(-)-Calcaridine B, a new chiral aminoimidazole-containing alkaloid from the marine sponge Leucetta chagosensis

LC-DAD/MS-based dereplication of organic extract of a calcareous sponge Leucetta chagosensis afforded one new chiral aminoimidazole-containing alkaloid, (-)-calcaridine B (1), along with one achiral imidazole analog leucettamine E (2) as well as one known imidazole derivative (2E, 9E)-pyronaamidine-...

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Bibliographic Details
Published in:Journal of asian natural products research 2019-11, Vol.21 (11), p.1123-1128
Main Authors: Tang, Wei-Zhuo, Yang, Zhong-Zhen, Sun, Fan, Wang, Shu-Ping, Yang, Fan, Jiao, Wei-Hua, Lin, Hou-Wen
Format: Article
Language:English
Subjects:
Alkaloids
Animals
Antineoplastic Agents
Biotechnology
chiral imidazole alkaloid
cytotoxicities
Cytotoxicity
human cell lines
Humans
Imidazole
inhibitory concentration 50
Leucetta
Leucetta chagosensis
liquid chromatography
Marine sponge
MCF-7 Cells
Molecular Structure
neoplasm cells
NMR
Nuclear magnetic resonance
nuclear magnetic resonance spectroscopy
Porifera
spectral analysis
Tumor cell lines
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Summary:LC-DAD/MS-based dereplication of organic extract of a calcareous sponge Leucetta chagosensis afforded one new chiral aminoimidazole-containing alkaloid, (-)-calcaridine B (1), along with one achiral imidazole analog leucettamine E (2) as well as one known imidazole derivative (2E, 9E)-pyronaamidine-9-(N-methylimine) (3). Their structures were elucidated on the basis of NMR spectroscopic analyses, and comparing with the literature. The cytotoxic activities of all isolates were evaluated against three human cancer cell lines, and compounds 1 and 3 exhibited mild cytotoxicities toward the MCF-7 cell line with IC 50 values of 25.3-24.2 μM, respectively.
ISSN:1028-6020
1477-2213
1477-2213
DOI:10.1080/10286020.2018.1499729