401)
Mario Figueroa, Huzefa Raja, Joseph O Falkinham rd, Audrey F Adcock, David J Kroll, Mansukh C Wani, Cedric J Pearce, Nicholas H Oberlies J Nat Prod. 2013 Jun 28;76(6):1007-15. doi: 10.1021/np3008842. Epub 2013 Jun 19.
An extract of the filamentous fungus Bionectria sp. (MSX 47401) showed both promising cytotoxic activity (>90% inhibition of H460 cell growth at 20 μg/mL) and antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). A bioactivity-directed fractionation study yielded one new peptaibol (1) and one new tetramic acid derivative (2), and the fungus biosynthesized diverse secondary metabolites with mannose-derived units. Five known compounds were also isolated: clonostachin (3), virgineone (4), virgineone aglycone (5), AGI-7 (6), and 5,6-dihydroxybisabolol (7). Compounds 5 and 7 have not been described previously from natural sources. Compound 1 represents the second member of the peptaibol structural class that contains an ester-linked sugar alcohol (mannitol) instead of an amide-linked amino alcohol, and peptaibols and tetramic acid derivatives have not been isolated previously from the same fungus. The structures of the new compounds were elucidated primarily by high-field NMR (950 and 700 MHz), HRESIMS/MS, and chemical degradations (Marfey's analysis). All compounds (except 6) were examined for antibacterial and antifungal activities. Compounds 2, 4, and 5 showed antimicrobial activity against S. aureus and several MRSA isolates.
2. Clonostachin, a novel peptaibol that inhibits platelet aggregation
T Chikanishi, K Hasumi, T Harada, N Kawasaki, A Endo J Antibiot (Tokyo). 1997 Feb;50(2):105-10. doi: 10.7164/antibiotics.50.105.
A novel peptaibol, designated clonostachin, was isolated from cultures of Clonostachys sp. F5898 by HP-20 and silica gel column chromatographies and reverse-phase HPLC. The structure of clonostachin was determined by Edman and chemical degradations, positive ion FAB-MS, EI-MS, and NMR analyses. Clonostachin was a linear tetradecapeptide with an N-terminal acetyl group and a C-terminal sugar alcohol. Clonostachin inhibited ADP-induced aggregation of human platelets by 80% at 150 microM.
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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 ╳
