23141-26-6

Upstream product

• 108-24-7 acetic anhydride 
• 22621-94-9 strictosamide 
• 61-54-1 tryptamine 
• 19351-63-4 secologanin 
• 343-94-2 tryptamine hydochloride 
• 19456-89-4 strictosidine 
• 27856-66-2 secologanin tetraacetate 

Relevant academic research and scientific papers

Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila

Hairy roots of Ophiorrhiza pumila, a rubiaceous camptothecin-producing plant, were obtained. From an investigation of the secondary metabolites, it was found that the hairy roots produced camptothecin and its related alkaloids, i.e. (3S)-pumiloside, (3S)- and (3R)-deoxypumilosides and strictosamide. We also isolated two new camptothecinoids, OPHR-23 and OPHR-17, the structures of which including the absolute configurations, were determined by spectroscopic analyses and chemical conversion from tryptamine and secologanin.

Isolation and Partial synthesis of 3(R)- and 3(S)-deoxypumiloside; structural revision of the key metabolite from the camptothecin producing plant, Ophiorrhiza pumila

Both the C-3 epimeric pair of 3(R)- and 3(S)-deoxypumiloside were found in Ophiorrizia pumila (Rubiaceae), a source plant of camptothecinoid metabolites. These structures were confirmed by spectroscopic analysis and partial stereoselective syntheses. The configuration at C-3 of the previously reported 'deoxypumiloside' is revised to 3(R) from 3(S).

Two chromone-secoiridoid glycosides and three indole alkaloid glycosides from Neonauclea sessilifolia

From the dried roots of Neonauclea sessilifolia, two new chromone-secoiridoid glycosides, sessilifoside and 7″-O-β-D-glucopyranosylsessilifoside, and three novel indole alkaloid glycosides, neonaucleosides A, B, and C, were isolated along with the main known glycosides, 5-hydroxy-2-methylchromone-7-O-β-D-apiofuranosyl-(1→6)- β-D-glucopyranoside, sweroside, loganin, grandifloroside, and quinovic acid 3β-O-β-D-quinovopyranoside-28-O-β-D-glucopyranoside. The structures of these new glycosides were determined by spectroscopic and chemical means. Neonaucleoside A and its C-3 epimer were prepared from secologanin and tryptamine.

Biogenetically patterned synthesis of camptothecin and 20- deoxycamptothecin

A biogenetically patterned synthetic route to the monoterpenoid quinoline alkaloids 20-deoxycamptothecin and (±)-camptothecin from secologanin and tryptamine via vincoside/strictosidine lactams has now been realized, and hence afforded likely biosynthetic intermediates for testing in vivo. (C) 2000 Elsevier Science Ltd.

Con figurative correlation and conformational analysis of strictosidine and vincoside derivatives

On the basis of the configuration of C-15 of the secologanin unit, using detailed NMR analysis, the configuration of C-3, the solution conformation around C-14, and the glucosidic bridge, as well as those of the dihydropyran and tetrahydropyridine rings, were determined in the vincosamide and strictosamide derivatives 4b and 5b. The stereochemical analysis was extended by chemical correlation to the 4-benzylated strictosidine and vincoside derivatives 3c and 3d. Experimental proof was presented for the interpretation of the 'anomalous' chemical shift of acetylated strictosamide derivatives.

Deeper insights into the stereostructure of strictosamide tetraacetate and methylisoalangiside tetraacetate, the key reference molecules in monoterpenoid indole- and isoquinoline glucoalkaloids

The highly shifted acetyl NMR signal of strictosamide tetraacetate, one of the most important reference molecules in the glucoindole alkaloid fields, is that on C2 of the glucose moiety. The signal that behaves similarly in methylisoalangiside tetraacetate was also confirmed to he that on C2.

The Alkaloids of Ophiorrhiza filistipula

Extraction of the fresh leaves of Ophiorrhiza filistipula (Rubiaceae) has yielded the alkaloids normalindine (2), 7-methoxycamptothecin (6) and strictosidinic acid (11).The configurations of the Strychnos alkaloids dolichantoside and isodolichantoside are revised.

PUMILOSIDE AND DEOXYPUMILOSIDE; PLAUSIBLE INTERMEDIATES OF CAMPTOTHECIN BIOSYNTHESIS

Pumiloside and deoxypumiloside, long-sought plausible intermediates of camptothecin biosynthesis, were found in Ophiorrhiza pumila (Rubiaceae).