Abstract
Activity-guided isolation of 80% acetone extract of Cornus alba, which is traditionally used as an anti-inflammatory, hemostatic and diuretic in Korea, yielded one novel compound, tentatively designated cornusiin H (13), together with 12 known compounds. The known compounds included four flavonoids (catechin (1), quercetin-3-O-β-d-glucuronide (2), quercetin-3-O-β-d-glucopyranoside (3), kaempferol-3-O-β-d-glucopyranoside (4)) and eight hydrolysable tannins (gallic acid (5), 2,6-di-O-galloyl-hamamelofuranoside (6), 2-galloyl-4-caffeoyl-l-threonic acid (7) 2,3-di-O-galloyl-4-caffeoyl-l-threonic acid (8), 1,2,3,4,6-penta-O-galloyl-β-d-glucopyranoside (9), cornusiin B (10), cornusiin A (11) and camptothin B (12)). All compounds exhibited potent 1,1-diphenyl-2-picrylhydrazyl (DPPH)-free radical scavenging activity. Especially, the radical scavenging activities of 6 and 9–13 were higher than that of vitamin C. Compounds 9, 11, 12 and 13 inhibited the production of nitric oxide (NO) in lipopolysaccharide-stimulated RAW264.7 cells to the same degree as NG-Monomethyl-l-arginine (l-NMMA). When the antiproliferative effects of the isolated compounds were assessed in prostate cancer cells, the dimeric ellagitannins (11–13) selectively inhibited LNCaP hormone-dependent prostate cancer cells. Flow cytometry analysis indicated that the dimeric ellagitannins induced apoptosis and S-phase arrest. These results suggest that dimeric ellagitannins from Cornus alba can be developed as functional materials or herbal medicines for prostate tumors such as benign prostate hyperplasia and early-stage prostate cancer.
Highlights
Prostate tumors can be categorized as benign prostate hyperplasia (BPH), which is an overgrowth of the prostate caused by extensive androgen-dependent tissue remodeling [1], and prostate cancer (PCa), which is a malignant tumor caused by oncogenic mutations, aberrant signaling or inflammatory conditions [2]
Twelve known compounds were identified as catechin (1) [18], quercetin-3-O-β-D-glucuronide
On 1 H-nuclear magnetic resonance (NMR), all signals were duplicated, and one pair of downfield-shifted anomeric proton signals were observed at δ 6.18, 6.18 (1.7 H in total, each d, J = 8.4 Hz, H-1R of each two forms). (Figure S3) These findings suggested that compound
Summary
Prostate tumors can be categorized as benign prostate hyperplasia (BPH), which is an overgrowth of the prostate caused by extensive androgen-dependent tissue remodeling [1], and prostate cancer (PCa), which is a malignant tumor caused by oncogenic mutations, aberrant signaling or inflammatory conditions [2]. The proliferation of prostate tissue which could make urination difficult is an important problem for BPH [3]. The α1 -Adrenergic agonists and 5α-reductase inhibitors are typically used to treat BPH, with the goals of improving urination and decreasing prostate growth. Hormonal therapy is used for early-stage prostate cancer. Being a typical chronic disease in middle-aged and old men, prostate tumors are likely to increase with age. BPH has been described in 62% of European middle-aged men [4]. PCa, Molecules 2016, 21, 137; doi:10.3390/molecules21020137 www.mdpi.com/journal/molecules
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