Oidiolactone A
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| Category | Bioactive by-products |
| Catalog number | BBF-03350 |
| CAS | 90578-11-3 |
| Molecular Weight | 320.3 |
| Molecular Formula | C17H20O6 |
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Description
Oidiolactone A is a diterpenoid produced by Oidiodendron griseum CL37215. It inhibits LPS-induced IL-1β and TNF-α activity with IC50 values of 1.5 and 4.7 µmol/L.
Specification
| Synonyms | PR-1388; PR 1388; PR1388 |
| IUPAC Name | (1S,2R,4S,5S,10S,14S,17R)-5-methoxy-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.02,4.04,9.014,17]heptadec-8-ene-7,15-dione |
| Canonical SMILES | CC12CCCC3(C1C(C4C5(C2=CC(=O)OC5OC)O4)OC3=O)C |
| InChI | InChI=1S/C17H20O6/c1-15-5-4-6-16(2)11(15)10(22-13(16)19)12-17(23-12)8(15)7-9(18)21-14(17)20-3/h7,10-12,14H,4-6H2,1-3H3/t10-,11+,12+,14-,15+,16-,17-/m0/s1 |
| InChI Key | VCIBPFWQFKTGGR-AGZKKFAISA-N |
Reference Reading
1. Nematicidal activities of 4-hydroxyphenylacetic acid and oidiolactone D produced by the fungus Oidiodendron sp
Kouhei Ohtani, Shozo Fujioka, Tsuyoshi Kawano, Atsumi Shimada, Yasuo Kimura Z Naturforsch C J Biosci. 2011 Jan-Feb;66(1-2):31-4.
Two nematicides, 4-hydroxyphenylacetic acid (4-HPA) (1) and oidiolactone D (2), were isolated from cultures of the fungus Oidiodendron sp., and their structures were identified by spectroscopic analyses. Compound 2 showed nematicidal activities against the root-lesion nematode, Pratylenchus penetrans, and the pine wood nematode, Bursaphelenchus xylophilus. Compound 1 was also active against these two nematodes but to a lesser extent.
2. Biologically active tetranorditerpenoids from the fungus Sclerotinia homoeocarpa causal agent of dollar spot in turfgrass
H M T Bandara Herath, Wimal H M W Herath, Paulo Carvalho, Shabana I Khan, Babu L Tekwani, Stephen O Duke, Maria Tomaso-Peterson, N P Dhammika Nanayakkara J Nat Prod. 2009 Dec;72(12):2091-7. doi: 10.1021/np900334k.
Nine new tetranorditerpenoid dilactones (2-10), together with two previously reported norditerpenoids dilactones (1, 11), and two known putative biosynthetic intermediates, oidiolactone-E (12) and 13, were isolated from an ethyl acetate extract of a culture medium of Sclerotinia homoeocarpa. Structures and absolute configurations of these compounds were determined by spectroscopic methods and confirmed by X-ray crystallographic analysis of representative compounds. Compounds were evaluated for herbicidal, antiplasmodial, and cytotoxic activities. Compounds 1, 2, 6, 7, and 11 were more active as growth inhibitors in a duckweed bioassay (I(50) values of 0.39-0.95 microM) than more than half of 26 commercial herbicides previously evaluated using the same bioassay. Some of these compounds exhibited strong antiplasmodial activities as well, but they also had cytotoxic activity, thus precluding them as potential antimalarial agents.
3. Total synthesis of oidiodendrolides and related norditerpene dilactones from a common precursor: metabolites CJ-14,445, LL-Z1271gamma, oidiolactones A, B, C, and D, and nagilactone F
Stephen Hanessian, Nicolas Boyer, Gone Jayapal Reddy, Benoît Deschênes-Simard Org Lett. 2009 Oct 15;11(20):4640-3. doi: 10.1021/ol901896c.
An efficient, high-yielding strategy has been developed for the asymmetric total synthesis of seven norditerpenoid dilactones known for their diverse biological properties. The three key steps employed to obtain a tricyclic lactone intermediate involved a Morita-Baylis-Hillman reaction, the stereocontrolled construction of a gamma-lactone through bromolactonization, and an efficient catalytic Reformatsky-type reaction. Access to CJ-14,445, LL-Z1271gamma, oidiolactones A, B, C, and D, and nagilactone F was possible from a common intermediate. Structures and stereochemistry were determined by X-ray analysis.
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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 ╳
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