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2.2 First Generation SHIP1 Agonist Pelorol and Analogues
The discovery of the SHIP enzyme by Dr. Gerald Krystal, 50 led to a collaboration in
which the Andersen natural product library of extracts was screened by Dr. Alice Mui in an
effort to discover small molecule activators of SHIP1. A methanol extract of the sponge
Dactylospongia elegans collected in Papua New Guinea exhibited promising activity in the
screening assay. Bioassay-guided fractionation of the extract led to the identification of the
meroterpenoid pelorol (2.1) as a selective SHIP1 activator (Figure 2.2). 51
Figure 2.2 The first selective SHIP1 activator marine natural product pelorol (2.1).
While biological evaluation of pelorol (2.1) was underway in the Mui and Andersen
labs, pelorol (2.1) was isolated by the Konig 52 and Schmitz 53 groups from the sponges
Dactylospongia elegans, and Petrosaspongia metachromia collected at the Great Barrier
Reef and Yap in the Federated States of Micronesia, respectively. In order to fully explore
the potential biological impact of this drug lead, the total synthesis of pelorol (2.1) was
completed by Lu Yang in the Andersen group, 51 along with a preliminary SAR study which
generated a small number of analogues.
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