Six terpenes shown in studies to be very promising to fight against cancercells.

FDA Disclaimer. *These statements have not been evaluated by the Food and Drug Administration. These products are not intended to diagnose, treat, cure or prevent any disease. *Consult your physician before beginning any exercise program. 

Humulene                        

Humulene is one of the main terpenes in hops, from which it gets its name. Humulene is also called alpha-caryophyllene. Like beta-caryophyllene, humulene is a cannabinoid and sesquiterpene, although it does not contain a cyclobutane ring. Humulene is a powerful anti-inflammatory and an anti-pain compound. It also has anti-cancer properties. Humulene is unique because, like THCv, it acts as an appetite suppressant, showing promise for weight loss treatments.

Aroma – Woody

Sources – Hops, Japanese Spicebush, ginseng, spearmint, ginger, common sage, Chinese Laurel Tree, Cannabis

Studies:

ANTIBACTERIAL

The antibacterial activity of basal fir oil (Abies balsamea) seen to be effective with Staphylococcus aureus. At 2.6 microg/mL, humulene was shown to have a minimum inhibitory concentration, the most potent of all the terpenes evaluated in the study.

Pichette A. Composition and antibacterial activity of Abies balsamea essential oil.

Phytother Res. 2006 May;20(5):371-3.

ANTI-INFLAMMATORY

Humulene was shown to be a good anti-inflammatory across a wide range of inflammatory markers. Its effects were comparable to dexamethasone in rat and mouse models. Humulene has been shown to have rapid onset and relatively good absorption with both oral and topical administration routes. In airway allergic inflammatory routes, humulene was shown to be effective orally or through aerosol.

Chaves JS. Pharmacokinetics and tissue distribution of the sesquiterpene alpha-humulene in mice. Planta Med. 2008 Nov;74(14):1678-83.

Fernandes ES. Anti-inflammatory effects of compounds alpha-humulene and (-)-trans-caryophyllene isolated from the essential oil of Cordia verbenacea.

Eur J Pharmacol. 2007 Aug 27;569(3):228-36. Epub 2007 May 22.

Alexandre P Rogerio. Preventive and therapeutic anti-inflammatory properties of the sesquiterpene α-humulene in experimental airways allergic inflammation.

Br J Pharmacol. 2009 Oct; 158(4): 1074–1087.

ANTI-CANCER

Humulene was elucidated to be potent against several solid tumor cell lines. The molecular mechanism involves producing reactive oxygen species, or free radicals, and depleting natural antioxidants in the cells. Humulene was also shown to work synergistically with beta-caryophyllene in delivering the molecule to cancer cells, thus increasing the cytotoxicity of humulene on several cancer cell lines.

Legault J. Antitumor activity of balsam fir oil: production of reactive oxygen species induced by alpha-humulene as possible mechanism of action. 

Planta Med. 2003 May;69(5):402-7.

Legault J. Potentiating effect of beta-caryophyllene on anticancer activity of alpha-humulene, isocaryophyllene and paclitaxel.

J Pharm Pharmacol. 2007 Dec;59(12):1643-7.

Tundis R. In vitro cytotoxic effects of Senecio stabianus Lacaita (Asteraceae) on human cancer cell lines.

Nat Prod Res. 2009;23(18):1707-18.

Type of Terpene: Sesquiterpene

CAS: 6753-98-6

Formula: C15H24

Molecular Mass: 204.35 g/mol

LD50: Estimated to be 45 mg/kg, always consult your doctor before attempting to medicate yourself

Storage: 2 – 8 C, proper ventilation, spark proof environment

Relative Density: 0.889 g/cm3 At 20 C

Melting Point: < 25 C

Boiling Point: 107 C

Flash Point: 90 C

Eucalyptol                        

Eucalyptol, also known as 1,8 cineole, has a fresh, strong eucalyptus, camphoraceous, minty odor. It is a cyclic ether monoterpene. Eucalyptol has been popularly used on the skin, gums, or other topical areas. The terpene is toxic to several species of bacteria including Staphylococcus aureus. Further research has proven eucalyptol to be a potential treatment for Alzheimer’s, as it lowered the inflammation caused by amyloid beta plaques. eucalyptol is also an anti-inflammatory for sinuses and the digestive system. As an antioxidant, eucalyptol was effective at preventing lipid oxidation. In addition, eucalyptol has been effective in battling leukemia and colon cancer cells. Asthma remedies have also been used with eucalyptol.

Aroma – Minty, camphor, spicy

Sources – Eucalyptus, camphor laurel, tea tree, bay leaves, mugwort, wormwood, mugwort, common sage, rosemary, or sweet basil, Cannabis

Studies:

ANTI-BACTERIAL

Eucalyptol demonstrated bactericidal activity against Escherichia coli, Enterobacter aerogenes, Serratia marcescens, and Staphylococcus aureus, proving to be a good anti-bacterial agent.

ALZHEIMER’S

Eucalyptol was used as treatment against PC12 brain cells exposed to amyloid beta plaques. Molecular analysis showed the terpene lowered the expression of NOS-2, COX-2 and NF-κB. In addition on the cellular level proinflammatory cytokines TNF-alpha, IL-1 beta, and IL-6 were reduced.

ANTI-INFLAMMATORY

Eucalyptol was able to mediate paw oedema and granulomas in a mice model. Eucalyptol was proven to lessen the effects of rhinosinusitis in a clinical trial. In regards to acute pancreatitis eucalyptol effectively reduced cerulein-induced histological damage, pancreatic edema, NF-κB expression, levels of MPO activity and MDA, while replenished the GSH depletion. Eucalyptol was also effective against colitis in rats upon induction by trinitrobenzene sulfonic acid (TNBS). A marked reduction in gross damage scores and wet weights of colonic segments were shown in rats pre-treated with the terpene.

ANTI-OXIDANT

Eucalyptol eluted to lessening the effects of cupric ion-mediated oxidation of lipoproteins, while simultaneously enhancing ferric ion removal ability in high-density lipoprotein. Also less lipids were found in the bloodstream in a fish model. This can also prove useful in mitagating arteriosclerosis.

INSECTICIDE

Eucalyptol demonstrated toxic activity against A. Albopictus larvae, with a LC50 = 267.130 ppm.

ANTI-CANCER

Apoptosis of human leukemia Molt 4B and HL-60 cells was induced by eucalyptol. Morphological changes showing apoptotic bodies and fragmentations of DNA were observed. Also in human colon cancer cell lines HCT116 and RKO eucalyptol was effective as evidenced by WST-8 and BrdU assays. Through inactivation of survivin and Akt, and activation of p38, these molecules induced cleaved PARP and caspase-3, ending in apoptosis.

ANTI-ASTHMA

In a lymphocyte and monocyte cell lines, eucalyptol significantly inhibited cytokine production of TNF-α, IL-1, IL-4, and IL-5. This can be inferred to control airway mucus hypersecretion by cytokine inhibition which would also be effective for sinusitis and COPD. There was also a clinical trial that found eucalyptol to be effective as well.

Type of Terpene: Monoterpene

CAS: 470-82-6

FEMA: 2465

Formula: C10H18O

Molecular Mass: 154.25 g/mol

LD50: 2,480 mg/kg

Storage: 2 – 8 C, proper ventilation, spark proof environment

Relative Density: 0.9225 at 20 C

Water Solubility: 0.1 g/l at 25 C

Melting Point: 1 C

Boiling Point: 176 C

Flash Point: 49 C

Limonene                        

Limonene has a strong citrus odor and flavor, the highest amounts are seen in citrus peels. Limonene is commonly used in perfume, house cleaners, food and medicine, partial due to it’s nice aroma and low toxicity. Limonene has been used as a house remedy for acne and athlete’s foot in the past.

Limonene has been shown to be a potent antidepressant and anti-anxiety treatment comparable to some traditional medicines. Limonene has also been inferred to be an anti-inflammatory, lowering or preventing key stages in the reaction. Limonene was elucidated in being a potential treatment for breast, prostate and pancreatic cancer.

Aroma – Citrus, orange, sweet, fresh

Sources – Citrus, Cannabis

Studies:

ANTIDEPRESSANT/ANTI-ANXIETY

Limonene demonstrated increased social interaction time and decreased immobility time, in the forced swim test using mice, indicating anxiolytic and antidepressant effects. The effects were comparable with the traditional anxiolytic diazepam and the antidepressant fluoxetine.

ANTI-INFLAMMATORY

Limonene was evaluated against human eosinophilic leukemia cells, specifically looking at reactive oxygen species (ROS), monocyte chemoattractant protein-1 (MCP-1), nuclear factor (NF) kappa B, and p38 mitogen-activated protein kinase. Limonene was found to inhibit cytokine and ROS production, while inactivating eosinophil migration.

ANTI-CANCER

Limonene has been attributed to induction of phase I and phase II enzymes that result in carcinogen detoxification. In two prostate cancer cell lines, limonene administration resulted in higher ROS generation, depletion of GSH, accompanied by increased caspase. In addition limonene results in differentiation of cancer cells as well. Breast and pancreatic cancer cell lines were also negatively affected.

ANTI-VIRAL

limonene was examined for its antiviral activity against herpes simplex virus type 1 (HSV-1) in vitro.

All antiviral assays were performed using RC-37 cells. Cytotoxicity was determined in a neutral red assay, antiviral assays were performed with HSV-1 strain KOS. The mode of antiviral action was evaluated at different periods during the viral replication cycle. Acyclovir was used as positive antiviral control.

limonene reduced viral infectivity by 100 %. The mode of antiviral action has been determined, only moderate antiviral effects were revealed by monoterpenes when these drugs were added to host cells prior infection or after entry of HSV into cells. However, Limonene exhibited high anti-HSV-1 activity by direct interaction with free virus particles. Limonene tested drugs interacted with HSV-1 in a dose-dependent manner thereby inactivating viral infection.

These results suggest that Limonene exhibit antiherpetic activity in the early phase of viral  multiplication and might be used as potential antiviral agents.

Type of Terpene: Monoterpene

CAS: 5989-27-5

FEMA: 2633

Formula: C10H16

Molecular Mass: 136.23 g/mol

LD50: Mice > 5,500 mg/kg

Storage: 2 – 8 C, proper ventilation, spark proof environment

Relative Density: 0.842 at 20 C

Melting Point: -74.3 C

Boiling Point: 176 C

Flash Point: 50 C

Terpinolene                        

Terpinolene is a common terpene primarily isolated from trees. It is present in high amounts in terpintine, which is used in the construction business as well. Terpinolene also goes by the name delta terpinene.

Terpinolene is not an analgesic or an anti-inflammatory, yet most cannabinoids and terpenoids are one of the two or both.

Terpinolene was concluded to be effective against several species of bacteria. Terpinolene is able to increase total antioxidant capacity levels in white blood cells without changing the total oxidative stress level. Terpinolene is further effective in fighting glial cell cancer and leukemia.

Aroma – Fresh, lemon, piney, citrus, sweet, woody

Sources – Pine, fir, apple, lilac, cumin, tea tree, Cannabis

Studies:

ANTIBACTERIAL

Terpinolene was elucidated to be toxic against, Bacillus subtilis, Staphylococcus aureus, Staphylococcus epidermidis and Escherichia coli through the disk susceptibility test minimum inhibitory concentrations measurements in a couple studies.

ANTI-OXIDANT

Genotoxic, oxidative and cytotoxic effects of terpinolene were explored with white blood cells. Genotoxicity was evaluated by micronucleus assay, sister chromatid exchanges assay, and 8-oxo-2-deoxyguanosine measurements. Cytotoxicity was detected by lactate dehydrogenase release and MTT assay. All assays were negative. Terpinolene treatment showed statistically significant increases of total antioxidant capacity levels in the cells without changing total oxidative stress levels. This antioxidant effect was also seen in preventing the oxidation of low density lipoprotein, which is helpful in combatting heart disease.

SEDATIVE

Nasal transmission of terpinolene was concluded to induce sleep in mice. Oral administration may prove more potent.

ANTI-CANCER

A key protein involved in progressing cancers, RAC-alpha serine/threonine-protein kinase, was shown to be reduced in leukemia cells with the treatment of terpinolene. Also brain  cancer cells were shown to be significantly affected by the terpene as well, and no signs of genetic damage were seen in the normal cells.

INSECTICIDE

Terpinolene demonstrated toxic effects against cockroaches, Blattella germanica,through contact as well as a fumigant.

Type of Terpene: Monoterpene

CAS: 586-62-9

FEMA: 3046

Formula: C10H16

Molecular Mass: 136.23 g/mol

LD50: > 4,000 mg/kg

Storage: Room temperature, proper ventilation, spark proof environment

Relative Density: 0.861 g/cm3

Water Solubility: 9.5 mg/L at 25 C

Boiling Point: 184 C    /    Flash Point: 64 C

Alpha Pinene                    

Pinene consists of two isomers, alpha and beta, depending on the position of the double bond within the molecule. It is an alkene and contains a highly reactive four membered ring perpendicular to the main ring, prone to skeletal rearrangements. Both the – and + enantiomers are seen in nature. – alpha pinene is mostly seen in European pines, and + alpha pinene mostly in North American pines. The racemic mixture is seen in eucalyptus and citrus oils. Pinene is used in nature with the ozone to condense aerosols that could harm the environment.

Aroma – Piney, earthy, woody

Sources – Conifer trees, eucalyptus, rosemary, sage, ironwort, Cannabis, citrus

Studies:

ANTI-INFLAMMATORY

With acute pancreatitis, alpha-pinene treatment reduced histological damage and myeloperoxidase activity in the pancreas and lungs. Furthermore, alpha-pinene pretreatment reduced the production of pancreatic tumor necrosis factor (TNF)-alpha, interleukin (IL)-1beta, and IL-6 during acute pancreatitis. In vitro, alpha-pinene inhibited cerulein-induced cell death and cytokine production in isolated cerulein-treated pancreatic acinar cells. This could point to alpha-pinene possibly having beneficial effects with pancreatic cancer and maybe diabetes. It has been shown that alpha pinene has anti-inflammatory effects in human chondrocytes, thus exhibiting potential antiosteoarthritic activity. + alpha pinene was shown to inhibit the interleukin -1beta- induced inflammatory and catabolic pathways, nuclear factor kappa-light-chain-enhancer of activated B cells and c-Jun N-terminal kinases activation, and the expressionof the inflammatory (iNOS) and catabolic (MMP-1 and -13) genes.

Bronchodilator

This terpene also acts as a powerful bronchodilator, opening airways for those with conditions like asthma or COPD.

ANTI-BACTERIAL 

As tested through solid medium diffusion procedure, pinene exhibited toxic effects against Staphylococcus aureus, S. epidermidis, Streptococcus pneumoniae and S. pyogene

ANTI-CANCER

Mice placed in an environment enriched with a-pinene demonstrated reduced melanoma growth, and tumor volume of the mice was about 40% smaller than that in the control mice. In another study, alpha-pinene was identified as an active anti-proliferative compound on liver cancer BEL-7402 cells using the MTT assay. Alpha-pinene inhibited BEL-7402 cells by arresting cell growth in the G2/M phase of the cell cycle, downregulating Cdc25C mRNA and protein expression, and reducing cycle dependence on kinase 1(CDK1) activity.

MEMORY ENHANCER

Alpha pinene has been shown to be a uncompetitive reversible inhibitor of red blood cell acetylcholinesterase in vitro. The essential oil of sage having, camphor, 1,8-cineole, bornyl acetate, alpha pinene and several other terpenes in much smaller concentrations were exposed to human cells. Since many memory-enhancing and dementia drugs are based on inhibiting cholinesterase to enhance cholinergic activity, it is thought that alpha pinene may act as an effective supplement for such conditions.

Type of Terpene: Monoterpene

CAS: 80-56-8

FEMA: 2902

Formula: C10H16

Molecular Mass: 136.23404 g/mol

LD50: Mice 3,700 mg/kg

Storage: 2 – 8 C, proper ventilation, spark proof environment

Relative Density: 0.858 g/mL at 25 C

Water Solubility: 0.00004 g/L at 20 C

Auto-ignition Temp: 255 C

Melting Point: -62.5 C

Boiling Point: 156 C

Flash Point: 33 C

B-Caryophyllene                    

Beta-caryophyllene is a sesquiterpene, with a sweet, woody, spicy, clove-like smell. It is a unique terpene due to its large size and structure. Due to these properties, beta-caryophyllene is able to activate several receptors in the body, including CB2, which is usually activated most by CBD. beta-caryophyllene has been shown to be an effective analgesic by regulating neuroinflammation and thermal hyperalgesia. Also as an antioxidant, beta-caryophyllene is effective as demonstrated by [preventing lipid oxidation and scavenging other radicals. As and anti-inflammatory beta-caryophyllene has been proven to mediate kidney inflammation and its side effects. In addition, beta-caryophyllene has been eluted to be a gastric-protective.

Aroma – Clove, Dry, Spicy, Sweet, Woody

Flavor – Spicy, Peppery, Woody, Camphoreous, Citrus

Studies:

ANALGESIC

The analgesic effects of beta-caryophyllene were evaluated in the rabbit conjunctival reflex test and in a rat phrenic nerve-hemidiaphragm preparation. Beta-caryophyllene attenuated thermal hyperalgesia and mechanical allodynia, and reduced spinal neuroinflammation. Also there were no signs of tolerance to the anti-hyperalgesic effects of BCP after prolonged treatment.

ANTI-OXIDANT

Beta-caryophyllene was demonstrated to have a high inhibitory capacity on lipid peroxidation and showed high scavenging activities against hydroxyl radicals and the superoxide anion.

Anti-Cancer

The present study reports a bioassay-guided isolation of β-caryophyllene from the essential oil of Aquilaria crassna. The structure of β-caryophyllene was confirmed using FT-IR, NMR and MS. The antimicrobial effect of β-caryophyllene was examined using human pathogenic bacterial and fungal strains. Its anti-oxidant properties were evaluated by DPPH and FRAP scavenging assays. The cytotoxicity of β-caryophyllene was tested against seven human cancer cell lines. The corresponding selectivity index was determined by testing its cytotoxicity on normal cells. The effects of β-caryophyllene were studied on a series of in vitro antitumor-promoting assays using colon cancer cells. Results showedthat β-caryophyllene demonstrated selective antibacterial activity against S. aureus (MIC 3 ± 1.0 μM) and more pronounced anti-fungal activity than kanamycin. β-Caryophyllene also displayed strong antioxidant effects. Additionally, β-caryophyllene exhibited selective anti-proliferative effects against colorectal cancer cells (IC50 19 μM). The results also showed that β-caryophyllene induces apoptosis via nuclear condensation and fragmentation pathways including disruption of mitochondrial membrane potential. Further, β-caryophyllene demonstrated potent inhibition against clonogenicity, migration, invasion and spheroid formation in colon cancer cells. These results prompt us to state that β-caryophyllene is the active principle responsible for the selective anticancer and antimicrobial activities of A. crassnia. β-Caryophyllene has great potential to be further developed as a promising chemotherapeutic agent against colorectal malignancies.

ANTI-INFLAMMATORY

In kidney cells, beta- caryophyllene successfully ameliorated cisplatin-induced kidney dysfunction, morphological damage, and renal inflammatory response. The effect of the compound was also correlated to mitigate oxidative and nitrative stress.

GASTRIC-PROTECTIVE

Caryophyllene was indicated to significantly inhibit gastric mucosal injuries induced by necrotizing agents, yet barely affects the secretion of gastric acid and pepsin. Caryophyllene produced anti-inflammatory effects, without indication of gastric mucosal damage typical of non-steroidal anti-inflammatory agents like aspirin and ibuprofen.

Type of Terpene: Sesquiterpene

CAS: 87-44-5

FEMA: 2252 

Formula: C15H24

Molecular Mass: 204.35 g/mol

LD50: Rat – >5,000mg/kg

Storage: 2 – 8 C, proper ventilation, spark proof environment