TY - JOUR
T1 - Bioactive Constituents from Radermachera boniana.
AU - Wang, Ming Zhong
AU - Xie, Wen Jian
AU - Guan, Yi Fu
AU - Song, Xun
AU - van Hung, Nguyen
AU - Cuong, Nguyen Manh
AU - Santarsiero, Bernard D.
AU - Fong, Harry H.S.
AU - Soejarto, D. Doel
AU - Zhang, Hong Jie
N1 - Funding Information:
The work described in this paper was supported by grants from the Hong Kong Baptist University (HKBU) Interdisciplinary Research Matching Scheme (RC-IRMS/12-13/03), the Research Grants Council of the Hong Kong Special Administrative Region, China (Project No. HKBU 12103014), the Faculty Research Grants, Hong Kong Baptist University (FRG2/14-15/047 and FRG1/13-14/029), the Hong Kong Scholars Program, and NIH Grants 3U01TW001015-10S1 and 2U01TW001015-11 A1 (administered by the Fogarty International Center as part of an International Cooperative Biodiversity Groups program, through funds from the NIH, NSF, and Foreign Agricultural Service of the USDA). The authors are grateful to the Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, and the Research Resources Center, University of Illinois at Chicago for support in the acquisition of the NMR, MS, IR, and UV data.
Publisher copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2016/6/1
Y1 - 2016/6/1
N2 - The bioassay-directed fractionation of the roots of Radermachera boniana Dop. (Bignoniaceae) led to the isolation of 17 naphthalene-based quinones and related derivatives including the new radermacherones A (1), B (2) and C (6), radermaquinone (3), and radermacherol (5). The absolute configuration of 2 was determined through X-ray crystallographic analysis. The isolates 3, hydroxy-β-isonaphthoquinone (4), 6, α-naphthoquinone (8), β-naphthoquinone (9), 3-hydroxy-β-naphthoquinone (10), 4-oxo-β-naphthoquinone (11), 2-acetyl-naphtha[2,3-b]furan-4,9-dione (BBI608) (12), 2-acetyl-7-methoxy-naphtho[2,3-b]furan-4,9-dione(13), stenocarpoquin-one B (14), dehydro-α-isonaphthoquinone (15) and 3-hydroxydehydro-α-isonaphthoquinone (16) showed cytotoxic activity in a cancer cell line panel comprising KB, Col-2, Lu-1 and MCF-7 with IC50 values ranging from 0.15-38.6 µM. Compounds 12 (known as BBI608) and its methoxy derivative, 13 with extended conjugation showed the highest cytotoxicity among the tested compounds with IC50 values ranging from 0.12-3.33 µM, but 13 showed much different cancer cell killing selectivity than 12.
AB - The bioassay-directed fractionation of the roots of Radermachera boniana Dop. (Bignoniaceae) led to the isolation of 17 naphthalene-based quinones and related derivatives including the new radermacherones A (1), B (2) and C (6), radermaquinone (3), and radermacherol (5). The absolute configuration of 2 was determined through X-ray crystallographic analysis. The isolates 3, hydroxy-β-isonaphthoquinone (4), 6, α-naphthoquinone (8), β-naphthoquinone (9), 3-hydroxy-β-naphthoquinone (10), 4-oxo-β-naphthoquinone (11), 2-acetyl-naphtha[2,3-b]furan-4,9-dione (BBI608) (12), 2-acetyl-7-methoxy-naphtho[2,3-b]furan-4,9-dione(13), stenocarpoquin-one B (14), dehydro-α-isonaphthoquinone (15) and 3-hydroxydehydro-α-isonaphthoquinone (16) showed cytotoxic activity in a cancer cell line panel comprising KB, Col-2, Lu-1 and MCF-7 with IC50 values ranging from 0.15-38.6 µM. Compounds 12 (known as BBI608) and its methoxy derivative, 13 with extended conjugation showed the highest cytotoxicity among the tested compounds with IC50 values ranging from 0.12-3.33 µM, but 13 showed much different cancer cell killing selectivity than 12.
KW - anti-proliferative
KW - bioassay-directed isolation
KW - cancer cell lines
KW - naphthalene-based quinones
KW - Radermachera boniana
KW - structure determination
UR - https://www.scopus.com/pages/publications/85040990332
U2 - 10.1002/slct.201600269
DO - 10.1002/slct.201600269
M3 - Journal article
AN - SCOPUS:85040990332
SN - 2365-6549
VL - 1
SP - 1575
EP - 1579
JO - ChemistrySelect
JF - ChemistrySelect
IS - 8
ER -
SDG 3 Good Health and Well-being