Ervatamia orientalis

In 1971, Knox and Stobbe isolated, from T. orientalis (Ervatamia orientalis), ervatamine (44, C21H26N203, MP 98°C), 20-epi-ervatamine (45, C2IH26N203, MP 187°C, [a]D —22°), and 19,20-dehydroervatamine (50, C21H24N203, MP 200°C, [a]D +53°C), which were the first examples of a novel class of 2-acylindole alkaloids, lacking the most common indolylethylamine moiety (151). 

Tabernanthe orientalis. This plant is now called Ervatamia orientalis, and is found in Western Australia. The leaves contain ibogaine, along with six minor alkaloids that are closely related, structurally. 

Miers. =Tabernaemontana affinis Muell. Arg.)/ dregamine and tabernaemon-tanine in the root bark of Tabemaemontana elegans Stapf./ in the leaves of T. coronaria R.Br./ and (together with vobasine) in the bark of Ervatamia orientalis (R.Br.) Turrell. ... 

Quite the most intriguing new indole alkaloidal structural type to appear this year is that of ervatamine (17b) which occurs, together with 20-epi-ervatamine (17c) and 19,20-dehydroervatamine (17a), in Ervatamia orientalis.26a A description of the degradations (Scheme 5) which led to the structural assignments is included in this sub-section on the basis of a possible biogenetic relationship to alkaloids in this class (see below). 

Knox, J.R. and J. Slobbe 1975. Indole al- haloids from Ervatamia orientalis. i. Isolation of alkaloids and structural identification of tvi o dimers AustralianJournal of Chemistry 28 1813. 

Ervatamine, 20-epiervatamine, and 19, 20-dehydroervatamine have been obtained from Ervatamia orientalis (Apocynaceae), a small tropical tree, and from other Ervatamia species (89). 

Knox J R, Slobbe J 1971 Three novel alkaloids from Ervatamia orientalis. Tetrahedron Lett 2149-2151... 

The importance of unequivocally identifying botanical material, and naming it correctly, complete with the authority, is well illustrated in a study of four distinct Ervatamia species, all of which have at some time been named E. orientalis, with consequent inevitable confusion.64 The leaves of E. orientalis (R. Brown) Domin (=Tabernaemontana orientalis R. Brown), from New Guinea, unlike the other... 

Catharanthine—Ibogamine-Cleavamine Group. Catharanthine is one of the alkaloids produced in suspension cultures of the 200 GW cell line of Catharanthus roseus, 2a and ibogamine has been found in the stem and root bark of Hazunta modesta var. modesta subvar. montana.62 Four Ervatamia species have been shown to contain several alkaloids of this group.64 Thus, E. orientalis (R. Brown) Domin contains voacangine, conopharyngine, pandine, and pandoline, E. daemeliana... 

The recent reports of the occurrences of these alkaloids are given in Table II. Pandoline (657) has been isolated from the leaves and stems of Melodinus polyadenus (Baill.) Boiteau 99, 373), from Ervatamia obtusius-cula Mgf. (373), and from the leaves of E. lifuana Boiteau 374), Tabemae-montana citrifolia L. 32), Stenosolen heterophyllus (Vahl) Mgf. 29, 375), and E. orientalis (R. Brown) Domin 374). 20-Epipandoline (658) occurs in the first four of these species, and pandine ( 9) in the last four, and also in the stems and leaves of Tabernaemontana pandacaqui Poir 376). 

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