Chaste Tree

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• History and Introduction
• Medical Use
• Precautions
• Chemical Constituents
• Other Interesting Facts
• Isolation and Synthesis*
• References

History and Introduction (Top)

Chaste berry tree or Vitex is a kind of pretty tree which is about 10-20 feet height, its leaves are about 3-4 inches in diameter. Chaste tree some time is confused with the butterfly bush since these 2 types of plants have similar flowers. Vitex-agunus-castus is one of a genus from the Verbenaceace family. Vitex ( chaste berry) has hard fruits which is used for synthesizing medicine.[1]

• Lilac Chaste tree
• Hemp tree
• Sage tree
• Indian Spice
• Agnus Castus
• Vitex
• Monk's Pepper
• Chase Berry
• Monk's Berry
• Manjing Zi

• Family Verbenaceae
• Vitex agnus-castus
• Vitex Millis
• Vitex Trifolial
[2]

Medical Use (Top)

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Nowaday, Vitex agnus-castus is used as woman's herb for treating female menstrual hormone imbalances. Chaste berry's chemical reagents helps reduce in bloating,breast swelling and irritability in women during their menstrual periods. The affected agents in chaste berry tree stimulate the production of the hormone in the human body. That helps regulate menstrual cycles, and relieve menstrual pain. In additon, the Vitex agnus-castus extract also treats premature ejaculation, arthristis, coughing, edema, and insufficent lactation.[3]

Precautions (Top)

Eventhough Vitex chaste berry extract increases the dopamine level in blood to avoid Parkinson disease, it can't be abused or overdosed, since the excess amount of dopamine may cause other diseases such as schizophrenia. Women who just gave birth should not take Vitex extract since it may lower the production of breast milk.[4] Several researchers found that Vitexin ( Chaste berry extract)can both decrease and increase the prolactin level in the body. The excess amount of prolactin in blood cause stop the menstrual periods, and that is a very dangerous matter to women. Moreover, too little prolactin may reduce the milk production to women who just gave birth.[10]

Beside the usefulness of Chaste berry extract, there are also side effects which may be harmful to our health such as, hair loss, fast heartbeats, itching, nausea, rash, headache, and bledding between menstrual cycles. Chaste berry extract should not be taken during prenancy. Therefore, it would be a great idea to avoid the side-effects is consulting a physican before taking Vitex extract as well as other herbals.[5]

Chemical Constituents (Top)

The part which is used the most in Chaste tree is its fruit. The fruits taste slightly bitter and spicy as pepper ( monk's pepper), and mainly contains 1,8- cineole, C₁₀H₁₈O. Vitex agnus-castus extract also contains many other chemical agents such as:

Volatile oils contents Agnoside Aucubin Eurostoside Casticin 3,6,7,4'-trtramethyllether of 6 hydoxy-camhpor oil Isovitexin Orientin Viticine Alpha-pinenes Beta-pinenes Camphene Prerotundi furan luteolin 1,8 cineole Crysopleneol D ; etc [6]

Permission is being requested 1,8 cineole molecule by Berman. Henrich and H. Nakamura

1,8 cineole is one of a affected agent which is mainly contained within the berries. This chemical substance has such a complicated physical property and is described as:

Other Interesting Facts (Top)

The acients in the past used Chaste tree to treat many other health prblems such as fever, indigestion, ameliorate dropsy. The leaves and seeds of the Chaste berry tree was used to treat the bites of snakes and spiders. Many years later, the Persian mixed Chaste berries with other herbs to synthesize the medicine for treating madness, calming hysteria, and epilepsy. The last interesting thing about Chaste berry tree is that people used chaste-tree to make baskets, furnitures because of its flexibility. Generally, Chaste berry tree ( Vitex agnus-castus) is very beneficial and useful to our lives.[7]

Isolation and Synthesis (Top)

• Common name: eucalyptol
• Chemical name: 1,3,3-trimethyl-2 oxabicyclo[2,2,2]octane
• Chemical formula: C₁₀H₈O
• Molecular mass: 154.249 g/mol
• CAS number: [470-82-6]
• Density: 0.9225 g/cm³
• Very insoluble in H₂O.
• Can be soluble in ether,chloroform, and ethanol
• Nonetoxic and unreative compound.
• Present mostly in eucalyptus leaf oil
.
• A symetrical, cyclic ether.
• An achiral molecule.
[11]

2D model (ChemSketch) of 1,8 Cineole

3D model (ChemSketch) of 1,8 Cineole

1,8-cineole and its isomer 1,4-cineole are both synthesized by the rearrangement of the reactants terpene, or isoprene (terpene is used more often). Strong acids such as acid sulfuric, H₂SO₄ and heteropoly acid, H₃PW₁₂O₄(PW) are very necessary for this type of reaction. These strong acids functions as the catalysts which helps convert the reactant ( terpene compound) into its isomerization, and this is a pathway or intermediate to produce 1,8-cineole and its isomer 1,4- cineole.[12]

Eventhough both acid sulfuric, H₂SO₄ and heteropoly acid (HPAs) are promoted as the effective catalyst in the reaction, heteropoly acid (PW) is selected to use in most reations because of its strength. Heteropoly acid (PW) is also combined with SiO₂ to form a most effective catalyst which helps increase the rate of the reaction.[12]

Solvent is also an important element for this type of reaction. Solvent shouldn't be water, H₂O since water lowers the acidity of heteropoly acid ( catalyst). Solvent should be some type of aqueous so that heteropoly acid can't be soluble within it (solvent). That helps to keep the strength of the catalyst during the whole reaction, and therefore increases the yield of product (isomerization of terpene compound). Here are some of the favorite solvents for this reaction: Cyclohexane, Acetonitrile (MeCN), Dimethyl Formamide (DMF), Nitrobenzene (PhNO₂)(a highly suggested solvent).[12]

In the above picture, the starting reactant is alpha-terpineol which is belong to the terpene family, and also used to synthesize 1,8 cineole (step 1). In the pathway between step 1 and step 2, one H⁺ is donated by the strong acid ( catalyst) to break the double bond of alpha-terpineol, and form a possitive cloud at the carbon number 1 of the cyclohexane ring. In the step 2, the possitive charge of the carbon number 1 and the lone-pair electrons of the Oxygen in the O-H group attract eachother. The attraction between possitive and negative charge formed another bond that connect between the oxygen (-) and the carbon #1 (+), and a 1,8-cineole molecule is produced eventually.

1,8 cineole is contained mostly in many kinds of volatile oil such as volatile present in Vitexin ( chaste berry), or other volatile oil from other herbs. In other words, the main source of 1,8 cineole is the volatile oil. In order to regconize the 1,8 cineole in a particular volatile oil, we need to use a substrate which is 1,1,6,6-tetraphenylhaxa-2,4-diyne-1,6-diol to bind with 1,8 cineole in volatile oil and form a crystal complex. This crystal complex is measured and regconized by both methods IR, H-1,, and NMR. After that, we apply the Kugelrohr vaccum technology to seperate or isolate 1,8 cineole from the crystal complex to collect pure 1,8-cineole. That's how 1,8 cineole is isolated from volatile oil.[13]

Other names for 1,8-cineole from Scifinder Data base

• P-menthane
• 1,8-epoxy (8 Cl)
• 1,8-Epoxy-p-menthane
• Eucalyptol
• Terpan
• p-cineole

References (Top)