A pair of new alkaloid stereo-isomers, stemocochinin (1) and isostemocochinin (2), was obtained from the roots of Stemona japonica Miq., along with seven known alkaloids, stemonamine (3), isostemonamine (4), maistemonine (5), isomaistemonine (6), croomine (7), stemonine (8), and protostemonine (9). The complete structure and stereochemistry of the pair of isomers were established by extensive analysis of the spectral data. Furthermore, our results indicated that S. japonica is chemically closer to S. sessilifolia than S. tuberosa, which are consistent with our previous DNA study on Stemona species.
Pharmacopoeia Commission of People's Republic of China. (2005) The Pharmacopoeia of the People's Republic of China, Part 1. Chemical Industry Publishing House, Beijing, P.R. China, 100.
4.
Jiangsu New Medical College. (1977) Dictionary of Chinese Traditional Medicine. Shanghai People's Publishing House, P.R. China, 858–861.
5.
GregerH. (2006) Structural relationships, distribution and biological activities of Stemona alkaloids. Planta Medica, 72, 99–113.
6.
JiangRW, HonPM, XuYT, ChanYM, XuHX, ShawPC, ButPPH. (2006) Isolation and chemotaxonomic significance of tuberostemospironine-type alkaloids from Stemona tuberosa. Phytochemistry, 67, 52–57.
7.
JiangRW, HonPM, ZhouY, ChanYM, XuYT, XuHX, GregerH, ShawPC, ButPPH. (2006) Alkaloids and chemical diversity of Stemona tuberosa. Journal of Natural Products, 69, 749–754.
8.
JiangRW, HonPM, ButPPH, ChungHS, LinG, YeWC, MakTCW. (2002) Isolation and stereochemistry of two new alkaloids from Stemona tuberosa Lour. Tetrahedron, 58, 6705–6712.
9.
JiangRW, YeWC, ShawPC, ButPPH, MakTCW. (2010) Absolute configuration of neostenine. Journal of Molecular Structure, 966, 18–22.
10.
XuYT, ShawPC, JiangRW, HonPM, ChanYM, ButPPH. (2010) Antitussive and central respiratory depressant effects of Stemona tuberosa. Journal of Ethnopharmacology, 128, 679–684.
11.
XuYT, HonPM, JiangRW, ChengL, LiSH, ChanYP, XuHX, ShawPC, ButPPH. (2006) Antitussive effects of Stemona tuberosa with different chemical profiles. Journal of Ethnopharmacology, 108, 46–53.
12.
KalteneggerE, BremB, MereiterK, KalchhauserH, KähligH, HoferO, VajodayaS, GregerH. (2003) Insecticidal pyrido[1,2-a]azepine alkaloids and related derivatives from Stemona species. Phytochemistry, 63, 803–816.
13.
TangCP, 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.
14.
YeY, QinGW, XuRS. (1994) Alkaloids of Stemona japonica. Journal of Natural Products, 57, 665–669.
15.
YangXZ, ZhuJY, TangCP, KeCQ, LinG, ChengTY, RuddJA, YeY. (2009) Alkaloids from roots of Stemona sessilifolia and their antitussive activities. Planta Medica, 75, 174–177.
16.
YeY, XuRS. (1992) Studies on new alkaloids of Stemona japonica. Chinese Chemical Letters, 3, 511–514.
17.
CongX, ZhaoH, GuillaumeD, XuG, LuY, ZhengQ. (1995) Crystal structure and NMR analysis of the alkaloid protostemotinine. Phytochemistry, 40, 615–617.
18.
GuoA, LinL, DengZ, CaiS, GuoS, LinW. (2008) New Stemona alkaloids from the roots of Stemona sessilifolia. Chemistry & Biodiversity, 5, 598–605.
19.
ZouCY, FuHZ, LeiHM, LiJ, LinW-H. (1999) New alkaloids from the roots of Stemona japonica Miq. Journal of Chinese Pharmaceutical Sciences, 8, 185–190.
20.
LinWH, CaiMS, YingBP, FengR. (1993) Studies on the chemical constituents of Croomia japonica Miq. Acta Pharmaceutica Sinica, 28, 202–206.
21.
LinLG, LeungHPH, ZhuJY, TangCP, KeCQ, RuddJA, LinG, YeY. (2008) Croomine- and tuberostemonine-type alkaloids from roots of Stemona tuberosa and their antitussive activity. Tetrahedron, 64, 10155–10161.
22.
GötzM, StrunzGM. (1975) Tuberostemonine and related compounds: The chemistry of Stemona alkaloids. In Alkaloids MTP International Review of Sciences Organic Chemistry Series One Vol. 9GiesnerG. (Ed). Butterworths, London, UK, 143–160.
