Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. J Sci Food Agric. 2023 Aug 30;103(11):5353-5363. doi: 10.1002/jsfa.12609. Epub
 2023 Apr 21.

Contribution of terpenes, methanethiol, and fermentative esters to sparkling 
wine aroma in relation to production technology, vintage, and aging: a case 
study on Durello wines.

Luzzini G(1), Slaghenaufi D(1), Facinelli D(1), Ugliano M(1).

Author information:
(1)Department of Biotechnology, University of Verona, Verona, Italy.

BACKGROUND: The present study aimed to assess the chemical and sensory 
variability existing across sparkling white wines of a single appellation in 
relation to production technique and aging, identifying the existence of 
specific aroma chemical and sensory (odor) signatures. For this purpose, we 
selected Durello, an emerging sparkling white wine from the Veneto region 
produced using either Charmat or Classico methods.
RESULTS: Comparison of Durello varietal volatiles profile with other Italian 
sparkling and still wines highlighted specific features of Durello, such as high 
content of 1,4-cineole and non-megastigmane norisoprenoids. The production 
technique (Charmat or Champenoise) impacted both the volatile chemical profile, 
influencing the content of esters, fatty acids, cyclic terpenoids, C6 alcohols, 
β-damascenone and methanethiol. With regard to wine age and vintage, an 
influence on esters, p-menthane-1,8-diol, cineoles and methyl salicylate was 
observed.
CONCLUSION: Sensory evaluation by means of a sorting task approach indicated the 
existence of two main types of odor profile, one clearly associated with 
Classico method. The main drivers of such aroma diversity were esters, 
1,4-cineole and methanethiol. © 2023 The Authors. Journal of The Science of Food 
and Agriculture published by John Wiley & Sons Ltd on behalf of Society of 
Chemical Industry.

© 2023 The Authors. Journal of The Science of Food and Agriculture published by 
John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

DOI: 10.1002/jsfa.12609
PMID: 37024446 [Indexed for MEDLINE]


2. J Pestic Sci. 2023 Feb 20;48(1):11-16. doi: 10.1584/jpestics.D22-051.

Synthesis and herbicidal activity of optically active cinmethylin, its 
enantiomer, and C3-substituted cinmethylin analogs.

Ogawa N(1), Toyoshima S(1), Sekikawa S(1), Ishijima M(1), Katagiri K(1), Uematsu 
C(1), Hirano T(2), Ootaka A(2), Suzuki J(2).

Author information:
(1)Department of Applied Chemistry, Meiji University.
(2)Hokko Chemical Industry Co., Ltd.

We investigated the synthesis and herbicidal activity of optically active 
cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs. Optically 
active cinmethylin could be obtained in seven steps with the Sharpless 
asymmetric dihydroxylation of α-terpinene. The synthesized cinmethylin and its 
enantiomer showed similar herbicidal activity, which was independent of the 
stereochemistry. Next, we synthesized cinmethylin analogs with various 
substituents at the C3 position. We found that analogs with methylene, oxime, 
ketone, or methyl groups at the C3 position show excellent herbicidal activity.

© 2023 Pesticide Science Society of Japan.

DOI: 10.1584/jpestics.D22-051
PMCID: PMC9978247
PMID: 36874636


3. Commun Chem. 2022 Sep 27;5(1):113. doi: 10.1038/s42004-022-00725-0.

Solvent-free dehydration, cyclization, and hydrogenation of linalool with a dual 
heterogeneous catalyst system to generate a high-performance sustainable 
aviation fuel.

Keller CL(1), Doppalapudi KR(1), Woodroffe JD(1), Harvey BG(2).

Author information:
(1)Research Department, Chemistry Division, US NAVY, NAWCWD, China Lake, CA, 
93555, USA.
(2)Research Department, Chemistry Division, US NAVY, NAWCWD, China Lake, CA, 
93555, USA. benjamin.g.harvey.civ@us.navy.mil.

The development of efficient catalytic methods for the synthesis of bio-based, 
full-performance jet fuels is critical for limiting the impacts of climate 
change while enabling a thriving modern society. To help address this need, 
here, linalool, a terpene alcohol that can be produced via fermentation of 
biomass sugars, was dehydrated, cyclized, and hydrogenated in a one-pot reaction 
under moderate reaction conditions. This sequence produced a biosynthetic fuel 
mixture primarily composed of 1-methyl-4-isopropylcyclohexane (p-menthane) and 
2,6-dimethyloctane (DMO). The reaction was promoted by a catalyst composed of 
commercial Amberlyst-15, H+ form, and 10% Pd/C. Two other terpenoid substrates 
(1,8-cineole and 1,4-cineole) were subjected to the same conditions and 
excellent conversion to high purity p-menthane was observed. The fuel mixture 
derived from linalool exhibits a 1.7% higher gravimetric heat of combustion and 
66% lower kinematic viscosity at -20 °C compared to the limits for conventional 
jet fuel. These properties suggest that isomerized hydrogenated linalool (IHL) 
can be blended with conventional jet fuel or synthetic paraffinic kerosenes to 
deliver high-performance sustainable aviation fuels for commercial and military 
applications.

© 2022. This is a U.S. Government work and not under copyright protection in the 
US; foreign copyright protection may apply.

DOI: 10.1038/s42004-022-00725-0
PMCID: PMC9814387
PMID: 36697844

Conflict of interest statement: A provisional patent describing methods for the 
conversion of linalool into jet fuel blendstocks has been filed. B.G.H., C.L.K., 
and K.R.D. are listed as inventors. J.D.W. declares no competing interests.


4. J Agric Food Chem. 2021 May 19;69(19):5491-5499. doi:
10.1021/acs.jafc.1c01321.  Epub 2021 May 11.

Selective β-Mono-Glycosylation of a C15-Hydroxylated Metabolite of the 
Agricultural Herbicide Cinmethylin Using Leloir Glycosyltransferases.

Jung J(1), Schmölzer K(1), Schachtschabel D(2), Speitling M(2), Nidetzky 
B(1)(3).

Author information:
(1)Austrian Centre of Industrial Biotechnology, Graz A-8010, Austria.
(2)BASF SE, Carl-Bosch-Strasse 38, Ludwigschafen 67056, Germany.
(3)Institute of Biotechnology and Biochemical Engineering, NAWI Graz, TU Graz, 
Graz A-8010, Austria.

Cinmethylin is a well-known benzyl-ether derivative of the natural terpene 
1,4-cineole that is used industrially as a pre-emergence herbicide in grass weed 
control for crop protection. Cinmethylin detoxification in plants has not been 
reported, but in animals, it prominently involves hydroxylation at the benzylic 
C15 methyl group. Here, we show enzymatic β-glycosylation of synthetic 
15-hydroxy-cinmethylin to prepare a putative phase II detoxification metabolite 
of the cinmethylin in plants. We examined eight Leloir glycosyltransferases for 
reactivity with 15-hydroxy cinmethylin and revealed the selective formation of 
15-hydroxy cinmethylin β-d-glucoside from uridine 5'-diphosphate (UDP)-glucose 
by the UGT71E5 from safflower (Carthamus tinctorius). The UGT71E5 showed a 
specific activity of 431 mU/mg, about 300-fold higher than that of apple (Malus 
domestica) UGT71A15 that also performed the desired 15-hydroxy cinmethylin 
mono-glycosylation. Bacterial glycosyltransferases (OleD from Streptomyces 
antibioticus, 2.9 mU/mg; GT1 from Bacillus cereus, 60 mU/mg) produced mixtures 
of 15-hydroxy cinmethylin mono- and disaccharide glycosides. Using UDP-glucose 
recycling with sucrose synthase, 15-hydroxy cinmethylin conversion with UGT71E5 
efficiently provided the β-mono-glucoside (≥95% yield; ∼9 mM) suitable for 
biological studies.

DOI: 10.1021/acs.jafc.1c01321
PMCID: PMC8278484
PMID: 33973475 [Indexed for MEDLINE]

Conflict of interest statement: The authors declare no competing financial 
interest.


5. J Ethnopharmacol. 2021 Oct 28;279:113627. doi: 10.1016/j.jep.2020.113627. Epub
 2020 Nov 25.

Sedative and hypnotic effects of Perilla frutescens essential oil through 
GABAergic system pathway.

Zhong Y(1), Zheng Q(2), Hu P(1), Huang X(1), Yang M(3), Ren G(4), Li J(1), Du 
Q(1), Liu S(1), Zhang K(1), Wu L(1), Zhu L(1), Guo Y(1), Li W(1), Xiao S(1), 
Shuai S(1), Zhang M(1).

Author information:
(1)Key Laboratory of Modern Preparation of Traditional Chinese Medicine, 
Ministry of Education, State Key Lab.of Innovation Drug and Effcient 
Energy-Saving Pharmaceutical Equipment, Jiangxi University of Traditional 
Chinese Medicine, Nanchang, 330004, China.
(2)Key Laboratory of Modern Preparation of Traditional Chinese Medicine, 
Ministry of Education, State Key Lab.of Innovation Drug and Effcient 
Energy-Saving Pharmaceutical Equipment, Jiangxi University of Traditional 
Chinese Medicine, Nanchang, 330004, China. Electronic address: 
zhengqin912006@163.com.
(3)Key Laboratory of Modern Preparation of Traditional Chinese Medicine, 
Ministry of Education, State Key Lab.of Innovation Drug and Effcient 
Energy-Saving Pharmaceutical Equipment, Jiangxi University of Traditional 
Chinese Medicine, Nanchang, 330004, China. Electronic address: 
yangming16@126.com.
(4)Traditional Chinese Medicine Hospital Affliated to Southwest Medical 
University, Luzhou, 646000, China.

ETHNOPHARMACOLOGICAL RELEVANCE: Traditional Chinese medicine believes that 
depression syndrome has become one of the core pathogenesis of insomnia. The 
pharmacology of traditional Chinese medicine points out that Perilla frutescens 
has the effect of regulating Qi and relieving depression, promoting Qi 
circulation to relieve pain, so Perilla frutescens may have the potential 
therapeutic effect on insomnia. Related studies have reported the sedative and 
hypnotic effects of Perilla frutescens, but these studies have not yet explored 
the mechanism of sedative and hypnotic effects of Perilla frutescens essential 
oil (PFEO) through inhalation administration.
AIM OF THE STUDY: The purpose of this study is to explore the underlying 
sedative and hypnotic mechanisms of PFEO through the GABAergic system pathways.
MATERIALS AND METHODS: Established the PCPA insomnia model of mice, The open 
field test, pentobarbital-induced falling asleep rate, latency of sleeping time, 
and duration of sleeping time experiments were used to evaluate the behavior of 
mice, the enzyme-linked immunosorbent assay was used to analyze the content of 
5-HT and GABA in hypothalamus and cerebral cortex. Immunohistochemical 
experiment, Western blot experiment and RT-PCR experiment were used to study the 
mechanism of PFEO through GABAergic pathway to regulate insomnia. The main 
volatile constituents of PFEO were analyzed by gas chromatography-mass 
spectrometry (GC-MS).
RESULTS: The inhalation of PFEO has sedative and hypnotic effects, which reduce 
significantly the autonomic activity of PCPA insomnia mice, increase falling 
asleep rate, shorten latency of sleeping time, and prolong duration of sleeping 
time; the results of enzyme-linked immunosorbent assay show that PFEO increase 
the content of 5-HT and GABA in hypothalamus and cerebral cortex. The results 
showed that inhalation of PFEO increase the expression of GABAAα1 and GABAAα2 
positive cells, increase the level of GABAAα1 and GABAAα2 protein and also 
increase the level of GABAAα1 mRNA and GABAAα2 mRNA in the hypothalamus and 
cerebral cortex. The highest content of PFEO is Perillaldehyde (54.37%), 
followed by 1,4-Cineole (7.42%), Acetaldehyde diethyl acetal (6.61%), D-Limonene 
(5.09%), Eucalyptol (4.94%), etc. CONCLUSION: The inhalation of PFEO has 
sedative and hypnotic effects, it is speculated that the mechanism of which may 
be the sedative and hypnotic effects through the GABAergic pathway.

Copyright © 2020 Elsevier B.V. All rights reserved.

DOI: 10.1016/j.jep.2020.113627
PMID: 33246117 [Indexed for MEDLINE]