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J Biol Chem, Vol. 273, Issue 5, 2669-2675, January 30, 1998
From the Medical Research Council Laboratory of Molecular Biology,
Hills Road, Cambridge, CB2 2QH, United Kingdom
Differentiation-inducing factor (DIF)-1 is a
chlorinated alkyl phenone released by developing
Dictyostelium amoebae, which induces them to differentiate
into stalk cells. A biosynthetic pathway for DIF-1 is proposed from
labeling, inhibitor, and enzymological experiments. Cells incorporate
36Cl
into DIF-1 during development, showing
that the chlorine atoms originate from chloride ions; peak
incorporation is at the first finger stage. DIF-1 synthesis can be
blocked by cerulenin, a polyketide synthase inhibitor, suggesting that
it is made from a polyketide. This is most likely the C12
polyketide (2,4,6-trihydroxyphenyl)-1-hexan-1-one (THPH). Feeding
experiments confirm that living cells can convert THPH to DIF-1.
Conversion requires both chlorination and methylation of THPH, and
enzymatic activities able to do this exist in cell lysates. The
chlorinating activity, assayed using 36Cl, is
stimulated by H2O2 and requires both soluble
and particulate components. It is specific for THPH and does not use
this compound after O-methylation. The
methyltransferase is soluble, uses
S-adenosyl-L-methionine as a co-substrate, has
a Km for dichloro-THPH of about 1.1 µM, and strongly prefers this substrate to close
analogues. Both chlorinating and methyltransferase activities
increase in development in parallel with DIF-1 production, and both are
greatly reduced in a mutant strain that makes little DIF-1. It is
proposed that DIF-1 is made by the initial assembly of a
C12 polyketide skeleton, which is then chlorinated and
methylated.
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