PMID- 30563240
OWN - NLM
STAT- MEDLINE
DCOM- 20190319
LR  - 20230106
IS  - 1660-3397 (Electronic)
IS  - 1660-3397 (Linking)
VI  - 16
IP  - 12
DP  - 2018 Dec 6
TI  - Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity 
      of the C-17 Side-Chain and Natural Agonists of Human 
      Farnesoid/Pregnane(-)X(-)Receptor.
LID - 10.3390/md16120488 [doi]
LID - 488
AB  - Ten new triterpenoid compounds with structure diversity of the C-17 side-chain, 
      including nine tirucallanes, named xylocarpols A(-)E (1(-)5) and agallochols A(-)D 
      (6(-)9), and an apotirucallane, named 25-dehydroxy protoxylogranatin B (10), were 
      isolated from the mangrove plants Xylocarpus granatum, Xylocarpus moluccensis, 
      and Excoecaria agallocha. The structures of these compounds were established by 
      HR-ESIMS and extensive one-dimensional (1D) and two-dimensional (2D) NMR 
      investigations. The absolute configurations of 1 and 2 were unequivocally 
      determined by single-crystal X-ray diffraction analyses, conducted with Cu Kalpha 
      radiation; whereas those of 4, 6(-)8 were assigned by a modified Mosher's method 
      and the comparison of experimental electronic circular dichroism (ECD) spectra. 
      Most notably, 5, 6, 7, and 9 displayed potent activation effects on 
      farnesoid(-)X(-)receptor (FXR) at the concentration of 10.0 muM; 10 exhibited very 
      significant agonistic effects on pregnane(-)X(-)receptor (PXR) at the concentration 
      of 10.0 nM.
FAU - Jiang, Zhong-Ping
AU  - Jiang ZP
AD  - Marine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu 
      Avenue West, Guangzhou 510632, China. jiangzhongping0113@163.com.
FAU - Luan, Zhi-Lin
AU  - Luan ZL
AD  - College of Pharmacy and Advanced Institute for Medical Sciences, Dalian Medical 
      University, Dalian 116044, China. zhilin_luan@sina.com.
FAU - Liu, Ruo-Xi
AU  - Liu RX
AD  - Marine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu 
      Avenue West, Guangzhou 510632, China. 13249133788@163.com.
FAU - Zhang, Qun
AU  - Zhang Q
AD  - Marine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu 
      Avenue West, Guangzhou 510632, China. zhangqun0917@163.com.
FAU - Ma, Xiao-Chi
AU  - Ma XC
AD  - College of Pharmacy and Advanced Institute for Medical Sciences, Dalian Medical 
      University, Dalian 116044, China. maxc1978@163.com.
FAU - Shen, Li
AU  - Shen L
AUID- ORCID: 0000-0001-5770-1607
AD  - Marine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu 
      Avenue West, Guangzhou 510632, China. shenli6052@jnu.edu.cn.
FAU - Wu, Jun
AU  - Wu J
AUID- ORCID: 0000-0003-0807-5229
AD  - School of Pharmaceutical Sciences, Southern Medical University, 1838 Guangzhou 
      Avenue North, Guangzhou 510515, China. wwujun68@smu.edu.cn.
LA  - eng
GR  - U1501221, 31770377, 81661148049, and 81601174/National Natural Science Foundation 
      of China/
GR  - 21617474/the Fundamental Research Funds for the Central Universities, P.R. China/
PT  - Journal Article
DEP - 20181206
PL  - Switzerland
TA  - Mar Drugs
JT  - Marine drugs
JID - 101213729
RN  - 0 (NR1I2 protein, human)
RN  - 0 (Plant Extracts)
RN  - 0 (Pregnane X Receptor)
RN  - 0 (Receptors, Cytoplasmic and Nuclear)
RN  - 0 (Triterpenes)
RN  - 0 (apotirucallane)
RN  - 0 (tirucallane)
RN  - 0C5V0MRU6P (farnesoid X-activated receptor)
SB  - IM
MH  - Circular Dichroism
MH  - Crystallography, X-Ray
MH  - Euphorbiaceae/chemistry
MH  - Magnetic Resonance Spectroscopy
MH  - Meliaceae/chemistry
MH  - Molecular Structure
MH  - Plant Extracts/chemistry/isolation & purification/*pharmacology
MH  - Pregnane X Receptor/*agonists
MH  - Receptors, Cytoplasmic and Nuclear/*agonists
MH  - Triterpenes/chemistry/isolation & purification/*pharmacology
MH  - Wetlands
PMC - PMC6315889
OTO - NOTNLM
OT  - apotirucallane
OT  - farnesoid-X-receptor
OT  - mangrove
OT  - pregnane-X-receptor
OT  - tirucallane
OT  - triterpenoid
COIS- The authors declare no conflict of interest.
EDAT- 2018/12/20 06:00
MHDA- 2019/03/20 06:00
PMCR- 2018/12/01
CRDT- 2018/12/20 06:00
PHST- 2018/11/08 00:00 [received]
PHST- 2018/11/27 00:00 [revised]
PHST- 2018/12/04 00:00 [accepted]
PHST- 2018/12/20 06:00 [entrez]
PHST- 2018/12/20 06:00 [pubmed]
PHST- 2019/03/20 06:00 [medline]
PHST- 2018/12/01 00:00 [pmc-release]
AID - md16120488 [pii]
AID - marinedrugs-16-00488 [pii]
AID - 10.3390/md16120488 [doi]
PST - epublish
SO  - Mar Drugs. 2018 Dec 6;16(12):488. doi: 10.3390/md16120488.