Cephalosporium aphidicola

Hanson JR, PB Reese, JA Takahashi, MR Wilson (1994) Biotransformation of some stemodane diterpenoids by Cephalosporium aphidicola. Phytochem 36 1391-1393. 

Cephalosporium aphidicola Petdi., Eumyc./tool fw cancer study MI... 

Also the biotransformation of a-pinene derivatives and other pinane monoterpenoids by Cephalosporium aphidicola has been described [101]. The best conversion was the oxidation of verbenol to verbenone (yield 61%). 

More recently, the fungal transformation of (-)-menthol by Cephalosporium aphidicola was reported [111]. Incubation of (-)-menthol with this fungus for 12 days yielded four new metabolites, 10-acetoxymenthol, 4a-hydroxymenthol, 3a-hydroxymenthol, and 10-hydroxymenthol and two known compounds identified as 7-hydroxymenthol and 9-hydroxymenthol. 

Very recently, the chemoenzymatic preparation of nootkatone from valencene was described [150]. Nootkatone was prepared from valencene by copper(I) iodide catalysed oxidation with tert-butyl hydroperoxide and hydroxylated at C-9 by Mucor plumbeus and Cephalosporium aphidicola. 

Aphidicolin is a diterpenoid metabolite of Cephalosporium aphidicola and Phoma betae. The strueture of aphidieolin (5.126) was established in 1972 through a eombination of ehemieal, spectroseopie and X-ray crystallographic studies. Unlike the ent-kaurene and gibberellin metabolites of G. fujikuroi, aphidicolin possesses an absolute stereochemistry that is steroid-like . It has attracted considerable interest as a specific inhibitor of DNA polymerase a and as a potential anti-viral and anti-tumour agent. 

Cephalosporolides A-G (e.g. 22) are a group of 10-membered macrolides isolated from Cephalosporium aphidicola (Ackland et al., 1985 Farooq et al., 1995) (Fig. 3). From the same fungus, a dimer with a thioether linkage,... 

Ackland MJ, Hanson JR, Hitchcock PB. The structure of thiobiscephalospororide A, a dimeric pentaketide macrolide from Cephalosporium aphidicola. J Chem Soc Perkin Trans 1 2755-2757, 1984. 

Farooq A, Gordon J, Hanson JR, Takahashi JA. Two Ci0 lactones from Cephalosporium aphidicola. Phytochemistry 38 557-558, 1995. 

Generally, terpenoids have been believed to be biosynthesized via acetate-mevalonate pathway. Aphidicolin, a tetracyclic diterpenoid isolated from moulds, Cephalosporium aphidicola [47] and Nigrospora sphaerica [48], was also proved to be biosynthesized from mevanonic acid [49]. In this pathway, isopentenyl pyrophosphate (IPP), geranylgeranyl diphosphate (GGPP), labdane-type and pimarane-type diterpenoids were proposed to be intermediate precursors of aphidicolin [50]. 

JtWimeth y f- 8, f /a metham> i taH cyclohepta[a naphthti-teM<9-dimcthanoU I Cl 69653 NSC-234714, CMHMC4 mol wt 338,49. C 70.97%, H 10.12%, O L8,9l%. Novel tetracyclic diterpene antibiotic with antiviral and antimitotic properties, isolated from Cephalosporium aphidicola Fetch, It is a specific inhibitor of DNA < -polymerase. Description and K-ray crystallographic dele ruin of structure K. M. 

Aphidicolin (89) is a diterpenoid tetraol produced by the mold Cephalosporium aphidicola. In 1972, Hesp and co-workers reported its isolation and structure [50]. Aphidicolin (89) displays marked activity against Herpes simplex type I virus in cultures of human embryonic cells, as well as antifeedant properties. Furthermore, aphidicolin (89) exhibits antitumor activity in the C6 mouse colon and B16 mouse melanosarcoma screens and has been shown to inhibit the growth of leukemic T- and B-lymphocytes [51]. Such results have stimulated interest in clinical investigations of the effectiveness of 89 against human tumors. 

C20H34O4, Mr 338.49, mp. 227-233°C, [a]p -h12 (CH3OH) diterpenoid with antibiotic and antiviral activity from Cephalosporium aphidicola and other... 

FIGURE 19.63 Biotransformation of ( ) menthoi (137b) by Cephalosporium aphidicola. (Modi ed from Atta-ur-Rahman, M. et al., J. Nat. Prod., 61, 1340, 1998.)... 

FIGURE 20.27 Biotransformation of 10-epi-glubulol (70) and ledol (75) by Cephalosporium aphidicola, Aspergillus niger, and Glomerella cingulata. 

Ambrox (391) and sclareolide (402) were incubated with the fungus Cephalosporium aphidicola for 10 days in shake culture to give 3[3-hydroxy- (396), 3p,6P-dihydroxy- (401g), 3P,12-dihydroxy- (401h),... 

Cephalosporium aphidicola bioconverted cedrol (414) into 417 (Hanson and Nasir, 1993). On the other hand, Corynesphora cassiicola produced 419 in addition to 417 (Abraham et al., 1987). It is noteworthy that Botrytis cinerea that damages many flowers, fruits and vegetables biotransformed cedrol into different metabolites (420-422) from those mentioned above (Aleu et al., 1999). 

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