|Hosokawa, Masashi - HOKKAIDO UNIV, JPN|
Submitted to: Proceedings of the US Japan Joint Panel on Toxic Microorgnisms
Publication Type: Proceedings
Publication Acceptance Date: November 9, 2003
Publication Date: November 15, 2003
Citation: Hou, C.T., Hosokawa, M. 2003. New value-added products from PUFAs. Proceedings of the US Japan Joint Panel on Toxic Microorgnisms. 32nd UJNR Food and Agriculture Panel Meeting, November 9-15, 2003, Tsukuba, Japan. p. 247-256. Interpretive Summary: Hydroxy fatty acids are used for synthesis of specialty chemicals, special military nylon, plastisizers, coatings and physiologically active agents. Recently, we found that Clavibacter strain ALA2 (a bacteria) converted 20-carbon and 22-carbon essential fatty acids into new hydroxy and epoxy fatty acids. Both fatty acids have their first double bond located at the third carbon (omega-3) position. Strain ALA2 also converted two other essential fatty acids having their first double bond at the sixth carbon (omega-6) position into products different in structures to those obtained from omega-3 fatty acids. New products synthesized from these fatty acids include five-member ring and six-member ring cyclic fatty acids. Thus, the structures of bioconversion products were different between omega-3 and omega-6 unsaturated fatty acids. Furanyl fatty acids (five-member ring) are known anticancer drugs. The new products have great potential to be used as bioactive agents and raw materials for synthesis of specialty chemicals. Application of these products either for bioactive agents or raw material for synthesis of specialty chemicals will benefit U.S. farmers.
Technical Abstract: Clavibacter sp. ALA2 converted linoleic acid to unique cyclic fatty acids such as diepoxy bicyclic fatty acids (DEOAs) and tetrahydrofuranyl fatty acids (THFAs) as well as trihydroxy fatty acids (THOAs). Last year, we reported that strain ALA2 also converted other polyunsaturated fatty acids (PUFAs) such as alpha-linolenic acid (18:3, n-3) to novel THFAs, 13,16- dihydroxy-12,15-epoxy-9(Z)-octadecenoic acid and 7,13,16-trihydroxy-12,15-epoxy-9(Z)-octadecenoic acid. Now, we found other n-3 and n-6 PUFAs were also converted by strain ALA2 into novel products. Eicosapentaenoic acid (20:5, n-3) and docosahexaenoic acid (22:6, n-3) were converted to 15,18- dihydroxy-14,17-epoxy-icosatrienoic acid and 17,20-dihydroxy-16,19-epoxy-4(Z), 7(Z),10(Z),13(Z)-docosatetraenoic acid, respectively. In contrast, gama-linolenic acid (18:3, n-6) was converted to DEOA, THFA and THOA similar to linoleic acid reported previously. Therefore, strain ALA2 biotransformed n-3 and n-6 PUFAs into different cyclic fatty acids with hydroxyl groups. It places hydroxy group and cyclic structure at the same position from omega-terminal despite the number of carbon chain and double bond of PUFAs.