Two new tuberostemonine alkaloids, tuberostemonine L (3) and tuberostemonine M (4) and a new stemofoline alkaloid, (3′S)-hydroxystemofoline (5), along with two known alkaloids, (2′S)-hydroxystemofoline (1) and neotuberostemonine (2) have been isolated from a root extract of an unidentified Stemona species (Stemona sp.). The structure and relative configuration of these new alkaloids has been determined by spectral data interpretation, while the 3′S configuration of 5 was determined from NMR analysis of its (R)- and (S)-Mosher esters.
PilliRA, RossoGB, de OliveiraMCF. (2005) The Stemona Alkaloids. In The Alkaloids, CordellGA (Ed.) Elsevier, Amsterdam, Vol 62, Chapter 2, pp 77–173.
2.
For recent papers on Stemona alkaloids not cited in reference [1] see: (a) SchinnerlJ, KalteneggerE, PacherT, VajrodayaS, HoferO, GregerH. (2005) New Pyrrolo[1,2-a]azepine Type Alkaloids from Stemona and Stichoneuron (Stemonaceae). Monatshefte fuer Chemie, 136, 1671–1680;
3.
MungkornasawakulP, MatthewsH, UngAT, PyneSG, JatisatienrA, LieW, SkeltonBW, WhiteAH. (2005) Confirmation of the structure of oxystemokerrin by single crystal X-ray structural analysis and a proposed biosynthesis. ACGC Chemical Research Communications, 19, 30–33;
4.
SastrarujiT, JatisatienrA, PyneSG, UngAT, LieW, WilliamsMC. (2005) Phytochemical Studies on Stemona Plants: Isolation of Stemofoline Alkaloids. Journal of Natural Products, 68, 1763–1767;
5.
GregerH. (2006) Structural relationships, distribution and biological activities of Stemona alkaloids. Planta Medica, 72, 99–113;
6.
JiangR-W, HonP-M, ZhouY, ChanY-M, XuY-T, XuH-X, GregerH, ShawP-C, ButPP-H. (2006) Alkaloids and Chemical Diversity of Stemona tuberose, Journal of Natural Products, 69, 749–754;
7.
JiangR-W, HonP-M, XuY-T, ChanY-M, XuH-X, ShawP-C, ButPP-H. (2006) Isolation and chemotaxonomic significance of tuberostemospironine-type alkaloids from Stemona tuberosa. Phytochemistry, 67, 52–57.
8.
MungkornasawakulP, PyneSG, JatisatienrA, SupyenD, LieW, UngAT, SkeltonBW, WhiteAH. (2003) Stemocurtisine, the first pyrido[1,2-a]azapine Stemona alkaloid. Journal of Natural Products, 66, 980–982.
9.
KalteneggerE, BremB, MereiterK, KalchhauserH, KahligH, HoferO, VajrodayaS, GregerH. (2003) Insecticidal pyrido [1,2-a]azepine alkaloids and related derivatives from Stemona species. Phytochemistry, 63, 803–816.
10.
MungkornasawakulP, PyneSG, JatisatienrA, SupyenD, JatisatienrC, LieW, UngAT, SkeltonBW, WhiteAH. (2004) Phytochemical and larvicidal studies on Stemona curtisii: structure of a new pyrido[1,2-a]azepine Stemona alkaloid. Journal of Natural Products, 67, 675–677.
11.
BremB, SegerC, PacherT, HoferO, VajrodayaS, GregerH. (2002) Feeding deterrence and contact toxicity of Stemona alkaloids - a source of potent natural insecticides. Journal of Agricultural and Food Chemistry, 50, 6383–6388.
12.
JiwajindaS, HiraiN, WatanabeK, SantisopasriV, ChuengsamarnyartN, KoshimizuK, OhigashiH. (2001) Occurrence of the insecticidal 16,17-didehydro-16(E)-stemofoline in Stemona collinsae. Phytochemistry, 56, 693–695.
13.
MungkornasawakulP, PyneSG, JatisatienrA, LieW, UngAT, IssakulK, SawatwanichA, SupyenD, JatisatienrC. (2004) Phytochemical studies on Stemona burkillii Prain: Two new dihydrostemofoline alkaloids. Journal of Natural Products, 67, 1740–1743.
14.
ChungH-S, HonP-M, LinG, ButPP-H, DongH. (2003) Antitussive activity of Stemona alkaloids from Stemona tuberosa. Planta Medica, 69, 914–920.
OhtaniI, KusumiT, KashmanY, KakisawaH. (1991) High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. Journal of the American Chemical Society, 113, 4092–4096.
