Aspergillus cellulosae

Dihydronootkatone (17), which shows that citrus odor possesses antitermite activity, was also treated in A. niger to obtain 115-mono- (18) and lll -dihydroxylated products (19) (the ratio 115 and 11/ = 3 2). On the other hand, Aspergillus cellulosae reduced ketone group at C2 of 17 to give 2a- (20) (75.7%) and 2p-hydroxynootkatone (21) (0.7%) (Furusawa et al., 2003) (Figure 20.11). Tetrahydronootkatone (22) also shows antitermite and mosquito-repellant activity. It was incu-... 

FIGURE 20.11 Biotransformation of dihydronootkatone (17) hy Aspergillus niger and Aspergillus cellulosae. 

FIGURE 20.57 Biotransformation of (3-cyclocostunoiide (170) by Aspergillus cellulosae andBotryosphaeria dothidea. 

FIGURE 20.59 Biotransformation of y-cyclocostunolide (171) by Aspergillus niger, Aspergillus cellulosae, and Botryosphaeria dothidea. 

Hashimoto, T., Y. Noma, Y. Goto, M. Tanaka, S. Takaoka, andY. Asakawa, 2004. Biotransformation of (-)-maa-lioxide >y Aspergillus niger t A Aspergillus cellulosae. 62 655-666. 

The biotransformation of (+)-limonene (68) was carried out by using Aspergillus cellulosae M-77 (Noma et al., 1992b) (Figure 14.32). It is important to note that (+)-limonene (68a) was mainly... 

Besides the hydrolysis of menthyl esters, the biotransformation of menthol and its enantiomers has also been published (Shukla et al., 1987 Asakawa et al., 1991). The fungal biotransformation of (-)-(137b) and ( f)-menthols (137b ) by Aspergillus niger and Aspergillus cellulosae was described... 

FIGURE 14.180 Biotransformation of (-l-)-fenchol (11a) by Aspergillus niger TBUYN-2, Aspergillus cellulosae IFO 4040, and the larvae of common cutworm, Spodptera litura. (Modified from Miyazawa, M. and Y. Miyamoto, 2004. Tetrahadron, 60 3091-3096 Noma, Y. and Y. Asakawa, 2005a. Book of Abstracts of the 36th ISEO, p. 32.)... 

Noma, Y, S. Yamasaki, and Asakawa Y. 1992b. Biotransformation of limonene and related compounds by Aspergillus cellulosae. Phytochemistry, 31 2125-2121. 

The same substrate (169) was cultivated for 3 days by Aspergillus cellulosae to afford a sole metabolite, lip,13-dihydro-a-cyclocostunolide (177). Possible metabolic pathways of 169 by both microorganisms were shown in Figure 15.55. 

FIGURE 15.57 Biotransformation of P-cyclocostunolide (170) hy Aspergillus cellulosae tind Botryosphaeria dothidea. 

When parthenolide (240) was treated in Aspergillus cellulosae for 5 days, two new metabolites, lip,13-dihydro-(247, 43.5%) and lla,13-dihydroparthenolides (248, 1.6%) were obtained together with the same metabolites (241, 5.3%, 243, 11.2%, 245, 10.4%) as described above (Figure 15.72). Possible metabolic root of240 has been shown in Hgure 15.73 (Hashimoto et al., 2005). 

When compound (249) was treated with Aspergillus niger in the presence of 1-aminobenzotriaz-ole, 249 was completely converted into llp,13-dihydro derivative (250) for 3 days however, further biodegradation did not occur for 10 days (Hashimoto et al., 1999, 2001). The same substrate (249) was cultivated with Aspergillus cellulosae IFO to furnish 11,13-dihydro- (250) (82%) for only one day and then the product (250) slowly oxidized into ll,13-dihydro-8P-hydroxycostuslactone (256) (1.6%) from 8 days (Hashimoto et al., 1999, 2001) (Figure 15.78). 

Maalioxide (349), mp 65-66°, [a]n -34.4° obtained from the liverwort, Plagiochila sciophila was inoculated and cultivated rotatory (100 rpm) in Czapek-peptone medium (pH 7.0) at 30°C for 2 days. (-)-Maalioxide (349) (100 mg OO mL) was added to the medium and further cultivated for 2 days to afford three metabolites, ip-hydroxy-(350), ip,9P-dihydroxy- (351), and ip,12-dihydroxy-maalioxides (352), of which 351 was predominant (53.6%). When the same substrate was cultured with Aspergillus cellulosae in the same medium for 9 days, 7P-hydroxymaalioxide (353) was obtained as a sole product in 30% yield. The same substrate (349) was also incubated with the fungus Mucor plumbeus to obtain a new metabolite, 9P-hydroxymaalioxide (354), together with two known hydroxylated products (350,353) (Wang et al., 2006). 

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