Antiaris toxicaria

An isomeric sugar, D-javose, is a constituent of two cardenolide glycosides (strophanthojavoside and antiarojavoside) found (42) in the seeds of Antiaris toxicaria Lesch. Degradative studies indicated (42) that javose had the structure 6-deoxy-2-0-methyl-D-allose (17) and this assignment was confirmed by two stereospecific syntheses. 

Latex from the wood of Antiaris toxicaria, a toxic Indonesian plant, has been used for arrow poison. From the root bark of the plants, antiarones A (17) and B (18) [39], the first examples of isoprenylated aurone derivative, have been isolated along with the unique dihydrochalcone derivatives, antiarones J (19) and K (20) [40], Fig. (2). These compounds (19 and 20) are biogenetically considered to be formed... 

Antiaris toxicaria Upas tree Antiarin A Javanese tree of the mulberry family, used as an arrow poison... 

Practically nothing is Jcnown concerning this sugar obtained by Kiliani on hydrolysis of a-antiarin, one of two glycosides isolated from the sap of the deadly upas tree, Antiaris toxicaria. The sugar has been obtained only as a sirup, but crystalline antiaronic acid has. served to characterize it as a hexomethylose isomeric with rhamnose, which is found in the hydrolysis products of 3-antiarin. 

Ailanthus intergrifolia Lam./White siris Alstonia scholaris (L.) R.Br./White cheesewood Amoora cucullata Roxb./Amoora Anthocephalus cadamba (Roxb.) Miq./Labula Antiaris toxicaria Lesch./—... 

Occurrence. 6-Deoxy-D-gulose (36) occurs in steroidal glycosides,160 for example, from the sap of the upas tree, Antiaris toxicaria,169 from the walldower, Cheiranthus cheiri,170 and from Digitalis canariensis var. isabelliana.162 It has also been described in the lipopolysaccharide O-antigen of Yersinia enterocolitica serotype 0 8.171... 

Relomycin (Table 7) was found in culture broths of S. hygroscopicus (242) and shown to be 20-dihydrotylosin by chemical and microbial reductions (242,243). Macrocin (3 -0-demethyltylosin), was found as a minor factor in tylosin (244). It is the immediate biosynthetic precursor of tylosin and can be produced by a biosynthetically blocked mutant of S. fradiae (245—248). 6-Deoxy-2-0-methyl-D-allose [921-90-4/, a neutral sugar in macrocin, is a constituent of cardiac glycosides from Antiaris toxicaria and named javose (9, R = H, R/ = CH3) (249). 2 "-0-Demethylmacrocin (DOMM) obtained from another mutant of S. fradiae (246,250—252), is the penultimate precursor of tylosin (245—248). Other mutant strains of S. fradiae yield shunt metabolites of tylosin in which mycinose is altered (251,252). CP-56,064 [88378-53-4] is an analogue of tylosin in which mycarose is replaced by amicetose (5, R = H, R = OH) (253). 

Sugar component of glycosides found in seeds of Antiaris toxicaria. 

CAR 97] Carter C.A., Forney R.W., Gray E.A. et al., Toxicarioside A. A new cardenolide isolated from Antiaris toxicaria latex-derived dart poison. Assignment of the IH- and 13C-NMR shifts for an antiarigenin aglycone . Tetrahedron, vol. 53, pp. 13557-13566, 1997. 

Antiaris toxicaria (Pers.) Leschen. (Moraceae) latex... 

---