A study of the hitherto unreported Stichoneuron halabalensis Inthachub led to the characterization of the known compounds (+)-α-tocopherol and (R)-(+)-goniothalamin; four known Stemona alkaloids, bisdehydoxystemoninine A (1), stemoninine (2), sessilistemonamine C (3) and sessilistemonamine A (4); and three new alkaloids, stichoneurine C (5), D (6) and E (7). The structures of these compounds were determined on the basis of their spectroscopic data. Alkaloid 7 showed significant inhibitory activity against electric eel acetylcholinesterase (AChE) (IC50 5.90±0.084 μM), while goniothalamin and compounds 1 and 2 showed significant inhibitory activities against human AChE (IC50 7.24±0.52, 5.52±0.13 and 3.74±0.09 μM, respectively).
InthachubP., VajrodayaS., DuyfjesB.E.E. (2009) Review of the genus Stichoneuron (Stemonaceae). Edinburgh Journal of Botany, 66, 213–228.
2.
(a) PilliR.A., RossoG.B., de OliveiraM.C.F. (2005) The Stemona alkaloids. In The alkaloids, Vol 62, Chapter 2. CordellG.A. (Ed.), Elsevier, Amsterdam. 77–173; (b) Greger H. (2006) Structural relationships, distribution and biological activities of Stemona alkaloids. Planta Medica, 72, 99–113; (c) Pilli RA, Rosso GB, de Oliveira MCF. (2010) The chemistry of Stemona alkaloids: An update. Natural Product Reports, 27, 1908–1937; (d) Kongkiatpaiboon S, Schinnerl J, Felsinge, S, Keeratinijakal V, Vajrodaya S, Gritsanapan W, Brecker L, Greger H. (2011) Structural relationships of Stemona alkaloids: Assessment of species-specific accumulation trends for exploiting their biological activities. Journal of Natural Products, 74, 1931–1938.
3.
(a) ButPP-H, ShawP-C, LinG., JiangR-W, XuY-T. (2012) Authentication and quality assessment of the antitussive herb Baibu (Radix Stemonae). Advances in Botanical Research, 62, 1–33;(b) Xu Y-T, Shaw P-C, Jiang R-W, Hon P-M, Chan Y-M, But PP-H. (2010) Antitussive and central respiratory depressant effects of Stemona tuberosa. Journal of Ethnopharmacology, 128, 679–684; (c) Zhou X, Leung PHH, Li N, Ye Y, Zhang L, Zuo Z, Lin G. (2009) Oral absorption and antitussive activity of tuberostemonine alkaloids from the roots of Stemona tuberosa. Planta Medica, 75, 575–580; (d) Yang X-Z, Zhu J-Y, Tang C-P, Ke C-Q, Lin G, Cheng T-Y, Rudd, JA, Ye Y. (2009) Alkaloids from roots of Stemona sessilifolia and their antitussive activities. Planta Medica, 75, 174–177; (e) Lin L-G, Leung HP-H, Zhu J.-Y, Tang C.-P, Ke, C-Q, Rudd JA, Lin G, Ye Y. (2008) Croomine- and tuberostemonine-type alkaloids from roots of Stemona tuberosa and their antitussive activity. Tetrahedron, 64, 10155–10161; (f) Lin L-G, Li KM, Tang C-P, Ke C-Q, Rudd JA, Lin G, Ye Y. (2008) Antitussive stemoninine alkaloids from the roots of Stemona tuberosa. Journal of Natural Products, 71, 1107–1110; (g) Lin L-G, Zhong Q-X, Cheng T-Y, Tang C-P, Ke C-Q, Lin G, Ye Y. (2006) Stemoninines from the roots of Stemona tuberosa. Journal of Natural Products, 69, 1051–1054; (h) Xu Y-T, Hon P-M, Jiang R-W, Cheng L, Li S-H, Chan Y-P, Xu H-X, Shaw PC, But PP-H (2006) Antitussive effects of Stemona tuberosa with different chemical profiles. Journal of Ethnopharmacology, 108, 46–53; (i) Chung H-S, Hon P-M, Lin G, But PP-H, Dong H. (2003) Antitussive activity of Stemona alkaloids from Stemona tuberosa. Planta Medica, 69, 914–920.
4.
(a) KongkiatpaiboonS., MikulicicS., KeeratinijakalV., GregerH., GritsanapanW. (2013) HPLC simultaneous analysis for quality assessment of Stemona curtisii roots and determination of their insecticidal activities. Industrial Crops and Products, 43, 648–653;(b) Phattharaphan N, Pitiyont B, Visetson S. (2010) Potential of Stemona sp. for Plutella xylostella control. Journal of Biopesticides, 3, 278–281; (c) Mungkornasawakul P, Chaiyong S, Sastraruji T, Jatisatienr A, Jatisatienr C, Pyne SG, Ung AT, Korth J, Lie W. (2009) Alkaloids from the roots of Stemona aphylla. Journal of Natural Products, 72, 848–851; (d) Tang C-P, Chen T, Velten R, Jeschke P, Ebbinghaus-Kintscher U, Geibel S, Ye Y. (2008) Alkaloids from stems and leaves of Stemona japonica and their insecticidal activities. Journal of Natural Products, 71, 112–116; (e) Sanguanpong U, Hummel HE. (2008) Toxicity of Stemona root against onion cutworm by using different contacting methods and solvents. Communications in Agricultural and Applied Biological Sciences, 73, 459–467; (f) Mungkornasawakul P, Pyne SG, Jatisatienr A, Supyen D, Jatisatienr C, Lie W, Ung AT, Skelton BW, White AH. (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; (g) Kaltenegger E, Brem B, Mereiter K, Kalchhauser H, Kahlig H, Hofer O, Vajrodaya S, Greger H. (2003) Insecticidal pyrido[1,2-a]azepine alkaloids and related derivatives from Stemona species. Phytochemistry, 63, 803–816; (h) Brem B, Seger C, Pacher T, Hofer O, Vajrodaya S, Greger H. (2002) Feeding deterrence and contact toxicity of Stemona alkaloids - a source of potent natural insecticides. Journal of Agricultural and Food Chemistry, 50, 6383–6388; (i) Jiwajinda S, Hirai N, Watanabe K, Santisopasri V, Chuengsamarnyart N, Koshimizu K, Ohigashi H. (2001) Occurrence of the insecticidal 16,17-didehydro-16(E)-stemofoline in Stemona collinsae. Phytochemistry, 56, 693–695; (j) Sakata K, Aoki K, Chang C-F, Sakurai A, Tamura S, Murakoshi S. (1978) Stemospironine, a new insecticidal alkaloid of Stemona japonica Miq., isolation, structural determination and activity. Agricultural and Biological Chemistry, 42, 457–463; (k) Kongkiatpaiboon S, Keeratinijakal V, Gritsanapan W. (2012) HPLC analysis of stemokerrine and oxystemokerrine in the Thai medicinal plant Stemona kerrii. Natural Product Communications, 7, 1277–1278.
5.
SastrarujiK., SastrarujiT., UngA.T., GriffithR., JatisatienrA., PyneS.G. (2012) Synthesis of stemofoline analogues as acetylcholinesterase inhibitors. Tetrahedron, 68, 7103–7115.
6.
PhuwapraisirisanP., PoapolathepA., PoapolathepS., Tip-pyangS. (2006) In vivo oxytoxin antagonistic effects of pyrrolizidine alkaloids from Stemona sp. and Asparagus racemosus. ACGC Chemical Research Communications, 20, 17–19.
7.
HosoyaT., YamasakiF., NakataA., RahmanA., KusumawatiI., ZainiN.C., MoritaH. (2011) Inhibitors of nitric oxide production from Stemona javanica. Planta Medica, 77, 256–258.
8.
(a) ChanmahasathienW., OhnumaS., AmbudkarS.V., LimtrakulP. (2011) Biochemical mechanism of modulation of human P-glycoprotein by stemofoline. Planta Medica, 77, 1990–1995;(b) Chanmahasathien W, Ampasavate C, Greger H, Limtrakul P. (2011) Stemona alkaloids, from traditional Thai medicine, increase chemosensitivity via P-glycoprotein-mediated multidrug resistance. Phytomedicine, 18, 199–204; (c) Limtrakul P, Siwanon S, Yodkeeree S, Duangrat C. (2007) Effect of Stemona curtisii root extract on P-glycoprotein and MRP-1 function in multidrug-resistant cancer cells. Phytomedicine, 14, 381–389.
9.
PyneS.G., UngA.T., JatisatienrA., MungkornasawakulP. (2007) The pyrido[1,2-a]azepine Stemona alkaloids. Maejo International Journal of Science and Technology, 1, 157–165.
10.
HitotsuyanagiY., UemuraG., TakeyaK. (2010) Sessilifoliamides K and L: new alkaloids from Stemona sessilifolia. Tetrahedron Letters, 51, 5694–5696.
11.
HitotsuyanagiY., TakedaE., FukayaH., TakeyaK. (2008) Sessilifoliamine A and sessilifoliamide J: new alkaloids from Stemona sessilifolia. Tetrahedron Letters, 49, 7376–7379.
12.
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.
13.
GregerH., SchinnerlJ., VajrodayaS., BreckerL., HoferO. (2009) Pandanus alkaloids in Stemonaceae: Finding of a plausible biogenetic origin of Stemona alkaloids. Journal of Natural Products, 72, 1708–1711.
14.
BakerJ.K., MyersC.W. (1991) One-dimensional and two dimensional 1H- and 13C-nuclear magnetic resonance (NMR) analysis of vitamin E raw materials or analytical references standards. Pharmaceutical Research, 8, 763–770.
15.
CavalheiroaA.J., YoshidaM. (2000) 6-[o-Arylalkenyl]–5,6-dihydro-a-pyrones from Cryptocarya moschata (Lauraceae). Phytochemistry53, 811–819.
16.
LinG.L., ZhongQ.X., ChengT.Y., TangC.P., KeC.Q., LinG., YeY. (2006) Stemoninines from the roots of Stemona tuberosa. Journal of Natural Products, 69, 1051–1054.
17.
ChengD., 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.
18.
WangP., LiuA.L., AnZ., LiZ.H., DuG.H., QinH.L. (2007) Novel alkaloids from the roots of Stemona sessilifolia. Chemistry & Biodiversity, 4, 523–560.
19.
SastrarujiT., JatistienrA., PyneS.G., UngA.T., LieW., WilliamsM.C. (2005) Phytochemical studies on Stemona plants: isolation of stemofoline alkaloids. Journal of Natural Products, 68, 1763–1767.