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Introduction Syringa pubescens Turcz. was reported to be abundant in the Funiu Mountains of Henan Province and can be used to treat hepatitis and cirrhosis. In order to develop and utilise the resource, a fast and simple technique to extract bioactive compounds is needed. Objectives Our aims were to provide an extraction technique of glycosides from S. pubescens and study the antioxidant activity of this material. Methods Box-Behnken design (BBD) was employed with three factors at three levels. The process parameters such as ethanol concentration (X1 ), temperature (X2 ), and solvent-solid ratio (X3 ) could significantly influence efficiency and yield of target compounds. High-performance liquid chromatography (HPLC) was used to determine the content of glycosides. DPPH (α,α-diphenyl-β-picrylhydrazyl), ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) and reducing power were used to evaluate the antioxidant activity of S. pubescens extract. Results The optimal parameters for the maximal extraction yield were obtained with ethanol concentration of 68%, temperature of 89°C, solvent-solid ratio of 46 mL/g, and time of 20 min. The S. pubescens extract showed strong antioxidant properties in vitro. Conclusion The findings indicated the potential application of solvothermal extraction method to extract bioactive compounds from S. pubescens Turcz. Furthermore, the S. pubescens extract could be used as an important resource of antioxidant activity.

Phytochemical investigation into the 70 % ethanol extract of Forsythia suspensa leaves afforded the isolation and identification of two new lignan glycosides, Phillyrigeninside B (1) and Phillyrigeninside C (2). The structure of compounds isolated were elucidated via extensive spectroscopy techniques, including ultraviolet (UV), infrared (IR) and Nuclear Magnetic Resonance (NMR). The inhibitory effect against LPS-induced NO production in macrophages and the antibacterial activity were tested for compounds 1–2. The study showed that the two isolated compounds were furofuran lignan glycosides, and exhibited moderate antibacterial and moderate anti-inflammatory activities. The work further confirmed that the leaves of F. suspensa are also a source of furofuran lignan glycosides with important development value and wide application prospect.

To assess the application value of the seeds of the traditional medicine Chishao (Radix Paeonia Rubra, the root of Paeonia veitchii Lynch), the thousand seed weight, oil and kernel contents of the seeds, composition and contents of the main fatty acids, the physical and chemical characteristics of the seeds oil, and proximate composition and phytochemical components of the seeds shell and seeds oil residue were evaluated in this study. In addition, bioactivities such as antitumour and antimicrobial activity of the oligostilbene compound from P. veitchii seeds shell, and the inhibitory activities of the monoterpene glycoside compounds in P. veitchii seeds oil residue were also evaluated using different in vitro biochemical assays. The results showed that the seeds of P. veitchii had high oil content, and the seeds oil was characterized by very high levels of unsaturated fatty acids. The seeds shell contained large amounts of cellulose, lignin, and oligostilbene compounds, and high levels of monoterpene glycosides and crude protein were found in the P. veitchii seeds oil residue. The results of the biological tests showed that total oligostilbene compounds from P. veitchii seeds shell had antibacterial activity and moderate anticancer effects in vitro, and the total monoterpene glycoside compounds in P. veitchii showed strong inhibitory activities against NO production. As a medical plant and industrial crop with broad prospects, P. veitchii can be planted in most regions of China. In the past, it was planted solely because of the medical use of the roots. The above proximate and phytochemical profile, and bioactivity results show that the seeds of P. veitchii have high utilization value with potential in the development of value-added products, representing another valuable part of P. veitchii in the near future.

The oil peony seed cake, one of the most important by-products during the seed oil preparation, contains numerous monoterpene glycosides. The development and optimization of a simple and reproducible method for simultaneous qualitative and quantitative determination of monoterpene glycosides from oil peony seed cakes would be a valuable work for its further utilization. In this study, an HPLC method using DAD detector was developed to analyse fifteen monoterpene glycosides in oil peony seed cakes. The optimum resolution of the fifteen monoterpene glycosides was achieved on an ODS-AQ column. Acetonitrile (solvent A) and 0.5% potassium dihydrogen phosphate solution (pH 2.8) (solvent B) were used as the mobile phase by a gradient elution. Paeoniflorin showed the highest content amongst 15 monoterpene glycosides. It accounted for more than half of the total content of the fifteen monoterpene glycosides (TCFMG) in oil peony seed cake, followed by oxypaeoniflorin and albiflorin. The samples of different cultivation areas contain the different contents of monoterpene glycosides, mainly determined by their geographical variation. The higher level contents of monoterpene glycoside are believed to have more potential in medicinal application. The method thus could be used to control the quality of products from oil peony seed cakes.

A phytochemical investigation of oil peony seed cake led to the isolation and identification of three new monoterpene glycosides called paeonirockosides A (1), B (2), and C (5), together with 21 known monoterpene glycosides. Their structures were elucidated through the extensive application of one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR) spectroscopy and a comparison with authentic standards. The inhibitory activity of the isolated compounds against nitric oxide (NO) production was evaluated on lipopolysaccharide (LPS)-activated RAW 264.7 macrophages. Compounds mudanpioside F (3), benzoylpaeoniflorin (11), benzoyloxypaeoniflorin (12), oxypaeonidanin (18) and pyrindylpaeoniflorin (22) and the 70% aqueous ethanol extract (AEE) exhibited potent inhibitory activity against NO production with IC50 values of 18.65, 23.32, 25.14, 40.8, 28.61 and 36.42 μM, respectively. Monoterpene glycosides from peony seed cake can be developed into a promising immunosuppressive drug.

Ultrasonic-assisted extraction of oil from Paeonia lactiflora Pall. seeds with hexane as the solvent was studied, and the chemical composition of the oil was analyzed by gas chromatography–mass spectrometry (GC–MS). Based on single-factor tests, the effects of the extraction parameters, including ultrasonic time, ultrasonic temperature and ultrasonic power, on the extraction yield of P. lactiflora seed oil were optimized by response surface methodology. The chemical constituents of the oil residue of P. lactiflora were isolated using a silica gel column: Toyopearl HW-40, Sephadex LH-20, and preparative HPLC chromatographies. The structures of the isolated compounds were elucidated based on 1H-NMR, 13C-NMR and MS data analysis. An HPLC method for the simultaneous determination of six monoterpene glycosides in the seed cake and seed shell of P. lactiflora was established. The optimum conditions were as follows: extraction time of 18 min, extraction temperature of 35 °C, and extraction power of 445 W. Under these conditions, the extraction yield values of the oil were 28.85%. The predominant fatty acids in P. lactiflora seed oil were linolenic acid (34.12%), linoleic acid (26.47%), and oleic acid (27.87%), among others. The percentage of unsaturated fatty acids relative to total fatty acids exceeded 85%. Eight monoterpene glycosides, including 4″-hydroxyl-albiflorin (1), oxypaeoniflorin (2), albiflorin (3), paeoniflorin (4), paeonidanin (5), albiflorin R1 (6), 4-O-methyl-paeoniflorin (7) and oxypaeonidanin (8), were isolated from the oil residue of P. lactiflora. All the compounds were isolated from the seeds of P. lactiflora for the first time. The contents of 4″-hydroxyl-albiflorin, oxypaeoniflorin, albiflorin, paeoniflorin, paeonidanin and albiflorin R1 in the oil residue of P. lactiflora were 0.0113%, 0.0277%, 0.0655%, 0.589%, 0.0118% and 0.00486%, respectively. The contents of monoterpene glycosides in the oil residue were higher than those in the seed shell of P. lactiflora. These findings indicated that the seeds of P. lactiflora could be a good bioresource for the preparation of edible oil and total monoterpene glycosides. Therefore, P. lactiflora seeds have important research value as well as development and utilization prospects.

Ultrasound-assisted extraction (UAE) of total monoterpene glycosides extract (TMGE) from oil peony seed cakes was investigated. The extraction yield was optimized using response surface methodology (RSM). The chemical constituents of the monoterpene glycosides extract were isolated by repeated column chromatography, and the contents of the main isolated monoterpene glycosides in the oil peony seed cakes were determined by HPLC. The optimum conditions were as follows: a liquid-to-solid ratio of 27 mL/g, ultrasonic extraction time of 16 min, ultrasonic extraction temperature of 26 °C, and ethanol concentration of 67%. Under these conditions, the extraction yield of TMGE was 10.24%. Twenty monoterpene glycosides were isolated from the oil peony seed cakes, and compounds 11-12, 16 and 20 showed strong inhibitory activities on NO production. TMGE from oil peony seed cakes can also to be used as promising immunosuppressive drug due to its high content of monoterpene glycosides and immune-inhibitory activity. PRACTICAL AAPPLICATION: The peony seed oil was authorized as a new food by the Ministry of Health of the People's Republic of China. Peony seed cake is one of the most important by-products in the preparation of peony seed oil, and accounts for approximately 40% of the total mass of the peony seed. Total monoterpene glycosides are the main active ingredient of oil peony seed cake. This research has optimized the extraction conditions of total monoterpene glycoside from seeds cake of Paeonia ostii, which will provide useful reference information for further studies, and offer related industries with helpful guidance in practice.

The phytochemical study of the roots of Phlomis umbrosa Turcz afforded a new phenylethanoid glycoside, 3-hydroxy-4-methoxy-β-phenylethoxy-O-[2,3-diacetyl-α-l-rhamnopyranosyl-(1 → 3)]-4-O-cis-feruloyl-[β-d-apiofuranosyl-(1 → 6)]-β-d-glucopyranoside (1), and two new 28-noroleanane-derived spirocyclic triterpenoids, phlomishexaol C (2) and phlomishexaol D (3). Their structures were elucidated on the basis of 1D and 2D NMR analyses, in combination with high-resolution MS experiment.

The phytochemical study of the roots of Phlomis umbrosa Turcz. afforded three new phenylethanoid glycosides, 3'''-acetyl-O-betonyoside D (1), 2''', 3'''-di-acetyl-O- betonyoside D (2), and 3''', 4'''-di-acetyl-O-betonyoside D (3), along with five known phenylethanoid glycosides. Their structures were elucidated on the basis of spectroscopic data. The antitumor activity of the isolated compounds was investigated.