Project Information
11 September, 2023
Karamehmet Mah. AVRUPA SERBEST BÖLGESİ Adnan Arisoy blv. NO: 13 İÇ KAPI NO: 106


Nigella sativa, or black cumin, is an annual flowering plant of the Ranunculaceae family, native to the Mediterranean, Pakistan and India. Black cumin has been used for many years to treat various diseases, including hypertension, diabetes, inflammation, cough, headache, fever and dizziness. Over the past decades, scientific studies have confirmed the pharmacological properties of Nigella sativa seeds and demonstrated its anti-inflammatory, antibacterial, antihistamine, antidiabetic, anticancer and antihypertensive activity.

Nigella sativa extracts contain oils, amino acids, proteins, carbohydrates, alkaloids, nitrogen compounds and minerals. In total, more than 100 compounds have been isolated from black cumin seeds, but many studies associate most of the pharmacological activity of Nigella sativa with the content of thymoquinone and its dimers, which are known for their anti-cancer activity.

Thymoquinone has been thoroughly studied and has been shown to have a number of therapeutic properties, including analgesic, antihypertensive, hypolipidemic, anti-inflammatory, antibacterial, antihistamine and anticancer activity. Thymoquinone can also be used as a neuroprotector, which reduces the risk of developing Alzheimer's disease.

In the production of Nigella sativa oil, the seeds, after appropriate heat treatment, are crushed to a powdery state, diluted with bidistilled water, hexane and centrifuged to separate the oily phase. This method of producing oil allows you to retain a larger amount of biologically active thymoquinone in it than with the methanol method.

This has been proven during in vivo and in vitro experiments on non-malignant fibroblasts, Hodgkin's lymphoma cells and colon carcinoma. The antiproliferative activity directed against cancer cells reached 90%, which also confirmed the high content of biologically active thymoquinone in the oil. At the same time, this effect did not affect non-malignant fibroblasts, so the use of such oil will not harm ordinary cells.


3-TUYAN (I) (sabinan, tanacetan, dihydrosabinen) – found in a small amount (1-2%) in sage oil. It is a colorless liquid with a pleasant smell. Tuyan is sometimes called "salvene", which actually has the structure of 2-methyl-3-methylene-5-heptene (cis- and trans-forms).

α-TUYEN (II) is a colorless liquid with a pungent odor resembling α-pinene. It exists in a dextrorotatory form (d-α-tuyen). The main hydrocarbon component of oleoresin (turpentine) Boswellia serrata, as well as essential oil of the leaves of hinoki (a coniferous tree growing on Taiwan). It is also found in orthodontic oil. The essential oil of the leaves of Eucalyptus dives is contained in the form of a mix of D- and DL-forms. In an acidic environment, especially when it`s heated, it turns into terpinene derivatives. Does not oxidize.

β-THUYENE (III) – sometimes co-exists with α-tuyen in essential oils.

TUYON (IV) – 3-ketosabinan. A component of many essential oils. In essential oils it is contained in the form of stereoisomers, which are called α- and β-thujones, but sometimes tujon and isotujon. The α-isomer in essential oils is sinistrorotating (l-thujone), and the β-thujone is dextrorotating (d-isotujone). Usually, there is a mixture of these two isomers in natural oils.

α-tuyon – 3-tuyon. The main component of the essential oil of Thuja (Thuja occidentalis), sage (Salvia officinalis), tansy (Tanacetum vulgare).

β-thujone – 3-isotujone, "tanacetone". The main component of the essential oil of tansy (Tanacetum vulgare) and wormwood (Artemisia absinthium).

Thujone can be obtained by oxidation of ethanol by a chromic mixture. Thujone is easily oxidized by permanganate to tuiaketonic acid, and by hypobromide to a-tuiadicarboxylic acid. When it`s heated at 200 degrees under pressure, thujone isomerizes into carvotanacetone.

It is used primarily for the preparation of artificial essential oils, in particular, sage oil and wormwoods oil.

THUJYL ALCOHOL (V) – exists in the form of four diastereomers, which have these names: thujyl alcohol, isobutyl alcohol, neo-thujyl alcohol and non-isobutyl alcohol. Each of these alcohols exists in D- and L- optically active modifications.

All these isomers are usually present in different proportions in essential oils.

Thujyl alcohol (VI) – 3-thujyl alcohol, 3-thujyanol, thuyol. Bicyclic, secondary alcohol, which is found in the free state (10%) and in the form of esters (14%) in Artemisia absinthium, Thuja plicata and Artemisia camphorata wormwood essential oil (40% alcohol and 12% ester). There is also a percents of thujyl alcohol in the essential oil of orthodon and Artemisia verlotorum.

L-thujyl alcohol, commonly found in essential oils, is a syrupy liquid with an odor reminiscent of carvomentol. Stable, not subject to isomerization when heated. It is poorly esterified because of the ease of formation in these reactions of thuyen.

Isobutyl alcohol (VII), neothujyl alcohol (VIII) and neoisothujyl alcohol (IX) co-exist with butyl alcohol in essential oils. D-Isobutyl alcohol, commonly found in these essential oils, has a sweet smell.

In addition to butyl alcohols, essential oils contain (sometimes in large quantities) their esters ETHYL ACETATE, ISOTUYYL ACETATE, NEOTUYYL ACETATE, NEOISOTUYYL ACETATE. They also contain in essential oils of Artemisia absinthium, Thuja plicata and Artemisia camphorata together with thujyl alcohol.

Among other derivatives of tuyan, TUI-3-EN-10-AL, α-TUIAMENTOL and β-TUIAMENTONE, as well as UMBELLULONE (X) and CIS-UMBELLULOL (XI) are mentioned.

UMBELLULONE (X) and CIS-UMBELLULOL (XI) – found in oil of California bay tree (Umbellularia californica) in an amount of 30-40%. An oily liquid with a minty smell that irritates the nasal mucous membranes. It has a strong pharmacological effect.

SABINENE (XII) is a monoterpene hydrocarbon of the tuyan structure, it`s found very often in various essential oils. It exists in two optical and racemic forms.

D-sabine is the main component (up to 30%) of the essential oil of Savin juniper (Juniperus sabina), is present in Ceylon cardamon oil, in the essential oil of marjoram (Origanum majorana), oil of orthodon.

L-sabinene – is found in oil from seeds of Xanthoxylum budrunga, in oil of Savin juniper (Juniperus sabina), Vitex negundo.

DL-sabinene – is found in kubeba oil and Murraya koenigii leaf`s oil. Over time, sabinene gives terpinene derivatives: α-terpinene, terpinene-4-ol and 1,4-terpin.

TRANS-SABINOL (XIII) is a bicyclic terpene alcohol found in the essential oil of Savin juniper (Juniperus sabina), cypress oil in the form of an optically active D-form. It has a faint, pleasant smell.

When dilute acids influence on sabinol, dehydration and ring rupture occur with the formation of p-cymol, as well as 1-p menten-4,6-diol.

Sanbinol co-exists with its esters CIS-SABINYL ACETATE and TRANS-SABINYL ACETATE, which are found in the essential oil of Savin juniper.

In many essential oils (especially mint, oregano), CIS-SABINE HYDRATE (XIV) and TRANS SABINE HYDRATE (XV) (4-tuyanol) are found. The content of these isomers is usually low (1-3%, up to 10%).

Extractive essential oils contain sabinenhydrate in a much larger amount (up to 50%), which indicates its instability under conditions of steam distillation.

Sabinenhydrate`s esters CIS-SABINE HYDRATE ACETATE and TRANS-SABINE HYDRATE ACETATE are also found sometimes with it.