Pedrolane, a Polycyclic Diterpene Scaffold Containing a Bicyclo[2.2.1]heptane System, from Euphorbia pedroi

Abstract

Pedrolide (1), a diterpenoid with an unprecedented carbon skeleton, pedrolane, containing a bicycle[2.2.1]heptane system, is reported. This structural feature is hypothesized to involve an intramolecular cyclization, via Michael addition, and a ring contraction, via 1,2-alkyl shift or a Pinacol rearrangement of rings A and B, from a tigliane-type 5/7/6/3-tetracyclic ring precursor. The structure of 1 was established using spectroscopic techniques, single-crystal X-ray diffraction, and ab initio calculations. Pedrolide reversed multidrug resistance mediated by P-glycoprotein.

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“…The novel diterpenoid skeleton of pedrolide 11 , from Euphorbia pedroi , has been named pedrolane. 9 The structure of pedrolide 11 was confirmed by X-ray analysis. A biosynthetic route to pedrolide 11 from a tigliane precursor has been suggested.…”

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“…It might be biosynthesized from a tigliane diterpenoid employing an intramolecular Michael addition and 1,2- alkyl shift rearrangement as the key steps. 212 …”

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“…)hydrazineylidene]dregamine (12). Obtained from reaction of compound 2 (20 mg, 0.054 mmol, 1 equiv.)…”

“…Aiming at finding effective compounds for reversing MDR, our group has evaluated several plant-derived compounds with different scaffolds as effective ABC-transporter inhibitors, e.g., [12][13][14], with those containing nitrogen substituents receiving particular attention [13][14][15]. Owing to indole alkaloids privileged scaffold, coupled with high bioactivity, including their ability as anticancer agents [16], our ongoing research has been focused on the generation of small libraries of indole alkaloids, from the African medicinal plant Tabernaemontana elegans, through isolation and further derivatization, to establish structure-activity relationships, concerning their ability for reversing MDR [13][14][15]17].…”