Firmosides A and B: two new sucrose ferulates from the aerial parts of Silene firma and evaluation of radical scavenging
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Firmosides A and B: two new sucrose ferulates from the aerial parts of Silene firma and evaluation of radical scavenging activities Nguyen Hoang Uyen1 · Retno Widyowati1,2 · Melanny Ika Sulistyowaty1,3 · Sachiko Sugimoto1 · Yoshi Yamano1 · Susumu Kawakami4 · Hideaki Otsuka4 · Katsuyoshi Matsunami1 Received: 16 May 2020 / Accepted: 23 June 2020 © The Japanese Society of Pharmacognosy 2020
Abstract Two new tri-ferulates of sucrose, firmosides A and B (1 and 2, respectively), together with 18 known compounds (3–20), were isolated from the aerial parts of Silene firma. The structures of the isolated compounds were elucidated by various spectroscopic methods, including 1D, 2D NMR, and high-resolution electro-spray ionization–mass spectrometry (HR-ESI–MS). All the isolated compounds were evaluated for their free radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. As a result, two new compounds (1, 2) and 11 demonstrated significant radical scavenging activity, implying the usefulness as antioxidant agents. Graphic Abstract R HO HO O
OH
O
O
O
O
O O
O
OH OH
O
OMe OH
MeO OH
OMe
1: 2:
R OH OAc
Keywords Silene firma · Ferulic acid · Radical scavenging activities · DPPH · Sucrose · Firmoside
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11418-020-01426-5) contains supplementary material, which is available to authorized users. * Katsuyoshi Matsunami matunami@hiroshima‑u.ac.jp 1
Graduate School of Biomedical and Health Sciences, Hiroshima University, 1‑2‑3 Kasumi, Minami‑ku, Hiroshima 734‑8553, Japan
Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy, Universitas Airlangga, Gedung Nanizar Zaman Joenoes, Kampus C Unair, Surabaya 60115, Indonesia
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3
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Airlangga, Gedung Nanizar Zaman Joenoes, Kampus C Unair, Surabaya 60115, Indonesia
4
Faculty of Pharmacy, Yasuda Women’s University, 6‑13‑1 Yasuhigashi, Asaminami‑ku, Hiroshima 731‑0153, Japan
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Vol.:(0123456789)
Journal of Natural Medicines
Introduction The genus Silene (family: Caryophyllaceae) comprises more than 700 species mainly distributed in the temperate zone of the northern hemisphere. The genus Silene includes several taxa previously treated as different genera, such as Coronaria, Cucubalus, Lychnis, Melandrium, Petrocopsis, and Viscaria [1]. Melandrium firmum Rohrbach is a synonym of Silene firma and is widely distributed in China, Korea, Russia, and Japan. S. firma is an annual or biennial herb. The stems erect and reach 30–100 cm in height, and the knots are sometimes dark violet. Leaves are opposite, lanceolate to ovate–lanceolate, 3–10 cm long, 1–3 cm wide, apex acute, and hairs in the margins. Flowers bloom from June to September, and the petals are white. The seeds are black, renal shape, 0.7 to 1 mm, with spines, and ripen from July to August [2, 3]. The dried aerial parts have been used for the treatment of anuria, breast cancer, gonorrhea, and
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