Tuesday, May 16, 2017

The Phytochemistry of Kratom.


Since the 1960s, 25 alkaloids were isolated and chemically characterized from M. speciosa. The alkaloid content varies according to geographical region and season. The alkaloid profile of M. speciosa is summarized in Table 1. The main indole alkaloids present in the young leaves of M. speciosa are mitragynine and its analogues, speciogynine, paynantheine and speciociliatine. In addition, a new alkaloid, 7-hydroxy-7H-mitragyine (7-hydroxymitragynine; 7- HMG) was isolatedas aminor constituent(Fig. 2; Seatonet al., 1960; Beckett et al., 1965b, 1969; Lee et al., 1967; Shellard et al., 1978a, 1978b; Ponglux et al., 1994; Leon et al., 2009; Orio et al., 2012). These alkaloids were also found in the methanolic extract of the mature leaves together with mitragynaline, pinoresinol, mitralactonal, mitrasulgynine and 3,4,5,6-tetradehydromitragynine as minor constituents (Takayama et al., 1998). In the ethyl acetate extract, nine corynanthe-type indole alkaloids were isolated namely, mitragynine, speciogynine, speciociliatine, paynantheine, 7-HMG, mitragynaline, corynantheidaline, corynantheidine and isocorynoxeine, whereas 9-methoxymitralactonine and mitralactonine were obtained as minor constituents (Takayama, 2004). Investigation of Malaysian M. speciosa found new types of alkaloids namely mitragynaline, corynantheidaline, mitragynalinic acid and corynantheidalinic acid (Houghton et al., 1991). The total alkaloid content from the leaves varies from 0.5% to 1.5%. An additional indole alkaloid found in the fruits of M. speciosa is 7-hydroxyspeciociliatine (Kitajima et al., 2007). Microbial transformation of the leaves was shown to yield two major metabolites: mitragynine pseudoindoxyl and hydroxyl mitragynine pseudoindoxyl (Zarembo et al., 1974). Mitragynine is, with 66% of the total alkaloid mixture, the most abundant active alkaloid derived from the leaves of M. speciosa (Shellard, 1974, 1989; Shellard et al., 1978a, 1978b; Jansen and Prast, 1988a; Takayama et al., 1998; Chittrakarn et al., 2008). It was first isolated by Hooper (1907) and again by Field (1921) and Ing and Raison (1939). Field (1921) isolated two new alkaloids from Mitragyna species: mitragynine (from M. speciosa) and mitraversine (from M. parvifolia). Mitragynine was assumed to be a physiologically active constituent having morphine-like properties. However, it should be noted that it may not be the most potent psychoactive component. In particular over more chronic

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