Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. World J Microbiol Biotechnol. 2024 Nov 2;40(12):375. doi: 
10.1007/s11274-024-04166-w.

Advances in the biosynthesis of D-allulose.

Zhang Y(1), Zhou Z(2), Luan H(1), Zhang X(1), Liu M(1), Wang K(1), Wang F(1), 
Feng W(1), Xu W(1), Song P(3).

Author information:
(1)School of Pharmaceutical Sciences and Food Engineering, Liaocheng University, 
Liaocheng, China.
(2)Shandong Aocter Biotechnology Co., Ltd, Liaocheng, 252000, China.
(3)School of Pharmaceutical Sciences and Food Engineering, Liaocheng University, 
Liaocheng, China. songpeng@lcu.edu.cn.

D-allulose is a rare monosaccharide and a C-3 epimer of D-fructose. It has 
physiological functions, such as antihyperglycemic, obesity-preventing, 
neuroprotective, and reactive oxygen species (ROS) scavenging effects, making it 
an ideal sugar substitute. The synthesis methods for D-allulose include chemical 
synthesis and biosynthesis. Chemical synthesis requires strict reaction 
conditions and tends to produce byproducts. Biosynthesis is mainly an enzymatic 
process. Enzymatic catalysis for the conversion of starch or glycerol to 
D-allulose is performed mainly by enzymes such as isoamylase (IA), glucose 
isomerase (GI), D-allulose 3-epimerase (DPE), D-allulose-6-phosphate 3-epimerase 
(A6PE), D-allulose 6-phosphate phosphatase (A6PP), ribitol 2-dehydrogenase 
(RDH), glycerophosphate kinase (GK), glycerophosphate oxidase (GPO), and 
dihydroxyacetone phosphate (DHAP)-dependent aldolase. Biosynthesis is a more 
energy-efficient process, producing fewer harmful by-products and pollutants, 
and significantly reducing negative environmental impacts. Furthermore, the 
specific catalytic activity of enzymes facilitates the production of compounds 
of higher purity, thereby facilitating the isolation and purification of the 
products. It has thus become the main method for producing D-allulose. This 
article reviews the progress in research on the biosynthetic production of 
D-allulose, focusing on the enzymes involved and their enzymatic properties, and 
discusses the production prospects for D-allulose.

© 2024. The Author(s), under exclusive licence to Springer Nature B.V.

DOI: 10.1007/s11274-024-04166-w
PMID: 39487344 [Indexed for MEDLINE]


2. J Food Sci. 2024 Oct;89(10):6296-6307. doi: 10.1111/1750-3841.17340. Epub 2024
 Sep 10.

Low-calorie d-allulose as a sucrose alternative modulates the physicochemical 
properties and volatile profile of sponge cake.

Xie X(1)(2), Yu L(1)(2), Lin Q(1)(2), Huang D(1)(2).

Author information:
(1)Department of Food Science and Technology, National University of Singapore, 
Singapore, Singapore.
(2)National University of Singapore (Suzhou) Research Institute, Suzhou, 
Jiangsu, P. R. China.

d-Allulose, a C-3 epimer of d-fructose, is a rare sugar with ∼70% of the 
sweetness of sucrose but a caloric content of only 0.4 kcal/g. Due to its 
low-calorie nature, d-allulose has garnered increasing interest in the food 
industry. This study was the first attempt to explore the effect of d-allulose 
as a sucrose replacer on the properties of sponge cake, a widely consumed 
high-sugar product. Substituting sucrose with d-allulose generated negligible 
impact on the batter system, while pronounced differences in physicochemical 
properties of cakes were detected, including specific volume, texture, 
microstructure, color, and antioxidant activity. In addition, sponge cake 
containing d-allulose displayed a distinctive aroma volatile profile, with more 
furans and pyrazines generation. Furthermore, correlations of physicochemical 
properties across all formulations were depicted, and the potential mechanism 
behind the property alterations modulated by d-allulose was revealed from the 
perspectives of starch gelatinization and browning reactions. Overall, this 
study provides insights into the application potential of d-allulose as a 
sucrose substitute in bakery product. PRACTICAL APPLICATION: This study 
elucidates the effect of d-allulose as a low-calorie sugar substitute on sponge 
cakes. This finding is valuable for the food industry, providing insights into a 
healthier alternative to traditional sugar in baked goods.

© 2024 The Author(s). Journal of Food Science published by Wiley Periodicals LLC 
on behalf of Institute of Food Technologists.

DOI: 10.1111/1750-3841.17340
PMID: 39256532 [Indexed for MEDLINE]


3. J Appl Glycosci (1999). 2024 Aug 20;71(3):73-80. doi: 
10.5458/jag.jag.JAG-2023_0019. eCollection 2024.

Metabolic Profiling of Rat Kidney Tissue Following Administration of D-Allulose.

Kanasaki A(1), Niibo M(1), Iida T(1).

Author information:
(1)1 Research and Development, Matsutani Chemical Industry Co., Ltd.

D-Allulose (D-psicose) is a rare sugar and a C-3 epimer of D-fructose. 
D-Allulose has been reported to have several health benefits via its alteration 
of both glucose and lipid metabolism. It was previously reported that D-allulose 
alters the hepatic metabolomic profile. Although the kidneys are crucial organs 
in metabolic regulation, the effects of D-allulose on renal metabolism have not 
yet been established. Therefore, this study was designed to capture the overall 
metabolic response in the kidneys to D-allulose. This was done by providing an 
AIN-93G diet to Wistar rats, with or without 3 % D-allulose, for four weeks. 
Renal tissue and blood samples were collected after a 3-hour fasting for 
evaluation of the renal metabolic profile and their related plasma parameters. 
D-Allulose increased renal weight without changes in the plasma indices 
associated with reduced renal function. Metabolic profiling identified a total 
of 264 peaks. As the contribution rate was too low in the principal component 
analysis results of the metabolic profiling results, we evaluated the 
metabolites that were significantly different between two groups and identified 
23 up-regulated and 26 down-regulated metabolites in the D-allulose group. 
D-Allulose also had significant influence on several metabolites involved in 
glucose metabolism, amino acid metabolism, and purine metabolism. Moreover, the 
levels of trimethylamine N-oxide and symmetric dimethylarginine, which are 
associated with several diseases such as chronic kidney disease and 
cardiovascular disease decreased following D-allulose diets. This study showed 
that D-allulose affects the renal metabolic profile, and our findings will help 
elucidate the function of D-allulose.

2024 by The Japanese Society of Applied Glycoscience.

DOI: 10.5458/jag.jag.JAG-2023_0019
PMCID: PMC11368711
PMID: 39234033

Conflict of interest statement: This study was funded by Matsutani Chemical 
Industry Co., Ltd. (Itami, Japan). A.K., M.N., and T.I. are employees of this 
company.


4. J Agric Food Chem. 2024 Jul 3;72(26):14821-14829. doi:
10.1021/acs.jafc.4c03219.  Epub 2024 Jun 19.

Enhanced Biosynthesis of d-Allulose from a d-Xylose-Methanol Mixture and Its 
Self-Inductive Detoxification by Using Antisense RNAs in Escherichia coli.

Guo Q(1), Zheng LJ(1)(2), Zheng SH(1), Zheng HD(1)(2), Lin XC(1), Fan LH(1)(2).

Author information:
(1)College of Chemical Engineering, Fujian Engineering Research Center of 
Advanced Manufacturing Technology for Fine Chemicals, Fuzhou University, Fuzhou 
350108, People's Republic of China.
(2)Qingyuan Innovation Laboratory, Quanzhou 362801, People's Republic of China.

d-Allulose, a C-3 epimer of d-fructose, has great market potential in food, 
healthcare, and medicine due to its excellent biochemical and physiological 
properties. Microbial fermentation for d-allulose production is being developed, 
which contributes to cost savings and environmental protection. A novel 
metabolic pathway for the biosynthesis of d-allulose from a d-xylose-methanol 
mixture has shown potential for industrial application. In this study, an 
artificial antisense RNA (asRNA) was introduced into engineered Escherichia coli 
to diminish the flow of pentose phosphate (PP) pathway, while the 
UDP-glucose-4-epimerase (GalE) was knocked out to prevent the synthesis of 
byproducts. As a result, the d-allulose yield on d-xylose was increased by 
35.1%. Then, we designed a d-xylose-sensitive translation control system to 
regulate the expression of the formaldehyde detoxification operon (FrmRAB), 
achieving self-inductive detoxification by cells. Finally, fed-batch 
fermentation was carried out to improve the productivity of the cell factory. 
The d-allulose titer reached 98.6 mM, with a yield of 0.615 mM/mM on d-xylose 
and a productivity of 0.969 mM/h.

DOI: 10.1021/acs.jafc.4c03219
PMID: 38897918 [Indexed for MEDLINE]


5. Crit Rev Food Sci Nutr. 2024 May 20:1-28. doi: 10.1080/10408398.2024.2350617. 
Online ahead of print.

D-allose, a typical rare sugar: properties, applications, and biosynthetic 
advances and challenges.

Tang X(1), Ravikumar Y(1), Zhang G(1), Yun J(2), Zhao M(1), Qi X(1)(2).

Author information:
(1)School of Food and Biological Engineering, Jiangsu University, Zhenjiang, 
China.
(2)School of Life Sciences, Guangzhou University, Guangzhou, China.

D-allose, a C-3 epimer of D-glucose and an aldose-ketose isomer of D-allulose, 
exhibits 80% of sucrose's sweetness while being remarkably low in calories and 
nontoxic, making it an appealing sucrose substitute. Its diverse physiological 
functions, particularly potent anticancer and antitumor effects, render it a 
promising candidate for clinical treatment, garnering sustained attention. 
However, its limited availability in natural sources and the challenges 
associated with chemical synthesis necessitate exploring biosynthetic strategies 
to enhance production. This overview encapsulates recent advancements in 
D-allose's physicochemical properties, physiological functions, applications, 
and biosynthesis. It also briefly discusses the crucial role of understanding 
aldoketose isomerase structure and optimizing its performance in D-allose 
synthesis. Furthermore, it delves into the challenges and future perspectives in 
D-allose bioproduction. Early efforts focused on identifying and characterizing 
enzymes responsible for D-allose production, followed by detailed crystal 
structure analysis to improve performance through molecular modification. 
Strategies such as enzyme immobilization and implementing multi-enzyme cascade 
reactions, utilizing more cost-effective feedstocks, were explored. Despite 
progress, challenges remain, including the lack of efficient high-throughput 
screening methods for enzyme modification, the need for food-grade expression 
systems, the establishment of ordered substrate channels in multi-enzyme cascade 
reactions, and the development of downstream separation and purification 
processes.

DOI: 10.1080/10408398.2024.2350617
PMID: 38764407