A New 9,10-Dihydrophenanthrene and Cell Proliferative 3,4-δ-Dehydrotocopherols from Stemona tuberosa

Abstract

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.

Dihydrophenanthrenes from a Sicilian Accession of Himantoglossum robertianum (Loisel.) P. Delforge Showed Antioxidant, Antimicrobial, and Antiproliferative Activities

“…These results match those previously reported by other researchers, which highlighted an anti-proliferative activity of phenanthrenes and 9,10-dihydrophenanthrenes on several cancer cell lines derived from different tumor types, such as leukemia, breast, colon, prostate, and lung cancer [10,55]. Notably, several papers reported that similar molecules, at comparable doses, are effective on cancer cells and well tolerated by normal cells, suggesting a possible selective toxicity [56][57][58][59].…”

Wound Healing and the Use of Medicinal Plants

“…Alkaloid and stilbenoid isolated from the root of Stemona tuberosa are reported to have anti-inflammatory [306] and antibacterial [307] effects, while the dehydrotocopherol derivatives have been found to scavenge oxygen and free radicals [308]. Tocopherols isolated from the root of Stemona tuberosa increase cell proliferation in the mouse fibroblast NIH3T3 cells, suggesting the potential use of these compounds as wound healing agents [309].…”

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

“…20,21 g-Dehydrotocopherol shows proliferative effects on mouse NIH 3T3 broblasts and a potential use as wound healing agent has been suggested. 21 As mentioned above, a-, b-, gand d-tocotrienols (14, 15, 16, 17) usually occur as trace vitamers, however, several plant tissues and oils accumulate higher amounts of tocotrienols. For example, a-tocotrienol was found in barley (76 mg/100 g), gand d-tocotrienol in palm oil (36 mg and 8 mg/100 g, respectively).…”

“… 20,21 γ-Dehydrotocopherol shows proliferative effects on mouse NIH 3T3 fibroblasts and a potential use as wound healing agent has been suggested. 21 …”