Ephedra species

D. J. McConnell. 1998. Ephedra species in vitro culture, micropropagation, and the production ephedrine and other alkaloids. In Bajaj, Y. P. S. (ed.). Biotechnology in Agriculture and Forestry 41. Medicinal and Aromatic Plants X. Springer-Verlag. New York. p. 154-193. 

The thought that transmethylation of noradrenaline may be an initial step in its deactivation in the body makes one wonder whether further transmethylation of adrenaline is also not a common biological process. As a result of studies of the various alkaloids of plants of the Ephedra species, it was noted that not only Z-ephedrine and its stereoisomer d-pseudoephedrine are present but also that -norephedrine, d-norpseudoephedrine, l-methylephedrine, and d-methylpseudoephedrine (8) are present. The quaternary tri-methylammonium compounds corresponding to these were not reported but very... 

Ephedra, Ma huang Ephedra species Diet aid stimulant bronchodilator Central nervous system toxicity, cardiac toxicity Avoid in patients at risk for stroke, myocardial infarction, uncontrolled blood pressure, seizures, general anxiety disorder... 

The oriental crude drug Ma Huang or Mao, prepared from certain species of the genus Ephedra, contains ephedrine, pseudoephedrine, and homologous compounds (2). Although alkaloids of the ephedrine type occur in several Ephedra species, only a few other plant sources are known (Table IV and V). 

The six optically active alkaloids ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, and the N-methylated N-methylephedrine and N-methylpseudoephedrine are described in detail in Reti s review (2). Two new alkaloids of related structure have since been identified in Ephedra species, namely, (9-benzoylpseudoephedrine (271) and the oxazolidine derivative ephe-droxane (272). The 4-quinolone derivative ephedralone, recently isolated from Ephedra alata (273), may be of similar biogenetic origin as the ephedrines. Ephedra species also contain macrocyclic alkaloids of more complex structure (275). The two major Ephedra alkaloids (—)-ephedrine and (+)-pseudoephedrine are diastereomers. (—)-Ephedrine has the erythro and (+)-pseudoephedrine has the threo configuration. 

The oriental crude drug Mao (Epedrae Herba) is contained in various oriental pharmaceutical preparations (255). Since the content of ephedrine alkaloids in this drug may vary with the Ephedra species used for its preparation and with, e.g., harvest conditions, it has been important to develop quantitative analytical methods in order to evaluate the quality. 

Ephedrine is a component of the traditional Chinese remedy Ma Huang, extracted from Ephedra species, it is also used in nasal sprays as a decongestant. Pseudoephedrine is the active component of the decongestant Sudafed (so should that be Pseudephed ). 

The isoquinoline alkaloids are the second largest group of alkaloids, numbering about 6000, and can be viewed as five subgroups—the simple tetrahydroisoquinolines, the benzylisoquinolines, the phenethylisoquinolines, the Amaryllidaceae alkaloids, and the monoterpene isoquinolines. In addition, there are a number of simple phenethylamine derivatives, including ephedrine (originally from Ephedra species, but now synthesized) and pseudoephedrine, used for asthma and nasal... 

Ephedra species vary widely in their ephedrine content. One of the most common Chinese cultivars, known as China 3, contains 1.39% ephedrine, 0.361% pseudoephedrine, and 0.069% methylephedrine (21). This mix is fairly typical for commercially grown ephedra plants. Noncommercial varieties of ephedra may contain no ephedrine at all (22), while others may contain more... 

Ephedrine and ist isomer pseudoephedrine are alkaloids in Ephedra species. Brochmann-Hans-sen and Baerheim Svendsen reported the first gas chromatographic separation of these two alkaloids in a study on the separation and identification of 11 sympathomimetic amines on a 1.15 % SE-30 packed column at 104°C. However, ephedrine and pseudoephedrine could not be separated as such, but were separated as their oxazolidine derivatives after treatment with acetone. A typical chromatogram is given in Tale 13.1. 

Yamasaki et al. applied gas chromatography to the separation and quantitative analysis of the alkaloids in some Ephedra species collected around the Himalayas. A satisfactory separation of the alkaloids and quantitative determination of L-ephedrine and D-pseudoephedrine was achieved using oxazolidine formation with acetone. ... 

Ephedrue herbu consists of the dried aerial parts of xerophytic Ephedra species belonging to the family Ephedraceae. The plant is a shrub, 0.5-1 m high with scale-like leaves that clasp the stem. 

Nowadays the Ephedra species are mainly used for extraction of the active ingredient, the alkaloid (-) ephedrine. Not only the classical Chinese species E. sinica Stapf. is used, but mainly the species E.pferardiana. Wall ex. Stapf and E. major Host. =E. nebrodensis Finco), which both grow in India and Pakistan, and E. distachya L., which grows in Southern France. 

Several amino alcohols have been isolated from Ephedra species ephedrine (3), norephedrine (1), pseudoephedrine (or t/ -ephedrine, 4), and norpseudoephedrine (2). The pseudocompounds are diastereomers of the corresponding alkaloids. 

Ephedrine C,oH,sNO 165.24 40/225 -6.3° (C2H5OH) Ephedra species, Aconitum napellus, Catha edulis, Taxus baccata, Sida cordifolia, Roemeria refracta 299-42-3... 

Other distinguishing features Has longer micropylar tubes than other Ephedra species cones with 2-3 seeds. 

Kim SY, Gao JJ, Kang HK (2000) Two flavonoids from the leaves of Moms alba induce differentiation of the human promyelocytic leukemia (HL-60) cell line. Biol Pharm BtrU 23(4) 451 55 Kim SR, Park MJ, Lee MK, Stmg SH, Park EJ, Kim J (2(X)2) Havonoids of Imda britannica protect cultured cortical cells from necrotic cell death induced by glutamate. Free Radic Biol Med 32(7) 596-604 Kim HK, Choi YH, Erkelens C, Lefeber AW, Verpoorte R (2005) Metabolic fingerprinting of Ephedra species using H-NMR spectroscopy and principal component analysis. Chem Pharm BtrU 53(1) 105-109... 

The crude drug Mao is prepared from the aboveground parts of Ephedra species (Ephedraceae). Mao is used for the manufacture of ephedrine hydrochloride, and is also used to prepare the Kampo medicine Sho-seiryu-to, etc. 

In Kampo medicine, gnarls and the subterranean part ( Mao-kon ) of Ephedra species are regarded as contradiaory to the action of Mao (the above-ground part). It is known that an extract of the subterranean part lowers blood pressure, whereas the extract of Mao raises blood pressure. Examination of the active constituents afforded ephedradines A—D [3]. Among these active constituents, the structure of ephedradine A was determined by X-ray crystallography of the brominated derivative [3]. Chemical structures of ephedradines B—D were determined by comparison of their spectroscopic data with those of ephedradine A [3,4]. 

Ephedrine, an alkaloid with an amphetamine-like structure, is currently used in pharmaceuticals, with potentials to affect nerves, muscle, blood pressure, and heart rate. In 2004, the US Food and Drug Administration (FDA) banned ephedrine alkaloids marketed for reasons other than asthma, colds, allergies, other disease, or traditional Asian use. Ephedrine and its derivatives (stereoisomers and diaste-reomers) are naturally found in varied proportions in different plant species such as Catha edulis [12], Roemeria refracta [48], Taxus baccata [20], Sida cordifolia [7], Pinellia ternata [24], Aconitum napellus [8], and Ephedra species [22, 29, 32, 37]. 

---