Phorboid 20-homovanillates modified on ring C to mimic the constitution and conformation of the ultrapotent vanilloid resiniferatoxin (RTX) and on the AB ring system to suppress the tumour-promoting potential of the terpenoid core were prepared. Several unexpected reactions were discovered,
The cover picture shows Euphorbia resinifera Berg and its constituent resiniferatoxin (RTX), a phorboid that acts as an ultrapotent biological analogue of capsaicin, the hot principle of chili pepper and the archetypal vanilloid. Ever since its isolation, interest within the organic community for phorbol has been high on account of its challenging structure, puzzling reactivity, and remarkable bioactivity. Diacyl derivatives of phorbol can act as ultrapotent analogues of the endolipid sn-1,2-diacylglycerol (DAG) and show powerful tumour-promoting properties. The more recent discovery that certain non-tumour-promoting phorbol derivatives and phorbol-related compounds can activate vanilloid receptors of the TRPV1 and TRPV4 type has made phorbol very interesting also for neurosciences.
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