Advances in chemistry and bioactivity of the genus Erythroxylum

Abstract

Erythroxylum P. Browne is the largest and most representative genus of Erythroxylaceae family. It contains approximately 230 species that are mainly distributed in tropical and subtropical regions. Some species in this genus, such as E. monogynum and E. coca, have been used as folk medicines in India or South America for a long history. It is well known that Erythroxylum plants are rich in tropane alkaloids, and the representative member cocaine shows remarkable activity in human central nervous system. However, many other types of active compounds have also been found in Erythroxylum along with the broadening and deepening of phytochemical research. To date, a total of 383 compounds from Erythroxylum have been reported, among which only 186 tropane alkaloids have been reviewed in 2010. In this review, we summarized all remained 197 compounds characterized from 53 Erythroxylum species from 1960 to 2021, which include diterpenes, triterpenes, alkaloids, flavonoids, and other derivates, providing a comprehensive overview of phytoconstituents profile of Erythroxylum plants. In addition, the biological activities of representative phytochemicals and crude extracts were also highlighted.

Keywords: Bioactivity; Erythroxylum; Natural products; Phytoconstituent.

Fig. 1

Skeletons of diterpenes found in Erythroxylum plants

Fig. 2

Chemical structures of bicyclic diterpenes (1–12) found in Erythroxylum plants

Fig. 3

Chemical structures of tricyclic diterpenes (13–33) found in Erythroxylum plants

Fig. 4

Chemical structures of tetracyclic diterpenes (34–77) found in Erythroxylum plants

Fig. 5

Chemical structures of triterpenoids (78–96) found in Erythroxylum plants

Fig. 6

Chemical structures of TAs (97–107) found in Erythroxylum plants after 2010

Fig. 7

Chemical structures of flavonoid aglycones found in Erythroxylum plants

Fig. 8

Chemical structures of other constituents (181–197) found in Erythroxylum plants

Fig. 9

The proposed cocaine biosynthesis pathway in E. coca. The following enzymes are depicted in the figure above: ADC (arginine decarboxylase), ODC (ornithine decarboxylase), AIH (armatine iminohydrolase), PMT (putrescine methyltransferase), MPO (N-methylputrescine oxidase), PYKS (pyrrolidine ketide synthase), P450 (cytochrome 450), MT (methyltransferase), MecgoR (methylecgonone reductase), CS (cocaine synthase)