Cheimonophyllon A
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| Category | Antibiotics |
| Catalog number | BBF-00530 |
| CAS | |
| Molecular Weight | 266.33 |
| Molecular Formula | C15H22O4 |
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Description
It is produced by the strain of Cheimonophyllum candidissiumun sing. It has nematode killing, cytotoxicity (L1210, HL60, BHK21) and weak antifungal bacterial activity.
Specification
| IUPAC Name | 2-[(1S,2S,5R,6S)-5-hydroxy-5-methyl-7-oxabicyclo[4.1.0]heptan-2-yl]-6-methylhept-1-ene-3,4-dione |
| Canonical SMILES | CC(C)CC(=O)C(=O)C(=C)C1CCC(C2C1O2)(C)O |
| InChI | InChI=1S/C15H22O4/c1-8(2)7-11(16)12(17)9(3)10-5-6-15(4,18)14-13(10)19-14/h8,10,13-14,18H,3,5-7H2,1-2,4H3/t10-,13-,14-,15+/m0/s1 |
| InChI Key | HFEZPWJQBSYZET-FBUXBERBSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
Reference Reading
1. Asymmetric total syntheses of (+)-cheimonophyllon e and (+)-cheimonophyllal
Ken-Ichi Takao, Tomohiro Tsujita, Manabu Hara, Kin-Ichi Tadano J Org Chem. 2002 Sep 20;67(19):6690-8. doi: 10.1021/jo0203140.
The highly enantiocontrolled total syntheses of natural (+)-cheimonophyllon E (5) and (+)-cheimonophyllal (6), biologically intriguing oxygenated bisabolane-type sesquiterpenoids, have been completed. The present synthetic strategy featured the use of an asymmetric aldol-type reaction for preparing in the first synthetic step an optically active 6-C-substituted 3-methyl-2-cyclohexenone derivative. Thus, a Mukaiyama aldol reaction of 1-methyl-3-silyloxy-1,3-cyclohexadiene 31 with alpha,beta-unsaturated aldehyde 11 in the presence of a chiral (acyloxy)borane (CAB)-type Yamamoto catalyst 33 proceeded with high levels of both diastereo- and enantioselectivities. The predominant aldol adduct, syn-9, was transformed into gamma,delta-epoxy allylic alcohol 8 by a nine-step sequence, including the substrate-controlled 1,2-reduction of enone, syn-12, also the epoxidation of allylic alcohol 15. Epoxy-alcohol 8 underwent 5-exo-cyclization in a high regioselective manner under acidic conditions to produce a bicyclic key intermediate (+)-7, which was eventually efficiently converted to (+)-cheimonophyllon E (5) or (+)-cheimonophyllal (6).
2. New nematicidal and antimicrobial compounds from the basidiomycete Cheimonophyllum candidissimum (Berk & Curt.) sing. I. Producing organism, fermentation, isolation, and biological activities
M Stadler, H Anke J Antibiot (Tokyo). 1994 Nov;47(11):1284-9. doi: 10.7164/antibiotics.47.1284.
Six new bisabolane type sesquiterpenoids, cheimonophyllons A (1), B (2), C (3), D (4), E (5), and cheimonophyllal (6) were isolated from the culture fluid of the basidiomycete, Cheimonophyllum candidissimum. The compounds exhibited nematicidal, weak antifungal and antibacterial as well as cytotoxic activities. The main product, cheimonophyllon A (1) (C15H22O4), was also active in the Ames mutagenicity test.
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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 ╳
