PMID- 37070562
OWN - NLM
STAT- MEDLINE
DCOM- 20230921
LR  - 20230927
IS  - 1460-4752 (Electronic)
IS  - 0265-0568 (Linking)
VI  - 40
IP  - 9
DP  - 2023 Sep 20
TI  - A chemoinformatic analysis on natural glycosides with respect to biological 
      origin and structural class.
PG  - 1464-1478
LID - 10.1039/d2np00089j [doi]
AB  - Covering: up to 202216.19% of reported natural products (NPs) in the Dictionary 
      of Natural Products (DNP) are glycosides. As one of the most important NPs' 
      structural modifications, glycosylation can change the NPs' polarity, making the 
      aglycones more amphipathic. However, until now, little is known about the general 
      distribution profile of the natural glycosides in different biological sources or 
      structural types. The reason, structural or species preferences of the natural 
      glycosylation remain unclear. In this highlight, chemoinformatic methods were 
      employed to analyze the natural glycosides from DNP, the most comprehensively 
      annotated NP database. We found that the glycosylation ratios of NPs from plants, 
      bacteria, animals and fungi decrease successively, which are 24.99%, 20.84%, 
      8.40% and 4.48%, respectively. Echinoderm-derived NPs (56.11%) are the most 
      frequently glycosylated, while those produced by molluscs (1.55%), vertebrates 
      (2.19%) and Rhodophyta (3.00%) are the opposite. Among the diverse structural 
      types, a large proportion of steroids (45.19%), tannins (44.78%) and flavonoids 
      (39.21%) are glycosides, yet aminoacids and peptides (5.16%), alkaloids (5.66%) 
      are comparatively less glycosylated. Even within the same biological source or 
      structural type, their glycosylation rates fluctuate drastically between sub- or 
      cross-categories. The substitute patterns of flavonoid and terpenoid glycosides 
      and the most frequently glycosylated scaffolds were identified. NPs with 
      different glycosylation levels occupy different chemical spaces of 
      physicochemical property and scaffold. These findings could help us to interpret 
      the preference of NPs' glycosylation and investigate how NP glycosylation could 
      aid NP-based drug discovery.
FAU - Chen, Yinliang
AU  - Chen Y
AUID- ORCID: 0000-0003-4336-5117
AD  - National Key Laboratory of Agricultural Microbiology, Agricultural Bioinformatics 
      Key Laboratory of Hubei Province, College of Informatics, Huazhong Agricultural 
      University, Wuhan, P. R. China. dxkong@mail.hzau.edu.cn.
FAU - Liu, Yi
AU  - Liu Y
AUID- ORCID: 0000-0002-5821-5739
AD  - National Key Laboratory of Agricultural Microbiology, Agricultural Bioinformatics 
      Key Laboratory of Hubei Province, College of Informatics, Huazhong Agricultural 
      University, Wuhan, P. R. China. dxkong@mail.hzau.edu.cn.
FAU - Chen, Nianhang
AU  - Chen N
AD  - National Key Laboratory of Agricultural Microbiology, Agricultural Bioinformatics 
      Key Laboratory of Hubei Province, College of Informatics, Huazhong Agricultural 
      University, Wuhan, P. R. China. dxkong@mail.hzau.edu.cn.
FAU - Jin, Yuting
AU  - Jin Y
AD  - National Key Laboratory of Agricultural Microbiology, Agricultural Bioinformatics 
      Key Laboratory of Hubei Province, College of Informatics, Huazhong Agricultural 
      University, Wuhan, P. R. China. dxkong@mail.hzau.edu.cn.
FAU - Yang, Ruofei
AU  - Yang R
AD  - National Key Laboratory of Agricultural Microbiology, Agricultural Bioinformatics 
      Key Laboratory of Hubei Province, College of Informatics, Huazhong Agricultural 
      University, Wuhan, P. R. China. dxkong@mail.hzau.edu.cn.
FAU - Yao, Hucheng
AU  - Yao H
AD  - National Key Laboratory of Agricultural Microbiology, Agricultural Bioinformatics 
      Key Laboratory of Hubei Province, College of Informatics, Huazhong Agricultural 
      University, Wuhan, P. R. China. dxkong@mail.hzau.edu.cn.
FAU - Kong, De-Xin
AU  - Kong DX
AUID- ORCID: 0000-0003-0744-116X
AD  - National Key Laboratory of Agricultural Microbiology, Agricultural Bioinformatics 
      Key Laboratory of Hubei Province, College of Informatics, Huazhong Agricultural 
      University, Wuhan, P. R. China. dxkong@mail.hzau.edu.cn.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PT  - Review
DEP - 20230920
PL  - England
TA  - Nat Prod Rep
JT  - Natural product reports
JID - 8502408
RN  - 0 (Glycosides)
RN  - 0 (Flavonoids)
RN  - 0 (Plant Extracts)
RN  - 0 (Biological Products)
SB  - IM
MH  - Animals
MH  - *Glycosides/chemistry
MH  - Cheminformatics
MH  - Flavonoids/chemistry
MH  - Plants
MH  - Plant Extracts
MH  - *Biological Products/chemistry
EDAT- 2023/04/19 06:00
MHDA- 2023/09/21 06:42
CRDT- 2023/04/18 06:02
PHST- 2023/09/21 06:42 [medline]
PHST- 2023/04/19 06:00 [pubmed]
PHST- 2023/04/18 06:02 [entrez]
AID - 10.1039/d2np00089j [doi]
PST - epublish
SO  - Nat Prod Rep. 2023 Sep 20;40(9):1464-1478. doi: 10.1039/d2np00089j.