New observations on the secondary chemistry of world Ephedra (Ephedraceae). Caveney S, Charlet DA, Freitag H, Maier-Stolte M,
Starratt AN.
For several millennia, stem extracts of Ephedra
(Ephedraceae, Gnetales)
have been used as folk medicines in both the
Old and New World. Some species were used
in treatments of questionable efficacy
for venereal disease in North America during
the last century. Many Eurasian species produce
phenylethylamine alkaloids, mostly ephedrine
and pseudoephedrine, that interact with
adrenergic receptors in the mammalian sympathetic
nervous system.
Asian Ephedra have been used recently
in the clandestine manufacture of a street drug,
methamphetamine.
Although ephedrine alkaloids
are not detectable in New World species of Ephedra, together with Asian species they contain
other nitrogen-containing
secondary metabolites with known
neuropharmacological activity. Many mesic and particularly xeric species
worldwide accumulate substantial amounts of
quinoline-2-carboxylic acids, or kynurenates,
in their aerial parts.
Many species of Ephedra accumulate
cyclopropyl amino acid analogues of glutamate and proline in their stems and roots, and particularly
in the seed endosperm.
Mesic species synthesize substantial amounts of
three
L-2-(carboxycyclopropyl)glycine stereomersrarely seen in nature.
A cyclopropyl analogue of proline with known antimicrobial activity,
cis-3,4-methanoproline, is found in large amounts in the stems and seeds of many Ephedra species.
The ability to synthesize cyclopropyl amino acids
may be an ancestral feature in the taxon.
The natural function in the taxon of these three groups
of secondary compounds remains to be established.
PMID: 11454619 [PubMed - as supplied by publisher]
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The chemistry intelligentsia are hereby called upon to identify
protocols applicable to the identified alkaloids above,
employable by your basic corner lab-tyro,
in the conversion of the materials into something that will,
you know,
like:
get you high, man.
