TY - JOUR
T1 - Structurally Diverse Alkaloids from the Seeds of Peganum harmala
AU - Wang, Kai Bo
AU - Li, Da Hong
AU - Bao, Yu
AU - Cao, Fei
AU - Wang, Wen Jing
AU - Lin, Clement
AU - Bin, Wen
AU - Bai, Jiao
AU - Pei, Yue Hu
AU - Jing, Yong Kui
AU - Yang, Danzhou
AU - Li, Zhan Lin
AU - Hua, Hui Ming
N1 - Funding Information:
The work was financially supported by the National Natural Science Foundation of China (Grant No. 81172958), the Basic Research Subject of Key Laboratory Supported by Educational Commission of Liaoning Province of China (No. LZ2014044), and the China Scholarships Council.
Publisher Copyright:
© 2017 The American Chemical Society and American Society of Pharmacognosy.
PY - 2017/2/24
Y1 - 2017/2/24
N2 - Investigation of the alkaloids from Peganum harmala seeds yielded two pairs of unique racemic pyrroloindole alkaloids, (±)-peganines A-B (1-2); two rare thiazole derivatives, peganumals A-B (3-4); six new β-carboline alkaloids, pegaharmines F-K (5-10); and 12 known analogues. Their structures, including stereochemistry, were elucidated through spectroscopic analyses, quantum chemistry calculations, and single-crystal X-ray diffraction. Notably, the incorporation of pyrrole and indole moieties in peganines A-B, thiazole fragments in peganumals A-B, and a C-1 α,β-unsaturated ester motif in pegaharmine F (5) are all rare, and their presence in the genus Peganum were demonstrated for the first time. All isolates were tested for antiproliferative activities against the HL-60, PC-3, and SGC-7901 cancer cell lines, and compounds 9, 11, 12, and 13 exhibited moderate cytotoxicity against HL-60 cancer cell lines with IC50 values in the range of 4.36-9.25 μM.
AB - Investigation of the alkaloids from Peganum harmala seeds yielded two pairs of unique racemic pyrroloindole alkaloids, (±)-peganines A-B (1-2); two rare thiazole derivatives, peganumals A-B (3-4); six new β-carboline alkaloids, pegaharmines F-K (5-10); and 12 known analogues. Their structures, including stereochemistry, were elucidated through spectroscopic analyses, quantum chemistry calculations, and single-crystal X-ray diffraction. Notably, the incorporation of pyrrole and indole moieties in peganines A-B, thiazole fragments in peganumals A-B, and a C-1 α,β-unsaturated ester motif in pegaharmine F (5) are all rare, and their presence in the genus Peganum were demonstrated for the first time. All isolates were tested for antiproliferative activities against the HL-60, PC-3, and SGC-7901 cancer cell lines, and compounds 9, 11, 12, and 13 exhibited moderate cytotoxicity against HL-60 cancer cell lines with IC50 values in the range of 4.36-9.25 μM.
UR - http://www.scopus.com/inward/record.url?scp=85013752398&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85013752398&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.6b01146
DO - 10.1021/acs.jnatprod.6b01146
M3 - Article
C2 - 28128938
AN - SCOPUS:85013752398
SN - 0163-3864
VL - 80
SP - 551
EP - 559
JO - Journal Of Natural Products
JF - Journal Of Natural Products
IS - 2
ER -