A flavonoid alkaloid also known as a flavoalkaloid is a type of
natural product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical syn ...
produced by plants that contains both a
flavonoid
Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.
Chemically, flavonoids ...
core structure and a nitrogen containing
substituent
A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...
so that the substance is also classified as an
alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...
.
The most common flavonoid alkaloids contain a nitrogen
heterocycle such as a
pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a d ...
or
piperidine which is covalently bonded to the A-ring of a
chromone
Chromone (or 1,4-benzopyrone) is a derivative of benzopyran with a substituted keto group on the pyran ring. It is an isomer of coumarin.
Derivatives of chromone are collectively known as ''chromones''. Most, though not all, chromones are also ...
. One flavonoid alkaloid, lilaline, was isolated from
Lilium candidum in 1987.
The synthesis of flavonoid alkaloids has been achieved
[Zhen, J., Dai, Y., Villani, T., Giurleo, D., Simon, J. and Wu, Q., 2017. Synthesis of novel flavonoid alkaloids as α-glucosidase inhibitors. Bioorganic & Medicinal Chemistry.]
Pharmacology
A number of flavonoid alkaloids have been discovered that possess diverse pharmacological activity that may have application in the treatment of a range of diseases. One example is
alvocidib, a potent
CDK9 kinase inhibitor
A protein kinase inhibitor is a type of enzyme inhibitor that blocks the action of one or more protein kinases. Protein kinases are enzymes that phosphorylate (add a phosphate, or PO4, group) to a protein and can modulate its function.
The phospha ...
that is being developed for the treatment of
chronic lymphocytic leukemia
Chronic lymphocytic leukemia (CLL) is a type of cancer in which the bone marrow makes too many lymphocytes (a type of white blood cell). Early on, there are typically no symptoms. Later, non-painful lymph node swelling, feeling tired, fever, nigh ...
(CLL) and
acute myeloid leukemia (AML).
Flavonoid alkaloids were also found to present alpha-glucosidase inhibitory activity through artificial organic synthesis.
[Zhen, J., Dai, Y., Villani, T., Giurleo, D., Simon, J. and Wu, Q., 2017. Synthesis of novel flavonoid alkaloids as α-glucosidase inhibitors. Bioorganic & Medicinal Chemistry.]
References
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alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...
Alkaloids found in plants