TY - JOUR
T1 - A new 9,10-dihydrophenanthrene and cell proliferative 3,4-δ-dehydrotocopherols from Stemona tuberosa
AU - Kil, Yun Seo
AU - Park, Jiyoung
AU - Han, Ah Reum
AU - Woo, Hyun Ae
AU - Seo, Eun Kyoung
N1 - Publisher Copyright:
© 2015 by the authors; licensee MDPI.
PY - 2015/4/1
Y1 - 2015/4/1
N2 - A new compound, 9,10-dihydro-5-methoxy-8-methyl-2,7-phenanthrenediol (1), was isolated from the roots of Stemona tuberosa Lour. (Stemonaceae) together with two new optically active compounds, (2S,4′R,8′R)-3,4-δ-dehydrotocopherol (2) and (2R,4′R,8′R)-3,4-δ-dehydrotocopherol (3). The structures of compounds 1-3 were determined on the basis of spectroscopic data analysis. Compounds 2 and 3 were each purified from a stereoisomeric mixture of 2 and 3 by preparative HPLC using a chiral column for the first time. The absolute configurations at C-2 of 2 and 3 were determined by Circular Dichroism (CD) experiments. As a part of the research to find natural wound healing agents, all isolates and the mixture of 2 and 3 were evaluated for their cell proliferative effects using a mouse fibroblast NIH3T3 and a HeLa human cervical cancer cell line. As a result, 1, 2, 3, or the mixture of 2 and 3 showed 41.6%, 78.4%, 118.6%, 38.2% increases of cell proliferation in the mouse fibroblast NIH3T3 respectively, compared to 28.4% increase of δ-tocopherol. Moreover, none of them induced cancer cell proliferation. Therefore, 3,4-δ-dehydrotocopherols, especially pure isomers 2 and 3 can be suggested as potential wound healing agents.
AB - A new compound, 9,10-dihydro-5-methoxy-8-methyl-2,7-phenanthrenediol (1), was isolated from the roots of Stemona tuberosa Lour. (Stemonaceae) together with two new optically active compounds, (2S,4′R,8′R)-3,4-δ-dehydrotocopherol (2) and (2R,4′R,8′R)-3,4-δ-dehydrotocopherol (3). The structures of compounds 1-3 were determined on the basis of spectroscopic data analysis. Compounds 2 and 3 were each purified from a stereoisomeric mixture of 2 and 3 by preparative HPLC using a chiral column for the first time. The absolute configurations at C-2 of 2 and 3 were determined by Circular Dichroism (CD) experiments. As a part of the research to find natural wound healing agents, all isolates and the mixture of 2 and 3 were evaluated for their cell proliferative effects using a mouse fibroblast NIH3T3 and a HeLa human cervical cancer cell line. As a result, 1, 2, 3, or the mixture of 2 and 3 showed 41.6%, 78.4%, 118.6%, 38.2% increases of cell proliferation in the mouse fibroblast NIH3T3 respectively, compared to 28.4% increase of δ-tocopherol. Moreover, none of them induced cancer cell proliferation. Therefore, 3,4-δ-dehydrotocopherols, especially pure isomers 2 and 3 can be suggested as potential wound healing agents.
KW - 3,4-δ-dehydrotocopherol
KW - 9,10-Dihydrophenanthrene
KW - Cell proliferation
KW - Chiral separation
KW - Stemona tuberosa
KW - Stemonaceae
UR - http://www.scopus.com/inward/record.url?scp=84928668428&partnerID=8YFLogxK
U2 - 10.3390/molecules20045965
DO - 10.3390/molecules20045965
M3 - Article
C2 - 25854758
AN - SCOPUS:84928668428
SN - 1420-3049
VL - 20
SP - 5965
EP - 5974
JO - Molecules
JF - Molecules
IS - 4
ER -