Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Food Funct. 2020 Jun 24;11(6):5257-5265. doi: 10.1039/d0fo00769b.

Unveiling the bioactivity of Allium triquetrum L. lipophilic fractions: chemical 
characterization and in vitro antibacterial activity against 
methicillin-resistant Staphylococcus aureus.

Rabah S(1), Kouachi K(2), Ramos PAB(3), Gomes AP(4), Almeida A(4), 
Haddadi-Guemghar H(1), Madani K(5), Silvestre AJD(6), Santos SAO(6).

Author information:
(1)Laboratoire de Biomathématiques, Biophysique, Biochimie et Scientométrie, 
Faculté des Sciences de la Nature et de la Vie, Université de Bejaia, 06000 
Bejaia, Algérie.
(2)Faculté des Sciences de la Nature et de la Vie, Département des Troncs 
Communs, Université de Bejaia, 06000 Bejaia, Algérie and Laboratoire de 
Physico-Chimie des Matériaux et Catalyse, Faculté des Sciences Exactes, 
Université de Bejaia, 06000 Bejaia, Algérie.
(3)CICECO - Aveiro Institute of Materials and Department of Chemistry, 
University of Aveiro, 3810-193 Aveiro, Portugal. santos.sonia@ua.pt and 
LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, 
Portugal.
(4)Department of Biology and CESAM, University of Aveiro, 3810-193 Aveiro, 
Portugal.
(5)Laboratoire de Biomathématiques, Biophysique, Biochimie et Scientométrie, 
Faculté des Sciences de la Nature et de la Vie, Université de Bejaia, 06000 
Bejaia, Algérie and Centre de recherche en technologie agro-alimentaire, Route 
de Targua-ouzemour, 06000 Bejaia, Algérie.
(6)CICECO - Aveiro Institute of Materials and Department of Chemistry, 
University of Aveiro, 3810-193 Aveiro, Portugal. santos.sonia@ua.pt.

The lipophilic composition of Allium triquetrum L. bulbs, flowers and leaves was 
studied for the first time by GC-MS. Sixty compounds were firstly identified in 
A. triquetrum L. Fatty acids represented the major lipophilic family among the 
studied extracts, with (9Z,12Z,15Z)-octadeca-9,12,15-trienoic and 
(9Z,12Z)-octadeca-9,12-dienoic acids being the major constituents of this 
family. A long chain aliphatic ketone, namely hentriacontan-16-one, was mainly 
found in flowers and leaves. Flowers and leaves were also found to be rich in 
long chain aliphatic alkanes and alcohols, respectively. Sterols, 
monoglycerides, aromatic compounds and long chain aliphatic aldehydes were found 
in lower amounts. The antibacterial activity of A. triquetrum bulb, flower and 
leaf extracts against methicillin-resistant Staphylococcus aureus (MRSA) growth 
was in vitro assessed. Bulb and flower extracts showed significant MRSA growth 
inhibition. Overall, these valuable findings can contribute to the valorization 
of A. triquetrum L. as a source of value-added phytochemicals, specifically as 
antibacterial agents and for nutraceutical applications.

DOI: 10.1039/d0fo00769b
PMID: 32458905 [Indexed for MEDLINE]


2. Lipids. 2016 Dec;51(12):1407-1420. doi: 10.1007/s11745-016-4208-z. Epub 2016
Oct  28.

Identification of Polyketides in the Cuticular Waxes of Triticum aestivum cv. 
Bethlehem.

Racovita RC(1), Jetter R(2)(3).

Author information:
(1)Department of Chemistry, The University of British Columbia, Vancouver, BC, 
V6T 1Z1, Canada.
(2)Department of Chemistry, The University of British Columbia, Vancouver, BC, 
V6T 1Z1, Canada. reinhard.jetter@botany.ubc.ca.
(3)Department of Botany, The University of British Columbia, Vancouver, BC, V6T 
1Z4, Canada. reinhard.jetter@botany.ubc.ca.

Cuticular waxes are complex mixtures consisting mostly of very-long-chain 
aliphatics with single, primary functional groups. However, the waxes of many 
plant species also include aliphatics with one or more functional groups 
residing on subterminal or mid-chain carbons. In the present work, the cuticular 
wax mixtures from flag leaf blades and peduncles of Triticum aestivum cv. 
Bethlehem were analyzed in a search for novel wax constituents with in-chain 
functionalities, potentially of polyketide origin. The structures of compounds 
belonging to six different compound classes were elucidated using gas 
chromatography-mass spectrometry of various derivatives. Among them, a series of 
2,4-ketols was identified, with odd carbon numbers ranging from C25 to C37 and 
peaking at C33. The analogous C33 2,4-diketone was identified as well, together 
with a pair of co-eluting C31 mid-chain β-ketol isomers 
(16-hydroxyhentriacontan-14-one and 14-hydroxyhentriacontan-16-one), a pair of 
co-eluting C30 mid-chain α-ketol isomers (15-hydroxytriacontan-14-one and 
14-hydroxytriacontan-15-one), the corresponding C30 14,15-diketone, and a pair 
of co-eluting C31 ketones (hentriacontan-14-one and hentriacontan-16-one). All 
newly discovered structures contain ketone functional groups, with similar 
C13H27 and C15H31 alkyl chains on either side of the functionalities, thus 
resembling the previously reported very-long-chain β-diketones dominating the 
wheat wax mixtures. Based on these structural characteristics, possible 
biosynthetic pathways leading to the newly identified polyketide-like compounds 
are proposed.

DOI: 10.1007/s11745-016-4208-z
PMID: 27796867 [Indexed for MEDLINE]


3. Chem Biodivers. 2014 Feb;11(2):217-32. doi: 10.1002/cbdv.201300127.

Nucleolipids of the cancerostatic 5-fluorouridine: synthesis, adherence to 
oligonucleotides, and incorporation in artificial lipid bilayers.

Malecki E(1), Ottenhaus V, Werz E, Knies C, Montilla Martinez M, Rosemeyer H.

Author information:
(1)Organic Materials Chemistry and Bioorganic Chemistry, Institute of Chemistry 
of New Materials, University of Osnabrück, Barbarastr. 7, D-49069 Osnabrück; 
Ionovation GmbH, Westerbreite 7, D-49084 Osnabrück.

5-Fluorouridine (1a) was converted to its N(3)-farnesylated nucleoterpene 
derivative 8 by direct alkylation with farnesyl bromide (4). Reaction of the 
cancerostatic 1a with either acetone, heptan-4-one, nonadecan-10-one, or 
hentriacontan-16-one afforded the 2',3'-O-ketals 2a-2d. Compound 2b was then 
first farnesylated (→5) and subsequently phosphitylated to give the 
phosphoramidite 6. The ketal 2c was directly 5'-phosphitylated without 
farnesylation of the base to give the phosphoramidite 7. Moreover, the recently 
prepared cyclic 2',3'-O-ketal 11 was 5'-phosphitylated to yield the 
phosphoramidite 12. The 2',3'-O-isopropylidene derivative 2a proved to be too 
labile to be converted to a phosphoramidite. All novel derivatives of 1a were 
unequivocally characterized by NMR and UV spectroscopy and ESI mass 
spectrometry, as well as by elemental analyses. The lipophilicity of the 
phosphoramidite precursors were characterized by both their retention times in 
RP-18 HPLC and by calculated log P values. The phosphoramidites 6, 7, and 12 
were exemplarily used for the preparation of four terminally lipophilized 
oligodeoxynucleotides carrying a cyanine-3 or a cyanine-5 residue at the 
5'-(n-1) position (i.e., 14-17). Their incorporation in an artificial lipid 
bilayer was studied by single-molecule fluorescence spectroscopy and 
fluorescence microscopy.

Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich.

DOI: 10.1002/cbdv.201300127
PMID: 24591313 [Indexed for MEDLINE]


4. An Acad Bras Cienc. 2003 Dec;75(4):431-9. doi:
10.1590/s0001-37652003000400003.  Epub 2003 Nov 4.

Epicuticular waxes from caatinga and cerrado species and their efficiency 
against water loss.

Oliveira AF(1), Meirelles ST, Salatino A.

Author information:
(1)Instituto de Biociências, Universidade de São Paulo, 05422-970 São Paulo, SP, 
Brasil. afer@ib.usp.br

The effects of the contents and chemical composition of the foliar epicuticular 
waxes of species from the caatinga (Aspidosperma pyrifolium, Capparis yco, 
Maytenus rigida and Ziziphus joazeiro) and cerrado (Aristolochia esperanzae, 
Didymopanax vinosum, Strychnos pseudoquina and Tocoyena formosa) were evaluated 
as to the resistance to water loss by means of an experimental device 
constructed for this purpose. In general, the waxes of the caatinga species 
investigated were more efficient against water loss than cerrado species. 
Increase of the thickness of the waxy deposits from 40 to 90 microg.cm-2 had no 
significant effect on the resistance to water loss. The chemistry of the wax 
constituents was shown to be an important factor to determine the degree of 
resistance to evaporation. n-Alkanes and alcoholic triterpenes were the most 
efficient barriers, while hentriacontan-16-one (a ketone) and ursolic acid (an 
acid triterpene) revealed low efficiency. The higher efficiency of the waxes of 
the leaves from caatinga species (mainly those of C. yco and Z. joazeiro) is 
probably accounted for the predominance of n-alkanes in their composition. The 
lower efficiency of the waxes of A. pyrifolium (caatinga), T. formosa and A. 
esperanzae (both species from the cerrado) is probably a consequence of the 
predominance of triterpenoids in the waxes of the two former species and 
hentriacontan-16-one in the latter.

DOI: 10.1590/s0001-37652003000400003
PMID: 14605678 [Indexed for MEDLINE]


5. Plant Physiol. 1998 Mar;116(3):901-11. doi: 10.1104/pp.116.3.901.

Epicuticular wax accumulation and fatty acid elongation activities are induced 
during leaf development of leeks.

Rhee Y(1), Hlousek-Radojcic A, Ponsamuel J, Liu D, Post-Beittenmiller D.

Author information:
(1)Plant Biology Division, The Samuel Roberts Noble Foundation, P.O. Box 2180, 
Ardmore, Oklahoma 73402, USA.

Epicuticular wax production was evaluated along the length of expanding leek 
(Allium porrum L.) leaves to gain insight into the regulation of wax production. 
Leaf segments from the bottom to the top were analyzed for (a) wax composition 
and load; (b) microsomal fatty acid elongase, plastidial fatty acid synthase, 
and acyl-acyl carrier protein (ACP) thioesterase activities; and (c) tissue and 
cellular morphological changes. The level of total wax, which was low at the 
bottom, increased 23-fold along the length of the leaf, whereas accumulation of 
the hentriacontan-16-one increased more than 1000-fold. The onset of wax 
accumulation was not linked to cell elongation but, rather, occurred several 
centimeters above the leaf base. Peak microsomal fatty acid elongation activity 
preceded the onset of wax accumulation, and the maximum fatty acid synthase 
activity was coincident with the onset. The C16:0- and C18:0-ACP-hydrolyzing 
activities changed relatively little along the leaf, whereas 
C18:1-ACP-hydrolyzing activity increased slightly prior to the peak elongase 
activity. Electron micrographic analyses revealed that wax crystal formation was 
asynchronous among cells in the initial stages of wax deposition, and 
morphological changes in the cuticle and cell wall preceded the appearance of 
wax crystals. These studies demonstrated that wax production and microsomal 
fatty acid elongation activities were induced within a defined and identifiable 
region of the expanding leek leaf and provide the foundation for future 
molecular studies.

DOI: 10.1104/pp.116.3.901
PMCID: PMC35092
PMID: 9501123