The withanolides comprise a class o

The withanolides comprise a class of naturally occurring C28-
steroidal lactones structurally based on the ergostane skeleton.
These compounds are generally polyoxygenated, and this profusion
of oxygen functions has led to several natural modifications
of the carbocyclic skeleton, as well as of the side-chain, resulting
in compounds with complex structural features. Their chemistry
and occurrence has been the subject of several reviews (Ray and
Gupta, 1994; Veleiro et al., 2005; Chen et al., 2011; Misico et al.,
2011). Withanolides are present almost exclusively in the
Solanaceae subfamily Solanoideae. Some clades of the subfam.
Solanoideae also contain withanolides with exclusive interesting
structural arrangements which can be considered at different
hierarchical levels as chemotaxonomic markers (Misico et al., 2011).
Deprea Raf. is a small neotropical genus from South America
comprising ten species (Cueva and Treviño, 2012; Barboza et al.,
2013). In Deprea only two species have been investigated, Deprea
orinocensis and Deprea subtriflora. A family of withajardins
(withajardins A–E) has been isolated from D. orinocensis (Luis
et al., 1994; Echeverri et al., 1995) and many of these compounds
exhibited leishmanicidal activity (Cardona et al., 2006). This
nucleus, characterized by the presence of a bicyclic side-chain
involving C-21 and C-25 has been only described in Deprea and
Tubocapsicum genera (Hsieh et al., 2007; Kiyota et al., 2008).
Regarding D. subtriflora [currently, Larnax subtriflora, (Hunziker,
2001)], a biology-guided study led to isolation of a family of highly
oxygenated C27 18-norwithanolides named subtrifloralactones
(subtrifloralactones A–L). Some of these subtrifloralactones
showed potential cancer chemopreventive activity (Su et al.,
2003a,b).
Based on morphological data, Hunziker (2001) placed the genus
in the tribe Solaneae subtribe Witheringiinae Reveal, while Sawyer
(2005), based on a morphological phylogenetic analysis, considered
Deprea to be a member of the tribe Physalideae Miers (Barboza
et al., 2013). Recently, Särkinen et al. (2013), from molecular phylogenetic
evidence, included Deprea in the tribe Physalideae, although
the genus was not assigned to any subtribe. As part of an ongoing
program here aimed at determining the content of withanolides
contributing to the taxonomic position of Deprea, report in herein
is the isolation of a set of both new and known withanolides from
Deprea bitteriana (Werderm.) N.W. Sawyer & Benítez, Deprea
cuyacensis (N.W. Sawyer & S. Leiva) S. Leiva & Lezama, and Deprea zamorae Barboza & S. Leiva