Page 63 - Read Online

Siddiqui et al. Chem Synth 2023;3:25 https://dx.doi.org/10.20517/cs.2023.02 Page 9 of 50

Figure 11. Microbial transformation of (-)-caryophyllene oxide (49) with Cephalosporium aphidicola, and Macrophomina phaseolina.

Figure 12. Microbial transformation of (-)-caryophyllene oxide (49) with Rhizopus stolonifer,Aspergillus niger, Gibberella fujikuroi, and
Fusarium lini.

Derivatives 52 (IC = 44.0 ± 0.2 μM), 53 (IC = 455.8 ± 0.1 μM), 54 (IC = 189.5 ± 0.2 μM), 55 (IC = 10.9 ±
50
50
50
50
0.2 μM), 56 (IC = 458.7 ± 0.5 μM), 57 (IC = 23.6 ± 0.1 μM), 58 (IC = 43.6 ± 0.3 μM), and 59 (IC = 154.6 ±
50
50
50
50
0.3 μM) showed a moderate to significant inhibitory potential against butyrylcholinesterase, as compared to
the substrate 49 (IC = 208.4 ± 0.8 μM).
50
Biotransformation of (+)-cycloisolongifol-5β-ol (60)
Cunninghamella elegans-mediated transformation of a cyclic sesquiterpene (+)-cycloisolongifol-5β-ol ((60)
afforded three new metabolites, cycloisolongifol-3β,5β-diol (61) (3.7%), cycloisolongifol-5β-ol-11-one (62)
(4%), and cycloisolongifol-3β, 5β, 11α-triol (63) (3%) [Figure 13].
[32]
Biotransformation of (-)-ambrox (64)
Fungal transformation of another perfumery sesquiterpene, (-)-ambrox (64) with Fusarium lini yielded four
compounds, ambrox-1α-ol (65) (2.7%), ambrox-1α,11α-diol (66) (1.3%), ambrox-1α,6α-diol (67) (3.2%), and
ambrox-1α,6α,11α-triol (68) (4.6%) [Figure 14]. Similarly, four more derivatives, ambrox-3-one (69) (1.3%),
ambrox-3β-ol (70) (1%), ambrox-3β,6β-diol (71) (1.9%), and tetranorlabdane-3, 8, 12-triol (72) (4.7%) of
substrate 64 were also synthesized through its biotransformation with Rhizopus stolonifer [Figure 15].
[33]