Mappia foetida

The Indian tree Nothapodytes foetida (syn. Mappia foetida) is an important source of camptothecin, the DNA topoisomerase I inhibitor possessing anti-cancer and anti-HIV activity of significant therapeutic importance. One of the minor components of the plant has been identified as 9-methoxy-20-(S)-mappicine, a tetracyclic derivative of the pentacyclic camptothecin. When the latter compound was treated for a short-time (7 min) with microwave irradiation, it was converted into 9-methoxymappicine ketone with an exceptionally high yield of 95%. This ketone was then easily transformed by baker s yeast into the target compound 9-methoxy-20-(S)-mappicine as illustrated in Fig. 15 [91]. 

Camptothecin (CPT, 1) is a natural compound isolated for the first time [1] from the wood of Camptotheca acuminata Decne (Nyssaceae), a deciduous plant (xi shu, happy tree) of Southeastern China, but produced also by the Indian Icacinacea Nothapodytes foetida (Wight) Sleumer (formerly Mappia foetida Miers) [2], and by some other plants [3], the two former being the major sources of the compound. 

Govindachari, T, R., Ravindranath, K. R. and Viswanathan, N. (1974) Mappicine, a minor alkaloid from Mappia foetida Miers. J. Chem. Soc., Perkin Trans. 1, 1215-1217. 

The first total synthesis of ( )-mappicine (218) (Scheme 39), a minor alkaloid of Mappia foetida, uses as starting material the potential camptothecin intermediate... 

Mappicine, a minor alkaloid of Mappia foetida, has the structure (113a). This was confirmed by converting camptothecin (114a) into the new alkaloid (Scheme 26). 

The initial source plant of camptothecin, Camptotheca acuminata, is a rare species found in southern regions of the People s Republic of China. Today, camptothecin is produced commercially not only from cultivated C. acuminata trees in mainland China but also from the roots of Nothapodytes nimmoniana (formerly known as both N. foetida and Mappia foetida), which is found in the southern regions of the Indian subcontinent (69). Interestingly, these two antineoplastic agents are particularly important both because of the clinical effectiveness of their derivatives as cancer chemotherapeutic agents and because they are prominent lead... 

In addition to Camptotheca acuminata (Nyssaceae), camptothecine (6) has been found in Nothapodytes (Mappia) foetida and Merilliodendron megacarpum (Icacinaceae), Ophionhiza mungos (Rubiaceae), and Ervatamia heyneana (Apocynaceae) (Cordell, 1981). This distribution is of considerable interest to plant systematists and phylogenists, as it reflects the same dichotomy seen in the distribution of other types of monoterpene iridoids. 

Minor alkaloid from Mappia foetida (Icacinaceae). Pale... 

Govindachari T R, Viswanathan N 1972 Alkaloids of Mappia foetida. Phytochemistry 11 3529-3531... 

---