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. 2012 Oct 22;3:298. doi: 10.3389/fimmu.2012.00298

Figure 3.

Figure 3

Biosynthetic schemes of SPM. (A) In humans, AA can be converted into 15S-H(p)-ETE through 15-LO and into 15R-H(p)-ETE by aspirin (ASA)-acetylated COX-2. Both intermediates can be further metabolized through 5-LO and enzymatic hydrolysis yielding LXA4 or 15-epi-LXA4. (B) E-series resolvins are biosynthesized via conversion of EPA by ASA-acetylated COX-2. Products of these reactions, 18S-H(p)-EPE and 18R-H(p)-EPE, are rapidly taken up by 5-LO and converted to 18S-RvE1 and RvE1. (C) The DHA metabolome includes several SPM biosynthesized via 15/5-LO and ASA-acetylated COX-2. Each SPM is biosynthesized via distinct biochemical routes involving stereocontrolled oxygenation, epoxide formation, and enzymatic hydrolysis. The main structures of key SPM and their biosynthetic routes (with precursors and main enzymes involved) are depicted (see text and Serhan and Petasis, 2011 for further details). The complete stereochemistry of each of these SPM is established, total organic synthesis achieved, and bioactions confirmed.