1 research outputs found
Efficient Semisynthesis of (β)-Pseudoirroratin A from (β)-Flexicaulin A and Assessment of Their Antitumor Activities
Accumulating evidence indicates that
natural <i>ent</i>-kaurane diterpenoids show great potential
for medical treatment of different pathological conditions including
cytotoxicity, antibacterial, and anti-inflammatory activity. Among
a variety of diterpenoids tested, (β)-pseudoirroratin A displayed
a promising antitumor property <i>in vitro</i> and <i>in vivo</i>. However, this diterpenoid could merely be isolated
in a limited amount from a rare source of <i>Isodon pseudoirrorata</i>. To overcome such scanty source, we developed a novel, facile, and
efficient semisynthetic strategy to prepare (β)-pseudoirroratin
A from natural (β)-flexicaulin A, which can be expediently
obtained from <i>I. flexicaulis</i> in a great quantity.
The three-dimensional structure and the absolute configuration of
our synthetic diterpenoid have been determined and confirmed with
the X-ray crystallographic analysis. More importantly, we demonstrated
for the first time that pseudoirroratin A exerted significant cytotoxicity
against human colorectal carcinoma cells via an induction of apoptosis,
as well as a remarkable suppression on tumor growth in a colon cancer
xenograft mouse model