Multiple Monohydroxylation Products from rac-Camphor by Marine Fungus <i>Botryosphaeria</i> sp. Isolated from Marine Alga <i>Bostrychia radicans</i>

Jesus, Hugo C. R. de; Jeller, Alex H.; Debonsi, Hosana M.; Alves, Péricles B.; Porto, André L. M.

doi:10.21577/0103-5053.20160262

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Short Report • J. Braz. Chem. Soc. 28 (03) • Mar 2017 • https://doi.org/10.21577/0103-5053.20160262 copy

Multiple Monohydroxylation Products from rac-Camphor by Marine Fungus Botryosphaeria sp. Isolated from Marine Alga Bostrychia radicans

Authorship SCIMAGO INSTITUTIONS RANKINGS

This manuscript describes the biooxidation of rac-camphor using whole cells of marine-derived fungus Botryosphaeria sp. CBMAI 1197. The main biotransformation products of this monoterpene were achieved via a hydroxylation reaction and occurred with 5 days of rac-camphor incubation. Products were identified by means of gas chromatography mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) data. The major hydroxylated products were 6-endo-hydroxycamphor, 6-exo-hydroxycamphor, 5-exo-hydroxycamphor, 5-endo-hydroxycamphor, 3-exo-hydroxycamphor and 8-hydroxycamphor. The 6-exo-hydroxycamphor was obtained through a retro-aldol reaction when 6-endo-hydroxycamphor was maintained in presence of CDCl₃; this isomerization was confirmed by ¹H NMR and GC-MS data.

Keywords:
terpene; hydroxylation; biocatalysis; marine endophytic fungi

	Experimental data for 6-endo-hydroxycamphor (3)	Literature data for 6-endo- hydroxy- camphor (3)⁹
Position	δ_H (J in Hz)^a a 1H NMR data (200 MHz, CDCl3); / ppm	δ_H (J in Hz)^b b 1H NMR data (400 MHz, CDCl3). / ppm
3-endo	1.99 (d, 18.0)	1.98 (d, 18.5)
3-exo	2.35-2.48 (m)	2.43 (ddd, 18.5, 5.0, 3.0)
4	2.15 (t, 4.0)	2.14 (dd, 5.0, 4.5)
5-endo	1.34 (dd, 14.0, 2.0)	1.33 (dd, 13.5, 2.5)
5-exo	2.50-2.61 (m)	2.54 (dddd, 13.5, 10.0, 4.5, 3)
6-exo	4.18 (dd, 8.0, 2.0)	4.16 (dd, 10, 2.5)
8 and 10	0.98 (s, 6H)	0.96 (s, 6H)
9	0.83 (s, 3H)	0.82 (s, 3H)

	Experimental data for 5-exo-hydroxy- camphor (5)	Literature data for 5-exo- hydroxy- camphor (5)⁹
Position	δ_H (J in Hz)^a a 1H NMR data (200 MHz, CDCl3); / ppm	δ_H (J in Hz)^b b 1H NMR data (400 MHz, CDCl3). / ppm
3-endo	1.70 (d, 18.0)	1.70 (d, 18.5)
3-exo	2.34 (d, 18.0, 6.0)	2.33 (dd, 18.5, 5.0)
4	2.16 (d, 6.0)	2.16 (dd, 5.0, 1.0)
5-endo	4.02 (dd, 6.0, 4.0)	4.02 (dd, 7.5, 3.5)
6-endo	1.85 (m)	1.85 (dd, 14.0, 7.5)
6-exo	1.81 (m)	1.79 (ddd, 14.0, 3.5, 1.0)
8	0.85 (s, 3H)	0.85 (s, 6H)
9	1.25 (s, 3H)	1,25 (s, 3H)
10	0.93 (s, 3H)	0.93 (s, 3H)

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