PRODUCTION OF (E)-11-OH-9- AND (E )-9-OH-10-OCTADECENOIC ACIDS
597
by Bacillus Strain NRRL BD-447: Identification of 7-Hydroxy-
17-oxo-9-cis-octadecenoic Acid, J. Am. Oil Chem. Soc. 76:
1023–1026 (1999).
of edible waste oil. Compound 1 may result from direct al-
lylic oxidation of oleic acid at C-11, and in fact it was ob-
tained by Knothe et al. (19) by chemical oxidation of oleic
acid with SeO2/tert-butylhydroperoxide. Compound 2 is a
fungitoxic chemical isolated from the timothy plant Epichloe
typhina (20) and was identified in the products of the action
of Pseudomonas sp. 42A2 on oleic acid (11), and by Kim
et al. (15) in the products of the action of P. aeruginosa on
oleic acid. Compound 3, reported by Koshino et al. (20), may
well proceed from the oxidation of oleic acid at C-9 and mi-
gration of the double bond to C-11. Allylic hydroxylations
with concomitant migration of double bonds are known to
occur in the cytochrome P-450 oxidation of fatty acids (21).
10. Parra, J.L., J. Pastor, F. Comelles, A. Manresa, and M.P. Bosch,
Studies of Biosurfactant Obtained from Olive Oil, Tenside Surf.
Det. 27:302–306 (1990).
11. Guerrero, A., I. Casals, M. Busquets, Y. León, and A. Manresa,
Oxidation of Oleic Acid to (E)-10-Hydroperoxy-8-octadecenoic
Acid and (E)-10-Hydroxy-8-octadecenoic Acids by
Pseudomonas sp. 42A2, Biochim. Biophys. Acta 1347:75–81
(1997).
12. Bastida, J., C. de Andrés, J. Culleré, M. Busquets, and A. Man-
resa, Biotransformation of Oleic Acid into 10-Hydroxy-8E-oc-
tadecenoic Acid by Pseudomonas sp. 42A2, Biotechnol. Lett.
21:1031–1035 (1999).
13. Hou, C.T., M.O. Bagby, R.D. Plattner, and S. Koritala, A Novel
Compound, 7,10-Dihydroxy-8(E)-octadecenoic Acid from
Oleic Acid by Bioconversion, J. Am. Oil Chem. Soc. 68:99–101
(1991).
ACKNOWLEDGMENTS
We gratefully acknowledge CICYT (projects PPQ 2000-0105-P4-
03 and AGL 20000-1695-C02-01), EC (FAIR CT96-1302), and
Comissionat per a Universitats i Recerca (1997SGR 00021 and
1999SGR00024) for financial support.
14. Gardner, H.W., and C.T. Hou, All (S) Stereoconfiguration of
7,10-Dihydroxy-8-(E)-octadecenoic Acid from Bioconversion
of Oleic Acid by Pseudomonas aeruginosa, Ibid. 76:1151–1156
(1999).
15. Kim, H., H.W. Gardner, and C.T. Hou, 10(S)-Hydroxy-8(E)-
octadecenoic Acid, an Intermediate in the Conversion of Oleic
Acid to 7,10-Dihydroxy-8(E)-octadecenoic Acid, Ibid. 77:
95–99 (2000).
16. Moore, J.A., and D.E. Reed, Diazomethane, in Organic Synthe-
sis, edited by V. Baumgarten, John Wiley & Sons, New York,
Vol. V, 1973, pp. 351–355.
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[Received October 17, 2000; accepted February 27, 2001]
JAOCS, Vol. 78, no. 6 (2001)