Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Sci Rep. 2024 Oct 28;14(1):25791. doi: 10.1038/s41598-024-74972-7.

Optimizing the extraction of essential oil yield from Pistacia lentiscus 
oleo-gum resin by superheated steam extraction using response surface 
methodology.

Ayub MA(1), Iram I(2), Waseem R(2), Ayub I(3), Hussain A(4), Abid MA(2), Iqbal 
SZ(5).

Author information:
(1)Department of Chemistry, University of Sahiwal, Sahiwal, 57000, Pakistan. 
adnanayub@uosahiwal.edu.pk.
(2)Department of Chemistry, University of Sahiwal, Sahiwal, 57000, Pakistan.
(3)Department of Zoology, Government College University Faisalabad, Faisalabad, 
38000, Pakistan.
(4)Institute of Chemistry, University of Okara, Okara, Punjab, 56300, Pakistan.
(5)Food Safety and Food Toxicology Lab, Department of Applied Chemistry, 
Government College University Faisalabad, Faisalabad, 38000, Pakistan.

Pistacia lentiscus L. is an aromatic plant containing a significant percentage 
of essential oil (EO) used in fragrance, pharmaceuticals, cosmetics, and the 
food industry. The purpose of this work is focused on the optimization of 
Pistacia lentiscus L. oleo gum resin EO yield extracted by superheated steam 
extraction (SHSE) by response surface methodology, including extraction 
parameters of particle size (0. 5 - 1 mm), temperature (140-180 °C) and time 
(90-150 min). The optimum conditions for Pistacia lentiscus L. EO extracted by 
SHSE were found to be (particle size: 0.75 mm, time: 120 min and temperature: 
160 ℃) which produced the highest EO yield of 5.7%. A regression model was 
developed, demonstrating a robust quadratic correlation with an R2 value of 
0.9991, making it suitable for predictions. Furthermore, the yield of Pistacia 
lentiscus L. EO extracted by SHSE was compared with the conventional steam and 
hydro distillation techniques. The study revealed that SHSE yielded higher 
quantities of EO than other extraction methods. GC-MS analyzed the chemical 
composition of Pistacia lentiscus L. EO. The predominant compound of Pistacia 
lentiscus L. EO was determined to be α-pinene, while the other identified 
compounds include trans-verbenol, verbenol, cis-verbenone, camphene, β-myrcene, 
d-limonene, cymene, α-myrtenol, α-campholenal, α-copaene, and α-thujene, whose 
content differed according to different extraction techniques. Overall, 
superheated steam extraction is an efficient technique for extracting Pistacia 
lentiscus L. essential oil that enhances EO yield, requiring less time for 
extraction.

© 2024. The Author(s).

DOI: 10.1038/s41598-024-74972-7
PMCID: PMC11519484
PMID: 39468086 [Indexed for MEDLINE]

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


2. Int J Biol Macromol. 2024 Oct 3;281(Pt 2):136202. doi: 
10.1016/j.ijbiomac.2024.136202. Online ahead of print.

Molecular and biochemical basis of interspecific variations in the 
organ-specific synthesis of floral terpenes between the domesticated cultivars 
and their wild relatives in Chrysanthemum.

Zhang W(1), Zhu Z(2), Li G(2), Chen S(3), Chen F(3), Chen F(4), Jiang Y(5).

Author information:
(1)Key Laboratory of Landscaping, Ministry of Agriculture and Rural Affairs, Key 
Laboratory of Biology of Ornamental Plants in East China, National Forestry and 
Grassland Administration, College of Horticulture, Nanjing Agricultural 
University, Nanjing 210095, China; National and Local Joint Engineering Research 
Center of Ecological Treatment Technology for Urban Water Pollution, College of 
Life and Environmental Science, Wenzhou University, Wenzhou 325035, China.
(2)Key Laboratory of Ministry of Education for Medicinal Plant Resource and 
Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource 
Development of Endangered Crude Drugs in Northwest China, College of Life 
Sciences, Shaanxi Normal University, Xi'an 710119, China.
(3)Key Laboratory of Landscaping, Ministry of Agriculture and Rural Affairs, Key 
Laboratory of Biology of Ornamental Plants in East China, National Forestry and 
Grassland Administration, College of Horticulture, Nanjing Agricultural 
University, Nanjing 210095, China.
(4)Department of Plant Sciences, University of Tennessee, Knoxville, TN 37996, 
USA.
(5)Key Laboratory of Landscaping, Ministry of Agriculture and Rural Affairs, Key 
Laboratory of Biology of Ornamental Plants in East China, National Forestry and 
Grassland Administration, College of Horticulture, Nanjing Agricultural 
University, Nanjing 210095, China. Electronic address: jiangyifan@njau.edu.cn.

Terpenoids, as the main components of the floral scent, exhibit interspecific 
variations and spatial specificity in Chrysanthemum genus. Here, we selected two 
primary species as the ancestors of C. morifolium along with two classic 
cultivars to investigate the influence of domestication on the variations in 
emission and production of floral terpenoids. The results indicated that the 
wild relatives emitted and accumulated higher levels of terpenoids in their disc 
florets and phyllaries & receptacles compared to the cultivars. Six gene modules 
associated with terpenoid production in three floral organs were characterized 
through WGCNA. Furthermore, 28 terpene synthase (TPS) genes were identified from 
both wild relatives and cultivars by comparative transcriptome database. In 
vitro enzymatic activity assay revealed that several products of monoterpenoids 
(α-pinene and α-terpinene) and sesquiterpenoids (β-farnesene, α-copaene and 
γ-curcumene), were commonly catalyzed by TPSs identified from wild relatives and 
cultivars. Nevertheless, we found that β-myrcene, β-elemene, β-cadinene and 
β-caryophyllene were predominantly produced by TPSs in the wild relatives, while 
d-limonene and β-copaene were specifically catalyzed by TPSs in the cultivars. 
It was also observed that the expression of the CiLSTPS3 gene could be 
associated with the emission and accumulation of β-caryophyllene in floral 
scent. Overall, the complex biochemical functions of TPSs, along with their 
varying expression patterns, significantly contribute to the interspecific 
variations of floral terpenoids in the Chrysanthemum genus. Our findings provide 
new insights into the molecular and biochemical mechanisms underlying the impact 
of domestication on the production of floral terpenoids in Chrysanthemum.

Copyright © 2024 Elsevier B.V. All rights reserved.

DOI: 10.1016/j.ijbiomac.2024.136202
PMID: 39366608

Conflict of interest statement: Declaration of competing interest The authors 
declare that they have no competing financial interests or personal 
relationships that could have appeared to influence the work reported in this 
paper.


3. Molecules. 2024 Aug 24;29(17):4008. doi: 10.3390/molecules29174008.

Wild Pepper (Piper laetispicum) Fruit Quality Traits at Different Developmental 
Stages.

Zhao Z(1)(2), Fang Y(1), Zhang D(2), Wang J(3), Huang Y(2), Hao C(3)(4), Fan 
R(1).

Author information:
(1)Tropical Croups Genetic Resources, Chinese Academy of Tropical Agricultural 
Science (CATAS), Haikou 571101, China.
(2)College of Tropical Crops, Yunnan Agricultural University, Pu'er 665099, 
China.
(3)Spice and Beverage Research Institute, Chinese Academy of Tropical 
Agricultural Science (CATAS), Wanning 571533, China.
(4)Key Laboratory of Genetic Resources Utilization of Spice and Beverage Crops, 
Ministry of Agriculture, Wanning 571533, China.

High-quality Piper laetispicum (Piper laetispicum C. DC) is the key to the 
development of foods, natural medicines, and cosmetics. Its crude fat, ash, 
piperine, protein, and aroma compounds were determined in this experiment. 
Principal component (PCA) and hierarchical cluster analyses (HCA) were used to 
evaluate the aroma compounds at different developmental stages. The main aroma 
compounds identified using steam distillation combined with GC-MS were sabinene 
(34.83-76.14%), α-copaene (5.11-19.51%), linalool (2.42-15.70%), 
trans-caryophyllene (2.37-6.57%), α-pinene (1.51-4.31%), and germacrene D 
(1.30-4.10%). The aroma metabolites at different developmental stages were 
analysed using non-targeted metabolomes, and linalool was found to be the most 
abundant. Based on the experimental results, there were more nutrient compounds 
in young Piper laetispicum than in the last three developmental stages. The 
aromatic metabolites contributed the most to PC1. There were also more different 
metabolites of aroma between the young and expanding stages. Therefore, 
regarding quality, young fruits have great potential.

DOI: 10.3390/molecules29174008
PMCID: PMC11396435
PMID: 39274856 [Indexed for MEDLINE]

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


4. Plants (Basel). 2024 Aug 25;13(17):2367. doi: 10.3390/plants13172367.

Analysis of the Volatile and Enantiomeric Compounds Emitted by Plumeria rubra L. 
Flowers Using HS-SPME-GC.

Calva J(1), Celi J(2), Benítez Á(3).

Author information:
(1)Departamento de Química, Universidad Técnica Particular de Loja, Loja 
1101608, Ecuador.
(2)Carrera de Bioquímica y Farmacia, Universidad Técnica Particular de Loja, 
Loja 1101608, Ecuador.
(3)Biodiversidad de Ecosistemas Tropicales-BIETROP, Herbario HUTPL, Departamento 
de Ciencias Biológicas y Agropecuarias, Universidad Técnica Particular de Loja 
(UTPL), San Cayetano s/n, Loja 1101608, Ecuador.

The volatile components emitted by fresh aromatic flowers of Plumeria rubra L., 
harvested in southern Ecuador during three different months were determined to 
evaluate the fluctuation of secondary metabolites. The volatile compounds were 
analyzed using headspace solid-phase microextraction (HS-SPME) followed by gas 
chromatography coupled to mass spectrometry (GC-MS) and a flame ionization 
detector (GC-FID) using two types of columns: a non-polar (DB-5ms) and polar 
column (HP-INNOWax). The principal chemical groups were hydrocarbon 
sesquiterpenes (43.5%; 40.0%), oxygenated sesquiterpenes (23.4%; 26.4%), 
oxygenated monoterpenes (14.0%; 11.2%), and hydrocarbon monoterpenes (12.7%; 
9.3%). The most representative constituents were (E,E)-α-Farnesene (40.9-41.2%; 
38.5-50.6%), (E)-nerolidol (21.4-32.6%; 23.2-33.0%), (E)-β-ocimene (4.2-12.5%; 
4.5-9.1%), (Z)-dihydro-apofarnesol (6.5-9.9%; 7.6-8.6%), linalool (5.6-8.3%; 
3.3-7.8%), and perillene (3.1-5.9%; 3.0-3.2%) in DB-5ms and HP-INNOWax, 
respectively. Finally, we reported for the first time the enantiomeric 
distribution of P. rubra flowers, where the enantiomers (1R,5R)-(+)-α-pinene, 
(S)-(-)-limonene, (S)-(+)-Linalool, and (1S,2R,6R,7R,8R)-(+)-α-copaene were 
present as enantiomerically pure substances, whereas (S)-(+)-(E)-Nerolidol and 
(R)-(+)-(E)-Nerolidol were observed as scalemic mixtures. This study provides 
the first comprehensive and comparative aroma profile of Plumeria rubra 
cultivated in southern Ecuador and gave us a clue to the variability of P. rubra 
chemotypes depending on the harvesting time, which could be used for future 
quality control or applications in phytopharmaceutical and food industries.

DOI: 10.3390/plants13172367
PMCID: PMC11397236
PMID: 39273851

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


5. J Nat Prod. 2024 Sep 27;87(9):2302-2309. doi: 10.1021/acs.jnatprod.4c00758.
Epub  2024 Aug 28.

Stereoselective Oxidation of α-Copaene, a Fire Ant Repellent Sesquiterpene from 
the Essential Oil of Dipterocarpus turbinatus.

George G(1), Shah FM(1), Ali A(1), Guddeti DK(1), Alowaifi N(1), Lee J(1), Chen 
J(2), Khan IA(1)(3), Li XC(1)(3).

Author information:
(1)National Center for Natural Products Research, Research Institute of 
Pharmaceutical Sciences, The University of Mississippi, University, Mississippi 
38677, United States.
(2)Biological Control of Pests Research Unit, USDA-ARS, Stoneville, Mississippi 
38776, United States.
(3)Department of Bio-Molecular Sciences, School of Pharmacy, The University of 
Mississippi, University, Mississippi 38677, United States.

Imported fire ants are significant agricultural pests. Repellents can be used to 
prevent foraging fire ants from entering sensitive areas, including electrical 
equipment, nursing homes, and hospitals. Bioassay-guided fractionation of the 
essential oil extracted from gurjun balsam (Dipterocarpus turbinatus) resulted 
in the identification of (-)-α-copaene (1) as the repellent constituent with a 
minimum repellent effective dose (MRED) of 15.6 μg/g against both red imported 
fire ants (Solenopsis invicta) and hybrid imported fire ants (Solenopsis invicta 
× Solenopsis richteri). Stereoselective oxidation of 1 via autoxidation and 
chemical methods produced (-)-5R-hydroperoxy-α-copaene (2), 
(+)-3S-hydroperoxycopa-4-ene (3), (-)-α-copaene oxide (4), (+)-β-copaen-4α-ol 
(5), copaenediol (6), and copaene ketol (7). Reduction of 2 and 3 with 
triphenylphosphine afforded (-)-5R-hydroxy-α-copaene (2a) and 
(+)-3S-hydroxycopa-4-ene (3a), respectively, which led to the structural 
revision of copa-3-en-2α-ol and copa-2-en-4-ol as 2a and 3, respectively. The 
configurational assignment of compound 4 in the literature was also clarified by 
the detailed analysis of 2D NMR spectroscopic data. Compounds 2-7 showed 
repellency with MREDs ranging from 3.9 to 15.6 μg/g against hybrid and red 
imported fire ants, indicating that chemical modification can enhance the 
repellent effect of (-)-α-copaene.

DOI: 10.1021/acs.jnatprod.4c00758
PMID: 39196851 [Indexed for MEDLINE]