Strictosidine Explained

Strictosidine is a natural chemical compound and is classified as a glucoalkaloid and a vinca alkaloid. It is formed by the Pictet–Spengler condensation reaction of tryptamine with secologanin, catalyzed by the enzyme strictosidine synthase. Thousands of strictosidine derivatives are sometimes referred to by the broad phrase of monoterpene indole alkaloids.^{[1] [2]} Strictosidine is an intermediate in the biosynthesis of numerous pharmaceutically valuable metabolites including quinine, camptothecin, ajmalicine, serpentine, vinblastine, vincristine and mitragynine.

Biosynthetic pathways help to define the subgroups of strictosidine derivatives.^{[3] [4]}

Distribution

Strictosidine is found in the following plant families:

• Apocynaceae

Here especially in Rhazya stricta and Catharanthus roseus.

• Loganiaceae
• Rubiaceae
• Icacinaceae
• Nyssaceae
• Alangiaceae

Recent efforts in metabolic engineering have permitted the synthesis of strictosidine by yeast (Saccharomyces cerevisiae).^[5] This was accomplished by adding 21 genes and 3 gene deletions.

Research

The involvement of the glucoalkaloid strictosidine in the antimicrobial and antifeedant activity of Catharanthus roseus leaves was studied. Strictosidine and its deglucosylation product, specifically formed by the enzyme strictosidine glucosidase, were found to be active against several microorganisms.^[6]

Notes and References

1. Mizukami H, Nordlöv H, Lee SL, Scott AI . Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cells . Biochemistry . 18 . 17 . 3760–3763 . August 1979 . 476085 . 10.1021/bi00584a018 .
2. Treimer JF, Zenk MH . Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation . European Journal of Biochemistry . 101 . 1 . 225–233 . November 1979 . 510306 . 10.1111/j.1432-1033.1979.tb04235.x . free .
3. Book: Plant Secondary Metabolism . Seigler DS . Springer . 1998 . 978-0-412-01981-4 .
4. Book: Biochemistry of Plant Secondary Metabolism . Wink M . Blackwell . 2010 . 978-0-8493-4085-7 .
5. Brown S, Clastre M, Courdavault V, O'Connor SE . De novo production of the plant-derived alkaloid strictosidine in yeast . Proceedings of the National Academy of Sciences of the United States of America . 112 . 11 . 3205–3210 . March 2015 . 25675512 . 4371906 . 10.1073/pnas.1423555112 . free . 2015PNAS..112.3205B .
6. Luijendijk TJ, van der Meijden E, Verpoorte R . Involvement of strictosidine as a defensive chemical inCatharanthus roseus . Journal of Chemical Ecology . 22 . 8 . 1355–66 . August 1996 . 24226242 . 10.1007/BF02027718 .