Halymecin A
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| Category | Antibiotics |
| Catalog number | BBF-01315 |
| CAS | 165561-10-4 |
| Molecular Weight | 805.04 |
| Molecular Formula | C42H76O14 |
| Purity | 95% |
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Description
It is produced by the strain of Fusarium sp. FE-71-1. It's an antibiotic produced by Marine microbes. Halymecin A had only weak antibacterial and fungal activity.
Specification
| IUPAC Name | (3R,5R)-5-[(3R,5R)-3-acetyloxy-5-[(3R,5R)-5-[(3R,5R)-3,5-dihydroxydecanoyl]oxy-3-hydroxydecanoyl]oxydecanoyl]oxy-3-hydroxydecanoic acid |
| Canonical SMILES | CCCCCC(CC(CC(=O)OC(CCCCC)CC(CC(=O)OC(CCCCC)CC(CC(=O)OC(CCCCC)CC(CC(=O)O)O)OC(=O)C)O)O)O |
| InChI | InChI=1S/C42H76O14/c1-6-10-14-18-31(44)22-32(45)26-40(50)54-36(20-16-12-8-3)24-34(47)27-41(51)56-37(21-17-13-9-4)28-38(53-30(5)43)29-42(52)55-35(19-15-11-7-2)23-33(46)25-39(48)49/h31-38,44-47H,6-29H2,1-5H3,(H,48,49)/t31-,32-,33-,34-,35-,36-,37-,38-/m1/s1 |
| InChI Key | OHOMGNIITZEKKL-NCUMTQOVSA-N |
Properties
| Appearance | Colorless Oily Matter |
| Antibiotic Activity Spectrum | Fungi |
| Solubility | Soluble in Dichloromethane |
Reference Reading
1. Antimicrobial activities of novel mannosyl lipids isolated from the biocontrol fungus Simplicillium lamellicola BCP against phytopathogenic bacteria
Quang Le Dang, Teak Soo Shin, Myung Soo Park, Yong Ho Choi, Gyung Ja Choi, Kyoung Soo Jang, In Seon Kim, Jin-Cheol Kim J Agric Food Chem. 2014 Apr 16;62(15):3363-70. doi: 10.1021/jf500361e. Epub 2014 Apr 4.
The antagonistic fungus Simplicillium lamellicola BCP has been developed as a microbial biopesticide that effectively controls the development of various plant diseases caused by both pathogenic bacteria and pathogenic fungi. Antibacterial bioassay-directed fractionation was used to isolate mannosyl lipids from S. lamellicola BCP, and the structures of these compounds were elucidated using spectral analysis and chemical degradation. Three novel mannosyl lipids were characterized and identified as halymecins F and G and (3R,5R)-3-O-β-D-mannosyl-3,5-dihydrodecanoic acid. Massoia lactone and (3R, 5R)-3-hydroxydecan-5-olide were also isolated from S. lamellicola BCP. The three novel compounds inhibited the growth of the majority of phytopathogenic bacteria that were tested, and halymecin F displayed the strongest antibacterial activity. Agrobacterium tumefaciens was the most sensitive to the three novel compounds, with IC₅₀ values ranging from 1.58 to 24.8 μg/mL. The ethyl acetate extract of the fermentation broth from the antagonistic fungus effectively reduced the bacterial wilt caused by Ralstonia solanacearum on tomato seedlings. These results indicate that S. lamellicola BCP suppresses the development of plant bacterial diseases through the production of antibacterial metabolites.
2. Halymecins, new antimicroalgal substances produced by fungi isolated from marine algae
C Chen, N Imamura, M Nishijima, K Adachi, M Sakai, H Sano J Antibiot (Tokyo). 1996 Oct;49(10):998-1005. doi: 10.7164/antibiotics.49.998.
Novel antimicroalgal substances halymecins A (1), B (2) and C (3) were isolated from the fermentation broth of a Fusarium sp. and halymecins D (4) and E (5) from an Acremonium sp. The structures of these halymecins, Fig. 1, were determined based on extensive 2D NMR studies as well as mass spectral data. These chemical structures are conjugates of di- and trihydroxydecanoic acid. Halymecin A showed antimicroalgal activity against Skeletonema costatum.
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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 ╳
