Genipin is a
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 ...
found in ''
Genipa americana
''Genipa americana'' () is a species of trees in the family Rubiaceae. It is native to the tropical forests of North and South America, as well as the Caribbean.
Description
''Genipa americana'' trees are up to 30 m tall and up to 60 cm d ...
'' fruit extract. It is an
aglycone An aglycone (aglycon or genin) is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid molecule.
Detection
A way to identify aglycone ...
derived from an
iridoid
Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, mos ...
glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...
called
geniposide
Geniposide, the glycoside form of genipin, is a bioactive iridoid glycoside that is found in a wide variety of medicinal herbs, such as ''Gardenia jasminoides (fruits) ''.
Geniposide shows several pharmacological effects (in vitro and in vivo) i ...
which is also present in fruit of ''
Gardenia jasminoides
''Gardenia jasminoides'', commonly known as gardenia, is an evergreen flowering plant in the coffee family Rubiaceae. It is native to parts of South-East Asia. Wild plants range from 30 centimetres to 3 metres (about 1 to 10 feet) in height. The ...
''.
Genipin is an excellent natural
cross-link
In chemistry and biology a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural ...
er for proteins, collagen, gelatin, and chitosan cross-linking. It has a low acute toxicity, with i.v. 382 mg/kg in mice, therefore, much less toxic than
glutaraldehyde
Glutaraldehyde is an organic compound with the formula . The molecule consists of a five carbon chain doubly terminated with formyl (CHO) groups. It is usually used as a solution in water, and such solutions exists as a collection of hydrates, c ...
and many other commonly used synthetic cross-linking reagents. Furthermore, genipin can be used as a regulating agent for drug delivery, as the raw material for gardenia blue pigment preparation, and as the intermediate for
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 ...
syntheses.
The blue color of genipin is stabilized in
milk
Milk is a white liquid food produced by the mammary glands of mammals. It is the primary source of nutrition for young mammals (including breastfed human infants) before they are able to digestion, digest solid food. Immune factors and immune ...
due to the natural
pH of milk
''
In vitro
''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology an ...
'' experiments have shown that genipin blocks the action of the transporter
uncoupling protein 2.
References
{{reflist
Iridoids
Diols
Carboxylate esters
Cyclopentenes