Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. ACS Catal. 2024 Jun 24;14(13):10295-10316. doi: 10.1021/acscatal.4c02355. 
eCollection 2024 Jul 5.

Hexa-Fe(III) Carboxylate Complexes Facilitate Aerobic Hydrocarbon Oxidative 
Functionalization: Rh Catalyzed Oxidative Coupling of Benzene and Ethylene to 
Form Styrene.

Bennett MT(1), Park KA(1), Musgrave CB 3rd(2), Brubaker JW(2), Dickie DA(2), 
Goddard WA 3rd(2), Gunnoe TB(1).

Author information:
(1)Department of Chemistry, University of Virginia, Charlottesville, Virginia 
22904, United States.
(2)Materials and Process Simulation Center, California Institute of Technology, 
Pasadena, California 91125, United States.

Fe(II) carboxylates react with dioxygen and carboxylic acid to form 
Fe6(μ-OH)2(μ3-O)2(μ-X)12(HX)2 (X = acetate or pivalate), which is an active 
oxidant for Rh-catalyzed arene alkenylation. Heating (150-200 °C) the catalyst 
precursor [(η2-C2H4)2Rh(μ-OAc)]2 with ethylene, benzene, Fe(II) carboxylate, and 
dioxygen yields styrene >30-fold faster than the reaction with dioxygen in the 
absence of the Fe(II) carboxylate additive. It is also demonstrated that 
Fe6(μ-OH)2(μ3-O)2(μ-X)12(HX)2 is an active oxidant under anaerobic conditions, 
and the reduced material can be reoxidized to Fe6(μ-OH)2(μ3-O)2(μ-X)12(HX)2 by 
dioxygen. At optimized conditions, a turnover frequency of ∼0.2 s-1 is achieved. 
Unlike analogous reactions with Cu(II) carboxylate oxidants, which undergo 
stoichiometric Cu(II)-mediated production of phenyl esters (e.g., phenyl 
acetate) as side products at temperatures ≥150 °C, no phenyl ester side product 
is observed when Fe carboxylate additives are used. Kinetic isotope effect 
experiments using C6H6 and C6D6 give k H/k D = 3.5(3), while the use of protio 
or monodeutero pivalic acid reveals a small KIE with k H/k D = 1.19(2). 
First-order dependencies on Fe(II) carboxylate and dioxygen concentration are 
observed in addition to complicated kinetic dependencies on the concentration of 
carboxylic acid and ethylene, both of which inhibit the reaction rate at a high 
concentration. Mechanistic studies are consistent with irreversible benzene C-H 
activation, ethylene insertion into the formed Rh-Ph bond, β-hydride 
elimination, and reaction of Rh-H with Fe6(μ-OH)2(μ3-O)2(μ-X)12(HX)2 to 
regenerate a Rh-carboxylate complex.

© 2024 The Authors. Published by American Chemical Society.

DOI: 10.1021/acscatal.4c02355
PMCID: PMC11232027
PMID: 38988649

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


2. JACS Au. 2024 Jun 12;4(6):2403-2410. doi: 10.1021/jacsau.4c00436. eCollection 
2024 Jun 24.

Mechanistic Rationale for Ketene Formation during Dabbing and Vaping.

Munger KR(1), Anreise KM(1), Jensen RP(2), Peyton DH(1), Strongin RM(1).

Author information:
(1)Department of Chemistry, Portland State University, Portland, Oregon 97217, 
United States.
(2)Florascience Inc., Milwaukie, Oregon 97222, United States.

Ketene is one of the most toxic vaping emissions identified to date. However, 
its high reactivity renders it relatively challenging to identify. In addition, 
certain theoretical studies have shown that realistic vaping temperature 
settings may betoo low to produce ketene. Each of these issues is addressed 
herein. First, an isotopically labeled acetate precursor is used for the 
identification of ketene with enhanced rigor in vaped aerosols. Second, 
discrepancies between theoretical and experimental findings are explained by 
accounting for the effects of aerobic (experimental) versus anaerobic (simulated 
and theoretical) pyrolysis conditions. This finding is also relevant to 
explaining the relatively low-temperature production of aerosol toxicants beyond 
ketene. Moreover, the study presented herein shows that ketene formation during 
vaping is not limited to molecules possessing a phenyl acetate substructure. 
This means that ketene emission during vaping, including from popular flavorants 
such as ethyl acetate, may be more prevalent than is currently known.

© 2024 The Authors. Published by American Chemical Society.

DOI: 10.1021/jacsau.4c00436
PMCID: PMC11200222
PMID: 38938801

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


3. J Phys Chem A. 2024 Jun 13;128(23):4685-4693. doi: 10.1021/acs.jpca.4c02181. 
Epub 2024 May 30.

N···C═O n → π* Interaction: Gas-Phase Electronic and Vibrational Spectroscopy 
Combined with Quantum Chemistry Calculations.

Panwaria P(1), Das A(1).

Author information:
(1)Department of Chemistry, Indian Institute of Science Education and Research 
Pune, Dr. Homi Bhabha Road, Pashan, Pune 411008, India.

Herein, we have used gas-phase electronic and vibrational spectroscopic 
techniques for the first time to study the N···C═O n → π* interaction in ethyl 
2-(2-(dimethylamino) phenyl) acetate (NMe2-Ph-EA). We have measured the 
electronic spectra of NMe2-Ph-EA in the mass channels of its two distinct 
fragments of m/z = 15 and 192 using a resonant two-photon ionization technique 
as there was extensive photofragmentation of NMe2-Ph-EA. Identical electronic 
spectra obtained in the mass channels of both fragments confirm the dissociation 
of NMe2-Ph-EA in the ionic state, and hence, the electronic spectrum of the 
fragment represents that of NMe2-Ph-EA only. UV-UV hole-burning spectroscopy 
proved the presence of a single conformer of NMe2-Ph-EA in the experiment. 
Detailed quantum chemistry calculations reveal the existence of a N···C═O n → π* 
interaction in all six low-energy conformers of NMe2-Ph-EA. A comparison of the 
IR spectrum of NMe2-Ph-EA acquired from the gas-phase experiment with those 
obtained from theoretical calculations indicates that the experimentally 
observed conformer has a N···C═O n → π* interaction. The present finding might 
be further valuable in drug design and their recognition based on the N···C═O n 
→ π* interaction.

DOI: 10.1021/acs.jpca.4c02181
PMID: 38814588


4. Foods. 2024 May 16;13(10):1546. doi: 10.3390/foods13101546.

Optimization of High-Density Fermentation Conditions for Saccharomycopsis 
fibuligera Y1402 through Response Surface Analysis.

Yuan H(1), Sun Q(1), Wang L(1), Fu Z(2), Zhou T(1), Ma J(1), Liu X(3), Fan 
G(1)(4), Teng C(1).

Author information:
(1)Key Laboratory of Geriatric Nutrition and Health (Beijing Technology and 
Business University), Ministry of Education, Beijing 100048, China.
(2)School of Biology and Food Science, Hebei Normal University for 
Nationalities, Chengde 067000, China.
(3)China Food Flavor and Nutrition Health Innovation Center, School of Food and 
Health, Beijing Technology and Business University, Beijing 100048, China.
(4)Sweet Code Nutrition & Health Institute, Zibo 256306, China.

Saccharomycopsis fibuligera, which produces enzymes like amylase and protease as 
well as flavor substances like β-phenyl ethanol and phenyl acetate, plays a 
crucial role in traditional fermented foods. However, this strain still lacks a 
high-density fermentation culture, which has had an impact on the strain's 
industrial application process. Therefore, this study investigated the 
optimization of medium ingredients and fermentation conditions for high-density 
fermentation of S. fibuligera Y1402 through single-factor design, 
Plackett-Burman design, steepest ascent test, and response surface analysis. The 
study found that glucose at 360.61 g/L, peptone at 50 g/L, yeast extract at 
14.65 g/L, KH2PO4 at 5.49 g/L, MgSO4 at 0.40 g/L, and CuSO4 at 0.01 g/L were the 
best medium ingredients for S. fibuligera Y1402. Under these conditions, after 
three days of fermentation, the total colony count reached 1.79 × 108 CFU/mL. 
The optimal fermentation conditions were determined to be an initial pH of 6.0, 
an inoculum size of 1.10%, a liquid volume of 12.5 mL/250 mL, a rotation speed 
of 120 r/min, a fermentation temperature of 21 °C and a fermentation time of 
53.50 h. When fermentation was conducted using the optimized medium and 
conditions, the total colony count achieved a remarkable value of 5.50 × 109 
CFU/mL, exhibiting a substantial increase of nearly 31 times the original value 
in the optimal culture medium. This significant advancement offers valuable 
insights and a reference for the industrial-scale production of S. fibuligera.

DOI: 10.3390/foods13101546
PMCID: PMC11121647
PMID: 38790845

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


5. Med Oncol. 2023 Dec 29;41(1):38. doi: 10.1007/s12032-023-02250-z.

Ammonia scavenger and glutamine synthetase inhibitors cocktail in targeting 
mTOR/β-catenin and MMP-14 for nitrogen homeostasis and liver cancer.

Elmetwalli A(1)(2), Nageh A(3), Youssef AI(4), Youssef M(5), Ahmed MAE(6), 
Noreldin AE(7), El-Sewedy T(4).

Author information:
(1)Department of Clinical Trial Research Unit and Drug Discovery, Egyptian Liver 
Research Institute and Hospital (ELRIAH), Mansoura, Egypt. 
dr.prof2011@gmail.com.
(2)Microbiology Division, Higher Technological Institute of Applied Health 
Sciences, Egyptian Liver Research Institute and Hospital (ELRIAH), Mansoura, 
Egypt. dr.prof2011@gmail.com.
(3)Fertility and Assisted Reproductive Techniques Unit, International Teaching 
Hospital, Tanta University, Tanta, Egypt.
(4)Department of Applied Medical Chemistry, Medical Research Institute, 
Alexandria University, Alexandria, Egypt.
(5)Department of Histochemistry and Cell Biology, Medical Research Institute, 
Alexandria University, Alexandria, Egypt.
(6)Department of Clinical Pathology, Military Medical Academy, Alexandria Armed 
Forces Hospitals, Alexandria, Egypt.
(7)Department of Histology and Cytology, Faculty of Veterinary Medicine, 
Damanhour University, Damanhour, 22511, Egypt.

The glutamine synthetase (GS) facilitates cancer cell growth by catalyzing de 
novo glutamine synthesis. This enzyme removes ammonia waste from the liver 
following the urea cycle. Since cancer development is associated with 
dysregulated urea cycles, there has been no investigation of GS's role in 
ammonia clearance. Here, we demonstrate that, although GS expression is 
increased in the setting of β-catenin oncogenic activation, it is insufficient 
to clear the ammonia waste burden due to the dysregulated urea cycle and may 
thus be unable to prevent cancer formation. In vivo study, a total of 165 male 
Swiss albino mice allocated in 11 groups were used, and liver cancer was induced 
by p-DAB. The activity of GS was evaluated along with the relative expression of 
mTOR, β-catenin, MMP-14, and GS genes in liver samples and HepG2 cells using 
qRT-PCR. Moreover, the cytotoxicity of the NH3 scavenger phenyl acetate (PA) 
and/or GS-inhibitor L-methionine sulfoximine (MSO) and the migratory potential 
of cells was assessed by MTT and wound healing assays, respectively. The Swiss 
target prediction algorithm was used to screen the mentioned compounds for 
probable targets. The treatment of the HepG2 cell line with PA plus MSO 
demonstrated strong cytotoxicity. The post-scratch remaining wound area (%) in 
the untreated HepG2 cells was 2.0%. In contrast, the remaining wound area (%) in 
the cells treated with PA, MSO, and PA + MSO for 48 h was 61.1, 55.8, and 78.5%, 
respectively. The combination of the two drugs had the greatest effect, 
resulting in the greatest decrease in the GS activity, β-catenin, and mTOR 
expression. MSO and PA are both capable of suppressing mTOR, a key player in the 
development of HCC, and MMP-14, a key player in the development of HCC. PA 
inhibited the MMP-14 enzyme more effectively than MSO, implying that PA might be 
a better way to target HCC as it inhibited MMP-14 more effectively than MSO. A 
large number of abnormal hepatocytes (5%) were found to be present in the HCC 
mice compared to mice in the control group as determined by the 
histopathological lesions scores. In contrast, PA, MSO, and PA + MSO showed a 
significant reduction in the hepatic lesions score either when protecting the 
liver or when treating the liver. The molecular docking study indicated that PA 
and MSO form a three-dimensional structure with NF-κB and COX-II, blocking their 
ability to promote cancer and cause gene mutations. PA and MSO could be used to 
manipulate GS activities to modulate ammonia levels, thus providing a potential 
treatment for ammonia homeostasis.

© 2023. The Author(s), under exclusive licence to Springer Science+Business 
Media, LLC, part of Springer Nature.

DOI: 10.1007/s12032-023-02250-z
PMID: 38157146 [Indexed for MEDLINE]