Chemical studies on monoterpenoid indole alkaloids from medicinal plant resources Gelsemium and Ophiorrhiza

Takayama H, Sakai S (1997) Gelsemium alkaloids. In: Cordell GA (ed) The alkaloids, vol 49. Academic, New York, pp 1–78 and references cited therein

Liu ZJ, Lu RR (1988) Gelsemium alkaloids. In: Brossi A (ed) The alkaloids, vol 33. Academic, New York, pp 83–140 and references cited therein

Rujjanawate C, Kanjanapothi D, Panthong A (2003) Pharmacological effect and toxicity of alkaloids from Gelsemium elegans Benth. J Ethnopharmacol 89:91–95. DOI 10.1016/S0378–8741(03)00267–8

Zhamg L, Lin J, Wu Z (2003) Advances in the study on chemical constituents and pharmacology of Gelsemium elegans (Gardn et Champ.) Benth. J Chin Med Mat 26:451–453

Chi D-B, Lei L-S, Jin H, Pang J-X, Jiang Y-P (2003) Study of koumine-induced apoptosis of human colon adenocarcinoma LoVo cells in vitro. Acad J First Med Coll PLA 23:911–913

Kitajima M, Arai Y, Takayama H, Aimi N (1998) A chemical study on “Yakatsu” stored in Shosoin Repository. Isolation and characterization of four indole alkaloids from a 1250-year-old sample of the Chinese toxic medicine. Proc Jpn Acad Ser B 74:159–163

Kogure N, Ishii N, Kitajima M, Wongseripipatana S, Takayama H (2006) Four novel gelsenicine-related oxindole alkaloids from the leaves of Gelsemium elegans Benth. Org Lett 8:3085–3088. DOI 10.1021/ol061062i

Lin L-Z, Cordell GA, Ni C-Z, Clardy J (1991) Oxindole alkaloids from Gelsemium elegans. Phytochemistry 30:1311–1315. DOI 10.1016/S0031–9422(00)95223–3

Kitajima M, Kogure N, Yamaguchi K, Takayama H, Aimi N (2003) Structure reinvestigation of gelsemoxonine, a constituent of Gelsemium elegans, reveals a novel, azetidine-containing indole alkaloid. Org Lett 5:2075–2078. DOI 10.1021/ol0344725

Kitajima M, Nakamura T, Kogure N, Ogawa M, Mitsuno Y, Ono K, Yano S, Aimi N, Takayama H (2006) Isolation of gelsedine-type indole alkaloids from Gelsemium elegans and evaluation of the cytotoxic activity of Gelsemium alkaloids for A431 epidermoid carcinoma cells. J Nat Prod 69:715–718. DOI 10.1021/np060016o

Kogure N, Nishiya C, Kitajima M, Takayama H (2005) Six new indole alkaloids from Gelsemium sempervirens Ait. f. Tetrahedron Lett 46:5857–5861. DOI 10.1016/j.tetlet.2005.06.136

Kitajima M, Urano A, Kogure N, Takayama H, Aimi N (2003) New oxindole alkaloids and iridoid from carolina jasmine (Gelsemium sempervirens Ait. f.). Chem Pharm Bull 51:1211–1214. DOI 10.1248/cpb.51.1211

Wall M E, Wani M C (1998) History and future prospects of camptothecin and taxol. In: Cordell G A (ed) The alkaloids, vol 50. Academic, New York, pp 509–535 and references cited therein

Wall ME, Wani MC, Cook CE, Palmer KH, McPhail AT, Sim GA (1966) Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. J Am Chem Soc 88:3888–3890. DOI 10.1021/ja00968a057

Tafur S, Nelson JD, DeLong DC, Svoboda GH (1976) Antiviral components of Ophiorrhiza mungos isolation of camptothecin and 10-methoxycamptothecin. Lloydia 39:261–262

Arbain D, Putra DP, Sargent MV (1993) The alkaloids of Ophiorrhiza filistipula. Aust J Chem 46:977–985

Thomas CJ, Rahier NJ, Hecht SM (2004) Camptothecin: current perspectives. Bioorg Med Chem 12:1585–1604. DOI 10.1016/j.bmc.2003.11.036 and references cited therein

Aimi N, Nishimura M, Miwa A, Hoshino H, Sakai S, Haginiwa J (1989) Pumiloside and deoxypumiloside; plausible intermediates of camptothecin biosynthesis. Tetrahedron Lett 30:4991–4994. DOI 10.1016/S0040–4039(01)80563–3

Aimi N, Hoshino H, Nishimura M, Sakai S, Haginiwa J (1990) Chaboside, first natural glycocamptothecin found from Ophiorrhiza pumila. Tetrahedron Lett 31:5169–5172. DOI 10.1016/S0040–4039(00)97833-X

Aimi N, Ueno M, Hoshino H, Sakai S (1992) Synthesis and absolute configuration of chaboside, first natural gluco-camptothecin. Tetrahedron Lett 33:5403–5404. DOI 10.1016/S0040–4039(00)79105–2

Kitajima M, Masumoto S, Takayama H, Aimi N (1997) Isolation and partial synthesis of 3(R)- and 3(S)-deoxypumilosides; structural revision of the key metabolites from the camptothecin producing plant, Ophiorrhiza pumila. Tetrahedron Lett 38:4255–4258. DOI 10.1016/S0040–4039(97)00858–7

Aimi N, Tsuyuki T, Murakami H, Sakai S, Haginiwa J (1985) Structure of ophiorines A and B; novel type gluco indole alkaloids isolated from Ophiorrhiza spp. Tetrahedron Lett 26:5299–5302. DOI 10.1016/S0040–4039(00)95021–4

Aimi N, Murakami H, Tsuyuki T, Nishiyama T, Sakai S, Haginiwa J (1986) Hydrolytic degradation of β-carboline-type monoterpenoid glucoindole alkaloids: a possible mechanism for harman formation in Ophiorrhiza and related rubiaceous plants. Chem Pharm Bull 34:3064–3066

Kitajima M, Fujii N, Yoshino F, Sudo H, Saito K, Aimi N, Takayama H (2005) Camptothecins and two new monoterpene glucosides from Ophiorrhiza liukiuensis. Chem Pharm Bull 53:1355–1358. DOI 10.1248/cpb.53.1355

Kitajima M, Fischer U, Nakamura M, Ohsawa M, Ueno M, Takayama H, Unger M, Stöckigt J, Aimi N (1998) Anthraquinones from Ophiorrhiza pumila tissue and cell cultures. Phytochemistry 48:107–111. DOI 10.1016/S0031–9422(97)00614–6

Kitajima M, Nakamura M, Takayama H, Saito K, Stöckigt J, Aimi N (1997) Constituents of regenerated plants of Ophiorrhiza pumila; formation of a new glycocamptothecin and predominant formation of (3R)-deoxypumiloside over (3S)-congener. Tetrahedron Lett 38:8997–9000. DOI 10.1016/S0040–4039(97)10404-X

Kitajima M, Nakamura M, Watanabe A, Takayama H, Aimi N. (1998) Synthesis and absolute configuration of 9-β-d-glucosyloxycamptothecin, a new gluco camptothecin isolated from Ophiorrhiza pumila regenerated plants. J Chem Soc Perkin Trans 1:389–390. DOI 10.1039/a708263k

Saito K, Sudo H, Yamazaki M, Koseki-Nakamura M, Kitajima M, Takayama H, Aimi N (2001) Feasible production of camptothecin by hairy root culture of Ophiorrhiza pumila. Plant Cell Rep 21:267–271. DOI: 10.1007/s002990100320

Kitajima M, Yoshida S, Yamagata K, Nakamura M, Takayama H, Saito K, Seki H, Aimi N (2002) Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila. Tetrahedron 58:9169–9178. DOI 10.1016/S0040–4020(02)01196–1

Sudo H, Yamakawa T, Yamazaki M, Aimi N, Saito K (2002) Bioreactor production of camptothecin by hairy root cultures of Ophiorrhiza pumila. Biotec Lett 24:359–363. DOI 10.1023/A:1014568904957

Kitajima M, Niwa M, Yanagisawa C, Takayama H, Sudo H, Saito K, Aimi N (2002) Camptothecin-related alkaloids from culture medium of hairy roots of Ophiorrhiza pumila. Nat Med 56:275

Hutchinson CR, Heckendorf AH, Straughn JL, Daddona PE, Cane DE (1979) Biosynthesis of camptothecin. 3. Definition of strictosamide as the penultimate biosynthetic precursor assisted by 13C and 2H NMR spectroscopy. J Am Chem Soc 101:3358–3369. DOI 10.1021/ja00506a037

Yamazaki Y, Kitajima M, Arita M, Takayama H, Sudo H, Yamazaki M, Aimi N, Saito K (2004) Biosynthesis of camptothecin. In silico and in vivo tracer study from [1-13C]glucose. Plant Physiol 134:161–170. DOI 10.1104/pp.103.029389