Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Molecules. 2018 Mar 4;23(3):576. doi: 10.3390/molecules23030576.

GC-MS Analysis of the Composition of the Essential Oil from Dendranthema indicum 
Var. Aromaticum Using Three Extraction Methods and Two Columns.

Fan S(1), Chang J(2), Zong Y(3), Hu G(4), Jia J(5).

Author information:
(1)School of Traditional Chinese MateriaMedica, Shenyang Pharmaceutical 
University, Shenyang 110016, China. threehedgehod@163.com.
(2)Fushun Drug Inspection and Testing Center, Fushun 113006, China. 
clikeshell@163.com.
(3)School of Traditional Chinese MateriaMedica, Shenyang Pharmaceutical 
University, Shenyang 110016, China. zongyufeng28@126.com.
(4)School of Traditional Chinese MateriaMedica, Shenyang Pharmaceutical 
University, Shenyang 110016, China. hugsh_2011@163.com.
(5)School of Traditional Chinese MateriaMedica, Shenyang Pharmaceutical 
University, Shenyang 110016, China. jiajingming@163.com.

Dendranthema indicum var. aromaticum, which is an aromatic plant with a strong 
and special fragrance throughout the whole plant, is used for the treatment of 
colds and headaches, and as a mosquito repellant in Shennongjia, Hubei province, 
China. To analyze the composition of the essential oil from this medicinal herb, 
we developed a gas chromatography-mass Spectrometry (GC-MS) method including 
microwave-assisted extraction, hydrodistillation and direct headspace analysis 
in two different stationary phase columns. In total, 115 volatile compounds were 
identified, of which 90 compounds were identified using Rxi-5MS and 78 using 
HP-INNOWAX. Our results revealed that the oil was mainly composed of five 
categories of compound: oxygenated monoterpenes (28.76-78.10%), oxygenated 
sesquiterpenes (4.27-38.06%), sesquiterpenes (3.22-11.57%), fatty hydrocarbons 
(1.65-9.81%) and monoterpenes (0-3.32%). The major constituents are α-thujone, 
β-thujone, cis-sabinol, sabinyl acetate and (-)-neointermedeol.However, the 
essential oil composition in the published literature differs significantly. 
Therefore, a cluster analysis was carried out using the top ten compositions in 
the reported literature as well as this study, using Minitab software. To 
provide detailed information on plant origin, the ITS1-5.8s-ITS2 region was 
amplified and sequenced (Accession No. MF668250). Besides, in order to provide a 
macroscopic view of the chemical composition, the biosynthetic pathway of the 
main components was summarized according to the Kyoto Encyclopedia of Genes and 
Genomes (KEGG) database and the published literatures.

DOI: 10.3390/molecules23030576
PMCID: PMC6017652
PMID: 29510531 [Indexed for MEDLINE]

Conflict of interest statement: The authors declare no conflict of interest.


2. Environ Sci Pollut Res Int. 2018 Mar;25(7):6466-6473. doi: 
10.1007/s11356-017-0822-4. Epub 2017 Dec 17.

Nanoemulsion of Dill essential oil as a green and potent larvicide against 
Anopheles stephensi.

Osanloo M(1), Sereshti H(2), Sedaghat MM(3), Amani A(4)(5).

Author information:
(1)Department of Medical Nanotechnology, School of Advanced Technologies in 
Medicine, Tehran University of Medical Sciences, Tehran, Iran.
(2)Department of Chemistry, Faculty of Science, University of Tehran, Tehran, 
Iran.
(3)Department of Medical Entomology and Vector Control, School of Public Health, 
Tehran University of Medical Sciences, Tehran, Iran.
(4)Department of Medical Nanotechnology, School of Advanced Technologies in 
Medicine, Tehran University of Medical Sciences, Tehran, Iran. 
aamani@tums.ac.ir.
(5)Medical Biomaterials research Center (MBRC), Tehran University of Medical 
Sciences, Tehran, Iran. aamani@tums.ac.ir.

Indiscriminate use of industrial larvicides causes environment pollution and 
resistance against the larvicides in mosquitoes. Essential oils (EOs) have many 
biological activities such as larvicidal effects which have been proposed as new 
alternatives for industrial ones. Many components of EOs are volatile, thus, 
should be formulated to retain their activity. Components of Dill EO were 
identified by GC-MS analysis. Larvicidal activity (LA) of bulk Dill EO 
(non-formulated) was evaluated against Anopheles stephensi in line with WHO 
guideline for lab tests. For the first time, nanoemulsions of Dill EO were 
prepared. Various nanoemulsions having fixed amounts of Dill EO 1.2%, comparable 
with lethal concentration (LC) at 90% of bulk Dill EO, were prepared having 
tween 20 (5-30%) with/out ethanol (5-30%). LA of two selected nanoemulsions were 
then evaluated and compared with that of bulk Dill EO. Five ingredients of oil, 
with high amounts, were identified as p-Cymenealpha (20.81%), alpha-Phellandrene 
(20.75%), Carvone (10.97%), Dill ether (9.88%), and cis-Sabinol (3.61%). LC of 
Dill EO at 50 and 90% were found as 38.8 and 65 ppm, respectively, against 3rd 
and 4th instar larvae of An. stephensi (Beech-Lab strain). Particle size (PS) 
ranges of nanoemulsions were 10.7-1880.0 nm. LA of optimum nanoemulsion (PS: 
10.7 nm) was significantly better than that of bulk Dill EO. The preparation 
showed stability against 200 times dilution during larvicidal tests and 
performed significantly better than the nanoemulsion which was not stable after 
dilution. To obtain improved efficiency against larvae using nanoemulsions of 
EOs, the nanoemulsion should be resistant against dilution. Such a stable and 
green nanoemulsion may be used as alternative to industrial larvicides.

DOI: 10.1007/s11356-017-0822-4
PMID: 29250730 [Indexed for MEDLINE]


3. J Sep Sci. 2014 Apr;37(8):990-6. doi: 10.1002/jssc.201301355. Epub 2014 Mar
13.

Rapid analysis of Origanum majorana L. fragrance using a nanofiber sheet, gas 
chromatography with mass spectrometry, and chemometrics.

Asadollahi-Baboli M(1), Aghakhani A.

Author information:
(1)Department of Science, Babol University of Technology, Babol, Mazandaran, 
Iran.

Headspace nanofiber sheet microextraction together with GC-MS and chemometrics 
resolution techniques were implemented to separate and identify the volatiles 
emitted by intact marjoram (Origanum majorana L.) and their relative 
concentrations. A novel polyaniline-nylon-6 nanofiber composite was applied for 
headspace microextraction. Characteristics such as high surface-to-volume ratio 
and π-π functional groups in polyaniline together with the NH and C=O functional 
groups in nylon-6 make the polyaniline-nylon-6 nanofiber composite a suitable 
candidate for the extraction of volatiles and semivolatiles. The extracted 
constituents were desorbed and injected into the GC-MS system under the optimum 
conditions. Chemometric resolution techniques were utilized to solve the 
baseline offset, asymmetric peaks, and overlapped peaks problems that arise from 
GC-MS analysis. By means of these techniques and resolving the overlapped peak 
clusters, the number of identified constituents was increased to 67 compounds. 
The major released constituents from the intact marjoram leaves are 4-terpineol, 
β-linalool, cis-sabinol, and trans-geraniol.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI: 10.1002/jssc.201301355
PMID: 24520037 [Indexed for MEDLINE]


4. Arch Biochem Biophys. 1987 Oct;258(1):287-91. doi:
10.1016/0003-9861(87)90346-8.

Metabolism of monoterpenes: specificity of the dehydrogenases responsible for 
the biosynthesis of camphor, 3-thujone, and 3-isothujone.

Dehal SS(1), Croteau R.

Author information:
(1)Institute of Biological Chemistry, Washington State University, Pullman 
99164-6340.

Sage (Salvia officinalis) is shown to contain two electrophoretically distinct 
dehydrogenases for the respective oxidations of (+)-borneol to (+)-camphor, and 
of (+)-cis-sabinol to (+)-sabinone en route to (-)-3-isothujone. Similarly, 
tansy (Tanacetum vulgare) is shown to contain two electrophoretically distinct 
dehydrogenases for the respective oxidations of (-)-borneol to (-)-camphor and 
of (+)-cis-sabinol to (+)-sabinone en route to (+)-3-thujone. These results 
demonstrate that separate dehydrogenases are responsible for the biosynthesis of 
camphor from borneol and of the thujyl ketones via cis-sabinol, and they also 
indicate that the previously reported oxidations of various thujanols by the 
borneol dehydrogenases are only coincidental activities not relevant to the 
formation of 3-thujone and 3-isothujone.

DOI: 10.1016/0003-9861(87)90346-8
PMID: 3310901 [Indexed for MEDLINE]


5. Arch Biochem Biophys. 1987 Jul;256(1):179-93. doi:
10.1016/0003-9861(87)90436-x.

Metabolism of monoterpenes: demonstration of the hydroxylation of (+)-sabinene 
to (+)-cis-sabinol by an enzyme preparation from sage (Salvia officinalis) 
leaves.

Karp F, Harris JL, Croteau R.

A microsomal preparation from the epidermis of Salvia officinalis leaves 
catalyzed the NADPH- and O2-dependent hydroxylation of the monoterpene olefin 
(+)-sabinene to (+)-cis-sabinol. The reaction catalyzed is a key step in the 
biosynthesis of C3-oxygenated thujane monoterpenes, and the hydroxylase is 
highly specific for (+)-sabinene as substrate. The hydroxylase from leaf 
homogenates was solubilized and characterized with regard to reaction 
conditions, inhibitors, and activators. Activity was partially inhibited by 
rabbit anti-rat cytochrome P-450 and by CO, and the latter inhibition was 
reversed by 450 nm light. A CO-difference spectrum and type I substrate binding 
spectrum were obtained. The hydroxylase meets most of the established criteria 
for a cytochrome P-450-dependent mixed function oxygenase and represents one of 
very few enzyme systems of this type to be isolated from leaves of a higher 
plant.

DOI: 10.1016/0003-9861(87)90436-x
PMID: 3111374 [Indexed for MEDLINE]