Stemona alkaloids form a unique class, which can be attributed to hemiterpenoid pyrrolidine- and monoterpenoid pyrrolidine-class alkaloids originated from L-ornithine and glutamic acid. By the end of 2013, approximately 183 Stemona alkaloids had been isolated from nature. The literature on Stemona alkaloids in the realms of chemical structure, synthesis, and bioactivities has been elegantly summarized and reviewed. We thus summarize in this review the biosynthesis, structural classification, and the intrinsic, biogenetic relationships of Stemona alkaloids. Based on the comprehensive consideration of biogenetic pathways and chemical features, the 183 Stemona alkaloids are classified into two classes (hemiterpenoid pyrrolidine- and monoterpenoid pyrrolidine) and fourteen types.
DuyfjesS.E. (1993) Stemonaceace, E. In Flora Malesiana, Ser. I, 399–409.
2.
TsiZ.H., DuyfjesB.E.E. (2000) Stemonaceace. In Flora of China, Vol. 24, WuZY, RavenPH. (Eds). Science Press, Beijing, 70–72.
3.
HitotsuyanagiY., TakadaE., FukayaH., TakeyaK. (2008) Sessilifoliamine A and sessilifoliamide J: new alkaloids from Stemona sessilifolia. Tetrahedron Letters, 49, 7376–7379.
4.
HitotsuyanagiY., UemuraG., TakeyaK. (2010) Sessilifoliamides K and L: new alkaloids from Stemona sessilifolia. Tetrahedron, 51, 5694–5696.
5.
PilliR.A., RossoG.B., OliveiraC.F. (2000) Recent progress in the Stemona alkaloids. Natural Product Reports, 17, 117–127.
6.
PilliR.A., RossoG.B., OliveiraM.C.F. (2005) The Stemona alkaloids. In The Alkaloids. Vol. 62, CordellGA, (Eds). Elsevier Science, New York, 77.
7.
PilliR.A., RossoG.B., OliveiraM.C.F. (2010) The chemistry of Stemona alkaloids: an update. Natural Product Reports, 27, 1908–1937.
8.
GregerH. (2006) Structural relationships, distribution and biological activities of Stemona alkaloids. Planta Medica, 72, 99–113.
9.
CordellG.A. (1981) Introduction to alkaloids. A biogenetic approach.New York, Wiley-InterScience, 1055.
10.
CordellG.A., ChoiT.Alkaloids and their biosynthesis. In Phytochemistry and Pharmacognosy section, Chemical Sciences, Engineering and Technology Resources, Encyclopedia of Life Support Systems (EOLSS). Developed under the Auspices of the UNESCO, EOLSS Publishers, Oxford, UK (http://www.eolss.net).
11.
DewickP.M. (2009) Medicinal Natural Products: A Biosynthetic Approach, 3rd Ed. John & Sons, 7–40, 311–326.
12.
WangF.P. (2008) Chemistry of Alkaloids.Chemical & Engineering Press, Beijing, 1–520.
13.
VerpoorteR., SchripsemaJ., LeerT. (1988) Cinchona alkaloids. In The Alkaloids. Vol. 34, BrossiA. (Ed). Academic Press, New York, 333.
14.
LiebischH.V. (1985) In Biochemistry of Alkaloids.MothesK. (Ed). VEB Drunckhaus, Berlin, 88–98.
15.
MenJ.L., TaylorW.I. (1965) An uniform numbering system for indole alkaloids. Experientia, 21, 508–509.
16.
GötzM., SrunzM. (1975) In The Alkaloids. Vol. 9, WiesnerG. (Ed). MTP, International Review of Sciences, Organic Chemistry, Series one, Butterworths, London, 143–160.
17.
SegerC., MereiterK., KalteneggerE., PacherT., GregerH., HoferO. (2004) Two pyrrolo[1,2-a] azepine type alkaloids from Stemona collinsae Craib: Structure elucidation, relationship to asparagamine A, and a new biogenetic concept of their formation. Chemistry & Biodiversity, 1, 265–279.
18.
GregerH., SchinnerK., VajrodayaS., BreckerL., HoferO. (2009) Pandanus alkaloids in Stemonaceae: Finding of a plausible biogenetic origin of Stemona alkaloids. Journal of Natural Products, 72, 1708–1711.
19.
MungkorsawakulP., MattewsH., UngA.T., PyneS.G., JatisatienrA., LieW., SkeltonB.W., WhiteA.H. (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.
20.
PyneS.G., UngA.T., JastisatienrA., MungkorsawakulP. (2007) The pyrido [1, 2-a]azepine Stemona alkaloids. Maejo International Journal of Science and Technology, 1, 157–165.
21.
McMurryJ., BegleyT. (2005) The Organic Chemistry of Biological Pathway.Roberts, Englewood, CO.
22.
SastrarujiT., JatisatienrA., PyneS.G., UngA.T., LieW., WilliamsM.C. (2005) Phytochemical studies on Stemona plants: Isolation of stemofoline alkaloids. Journal of Natural Products, 68, 1763–1767.
23.
ZhangJ., ZengF.J. (2013) Comparison on different ways of extracting volatile oils from Stemona tuberosa. Chinese Journal of Ethnomedicine and Ethnopharmacy, 31–33.
24.
LinW.H., YeY., XuR.S. (1992) Chemical studies on new Stemona alkaloids from Stemona tuberosa. Journal of Natural Products, 55, 571–576.
25.
KeC.Q., HeZ.S., YangY.P., YeY. (2003) A novel alkaloid from Stemona parviflora. Chinese Chemical Letters, 14, 173–175.
26.
LinL.G., DiebP.H., TangC.P., KeC.Q., YangX.Z., YeY. (2007) Alkaloids from the roots of Stemona cochinchinensis. Helvetica Chimica Acta, 90, 2167–2177.
27.
KakutaD., HitotsuyanajiY., MatsuuraN., FukayaH., TakeyaK. (2003) Structures of new alkaloids sessilifoliamides A-D from Stemona sessilifolia. Tetrahedron, 59, 7779–7786.
28.
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.
29.
MungkornasawakulP., PyneS.G., JatisatienrA., SupyenD., LieW., UngA.T., SkeltonB.W., WhiteA.H. (2003) Stemocurtisine, the first pyrido [1, 2-a]azapine Stemona alkaloids. Journal of Natural Products, 66, 980–982.
30.
ChaiyongS., JatisatienrA., MungkornasawakulP., SatrarujiT., PyneS.G., UngA.T., UrathamakulT., LieW. (2010) Phytochemical investigations of Stemona curtisii and synthetic studies on Stemona curtisine alkaloids. Journal of Natural Products, 73, 1833–1836.
31.
SchinneriJ., BremB., ButP.P.H., VajrodayaS., HoferO., GregerH. (2007) Pyrrolo- and pyridoazepine alkaloids as chemical markers in Stemona species. Phytochemistry, 68, 1417–1427.
32.
SakataK., AokiK., ChangC.F., SakuraiA., TamuraS., MurakoshiS. (1978) Stemospironine, a new insecticidal alkaloid of Stemona japonica Miq. isolation, structural determination and activities. Agricultural and Biological Chemistry, 42, 457–463.
KosteckiK., EngelmeierD., PacherT., HoferO., VajrodayaS., GregerH. (2004) Dihydrophenanthrens and other antifungal stilbenoids from Stemona cf. pierrei. Phytochemistry, 65, 99–106.
35.
YangX.Z., ZhuJ.Y., TangC.P., KeC.Q., LinG., ChengT.Y., RuddJ.A., YeY. (2009) Alkaloids from roots of Stemona sessilifolia and their antitussive activities. Planta Medica, 75, 174–177.
36.
KuoC., ChuT. (1978) A study of Stemona alkaloids. I. Acta Chimica Sinica, 36, 291–296;Chemical Abstracts (1979), 90, 164717y.
37.
LinW.H., XuR.S., ZhongQ.X. (1991) Chemical studies on Stemona alkaloids. Acta Chimica Sinica, 49, 927–931.
38.
XuR.S., TangZ.J., FengS.C., YangY.P., LinW.H., ZhongQ.X., ZhongY. (1991) Studies on bioactive components from Chinese medical plants. The Memórias do Instituto Oswaldo Cruz, 86, Suppl. II, 55–59.
39.
WangY.Z., TangC.P., DienP.H., YeY. (2007) Alkaloids from the roots of Stemona saxorum. Journal of Natural Products, 70, 1356–1359.
40.
LinL.G., LeungH.P.H., ZhuJ.Y., TangC.P., KeC.Q., RuddJ.A., LinG., YeY. (2008) Croomine- and tuberostemonine-type alkaloids from roots of Stemona tuberosa. Tetrahedron, 64, 10155–10167.
41.
HitotsuyanagiY., FukayaH., TakedaE., MatsudaS., SaishuY., ZhuS., KomatosuK., TakeyaK. (2013) Isolation of stemona-amine B and stemona-lactams M-R. Tetrahedron, 69, 6297–6304.
42.
NoroT., FukushimaS., UenoA., MiyaseT., IitakaY., SaikiY. (1979) A new alkaloid, croomine, from Croomia heterosepala Okuyama, Chemical and Pharmaceutical Bulletin, 27, 1495–1497.
43.
LinW.H., CaiM.S., YingB.P., FengR. (1993) Studies on the chemical constituents of Croomia japonica Miq. Acta Pharmaceutica Sinica, 28, 202–206.
44.
JiangR.W., HonP.M., XuY.T., ChanY.M., XuH.X., ShawP.C., ButP.P.H. (2006) Isolation and chemotaxonomic significance of tuberostemospironine-type alkaloids from Stemona tuberosa. Phytochemistry, 67, 52–57.
45.
SchinnerlJ., KalteneggerE., PacherT., VajrodayaS., HoferO., GregerH. (2005) New pyrrolo [1. 2-a]azepine type alkaloids from Stemona and Stichoneuron (Stemonaceae). Monatshefte fur Chemie, 136, 1671–1680.
46.
XuR.S., LuY.J., ChuJ.H., IwashitaT., NaokiH., NayaY., NakanishiK. (1982) Studies on some new Stemona alkaloids: a diagnostically useful 1H NMR line-broadening effect. Tetrahedron, 38, 2667–2670.
47.
JiangR.W., HonP.M., ZhouY., ChanY.M., XuY.T., XuH.X., GregerH., ShawP.C., ButP.P.H. (2006) Alkaloids and chemical diversity of Stemona tuberosa. Journal of Natural Products, 69, 749–754.
48.
YueY., DengA.J., XuD.S., QinH.L. (2013) Two new Stemona alkaloids from Stemona tuberosa Lour. Journal of Asian Natural Products Research, 15, 145–150.
49.
PudjiastutiP., PyneS.G., SugiyantoS., LieW. (2012) Isolation of tuberospironine A, a novel croomine derivative from Stemona tuberosa Lour. Phytochemistry Letters, 5, 358–360.
TangC.T., ChenT., VeltenR., JeschkeP., Ebbinghaus-KintscherU., GeibelS., YeY. (2008) Alkaloids from stems and leaves of Stemona japonica and their insecticidal activities. Journal of Natural Products, 71, 112–116.
52.
LinL.G., TangC.P., DienP.H., XuR.S., YeY. (2007) Cochinchistemonine, a novel skeleton alkaloid from Stemona cochinchinensis. Tetrahedron Letters, 48, 1559–1561.
53.
LaiD.H., YangZ.D., XueW.W., ShengJ., ShiY., YaoX.J. (2013) Isolation, characterization and acetylcholinesterase inhibitory activity of alkaloids from roots of Stemona sessilifolia. Fitoterapia, 89, 257–264.
LinW.H., FuH.Z. (1999) Three new alkaloids from the roots of Stemona tuberosa Lour. Journal of Chinese Pharmaceutical Sciences, 8, 1–7.
56.
GuoA., JiaL., DengZ.W., CaiS.Q., GuoS.X., LinW.H. (2008) New Stemona alkaloids from the roots of Stemona sessilifolia, Chemistry & Biodiversity, 5, 598–605.
57.
MungkornasawakulP., ChaiyongS., SastrarujiT., JatisatienrA., JatisatienerC., PyneS.G., UngA.T., KorthJ., LieW. (2009) Alkaloids from the roots of Stemona aphylla. Journal of Natural Products, 72, 848–851.
58.
YeY., XuR.S. (1992) Studies on new alkaloids of Stemona japonica. Chinese Chemical Letters, 3, 511–514.
59.
YeY., QinG.W., XuR.S. (1994) Alkaloids of Stemona japonica. Journal of Natural Products, 57, 665–669.
60.
LinW.H., YeY., XuR.S. (1991) Studies on new alkaloids of Stemona mairei. Chinese Chemical Letters, 2, 369–370.
61.
LinW.H., YeY., XuR.S. (1991) Studies on new alkaloids of Stemona mairei. Youji Huaxue, 11, 500–503;Chemical Abstracts (1992), 116, 148183w.
62.
CongX.D., ZhaoH.R., GuiillaumeG., XuG.J., LuY., ZhengQ.T. (1995) Crystal structure and NMR analysis of the alkaloid protostemotinine. Phytochemistry, 40, 615–617.
63.
MungkornasawakulP., PyneS.G., JatisatienrA., LieW., UngA.T., IssakulK., SawatwanichA., SupyenD., JatisatienrC. (2004) Phytochemical studies on Stemona burkillii Prain: two new dihydrostemofoline alkaloids. Journal of Natural Products, 67, 1740–1743.
64.
SastrarujiT., ChaiyongS., PyneS.G., UngA.T., LieW. (2011) Phytochemical studies on Stemona aphylla: isolation of a new stemofoline alkaloid and six new Stemona stemofurans. Journal of Natural Products, 74, 60–64.
65.
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.
66.
LinW.H., XuR.S., ZhongQ.X. (1991) Chemical studies on Stemona alkaloids II. Studies on the minor alkaloids of Stemona parviflora Wright C. H. Acta Chimica Sinica, 49, 1034–1037.
67.
SastrarujiT., JatisatienrA., IssakulK., PyneS.G., UngA.T., LieW., WilliamsM.C. (2006) Phytochmical studies on Stemona plants: isolation of new tuberostemonine and stemofoline alkaloids, Natural Product Communications, 1, 813–818.
68.
KendeA.S., SmalleyT.L., HungH. (1999) Total synthnsis of (±)-isostemofoline. Journal of the American Chemical Society, 121, 7431–7432.
69.
JiwajindaS., HiraiN., WatanabeK., SantisopasriV., ChuengsamarnyartN., KoshimizuK., OhigashiH. (2001) Occurrence of the insecticidal 16, 17-dihydro-15 (E)-stemofoline in Stemona collinsae. Phytochemistry, 56, 693–695.
70.
SastrarujiK., PyneS.G., UngA.T., MungkornasawakulP., LieW., JatisatienrA. (2009) Structural revision of stemoburkilline from an E-allene to a Z-allene. Journal of Natural Products, 72, 316–318.
71.
MungkornasawakulP., PyneS.G., JatisatienrA., SupyenD., JatisatienrC., LieW., UngA.T., SkeltonB.W., WhiteA.H. (2004) Phytochemical and larvicidal studies on Stemona curtisii: structure of a new pyrido [1. 2-a]azepine Stemona alkaloid. Journal Natural Products, 67, 675–677.
HitotsuyanagiY., ShigemoriG., FukuyaH., HikitaH., ZhuS., KomatsuK., TakeyaK. (2013) Stemona-amines C-E, new alkaloids from Stemona tuberosa. Tetrahedron Letters, 54, 6995–6998.
74.
LinW.H., WangL., QiaoL., CaiM.S. (1993) Two minor alkaloids from the roots of Stemona tuberosa L. Chinese Chemical Letters, 4, 1067–1070.
75.
ChengD.L., GuoJ., ChuT.T. (1988) A study of Stemona alkaloids. III. Application of 2D NMR spectroscopy in the structure determination of stemoninine. Journal of Natural Products, 51, 202–211.
76.
GuoJ. (1981) A study of Stemona alkaloids II. Acta Chimica Sinica, 39, 865–868.
77.
KyeP.T., KimV.N., DungN.X. (1992) Isolation of Stemona LG. from the roots of Vietnamese Stemona tuberosa Lour. Chemical Abstracts, 117, 108076c
78.
LinW.H., MaL., CaiM.S., BarnesR.A. (1994) Two minor alkaloids from roots of Stemona tuberosa. Phytochemistry, 36, 1333–1335.
79.
LinL.G., LiK.M., KeC.Q., RuddJ.A., LinG., YeY. (2008) Antitussive stemoninine alkaloids from the roots of Stemona tuberosa. Journal of Natural Products, 71, 1107–1110.
80.
LinL.G., ZhongH.X., ChengT.Y., TangC.P., KeC.Q., LinG., YeY. (2006) Stemoninines from the roots of Stemona tuberosa. Journal of Natural Products, 69, 1051–1054.
81.
WangF., LiuA.L., AnZ., LiZ.H., DuG.H., QinH.L. (2007) Novel alkaloids from the roots of Stemona sessilifolia. Chemistry & Biodiversity, 4, 523–530.
82.
WangP., LiuA.L., LiZ.H., DuG.H., QinH.L. (2008) Stemoninine-type alkaloids from the roots of Stemona sessilifolia. Journal of Asian Natural Products Research, 10, 311–314.
83.
LinW.H., YinB.P., TangZ.J., XuR.S. (1990) The structure of parvistemonine. Acta Chimica Sinica, 48, 811–814.
84.
GaoY., WangJ., ZhangC.F., XuX.H., ZhangM., KongL.Y. (2014) Seven new alkaloids from the roots of Stemona tuberosa. Tetrahedron, 70, 967–974.
85.
ChungH.S., HonP.M., LinG., ButP.P.H., DongH. (2003) Antitussive activity of Stemona alkaloids from Stemona tuberosa. Planta Medica, 69, 914–920.
86.
PhamH.D., YuB.W., ChauV.M., YeY., QinQ.W. (2002) Alkaloids from Stemona collinsae. Journal of Asian Natural Products Research, 4, 81–85.
JiangR.W., HonP.M., ButP.P.H., ChungH.S., LinG., YeW.C., MakT.C.W. (2002) Isolation and stereochemistry of two new alkaloids from Stemona tuberosa. Tetrahedron, 58, 6705–6712.
89.
HitotsuyanagiY., HikiitaM., UemuraG., FukayaH., TakeyaK. (2011) Structures of stemoxazolidinones A-F, alkaloids from Stemona sessilifolia. Tetrahedron, 67, 455–461.
90.
LiuS.W., FuH.Z., LinW.H. (1999) Alkaloids from the roots of Stemona tuberosa. Acta Pharmaceutica Sinica, 34, 372–375.
91.
ZhongY., GaoY., GuoQ.P., LiW.M. (2010) Two new alkaloids from Stemona tuberosa. Helvetica Chimica Acta, 93, 133–138.
92.
HitotsuyanagiY., HikitaM., OdaT., KakutaD., FukayaH., TakeyaK. (2007) Structures of four new alkaloids from Stemona sessilifolia. Tetrahedron, 63, 1008–1013.
93.
LinW.H., XuR.S., WangR.J., MakT.C.W. (1991) Molecular structure of tuberostemonone. Journal of Crystallographic and Spectroscopic Research, 21, 189–194.
94.
WangP., QinH.L., LiZ.H., LiuA.L., DuG.H. (2007) A new alkaloid from Stemona sessilifolia. Chinese Chemical Letters, 18, 152–154.
95.
HitotsuyanagiY., HikitaM., NakadaK., FukayaH., TakeyaK. (2007) Sessilifoliamide I, a new alkaloid from Stemona sessilifolia. Heterocycles, 71, 2035–2040.
