Monordens

Characterisation of the antibiotic monordene (also referred to as radicicol) with the elemental composition Cig/Zz/OgCl isolated from Monosporium bonorden gave the macrolide structure 1. The relative configuration of the H atoms on the two conjugated double bonds (6,7-cis, %,9-trans-) could be deduced from the 60 MHz H NMR spectrum The relative configuration of the C atoms 2-5, which encompass the oxirane ring as a partial structure, has yet to be established. 

The reference compound methyloxirane gives the H NMR spectrum 11a shown with expanded multiplets. What information regarding its relative configuration can be deduced from the expanded H multiplets of monordene displayed in 11b ... 

Again following the principle that the same coupling constant holds for the coupling partner, the H shift values of the protons on the positions C-1 to C-9 of monordene can be assigned (A, Sh), as can the multiplicities and the coupling constants (B, Hz). 

Mirrington RN, Ritchie E, Shoppee GW, Sternhell S, Taylor WG, Some metabolites oiNectria radicicola Gerlach Nilsson (Syn. Cylindrocarpon radicicolaSffr.) the structure of radicicol (monorden), Aust J Chem 19 1265—1284, 1966. 

Aral M, Yamamoto K, Namatame I, Tomoda H, Omura S, New monordens produced by amidepsine-producing fungus Humicola sp. Y 0-23 A2, J Antibiotics... 

Initial attention in the development of Hsp90 inhibitors as anticancer agents was focused on two natural products, geldanamycin (compound 43, Fig. 8) and radicicol (also called monorden, compound 44, Fig. 8). These compounds bind into the ATP-binding cleft of the N-terminal domain of Hsp90 preventing the chaperone from cycling between its ADP and ATP-bound... 

Wicklow DT, Joshi BK, Gamble WR, Gloer JB, Dowd PF (1998) Antifungal Metabolites (Monorden, Monocillin IV, and Cerebrosides) from Humicola fuscoatra Traaen NRRL 22980, Mycoparasite of Aspergillus flavus Sclerotia. Appl Environ Microbiol 64 4482... 

Yamamoto K, Hatano H, Arai M, Shiomi K, Tomoda H, Omura S (2003) Structure Elucidation of New Monordens Produced by Humicola sp. FO-2942. J Antibiot 56 533... 

McCapra, F., Scott, A. L, Delmotte, P Delmotte-Plaquee, J., Bhacca, N. S. (1964). The constitution of monorden, an antibiotic with tranquihsing action. Tetrahedron Lett., 5, 869-875. 

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