1National Center for Natural Products Research, School of Pharmacy,
University of Mississippi, University, MS, USA
2Department of Pharmacognosy, Faculty of Pharmacy, Minia University,
3Department of Pharmacognosy, Faculty of Pharmacy, Near East University,
4Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University,
5Department of Pharmaceutics and Drug Delivery, School of Pharmacy,
University of Mississippi, MS, USA
Mahmoud A. ElSohly, National Center for Natural Products Research,
School of Pharmacy, University of Mississippi, University, MS 38677, USA.
Email: melsohly@ olemiss. edu
Bioactive Natural Products from Terrestrial and Marine Resources, Especially Terpenes, but not limited to- Original Article
Natural Product Communications
Volume 15(5): 1–7
© The Author(s) 2020
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Chemical Composition of Volatile Oils of
Fresh and Air- Dried Buds of Cannabis
chemovars, Their Insecticidal and
Amira S. Wanas1,2, Mohamed M. Radwan1, Suman Chandra1, Hemant Lata1, Zlatko Mehmedic1,
Abbas Ali1, KHC Baser3, Betul Demirci4, and Mahmoud A. ElSohly1,5
The volatile oils of fresh and air- dried buds of 3 different varieties of Cannabis, namely, high cannabidiol (CBD) chemotype, inter-
mediate CBD/tetrahydrocannabinol (THC) chemotype, and high THC chemotype were prepared by hydrodistillation. Gas chro-
matography analysis of the volatile oils resulted in the identification of 71 compounds, of which 33 were monoterpenes and 38
were sesquiterpenes. The volatile oil obtained from the THC chemotype showed an increase in the ratio of the sesquiterpenes to
monoterpenes content. The content of terpinolene was dramatically decreased upon drying of THC chemotype. Moderate increase
in β-caryophyllene and caryophyllene oxide was observed. However, there was no detectable change in the percentage of mono-
terpenes and sesquiterpenes content in both the intermediate type and CBD chemotype upon drying. The insecticidal activity of
the volatile oils was evaluated. The oil obtained from the fresh and dried high CBD cannabis showed good biting deterrent activity
at 10 ug/cm2 compared with N,N- diethyl- meta- toluamide at 4.78 µg/cm2, and good larvicidal activity.
cannabis essential oils, gas chromatography, insecticidal, larvicidal
Received: February 20th, 2020; Accepted: April 21st, 2020.
Terpenes are the main fragrant compounds in plant resins and
volatile oils responsible for the plants’ distinctive smells.
Terpenes in Cannabis plants are responsible for strain- specific
variations in the smell of the plants.1 The distinct scent of a
cannabis cultivar is the result of the balance of the different
terpenes produced by that particular plant’s breeding.2
Cannabis sativa plants are particularly rich in terpenes, repre-
sented by 120 compounds that are typically monoterpenes and
sesquiterpenes.3 The most common terpenes in cannabis are
β-caryophyllene, myrcene, limonene, α-pinene, β-pinene, α-hu-
mulene, and linalool.1 Monoterpenes are predominant in fresh
plant material but their yield diminishes upon drying and stor-
age,4,5 resulting in a higher relative proportion of sesquiter-
penes in dried cannabis.
Terpenoids play various ecological roles and their composi-
tion is under genetic control.6 They are considered as a contrib-
uting factor that determines plant community properties and
ecosystem functions and thought to have evolved primarily as
defense compounds. In addition, certain terpenoids in the mix-
ture may be recycled into the plant’s primary metabolism.
Other compounds are emitted into the environment, through
volatilization, decomposition of the plant, or by exudation,
playing a major role in numerous interactions. The remarkable
stickiness of cannabis exudates traps insects as it has insecti-
cidal and repellent activities7 and provides a synergistic mecha-
nochemical defense in combination with the insecticidal
phytocannabinoid acids, mainly tetrahydrocannabinolic acid
(THCA), cannabidiolic acid (CBDA), and cannabichromenic
acid (CBCA). These cannabinoids are biosynthesized from the
Natural Product Communications
common substrate, cannabigerolic acid, in the storage cavity of
the glandular trichomes.8
The lipophilic nature of terpenes increases the blood–brain
barrier permeability leading to many sites of pharmacological
actions.9 The therapeutic potential of terpenes are numerous,
including anti- inflammatory, anti- oxidant, analgesic, anticonvul-
sant, antidepressant, anticancer, antimutagenic, anesthetic, anti-
nociceptive, antihistaminic, and antispasmodic activities.1,10
Limonene displayed antinociceptive activity in chemical
nociceptive mice models and causes peripheral analgesia
through opioid receptors stimulation.11 Myrcene has potent
anti- inflammatory, analgesic, and anxiolytic properties.12
β-Caryophyllene (BCP) is the most common sesquiterpenoid
in cannabis plants and extracts, especially after heat decarbox-
ylation,13 was shown to be a selective natural CB2 receptor ago-
nist without psychoactivity.14
Literature reports suggest that besides the individual activi-
ties of terpenes, they are responsible for improving the canna-
binoids activities, a phenomenon referred to as known “the
entourage effect” especially in the treatment of pain.15
In continuation of our investigation of the cannabis volatile
oil,16 herein, we examined the different chemical composition
of the volatile oil of the cannabis chemotypes before and after
drying as well as their insecticidal activity.
Results and Discussion
The volatile oils of fresh (F) and air- dried buds (D) of 3 differ-
ent chemotypes of cannabis plant including CBD chemotype
(fiber type), CBD/THC chemotype (intermediate type), and
THC chemotype (drug type) were prepared by hydrodistilla-
tion. Gas chromatography (GC)–mass spectrometry (MS) and
GC/flame- ionization detector (FID) were used to analyze the
prepared volatile oils.
The GC–MS analysis resulted in the identification of 71
compounds with 33 monoterpenes and 38 sesquiterpenes. The
identification was based on a direct comparison with authentic
samples and/or by comparing the retention times and mass
spectral fragmentation with the data published by “Başer
Library of Essential Oil Constituents” and Wiley GC/MS
Library, MassFinder 3 Library. The percentage of each com-
pound was determined depending on its relative response in
the FID chromatograms. Table1 shows a list of all identified
compounds, relative retention indices, and their percentage
Generally, the composition of the different essential oils
varied and the percentage of monoterpenes decreased upon
drying. The collected data shows the change in the percentage
of the monoterpenes and the sesquiterpenes content in each
chemotype due to drying.
On drying of CBD chemotype, it was observed that the
monoterpenes content of the volatile oil was higher in the oil of
the fresh material (58.7%) than in the dried one (46.5%) (Table2).
The oil of the fresh fiber type (CBD chemovar) was rich in
myrcene (27.5%) and limonene (14%). An obvious increase in the
caryophyllene oxide content from 3.4% to 10.3% along with a
10% reduction in the myrcene content from 27.5% to 17.1% and
a slight change of the limonene from 17% to 14% were the most
significant changes on drying.
An increase in the percentage of sesquiterpenes from 61.0%
to 71.6% and a reduction of monoterpene content from 33.7%
to 25.5% was observed as a result of drying the THC chemo-
type plant material (Table2). The volatile oil of the fresh drug
type showed significant content of β-caryophyllene and ter-
pinolene compared with the other 2 types. Terpinolene content
was shown to decrease upon drying ranging from 9.4% to
1.7%. Moderate increase in β-caryophyllene and caryophyllene
oxide was observed.
However, there was no detectable change in the percentage
of the monoterpenes and sesquiterpenes content of the oil of
the intermediate chemovar upon drying. Its freshly prepared
oil was rich in α-pinene, β-pinene, and limonene. The relative
concentration of these compounds only slightly changed on
drying. The chemical structures of the major components of
the essential oil of cannabis are shown in Figure1.
Biting deterrent activity of these volatile oils was deter-
mined by using K&D bioassay.17 All the essential oils showed
higher biting deterrence activity than the solvent control, etha-
nol. The biting deterrent activity of essential oil of MX-2- F,
VI-2- F, and A-17–2- F was similar to N,N- diethyl- meta-
toluamide (DEET), whereas the activity of all the other essen-
tial oils was significantly lower than DEET (Figure2). Biting
deterrent activity of MX-2- D and VI-2- D was similar to etha-
nol. The oil obtained from the fresh and dried CBD chemo-
type cannabis showed good biting deterrent activity at 10 ug/
cm2 compared with DEET at 4.78 ug/cm2. Biting deterrent
activity of the essential oils is given in Figure2.
Out of 6 essential oils tested in our screening bioassay, only
4 oils showed larvicidal activity against 1- day old Aedes aegypti
larvae, whereas the others were inactive at the maximum dose
of 125 ppm (Table3). The 50% lethal concentration (LC50)
values for these 4 oils ranged between 21.5 and 27.5 ppm.
Based on 95% confidence interval (CI), LC50 values of VI-2- D
and A-17-2- F were similar to VI-2- F, whereas these values were
significantly lower than A-17-2- F. However, these variations
among the essential oils are very small. These data suggest that
some compounds or their combinations were responsible for
this activity. Further studies should focus on the testing of the
pure compounds from these oils to identify the compounds
responsible for these insecticidal activities.
Indoor and outdoor C. sativa plants of 3 chemotypes (high
THC, THC/CBD, and high CBD) were grown at the University
of Mississippi. Outdoor grown plants were harvested in 2014
Wanas etal. 3
Table 1. The Chemical Composition of the Volatile Oils Prepared From Fresh and Dried Cannabis Samples.
Fiber type Intermediate type Drug type
RRI Compound V1-2- F V1-2- F (%) V1-2- D
1032 α-Pinene 2.2 4.0 15.4 15.6 3.6 6.0
1035 α-Thujene 0.1 0.2 0.2 0.2 0.2 0.3
1076 Camphene tr 0.1 0.3 0.3 0.1 0.2
1118 β-Pinene 1.5 2.1 7.8 7.5 2.3 3.5
1132 Sabinene 0.1 - - - 0.1 tr
1159 δ-3- Carene 0.3 - - - 0.3 0.3
1174 Myrcene 27.5 17.1 7.9 9.8 10.3 6.9
1188 α-Terpinene - - - - 0.2 -
1203 Limonene 14.0 17.0 33.0 27.1 1.2 1.9
1218 β-Phellandrene 0.6 0.2 0.1 0.2 0.6 0.4
1246 (Z)-β-Ocimene 0.2 tr 0.1 0.1 0.1 tr
1266 (E)-β-Ocimene 2.2 - 0.3 0.7 2.8 0.5
1280 p- Cymene 0.5 0.6 0.1 0.1 0.3 0.6
1290 Terpinolene 2.7 tr - 0.3 9.4 1.7
1429 Perillene tr 0.2 - - - -
1452 α,ρ-Dimethylstyrene 0.1 0.3 - - 0.2 tr
1474 trans- Sabinene hydrate 0.1 tr 0.1 0.1 tr tr
1477 4,8- Epoxyterpinolene 0.5 0.4 - 0.1 0.2 tr
1498 (E)- b- Ocimene epoxide 0.1 tr 0.1 - - -
1553 Linalool 0.3 0.3 1.0 0.9 0.6 0.8
1589 Isocaryophyllene 0.1 tr 0.2 0.2 0.2 tr
1594 trans-β-Bergamotene 0.5 0.9 0.3 0.3 0.6 0.7
1596 α-Guaiene 2.8 2.3 0.7 0.8 3.0 3.7
1611 Terpinen-4- ol 0.1 0.2 0.1 0.1 0.1 0.1
1612 β-Caryophyllene 7.6 6.2 6.6 9.0 16.5 20.7
1639 trans- p- Mentha-2,8- dien-1- ol 0.1 tr 0.2 tr - -
1650 γ-Elemene 0.1 tr 0.1 0.1 0.4 0.2
1661 Alloaromadendrene 0.1 0.2 - tr - -
1668 (Z)-β-Farnesene 0.4 0.4 0.2 0.4 0.7 0.7
1670 trans- Pinocarveol - - 0.2 0.1 - -
1687 α-Humulene 2.6 2.9 3.3 3.8 5.1 6.1
1688 Selina-4,11- diene 0.2 0.2 0.1 0.1 0.3 0.3
1704 γ-Muurolene - - 0.2 0.1 0.4 0.4
1706 α-Terpineol 0.6 0.8 0.9 0.9 0.3 0.3
1730 δ-Guaiene (=α-Bulnesene) 5.5 4.6 1.4 1.6 6.6 8.2
1740 Valencene - - 0.4 0.4 - -
1741 β-Bisabolene 0.9 1.0 tr -- 0.6 0.7
1742 β-Selinene 1.1 1.5 1.3 1.3 1.7 2.0
1744 α-Selinene 1.0 1.1 0.6 0.7 1.8 2.0
1747 Isoeremophilene 0.2 0.4 0.2 0.3 0.5 0.8
1751 Carvone - - 0.1 0.1 - -
1755 Bicyclogermacrene - - 0.2 - 0.2 0.3
1758 (E,E)-α-Farnesene 0.3 - - - 1.1 0.4
1773 δ-Cadinene 0.1 - - 0.1 0.2 tr
1776 γ-Cadinene 0.1 - - tr 0.2 tr
1785 7- epi-α-Selinene - - 0.2 0.2 - -
1784 (E)-α-Bisabolene 1.1 0.1 - 0.3 0.6 0.6
1796 Selina-3,7(11)- diene 4.1 3.7 2.5 3.0 9.1 13.2
1804 Myrtenol - - 0.1 0.1 - -
1830 2,6- Dimethyl-3(E),5(E),7 octatriene-2- ol 0.2 - 0.1 0.1 0.2 tr
1845 trans- Carveol 0.1 0.1 0.1 tr - -
1854 Germacrene- B 0.5 0.4 0.6 0.5 5.1 2.7
1864 p- Cymen-8- ol 1.6 2.5 0.1 0.2 0.5 1.6
Natural Product Communications
and indoor grown plants produced in 2017. Voucher speci-
mens from each variety were kept at the Coy Waller Laboratory,
University of Mississippi with codes CFP- MX, CFP- V1, and
CFP- A17 for high THC, high CBD, and THC/CBD, respec-
tively. Fresh mature buds of the 3 cannabis chemotypes were
harvested and divided into 2 equal parts of each chemotype.
One part of each kept fresh, while the other part air- dried at
room temperature for 1 week.
Preparation of the Volatile Oil
The volatile oil from each variety of fresh and dried plant
material was prepared by steam distillation using the Clevenger
apparatus. The terpene content of the prepared volatile oils
was determined by GC- FID analysis.
The GC- FID analysis was carried out using an Agilent 6890N
GC system, with the detector temperature set at 300°C. To
obtain the same elution order as with the GC–MS method,
simultaneous auto- injection was done on a duplicate of the
same column applying the same operational conditions.
Relative percentage amounts of the separated compounds
were calculated from the FID chromatograms. The analysis
results are given in Table1.
Identification of the essential oil components was carried
out by comparison of their relative retention times with those
of authentic samples or by comparison of their relative reten-
tion index (RRI) to a series of n- alkanes. Alternatively, com-
puter matching against commercial18,19 and in- house “Başer
Library of Essential Oil Constituents” built up by genuine
compounds and components of known oils, as well as MS lit-
erature data20,21 was also used for the identification.
The GC–MS analysis was carried out with an Agilent 5975 GC-
MSD system. Innowax FSC column (60 m × 0.25 mm internal
diameter and 0.25 μm film thickness) was used with helium as
carrier gas (0.8 mL/min). GC oven temperature was kept at
60°C for 10 minutes and programmed to 220°C at a rate of
4°C/min, and kept constant at 220°C for 10 minutes and then
programmed to 240°C at a rate of 1°C/min. Split ratio was
Fiber type Intermediate type Drug type
1882 cis- Carveol 0.1 0.2 0.2 0.1 - -
2001 Isocaryophyllene oxide 0.5 1.8 1.0 0.7 0.1 0.5
2008 Caryophyllene oxide 3.4 10.3 5.4 5.0 1.7 3.9
2030 Methyl eugenol 0.1 0.2 0.1 0.2 0.1 0.2
2045 Humulene epoxide- I 0.1 0.2 0.1 0.1 0.1 tr
2050 (E)- Nerolidol 0.3 0.7 0.4 0.5 0.5 0.3
2071 Humulene epoxide- II 0.9 3.0 1.8 1.6 0.4 0.8
2081 Humulene epoxide- III 0.3 1.9 tr 0.1 tr 0.2
2103 Guaiol - - - - 0.3 -
2127 10- epi−γ-Eudesmol - - - 0.3 -
2232 α-Bisabolol - 3.5 0.6 0.6 1.8 1.6
2250 α-Eudesmol - - - - 0.3 tr
2257 β-Eudesmol - - - - 0.3 tr
2269 Dimyrcene II- b - tr - - - -
2273 Porosadienol 0.3 0.5 - 0.4 0.6 0.4
2324 Caryophylla-2(12),6(13)- dien-5α-ol
0.2 0.3 0.2 0.2 0.3 tr
2389 Caryophylla-2(12),6- dien-5α-ol (=Caryophyllenol
- - - 0.2 0.3 -
2392 Caryophylla-2(12),6- dien-5β-ol (=Caryophyllenol
0.1 0.4 0.2 0.2 0.2 0.2
RRI, relative retention indices; tr, traces (<0.1%).
RRI calculated against n- alkanes. Percentage calculated from flame ionization detector data.
Table 1. Continued
Table 2. Monoterpenes and Sesquiterpenes Contents of Cannabis
Chemotype Monoterpenes (%) Sesquiterpenes (%)
V1-2- F 58.7 48.6
V1-2- D 46.5 35.6
A17-2- F 68.3 29.1
A17-2- D 64.3 32.8
MX-2- F 33.7 61.0
MX-2- D 25.5 71.6
Wanas etal. 5
adjusted at 40:1. The injector temperature was set at 250°C.
Mass spectra were recorded at 70 eV. Mass range was from m/z
Yellow fever mosquitoes used in these studies were from a lab-
oratory colony maintained at the Mosquito and Fly Research
Unit, Center for Medical, Agricultural and Veterinary
Entomology, USDA- ARS, Gainesville, Florida, since 1952.
Mosquitoes were reared to the adult stage by feeding the larvae
on a larval diet of 2% slurry of 3:2 Beef Liver powder (now
Foods, Bloomingdale, Illinois) and Brewer’s yeast (Lewis
Laboratories Ltd., Westport, CT, USA). The eggs were hatched
and the larvae reared to pupal stage in an environment con-
trolled room maintained at 27 ± 2°C and 60 ± 10% relative
humidity in a photoperiod regimen of 12:12 (L:D) hour. The
adult mosquitoes were maintained in the laboratory using the
procedures described by Ali et al.22
In Vitro K&D Bioassay
Bioassays were conducted using a 6- celled in vitro Klun and
Debboun (K&D) bioassay system.17 Briefly, the bioassay sys-
tem consists of 6 (3 × 4 cm) wells each of which contains
approximately 6 mL of the feeding solution. As described by
Ali et al,22 a feeding solution consisting of citrate phosphate
dextrose adenine (CPDA-1) and adenosine triphosphate (ATP)
was used instead of blood. All the compounds were tested in
this study, and DEET, 97%, N, N- diethyl- meta- toluamide
(Cas# 134–62-3, Sigma- Aldrich, St. Louis, MO, USA) at 25
nmol/cm2 was used as a positive control. All the treatments
were freshly prepared in molecular biology grade 100% etha-
nol. The temperature of the feeding solution in the reservoirs
Figure 1. Chemical structures of the major components of volatile oils of cannabis.
Natural Product Communications
was maintained at 37°C by using a circulatory bath. The reser-
voirs were covered with a layer of collagen membrane (Devro,
Sandy Run, SC, USA). The test samples were randomly applied
to 6 (4 × 5 cm) marked areas of organdy (A fine, thin cotton
fabric) and positioned over the membrane- covered CPDA-1 +
ATP solution. The K&D module containing 5 female mosqui-
toes per cell was positioned over treated organdy and trap
doors were opened to expose the treatments to the females.
The number of mosquitoes biting through treated organdy in
each cell was recorded after a 3- minute exposure and mosqui-
toes were prodded back into the cells to check the actual
feeding. A replicate consisted of 6 treatments: 4 test samples,
DEET, and ethanol- treated organdy as solvent control.
Treatments were replicated 5 times.
Bioassays were conducted using the bioassay system described
by Pridgeon et al.23 Further methods and statistical analyses
were done as previously described by Ali et al.22
Dimethylsulfoxide was used as a solvent to prepare the treat-
ments and was also used as a negative control. Permethrin
Figure 2. Mean bting deterrence index (BDI) values of essential oils of cannabis chemovars against Aedes aegypti. All the essential oils were
tested at 10 ug/cm2. Ethanol was the solvent control and N,N- diethyl- meta- toluamide (DEET) at 25 nmol/cm2 was used as positive control.
Means were separated by using Ryan–Einot–Gabriel–Welsch multiple range test (P ≤ 0.05).
Table 3. Toxicity of Essential Oils of Cannabis Chemovars Against 1- Day- Old Aedes Aegypti Larvae at 24 Hours Post- Treatment.
Essential oil LC50 (95% CI)LC90 (95% CI)χ2df
MX-2- F >125
MX-2- D >125
V1-2- F 23.3 (20.8-26.1) 38.9 (33.7-48.1) 61.3 48
V1-2- D 21.5 (19.1-24.2) 38.7 (33.2-48.5) 67.8 48
A-17-2- F 21.8 (19.3-24.6) 40.6 (34.6-51.2) 70.5 48
A-17-2- D 27.5 (24.7-30.5) 42.6 (37.3-52.1) 52.5 48
df, degree of freedom; CI, confidence interval; LC50, 50% lethal concentration; LC90, 90% lethal concentration.
LC50 and LC90 values are in ppm.
aPositive standard, purity 46.1% and 53.2% for cis and trans, respectively.
Wanas etal. 7
(95.7%) (Chem Service, Inc. West Chester, PA, USA) was used
as a positive control.
Proportion not biting (PNB) was calculated using the proce-
dure described by Ali et al.22
PNB = 1
−(Total number of females biting
Total number of females )
Data on the PNB were analyzed using SAS Proc ANOVA
(SAS Institute, Inc., Carry, NC, USA, 2007) and means were
separated using Ryan–Einot–Gabriel–Welsch multiple range
test. LC50 values for larvicidal data were calculated by using
SAS, Proc Probit.
Declaration of Conf licting Interests
The author(s) declared no potential conflicts of interest with respect
to the research, authorship, and/or publication of this article.
The author(s) disclosed receipt of the following financial support
for the research, authorship, and/or publication of this article: this
work was supported in part by the National Institute on Drug Abuse,
contract # N01DA-15-7793.
Mahmoud A. ElSohly https:// orcid. org/ 0000- 0002- 0019- 2001
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