Three New Oligostilbenes from the Seeds of Paeonia suffruticosa

Abstract

NotePaeonia suffruticosa ANDR. (Paeoniaceae) is found extensively in China. It is an important Chinese medicinal plant from the section Moutan of the genus Paeonia. This genus consists of ca. 35 species placed in three sections: Moutan, Oneapia, and Paeonia.1) The root cortex of this plant (Chinese name: mudanpi) is a well-known Chinese herbal medicine widely used as an analgesic, anaphylactic, antioxidative, and antiinflammatory agent. Numerous studies on the chemistry and pharmacology of this species have been performed.2) Previous phytochemical studies indicated that stilbenes were the primary bioactivity constituents of peony seeds. These stilbenes exhibit potent biological activities such as cytotoxic, antimutagenic, ecdysteroid antagonist, antioxidant, hyperpigmentation, antitumor, and anti-inflammatory activity and can improve bone disease. [3][4][5][6][7][8] In the course of searching for new bioactive natural products from the seeds of this plant, 11 stilbenes, trans-(1) and cis-suffruticosol D (2), trans-resveratrol (3), 9) trans-e-viniferin (4), 7)cis-e-viniferin (5), 7) gnetin H (6), 7) cis-gnetin H (7), suffruticosol A (8),3) suffruticosol B (9), 3) suffruticosol C (10), 3) and cis-ampelopsin E (11), 10) were isolated from the ethyl acetate extract of the seeds of P. suffruticosa. Among them, 1, 2, and 7 were new compounds. Here, we report the isolation and extensive structural elucidation of the new compounds. Results and Discussiontrans-Suffruticosol D (1) Three new oligostilbenes, trans-suffruticosol D (1), cis-suffruticosol D (2), and cis-gnetin H (7), were isolated along with the eight known stilbenes, trans-resveratrol (3), trans-e e-viniferin (4), cis-e e-viniferin (5), gnetin H (6), suffruticosol A (8), suffruticosol B (9), suffruticosol C (10), and cis-ampelopsin E (11) from the seeds of Paeonia suffruticosa. Compounds 3-6 were isolated for the first time from this plant species, and compound 11 was isolated for the first time from the genus Paeonia. The structures of the new compounds were elucidated based on spectral analyses, including 1D and 2D NMR experiments. The absolute configuration of compound 1 was determined by quantum chemical calculation of the electronic circular dichroism and comparison with the experimental circular dichroism spectrum.

Anti‑proliferative and anti‑metastasis effects of ten oligostilbenes from the seeds of Paeonia suffruticosa on human cancer cells

“…Thirdly, the steric arrangement and conformation of oligostilbenes also affected their antitumor activity. cis-and trans-suffruticosol D and cis-and trans-gnetin H are both trimers of resveratrol and both possess seven hydroxyl groups, differing only in their three-dimensional structures (16). Generally cis-and trans-gnetin H was 2-10 times more potent than cis-and trans-suffruticosol D, indicating that three-dimensional structures have a significant effect on cytotoxicity.…”

“…In 2003, Kang et al (7) isolated viniferin, trans-gnetin H and suffruticosol B from P. lactiflora and evaluated their effects on the proliferation and apoptosis of HL-60 cells. In our previous studies, we conducted several phytochemical analyses of the seedcases of P. suffruticosa and found that oligostilbenes were the major active ingredients, accounting for ~20% of the content (up to 200 mg/g) (9,10,16,17). In addition to their high abundance, some oligostilbenes identified in the seeds of Paeonia, such as suffruticosol A-C, have never been reported in other plants.…”

“…The ten oligostilbenes, trans-resveratrol, cis-ε-viniferin, trans-ε-viniferin, suffr uticosol A, suffr uticosol B, suffr uticosol C, cis-suffruticosol D, trans-suffruticosol D, cis-gnetin H and trans-gnetin H, were simultaneously purified from the dried seeds of P. suffruticosa as described previously (16). Their structures were characterized by ultraviolet (UV), infrared (IR), mass and nuclear magnetic resonance (NMR) spectroscopy, and the purities of all compounds were determined to be >95% (16). The compounds were resuspended in dimethyl sulfoxide (DMSO) (Sigma-Aldrich; Merck Millipore, Darmstadt, Germany) to yield a concentration of 10 mM, and stored at 4˚C.…”

In vitro antitumor effects of two novel oligostilbenes, cis- and trans-suffruticosol D, isolated from Paeonia suffruticosa seeds

“…This genus comprises ~35 species that are classified into three groups: Oneapia, Paeonia, and Moutan (5). The Cortex Moutan (root cortex) of Paeonia has been recorded by China's Pharmacopoeia as a significant source of herbal medicine (6).…”

“…The Cortex Moutan (root cortex) of Paeonia has been recorded by China's Pharmacopoeia as a significant source of herbal medicine (6). Extracts of Paeonia have been shown to possess cytotoxic, antitumor, anti-inflammatory and anti-oxidative activities (5). Previous photochemical research on Paeonia identified >260 bioactive compounds, including phenols, monoterpenoidglucosides, paeonols, flavonoids, tannins, steroids, triterpenoids and stilbenes (7).…”