PMID- 32132285
OWN - NLM
STAT- MEDLINE
DCOM- 20200313
LR  - 20200313
IS  - 2053-2296 (Electronic)
IS  - 2053-2296 (Linking)
VI  - 76
IP  - Pt 3
DP  - 2020 Mar 1
TI  - Characterization, crystal structure and cytotoxic activity of a rare iridoid 
      glycoside from Lonicera saccata.
PG  - 269-275
LID - 10.1107/S2053229620001977 [doi]
AB  - A new iridoid glycoside, methyl 
      (3R,4R,4aS,7S,7aR)-3-hydroxy-7-methyl-5-oxooctahydrocyclopenta[c]pyran-4-carboxylate-3-O-beta-D-(1'S,2'R,3'S,4'S,5'R)-glucopyranoside, 
      named loniceroside A, C(17)H(26)O(10), (1), was obtained from the aerial parts of 
      Lonicera saccata. Its structure was established based on an analysis of 
      spectroscopic data, including 1D NMR, 2D NMR and HRESIMS, and the configurations 
      of the chiral C atoms were determined by X-ray crystallographic analysis. The 
      single-crystal structure reveals that the cyclopenta[c]pyran scaffold is formed 
      from a five-membered ring and a chair-like six-membered ring connected through 
      two bridgehead chiral C atoms. In the solid state, the glucose group of (1) plays 
      an important role in constructing an unusual supramolecular motif. The structure 
      analysis revealed adjacent molecules linked together through intermolecular 
      O-H...O hydrogen bonds to generate a banded structure. Furthermore, the banded 
      structures are linked into a three-dimensional network by interesting hydrogen 
      bonds. Biogenetically, compound (1) carries a glucopyranosyloxy moiety at the C-3 
      position, representing a rare structural feature for naturally occurring iridoid 
      glycosides. The growth inhibitory effects against human cervical carcinoma cells 
      (Hela), human lung adenocarcinoma cells (A549), human acute mononuclear 
      granulocyte leukaemia (THP-1) and the human liver hepatocellular carcinoma cell 
      line (HepG2) were evaluated by the MTT method.
FAU - Qu, Zhaoxia
AU  - Qu Z
AD  - School of Pharmacy, The Key Laboratory of Prescription Effect and Clinical 
      Evaluation of State Administration of Traditional Chinese Medicine of China, 
      Binzhou Medical University, Guanhai Road 346#, Yantai, Shandong 264003, People's 
      Republic of China.
FAU - Ma, Li
AU  - Ma L
AD  - Yantai Stomatological Hospital, Yantai, Shandong 264001, People's Republic of 
      China.
FAU - Zhang, Qi
AU  - Zhang Q
AD  - School of Pharmacy, The Key Laboratory of Prescription Effect and Clinical 
      Evaluation of State Administration of Traditional Chinese Medicine of China, 
      Binzhou Medical University, Guanhai Road 346#, Yantai, Shandong 264003, People's 
      Republic of China.
FAU - Yang, Renyong
AU  - Yang R
AD  - School of Pharmacy, The Key Laboratory of Prescription Effect and Clinical 
      Evaluation of State Administration of Traditional Chinese Medicine of China, 
      Binzhou Medical University, Guanhai Road 346#, Yantai, Shandong 264003, People's 
      Republic of China.
FAU - Hou, Guige
AU  - Hou G
AD  - School of Pharmacy, The Key Laboratory of Prescription Effect and Clinical 
      Evaluation of State Administration of Traditional Chinese Medicine of China, 
      Binzhou Medical University, Guanhai Road 346#, Yantai, Shandong 264003, People's 
      Republic of China.
FAU - Wang, Yanan
AU  - Wang Y
AD  - State Key Laboratory of Bioactive Substance and Function of Natural Medicines, 
      Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union 
      Medical College, Beijing 100050, People's Republic of China.
FAU - Zhao, Feng
AU  - Zhao F
AD  - School of Pharmacy, The Key Laboratory of Prescription Effect and Clinical 
      Evaluation of State Administration of Traditional Chinese Medicine of China, 
      Binzhou Medical University, Guanhai Road 346#, Yantai, Shandong 264003, People's 
      Republic of China.
LA  - eng
GR  - 81703391/National Natural Science Foundation of China/International
GR  - 2016-I2M-3-010/CAMS Innovation Fund for Medical Sciences/International
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20200218
PL  - England
TA  - Acta Crystallogr C Struct Chem
JT  - Acta crystallographica. Section C, Structural chemistry
JID - 101620313
RN  - 0 (Cytotoxins)
RN  - 0 (Iridoid Glycosides)
SB  - IM
MH  - Crystallography, X-Ray
MH  - Cytotoxins/isolation & purification/*pharmacology
MH  - Humans
MH  - Hydrogen Bonding
MH  - Iridoid Glycosides/isolation & purification/*pharmacology
MH  - Lonicera/*chemistry
MH  - Magnetic Resonance Spectroscopy
MH  - Molecular Structure
OTO - NOTNLM
OT  - Lonicera
OT  - Lonicera saccata
OT  - crystal structure
OT  - cytotoxic activity
OT  - iridoid glycoside
OT  - monoterpenoid
EDAT- 2020/03/07 06:00
MHDA- 2020/03/14 06:00
CRDT- 2020/03/06 06:00
PHST- 2019/11/12 00:00 [received]
PHST- 2020/02/11 00:00 [accepted]
PHST- 2020/03/06 06:00 [entrez]
PHST- 2020/03/07 06:00 [pubmed]
PHST- 2020/03/14 06:00 [medline]
AID - S2053229620001977 [pii]
AID - 10.1107/S2053229620001977 [doi]
PST - ppublish
SO  - Acta Crystallogr C Struct Chem. 2020 Mar 1;76(Pt 3):269-275. doi: 
      10.1107/S2053229620001977. Epub 2020 Feb 18.