β-pinene

β-pinene) found in plants is an organic monoterpene compound, and is one of the most abundant compounds released by forest trees. If oxidized in air, the allylic products of the pinocarveol and myrtenol family prevail. α-pinene, which is a colorless liquid soluble in  alcohol, but not water, is one of the two isomers of pinene.

Owing to its woody-green pine-like smell, beta-pinene has been used as a flavoring and fragrance agent.  It’s is pretty common in essential oils and is also used in cooking to provide flavoring effects to the food, and also to act as a preservative.

The botanical families that contain β-pinene are Humulus lupulus, Clausena anisata, Cuminum cyminum, Pinus pinaster, Cannabis sativa, and Cannabis indica.

Uses of beta-Pinene:

Anti-depressant:

Antidepressant-like activity is seen in essential oils that contain β-pinene and Linalool, which are two most volatile monoterpenes.

These are components of many aromatic plants used in folk medicine around the world to relieve anxiety and depression.

A study in 2015 suggested that, linalool and beta-pinene act on the monoaminergic system by reflecting their biological activity on several receptors of the system. Since these constituents focus on multiple receptors, the resulting effects are more potent and long lasting when compared to those that focus on only a single receptor.

Linalool and beta-pinene act in balancing the brain chemistry in these receptors (multiple receptors) resulting in alterations of mood and depression.

Another study in 2012 on ‘Antidepressant activity of Litsea glaucescens essential oil: identification of β-pinene and linalool as active principles’ displayed evidence that, β-pinene and linalool which were active constituents of L. glaucescens essential oil played a role in promoting antidepressant activity.  As a result, the use of L. glaucescens to treat depression was initiated in Mexican Traditional Medicine.

Antibacterial Activities:

beta-Pinene also possesses antibacterial activities.  A study on Rosmarinus officinalis L. essential oil and three of its main components α-pinene (19.43%), 1,8-cineole (27.23%), and β-pinene (6.71%) were studied to understand the in vitro antibacterial behavior and toxicology characteristics. During the study, essential oils of R. officinalis L., α-pinene and β-pinene were treated on Gram-positive, and Gram- negative bacteria. The results showed that Gram-positive bacteria were more responsive to the oil.

Another study on Biological Activities of a-Pinene and β-Pinene Enantiomers conducted in the year 2012 suggested, “This study showed that only the positive enantiomers of pinene have antimicrobial activity against -pinene, C. albicans, C. neoformans, R. oryzae and MRSA. The additive and synergistic effects of (+) – and (+)-β-pinene standards combined with commercial antimicrobials are important as they reduced the MIC of combined substances, maintained the antimicrobial activity and decreased toxicity.”

Cytotoxic Activity:

Most essential oils are used in the industries of food, cosmetics, pharmaceutical and sanitary for their diverse activities that support insecticidal, anti-parasitical, bactericidal, and fungicidal properties.

Keeping this in mind, for several centuries specialists have tested essential oils from more than 20 plant families for the past 10 years. An experiment as such is what is mentioned below which proves the cytotoxic activity of beta-Pinene.

beta-Pinene is seen to show cytotoxic activity towards cancer cells. In the year 2014 a study on ‘Anticancer activity of essential oils and their chemical components’ proved, that essential oil of Schefflera heptaphylla (L.) Frodin and its major compound beta-pinene ((-)-beta-pinene and (+)-beta-pinene) showed significant anti-proliferative activity against A375 cancer cell lines. There by preventing the growth of cancer cells related to skin cancer.

Antimicrobial Activity:

Several studies were conducted to identify and prove the antimicrobial activity of beta-Pinene. One of such studies was in the year 2012 where β-pinene an essential component of Rosmarinus officinalis L. essential oil proved positive.

During the course of this study, the anticancer, and antibacterial activities of the oil of Rosmarinus officinalis L were assessed and the three main constituents of the oil 1,8-cineole, α-pinene and β-pinene was brought under consideration.

The result- the oil of Rosmarinus officinalis L exhibited the strongest antibacterial and cytotoxic activities towards SK-OV-3, HO-8910 and Bel-7402 human tumor cell lines, which were in order: Rosmarinus officinalis L. essential oil > α-pinene > β-pinene > 1,8-cineole.

Reference Links:

  1. beta-Pinene by Wikipedia
  2. Biological activities of α-pinene and β-pinene enantiomers by Institute of Microbiology Paulo de Góes, Rio de Janeiro, Brazil, PubMed
  3. Antibacterial Activity and Anticancer Activity of Rosmarinus officinalis L. Essential Oil Compared to That of Its Main Components by Wei Wang, Nan Li, Meng Luo, Yuangang Zu and Thomas Efferth, published in Molecular Diversity Preservation International Journal.
  4. Antidepressant activity of Litsea glaucescens essential oil: identification of β-pinene and linalool as active principles, published in the Journal of Ethnopharmacology and PubMed

α-Pinene

α-Pinene is a productive chemical constituent that’s seen in various species of coniferous trees especially the Pine. It’s also seen in Rosemary as well. α-pinene is more commonly seen in European pines; it is one of the two isomers of pine and an organic compound seen in the terpene class.

A mixture of α-pinene and α-isomer is seen in Eucalyptus oil and Orange peel oil. The chemical substance is also seen in Juniper berries and tea tree oil. The concentration and quantity of the chemical compound present in the oil depends on the temperature and availability of sunlight.

α-Pinene is seen in several essential oils and exhibits anti-inflammatory and antimicrobial properties, and acts as a broad-spectrum antibiotic. It also functions as an acetyl cholinesterase inhibitor and as a bronchodilator as well.

In ancient times, drops of the resin were collected from the bark of the trees to treat ailments. The resin collected was mixed with wine, milk or water to treat respiratory illnesses especially the ones that lead to congestion of the airway. The mixture was used as an expectorant to create relief.

The mixture of the resin were also used internally and externally to treat parasitic infections. Mixed with bees wax or animal fat, alpha-pinene was used as an antimicrobial ointment or an analgesic balm.

In the 1600, the Dutch used Juniper berries to create an alcoholic tonic which is now commonly known as Gin. This was even used as a medical aid in the ancient times. The French distilled the chemical compound from the bark of Juniper trees to create a product to treat skin diseases like eczema.

The resins containing α-Pinene called melaleuca was also put to use in the Aborigine cultures of ancient Australia to treat open wounds and prevent further infection, and also to treat fungal infections of the feet as well.

Likewise several cultures around the world used α-Pinene as tinctures, in teas and in topical formulations. As of today, this chemical constituent is being used in mouthwashes, cough lozenges, cold and chest ointments.

Antibacterial cytotoxic activity of α-Pinene:

A study conducted on Rosmarinus officinalis L. Essential Oil which contains 1,8-cineole (27.23%), α-pinene (19.43%) and β-pinene (6.71%) as its major constituents; was performed to identify the cytotoxic and antibacterial activity of the oil. The results suggested that R. officinalis L. essential oil was extremely effective towards three different kinds of cancer cells and exhibited the highest antibacterial activity.

Antimicrobial properties of α-Pinene:

Several studies have been carried out to understand the antimicrobial activities of α-pinene. One of these studies was on Biological Activities of α-Pinene and β-Pinene Enantiomers. This study was to understand the effect of the chemical substances on bacterial and fungal cells.

The study proved that α-Pinene projected an incredible amount of microbicidal activity against all fungi and bacteria when treated with MICs that ranged from 117 to 4,150 µg/mL.

Anti-inflammatory effects of α-Pinene:

Studies have proved that α-pinene exhibits anti-inflammatory effects in human Chondrocytes; keeping this in mind a study was carried out to establish an understanding on α-pinene and its anti-osteoarthritic activity.

The results focused positive feedback on the effects of α-pinene as an anti-inflammatory, anti-catabolic and anti-osteoarthritic and should be studied further for its promising activity as an anti-osteoarthritic drug.

Reference links:

  1. Antibacterial Activity and Anticancer Activity of Rosmarinus officinalis L. Essential Oil Compared to That of Its Main Components by Wei Wang, Nan Li, Meng Luo, Yuangang Zu and Thomas Efferth, published in Molecular Diversity Preservation International Journal.
  2. What are the medical uses of alpha-pinene? By WiseGeek
  3. Anti-inflammatory and Chondroprotective Activity of (+)-α-Pinene: Structural and Enantiomeric Selectivity by University of Coimbra, Portugal, published in the Journal of Natural Products.

Patchouli alcohol

Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in Patchouli. It also goes by the name, Patchouli camphor;(–)-patchoulol; (1R, 3R, 6S, 7S, 8S)-patchoulol, patchouli alcohol.

The (−)-optical isomer is one of the organic compound that imparts the scent of patchouli; it’s a colorless to pale yellow crystalline solid. Due to its pleasant fragrance, it is used as an important material in perfumery.

The oil has proven activity as anti microbial, inhibiting platelet activating factor (PAF), antiseptic, antiviral, sedative agents, and antifungal.

The organo nitrogen compounds of the oil functions with biological activities as a vasodilator, antiviral, antidepressants, antimicrobial, anti-schistosomal, anti-inflammatory, analgesic, antitumor, and anticonvulsant. The chemotherapy drug Taxol is also synthesized from this very oil.

Therapeutic uses of Patchouli alcohol:

Some studies reported the potential of patchouli oil for medicinal application. This compound is commonly associated to biological and physiological activity for disorders of the central nervous system and its capability to cooperate with receptors of the body.

The most prominent remedial attributes of Patchouli alcohol are:

Patchouli alcohol as an antioxidant:

A study on ‘Antioxidant Activities and Volatile Constituents of Various Essential Oils’ was carried out in the year 2007. During the process, thirteen essential oils were analyzed to determine their antioxidant activity using three different assay systems.

The main compounds seen in the oil which showed extensive antioxidant traits were, limonene (composition, 74.6%) in celery seed, benzyl acetate (22.9%) in jasmine, α-pinene (33.7%) in juniper berry, myristicin (44%) in parsley seed, patchouli alcohol (28.8%) in patchouli, citronellol (34.2%) found in rose, and germacrene (19.1%)  seen in ylang−ylang.

Bacterostatic, antifungal & larvicidal activity of Patchouli alcohol:

In 2004 a study to check the larvicidal activity of the essential oil of Teucrium leucocladum Boiss was conducted. During this study, the chemical composition of the water-distilled essential oil and n-hexane–ether extract of Teucrium leucocladum Boiss were identified by GLC and GLC–MS techniques. As a result 72 compounds were identified.

The sesquiterpene alcohols, patchouli alcohol (31.24% and 29.66%) and α-cadinol (9.29% and 21.54%) were the main components in the oil.

On analyzing the resulting extracts to identify their antifungal and bacterostatic activities, it was proved that they showed broad and potent activity against Bacillus subtilis, Candida albicans and Pseudomonas aeruginosa.

Patchouli alcohol as an Anti-inflammatory:

‘Anti-inflammatory activity of patchouli alcohol in RAW264.7 and HT-29 cells’ study performed in the year 2013 states that “PA inhibits the production of inflammatory mediators.” During the study, it was analyzed and documented to check if the PA brings on a reduction in the production of inflammatory mediators through down regulation of the NF-κB and ERK pathway.”

The above mentioned results suggested that PA shows anti-inflammatory activities through suppressing ERK-mediated NF-κB pathway in mouse macrophage and human colorectal cancer cells.

Antibacterial activity of Patchouli oil:

A study on the antimicrobial tests of patchouli oil was carried out by using a technology called molecular docking and antimicrobial test done in vitro. In the study, five biological macromolecule enzymes, required by the bacteria in the process of biosynthesis were selected as the objective molecules.

“A group of antibiotics benzyl penicillin, sulfadiazine, trimethoprim, rifampicin and ciprofloxacin, commonly known as antibacterial drugs, were selected as reference compounds.” The 3 three-dimensional of the 5 reference compounds used and the 26 compounds from patchouli oil were analyzed using surflex-dock software.

Here patchouli oil and its two major compounds, pogostone, and (-)-patchouli alcohol which exceeded 60% in patchouli oil samples, were selected antibacterial agents. The conclusion: “Molecular docking technology and antimicrobial test in vitro proved that patchouli oil had strong antimicrobial effects.” Of which, pogostone and (-)-patchouli alcohol displayed effective antimicrobial activity.

Reference Links:

  1. Patchoulol by Wikipedia
  2. Anti-inflammatory activity of patchouli alcohol in RAW264.7 and HT-29 cells, by Department of Nutrition and Food Science, University of Maryland, published in Food Chemical Toxicology
  3. Evaluation of the Antibacterial Activity of Patchouli Oil, published in the Iranian Journal of Pharmaceutical Research and PubMed