Magellanine
Encyclopedia
-Magellanine is a member of the Lycopodium
Lycopodium
Lycopodium is a genus of clubmosses, also known as ground pines or creeping cedar, in the family Lycopodiaceae, a family of fern-allies...

alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

 class of natural products. It was isolated from the club moss Lycopodium magellanicum
Lycopodium magellanicum
Lycopodium magellanicum is a species of club moss that falls into the Lycopodium genus. A number of natural products have been isolated from this plant, including magellanine, magellaninone, panticuline, acetyldihydrolycopodine, acetylfawcettiine, clavolonine , deacetylfawcettiine, fawcettiine,...

in 1976. It has been synthesized five times, with the first synthesis
Chemical synthesis
In chemistry, chemical synthesis is purposeful execution of chemical reactions to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...

 having been completed by the Larry E. Overman
Larry E. Overman
Larry E. Overman is Distinguished Professor of Chemistry at the University of California, Irvine. He was born in Chicago in 1943. Overman obtained a B.A. degree from Earlham College in 1965. and he completed his Ph.D. in chemistry from the University of Wisconsin–Madison in 1969, under Howard...

 group at the University of California, Irvine
University of California, Irvine
The University of California, Irvine , founded in 1965, is one of the ten campuses of the University of California, located in Irvine, California, USA...

 in 1993. It has also been synthesized by the Leo Paquette
Leo Paquette
Leo Armand Paquette is an American organic chemist. He received his Ph.D. in 1959 from the Massachusetts Institute of Technology and has been a Professor of Chemistry at the Ohio State University since 1969. He is the author of over 1000 papers and has also edited works such as the Encyclopedia...

 group in 1993 at The Ohio State University, the Chun-Chen Liao group in 2002 at National Tsing Hua University
National Tsing Hua University
National Tsing Hua University is one of the most prestigious universities in Taiwan. The university has a strong reputation in the studies of science and engineering. Times Higher Education - World University Rankings is107in the world. Engineering and Science are the best in Taiwan...

, the Miyuki Ishikazi and Tamiko Takahashi groups in 2005 at the Josai International University
Josai International University
is a private university in Tōgane, Chiba, Japan, established in 1992.-External links:*...

 and Tokyo University of Science
Tokyo University of Science
Tokyo University of Science is a private university of science and technology in Japan...

, and the Chisato Mukai group in 2007 at the Kanazawa University
Kanazawa University
is a national university of Japan located in the city of Kanazawa, the capital of Ishikawa Prefecture.Kanazawa University is divided into two main campuses: Kakuma and Takaramachi. Student enrollment is about 11,000 including 350 international students....

. One partial synthesis was completed by the A. I. Meyers group in 1995 at Colorado State University
Colorado State University
Colorado State University is a public research university located in Fort Collins, Colorado. The university is the state's land grant university, and the flagship university of the Colorado State University System.The enrollment is approximately 29,932 students, including resident and...

.

Biosynthetically, it is thought to have been derived from lysine
Lysine
Lysine is an α-amino acid with the chemical formula HO2CCH4NH2. It is an essential amino acid, which means that the human body cannot synthesize it. Its codons are AAA and AAG....

. This was determined by conducting feeding studies of radiolabeled precursors.
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