(−)-Magellanine is a member of the ''

Lycopodium ''Lycopodium'' (from Ancient Greek ''lykos'', wolf and ''podion'', diminutive of ''pous'', foot) is a genus of clubmosses, also known as ground pines or creeping cedars, in the family Lycopodiaceae. Two very different circumscriptions of the gen ...

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

class of natural products. It was isolated from the club moss '' Lycopodium magellanicum'' in 1976. It has been synthesized five times, with the first

synthesis Synthesis or synthesize may refer to: Science Chemistry and biochemistry *Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors **Organic synthesis, the chemical synthesis of organi ...

having been completed by the

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 Unive ...

group at the

University of California, Irvine The University of California, Irvine (UCI or UC Irvine) is a Public university, public Land-grant university, land-grant research university in Irvine, California, United States. One of the ten campuses of the University of California system, U ...

in 1993. It has also been synthesized by the

Leo Paquette Leo Armand Paquette ( – January 21, 2019) was an American organic chemist. Biography Paquette was born on July 15, 1934, in Worcester, Massachusetts. He received a Bachelor of Science (B.S.) in 1956 from the College of the Holy Cross and a P ...

group in 1993 at

Ohio State University The Ohio State University (Ohio State or OSU) is a public university, public Land-grant university, land-grant research university in Columbus, Ohio, United States. A member of the University System of Ohio, it was founded in 1870. It is one ...

, the Chun-Chen Liao group in 2002 at

National Tsing Hua University National Tsing Hua University (NTHU) is a public research university in Hsinchu, Taiwan. It was first founded in Beijing. After the Chinese Civil War, president Mei Yiqi and other academics relocated with the retreating Nationalist government to ...

, the Miyuki Ishikazi and Tamiko Takahashi groups in 2005 at the

Josai International University , JIU, is a private university established in 1992, with two campuses, one in Tōgane, Chiba Prefecture, Japan, and one in Kioi-chō, Chiyoda-ku , known as Chiyoda City in English,Tokyo University of Science , formerly "Science University of Tokyo" or TUS, informally or simply is a private research university located in Shinjuku, Tokyo, Japan. History Tokyo University of Science was founded in 1881 as The Tokyo Academy of Physics by 21 graduate ...

, and the Chisato Mukai group in 2007 at the

Kanazawa University Kanazawa University (, abbreviated to ) is a Japanese Japanese national university, national university in the city of Kanazawa, Ishikawa, Kanazawa, the capital of Ishikawa Prefecture. The university was founded in 1949, although it can trace it ...

. One partial synthesis was completed by the A. I. Meyers group in 1995 at

Colorado State University Colorado State University (Colorado State or CSU) is a Public university, public Land-grant university, land-grant research university in Fort Collins, Colorado, United States. It is the flagship university of the Colorado State University Syst ...

. Biosynthetically, it is thought to have been derived from

lysine Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. Lysine contains an α-amino group (which is in the protonated form when the lysine is dissolved in water at physiological pH), an α-carboxylic acid group ( ...

. This was determined by conducting feeding studies of radiolabeled precursors.{{cite journal , year = 2004 , title = Biosynthesis of the ''Lycopodium'' Alkaloids , journal = Nat. Prod. Rep. , volume = 21 , pages = 752–772 , doi=10.1039/b409720n , last1 = Ma , first1 = Xiaoqiang , last2 = Gang , first2 = David R.

References

Alkaloids