Tabernaemontana, (Apocynaceae), a review of it’s taxonomy, phytochemistry, ethnobotany and pharmacology.


Van Beek et al
J of Ethnopharmacology #10: 1- , 1984.

This paper is a broad analysis of current knowledge on the genus Tabernaemontana, which in this paper includes Ervatamia spp and others as synonyms for members of this genus. The authors of this paper classify Ervatamia orientalis as a synonym for Tabernaemontana orientalis, and also state that many of the previously described species such as E. angustisepala and E. pubescens can in fact be considered synonyms for T. orientalis also. It seems that many members of this genus have been described at different times and places, with quite a few different names, and can therefore have many synonyms.
Previously as far as I was aware, most botanists in Australia recognised three species, under the name of Ervatamia ( E. orientalis, E. angustisepala, E. pubescens. ). In this report E. orientalis is considered a synonym for Tabernaemontana orientalis, as is E. angustisepala and E. pubescens. Recently the catalogue of Queensland native and naturalised plants (1993) described two species, Tabernaemontana orientalis and T. pandacaqui, as being found in Queensland. T. pandacaqui is apparently a synonym for either E. angustisepala and/ or E. pubescens here. In the Flora of the Kimberley region (1992), E. orientalis and E. pubescens are described, but a note states that both these may be synonyms for T. pandacaqui.
There has been a lot of name changes and confusion amongst many of the species in all the genera mentioned. Some species seem to have been described up to five times with different names, or varieties.
T. orientalis is a widely distributed species, known from Indonesia, New Guinea, northern Australia and the pacific region. It is very closely related to T. divaricata, a plant indigenous to India, and also known as Ervatamia divaricata, T. coronaria is also a synonym for this species. This is a list of the alkaloids ( alkaloids related to or structurally like ibogaine in italics ) obtained from various parts of specimens identified as stated in this study.


legend for plant parts; l = leaves, tw = twigs, bark = bark(!), sb = stem bark, rt bark = root bark, unk = unrecorded as to which part of the plant was used.

Tabernaemontana orientalis.
synonyms E. orientalis, E. pubescens (?), E. angustisepala (?) and others...

   alkaloid            plant part        mol wt        specimen from..

 Akuammidine              unk          352.1787          Qld
 Dregamine              l & tw         354.1943          Loyalty Is 
                          bark                           Qld
		          unk				 New Hebrides
 Tabernaemontanine       l & tw        354.1943 	 Loyalty Is
			  bark                           Qld
         		  unk			         New Hebrides
 Ervatamine	         l & sb        354.1943          Qld
			 l & tw			   	 Loyalty Is
19,20-dehydro-ervatamine l & sb	       352.178	         Qld
 20-epi-ervatamine      l & tw	       354.1943	         Loyalty Is
 		           sb				 Qld
 Apparacine                l	       264.1626	         Qld
 Conopharyngine         l & tw	       398.2205        	 Loyalty Is
                          unk				 New Guinea
		          unk				 Qld
 Coronaridine           l & tw         338.1994          Loyalty Is
                          unk				 New Hebrides
 Ibogaine                  l	       310.2045		 Qld
 Iboxygaine	        l & unk	       326.1994		 Qld
 Voacangine		l & tw	       368.2100		 Loyalty Is
			  unk				 Qld
		          unk			         New Guinea
 Isovoacangine           unk	       368.2100          New Hebrides
 Voacristine		bark	       384.2049		 Qld
 Pandoline	       l & tw	       354.1943  	 Loyalty Is
			unk				 New Guinea
 20-epi-pandoline      l & tw	       354.1943		 Loyalty Is
			unk			         New Guinea
 Pandine	       l & tw          352.1787		 Loyalty Is
			unk			         New Guinea
 Voacamine		bark	       704.3938		 Qld
 16-decarbo-methoxy-	bark	       646.3883		 Qld
 voacamine			
 16-decarbo-methoxy-	bark	       648.4039		 Qld
 19’,20’-dihydrovoacamine
 16-decarbo-methoxy-	bark           648.4039		 Qld
 19,20-dihydro-20-epi-voacamine 

The alkaloids voacamine, 16-decarbomethoxy-19,20-dihydrovoacamine and 16 decarbomethoxy-19,20-dihydro-20-epi-voacamine are actually dimeric alkaloids constructed from a single ibogaine molecule combined with either a dregamine or tabernaemontanine molecule. All these alkaloids, apart from ibogaine were found together in the bark of the species from Qld. Apart from apparacine, ibogaine and iboxygaine have lower molecular weights than any other alkaloids reported from this species.


Tabernaemontana pandacaqui.
synonymous with Ervatamia angustisepala(?).

   alkaloid         plant part        mol wt           specimen from..

 Pericyclivine	      leaf           322.1681           Phillipines
 Tabernaemontanine    leaf           354.1943	        Phillipines 
20-epi-Lochneridine   leaf	     340.1787	        Phillipines  
Coronaridine          bark	     338.1994	        Phillipines
		      bark				Jamaica
(-)-Ibogamine         bark	     280.1939	        Jamaica
Iboxygaine	      bark	     326.1994	        Jamaica
Tabernanthine         bark	     310.2045	        Jamaica 
iso-Voacangine	      bark           368.2100	        Jamaica
Voacristine	      bark           384.2049	        Jamaica (?) 
Ervafoline	      leaf	     644.3362           Phillipines
Ervafolidine	      leaf	     662.3468	        Phillipines
iso-Ervafolidine      leaf	     662.3468	        Phillipines

Ervafoline, Ervafolidine and iso-Ervafolidine are dimeric alkaloids, containing a single ibogan type molecule combined with another molecule of a related type of alkaloid called plumeran.


Tabernaemontana divaricata.
synonyms Ervatamia divaricata, E.coronaria, T. coronaria and others...closely related to T. orientalis.

   alkaloid        plant part         mol wt            specimen from..

Dregamine	   leaf ; stem	     354.1943 		India ; Florida
Tabernaemontanine  leaf; bark 	     354.1943		India ; Pakistan
		 roots; stem				Florida ; Egypt 
Vobasine	leaf; stem; root     352.1787		Egypt
Apparicine	    flower 	     264.1626		Cuba
Voaphylline	  flower; leaf	     296.1889		Cuba ; India
N-methylvoaphylline flower; leaf     310.2045		Cuba
Lochnericine	      leaf	     352.1787		India
Tabersonine	     flower 	     336.1838		Cuba
Coronaridine	   leaf; rt bark     338.1994	      India ; Cuba ;Florida	
		  stem; seed; unk		       Bangladesh ; Brazil
5-hydroxy-6-oxo-    rt bark	     368.1736		India
coronaridine
3-oxo-coronaridine  rt bark	     352.1787		India
5-oxo-coronaridine   rt bark	     352.1787		India
6-oxo-coronaridine   rt bark	     352.1787		India
Coronaridine-hydroxy- rt bark	     354.1943		India
indolenine
(+)-Heyneanine	    rt bark	     354.1943		India
(-)-Heyneanine	    rt bark	     354.1943		India
(-)-Ibogamine	    rt bark; stem    280.1939		India ; Cuba
Voacangine  	    leaf; stem	     368.2100		India ; Cuba
iso-Voacangine	     stem	     368.2100		India
Voacristine	     leaf	     384.2049		India
iso-Voacristine	  leaf; flower	     384.2049		India
3,14; 4,19-tetrahydro-	flower	     250.1470		Cuba
olivacine
Voacamine	     rt bark	     704.3938		India

Some of the alkaloids recorded such as the n-oxo- and hydroxy-indolenine types are probably not present in the fresh or living material, but are formed by oxidation, either as the plant dries or if the alkaloids are extracted the process involved may create them. Ibogan type alkaloids seem to oxidise quite readily, eg up to 50% of the alkaloids may be lost in drying the plant material.


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