Strictosidine is a natural

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

and is classified as a glucoalkaloid and a

vinca alkaloid ''Vinca'' alkaloids are a set of anti-mitotic and anti-microtubule alkaloid agents originally derived from the periwinkle plant ''Catharanthus roseus'' (basionym ''Vinca rosea'') and other ''vinca'' plants. They block beta-tubulin polymerizatio ...

. It is formed by the Pictet–Spengler

condensation reaction In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole ─ a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the f ...

with

secologanin Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively. Biosynthesis Secologanin b ...

, catalyzed by the enzyme

strictosidine synthase Strictosidine synthase (EC 4.3.3.2) is an enzyme in alkaloid biosynthesis that catalyses the condensation of tryptamine with secologanin to form strictosidine in a formal Pictet–Spengler reaction: :3-α(''S'')-strictosidine + H2O = tryptamine + ...

. Thousands of strictosidine

derivatives The derivative of a function is the rate of change of the function's output relative to its input value. Derivative may also refer to: In mathematics and economics * Brzozowski derivative in the theory of formal languages * Formal derivative, an ...

are sometimes referred to by the broad phrase of

monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...

indole alkaloids Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known differe ...

. Strictosidine is an intermediate in the

biosynthesis Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. ...

of numerous pharmaceutically valuable metabolites including

quinine Quinine is a medication used to treat malaria and babesiosis. This includes the treatment of malaria due to ''Plasmodium falciparum'' that is resistant to chloroquine when artesunate is not available. While sometimes used for nocturnal leg cr ...

camptothecin Camptothecin (CPT) is a topoisomerase inhibitor. It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of natural products for anticancer drugs. It was isolated from the bark and stem of ''Camptotheca acuminata'' (Campt ...

ajmalicine Ajmalicine, also known as δ-yohimbine or raubasine, is an antihypertensive drug used in the treatment of high blood pressure. It has been marketed under numerous brand names including Card-Lamuran, Circolene, Cristanyl, Duxil, Duxor, Hydroxysarp ...

, serpentine,

vinblastine Vinblastine (VBL), sold under the brand name Velban among others, is a chemotherapy medication, typically used with other medications, to treat a number of types of cancer. This includes Hodgkin's lymphoma, non-small cell lung cancer, bladder ca ...

vincristine Vincristine, also known as leurocristine and marketed under the brand name Oncovin among others, is a chemotherapy medication used to treat a number of types of cancer. This includes acute lymphocytic leukemia, acute myeloid leukemia, Hodgkin's ...

and

mitragynine Mitragynine is an indole-based alkaloid and the most abundant active alkaloid in the Southeast Asian plant ''Mitragyna speciosa'', commonly known as '' kratom.'' The total alkaloid concentration in dried leaves ranges from 0.5 to 1.5%. In Thai va ...

. Biosynthetic pathways help to define the subgroups of strictosidine derivatives.

Distribution

Strictosidine is found in the following plant families: *

Apocynaceae Apocynaceae (from ''Apocynum'', Greek for "dog-away") is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison Members of the ...

Here especially in

Rhazya stricta ''Rhazya stricta'' (Persian: اشورک Eshvarak) is a native poisonous plant in Southern Iran, Afghanistan, Pakistan, India, Iraq, Oman, Yemen, and Saudi Arabia.Muẓaffariān, Walī Allāh. 1996. A dictionary of Iranian plant names: Latin, Engl ...

and

Catharanthus roseus ''Catharanthus roseus'', commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, is a species of flowering plant in the family Apocynaceae. It is native and endemic to M ...

. *

Loganiaceae The Loganiaceae are a family of flowering plants classified in order Gentianales. The family includes up to 13 genera, distributed around the world's tropics. There are not any great morphological characteristics to distinguish these taxa from o ...

Rubiaceae The Rubiaceae are a family of flowering plants, commonly known as the coffee, madder, or bedstraw family. It consists of terrestrial trees, shrubs, lianas, or herbs that are recognizable by simple, opposite leaves with interpetiolar stipules ...

Icacinaceae The Icacinaceae, also called the white pear family, are a family of flowering plants,"Icacinaceae" At: Angiosperm Phylogeny Website At: Missouri Botanical Garden Website (see ''External links'' below). consisting of trees, shrubs, and lianas, pri ...

Nyssaceae Nyssaceae is a family of flowering trees sometimes included in the dogwood family (Cornaceae). Nyssaceae is composed of 37 known species in the following five genera:Averyanov, L. V. & Hiep, N. T. (2002). ''Diplopanax vietnamensis'', a New Specie ...

Alangiaceae Alangiaceae was recognized as a small family of small dicotyledon trees, shrubs or lianas, closely related to the Cornaceae (dogwood family). There is only one genus, ''Alangium'', with seventeen species. The APG II states that Alangiaceae is a ...

Recent efforts in metabolic engineering have permitted the synthesis of strictosidine by yeast (''

Saccharomyces cerevisiae ''Saccharomyces cerevisiae'' () (brewer's yeast or baker's yeast) is a species of yeast (single-celled fungus microorganisms). The species has been instrumental in winemaking, baking, and brewing since ancient times. It is believed to have been o ...

''). 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.Luijendijk, T. J. C., van der Meijden, E. & Verpoorte, R. (1996). Involvement of strictosidine as a defensive chemical inCatharanthus roseus. Journal of Chemical Ecology, 22(8), 1355–1366. https://doi.org/10.1007/bf02027718

References

{{Reflist Indole alkaloids Glucosides Vinyl compounds