A novel diterpenoid, gaditanone (2), which possesses an unprecedented 5/6/4/6-fused gaditanane tetracyclic ring skeleton, and a new jatrophane (1) were isolated from the aerial parts of Euphorbia gaditana. The chemical structures and absolute configurations were determined by extensive spectroscopic NMR studies and ECD data analysis. A proposed biosynthetic pathway is presented for compound 2.
A small library of
phorbol 12,13-diesters bearing low lipophilicity
ester chains was prepared as potential neurogenic agents in the adult
brain. They were also used in a targeted UHPLC–HRMS screening
of the latex of Euphorbia resinifera. Two new 12-deoxy-16-hydroxyphorbol 13,16-diesters were isolated,
and their structures were deduced using two-dimensional NMR spectroscopy
and NOE experiments. The ability of natural and synthetic compounds
to stimulate transforming growth factor alpha (TFGα) release,
to increase neural progenitor cell proliferation, and to stimulate
neurogenesis was evaluated. All compounds that facilitated TGFα
release promoted neural progenitor cell proliferation. The presence
of two acyloxy moieties on the tigliane skeleton led to higher levels
of activity, which decreased when a free hydroxyl group was at C-12.
Remarkably, the compound bearing isobutyryloxy groups was the most
potent on the TGFα assay and at inducing neural progenitor cell
proliferation in vitro, also leading to enhanced
neurogenesis in vivo when administered intranasally
to mice.
Two new macrocyclic diterpenes, 2-epi-latazienone (4) and 15-acetoxy-7-nicotinoyloxy-3,8-di-(2-methylpropanoyloxy)-4H,9H,11H-lathyra-5E,12E-dien-14-one (5), and three known lathyrane-type diterpenes (1-3) were isolated from Euphorbia laurifolia latex. Their structures were determined on the basis of a detailed analysis of their 1D and 2D NMR spectroscopic and mass spectral data.
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