Ervatamia

Fig. 38. Ervatamia pandacaqui (Poir.) Pichon. Flora of The Philippines. Herbarium Vadense (WAG). Botanical identification A.J.M. Leuwenberg, 1987. Geographical localization Pinamalayan, Mindanao. Field collector Ramos. June, 1922. 

In China, the bark and leaves are used for the treatment of fractures. The roots are used in Malaysia to recover from childbirth and exhaustion, and a paste of the plant is used to treat orchitis. The plant contains indole alkaloids such as conodurinine, 19 (S) hydroxyconoduramin, 19 (S)-hydroxyervahanine A, and related iboga alkaloid congeners, and like the species mentioned earlier, and in fact the genera Ervatamia, in general, would be worth investigating for serotoninergic activities (17). 

The already known geissoschizol (7, C19H24N20, MP 224-226°C, [a]D -70°) 184) and its 10-hydroxy derivative (8, C19H24N202, MP 264°C) (184), were isolated from the roots of T. bufalina (Ervatamia hainanensis) (53). The detailed analysis of the H-NMR spectra of 7 and 8 diacetate were reported (Table III) and the assignment of all of the protons was made by application of consecutive double-resonance experiments. 

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). 

The above sequence mimics the proposed biosynthesis of Ervatamia alkaloids and in this context Thai and Mansuy (190) set out to determine whether an enzyme preparation would be able to promote the same transformation. By incubation of dregamine hydrochloride with a suspension of liver microsomes from a rat pretreated with phenobarbital (as a good inducer of P-450 cytochromes) in the presence of NADPH and 02, 20-epiervatamine (45) was formed together with the major metabolite Nl -demethyldregamine. It is well known that microsomal reaction on tertiary amines results in Af-oxide formation or N-deal-kylation. Thus it is likely that 45 was derived either from a rearrangement of dregamine JV4-oxide, catalyzed by the iron cytochrome P-450 or from one-electron oxidation of 30. 

A new amorphous alkaloid has been recently isolated from the Chinese plant T. bufalina (Ervatamia hainanensis) collected on Hainan Island (53). Its mass spectrum showed a molecular ion at m/z 382, corresponding to C23H30N2O3. From the fragmentation pattern, this compound would appear to be a coronaridine derivative in which a C2H50 unit is attached to the aliphatic moiety of the molecule. The structure 111 with (S) configuration at C-3 was determined by a detailed analysis of its H-NMR spectrum (Table IV) in comparison with the data of other ibogan alkaloids. 

Finally, two phenolic derivatives of coronaridine were isolated 10-hy-droxycoronaridine (98, C21H26N203) from the wood and stem bark of T. hey-neana (Ervatamia heyneana) (128) and 11-hydroxycoronaridine (99, amorphous, [a]D —34°) from T. attenuata (47). Both gave characteristic UV spectra with bathochromic shifts on addition of alkali, in agreement with the proposed... 

The corresponding A4-oxide (132, C22H26N205, [a]D +86.6°) isolated from T. heyneana (Ervatamia heyneana) shows loss of 16 amu from M+ and subsequent fragmentation similar to that of other 3,6-oxidovoacangines (128). Skeletal... 

The related alkaloids ervaticine (15) and apparicine (16a) have been isolated from the leaves of Ervatamia coronaria (85H(23)2975) and from the wood of Vallesia antillana (77MI249), respectively. The latter exhibits high antibacterial activity. Subsequently, 16(S)-hydroxy-16,22-dihydroapparicine (16b) was isolated from the leaves of T. dichotoma (84JNP835). 

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. 

Ervatamia, Gabunia, Hazunta, Muntafara, Pagiantha, Pandaca, Peschiera, Phrissocarpus, and Stenosolen, All of these contain alkaloids related to Ibogaine. 

Ervatamia pandacaqui (Poir.) Pichon (Tabernaemontana cuminingiana A. DC., Taber-... 

Fig. 39. Ervatamia corymbosa (Roxb.) King Gamble. Flora of Malaya. Field No 104429. Geographical localization Krau Game Reserve, G. Benom, Central Pahang in primary forest hillside, altitude 1000 feet. Field collector S. Chelliah, 7/14/1967. Botanical identification A.J.M Leeuwenberg, 1986. Herbarium Vadense.

The first extractions of Strempeliopsis strempelioides K. Schum. (Family Apo-cynaceae), from Cuba, reveal that it is rich in alkaloids. The leaves and stem bark contain, amongst others, (+)-tubotaiwine and (+)-condylocarpine, and the stem bark also contains (-)-apparicine.80 Apparicine (pericalline) also occurs, together with O-acetylvallesamine, 19,20-dihydrocondylocarpine, and eleven other alkaloids, in the wood and stem bark of Ervatamia heyneana (Wall.) T. Cooke,81 and... 

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