Iridoids fromCoelospermum billardieri

N-Methylisosalsoline from Hammada scoparia

“…For related literature on Hammada scoparia and isoquinoline alkaloids, see: Baker (1996); Benkrief et al (1990); Carling & Sandberg (1970); El-Shazly & Wink (2003); El-Shazly et al (2005); Iwasa et al (2001); Jarraya & Damak (2001); Vetulani et al (2001Vetulani et al ( , 2003.…”

“…Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999). Hammada scoparia has been reported to contain the alkaloids carnegine and N-methylisosalsoline as major tetrahydroisoquinoline alkaloids in addition to other minor alkaloids (Benkrief et al, 1990, Jarraya & Damak 2001El-Shazly & Wink, 2003).…”

“…mg; fraction 3 eluted with dichloromethane) and the second (white rosette crystals) is N-methylisosalsoline (545 mg; fraction 7 eluted with dichloromethane-methanol, 94-6, v-v). These alkaloids were previously isolated from Hammada scoparia (Carling & Sandberg, 1970;Benkrief et al, 1990;Jarraya & Damak, 2001;El-Shazly & Wink, 2003). Their structures were determined on the basis of their spectral data such as UV, MS, 1 H NMR and H-H COSY, 13 Suitable white X-ray quality crystals of this compound were obtained by recrystallization from methanol.…”

Recent progress in the chemistry of indole alkaloids and mould metabolites

“…26 Details of the syntheses of murrayaquinone A and pyrayaquinones A and B have also been p~blished.~' Me (37) Cryptolepine y-Harmine (36), which is claimed to be the first y-carboline derivative to be isolated from a plant source, has been extracted from the seeds of Peganum harmala; harmine was also isolated. 28 Proton and I3C NMR data for cryptolepine (37) have been obtained and complete assignments made. 29 The first synthesis of (+)-duocarmycin A (38), one of a group of novel anti-tumour antibiotics isolated recently2j from a Streptomyces species, has been reported,30 in which the critical stages involve the construction of the oxindole-indoline (39) by the Gassman oxindole synthesis from the indoline (40), and the formation of the cyclopropane ring from the penultimate compound (4 1) by base-catalysed elimination of methane sulfonic acid (Scheme 6); the other stages in the sequence were unexceptional.…”