Three new glycosides from the whole plant of Clematis lasiandra Maxim and their cytotoxicity

Phytochemical investigation on the whole plant of Clematis lasiandra Maxim led to the isolation of two new phenolic glycosides (1 and 2), one new lignanoid glycoside (3), together with three known lignanoid glycosides (4–6). The structures of the new compounds were elucidated as 4-O-β-d-galactopyranosyl-ethyl-E-caffeate (1), 4-O-β-d-galactopyranosyl-3-hydroxyl-phenylethene (2) and (8R)-3,3′-dimethoxy-4,4′,9,9′-tetrahydroxy-5′,8-lignan 3′-O-β-d-glucopyranoside (3), on the basis of extensive spectral analysis and chemical evidence. The characteristic of the polymerized C-5′–C-8 type lignanoid aglycone in glycoside 3 was found from genus Clematis for the first time. Compounds 1–6 were evaluated for their cytotoxicity against human tumor cell lines HL-60, Hep-G2 and SGC-7901, the new glycosides 1 and 2 showed significant cytotoxicity against those three tumor cell lines with IC₅₀ in the range from 9.73 to 22.31 μM, while lignanoid glycosides 3–6 showed weak cytotoxicity to those test cell lines with IC₅₀ value more than 52.71 μM.     

Secondary metabolites from the stem bark of Juglans mandshurica

A pair of new dibenz[cd,lm]perylene derivatives, juglanperylenone A (1a) and juglanperylenone B (1b), along with ten known compounds, including four anthraquinones (2–5), two coumarins (6–7) and four triterpenoids (8–11), were isolated from the stem bark of Juglans mandshurica Maxim. Their structures were elucidated on the basis of spectroscopic evidence, including 1D and 2D NMR, HR-TOF-MS, and by comparison with literature data. In addition, the chemotaxonomic significance of the isolates was also discussed in this paper.     

Three new triterpenoid saponins from the aerial parts of Lysimachia foenum-graecum

A further phytochemical investigation of the aerial parts of Lysimachia foenum-graecum Hance led to the isolation of three new oleanane-type triterpenoid saponins, foegraecumosides L–N (1–3), along with one known saponin, 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosyl-cyclamiretin A (4). Their structures were elucidated by spectroscopic data analyses and chemical methods Compounds 1−4 were evaluated for their cytotoxicity against NCI-H460, MGC-803, HepG2, and T24 human cancer cell lines, and compound 4 showed moderate activity against all tested cell lines. Furthermore, the cytotoxicity of compound 4 was tested on drug-sensitive and drug-resistant lung cancer cell lines (A549 and A549/CDDP, respectively).     

Chemical constituents isolated from the roots of Sanguisorba officinalis L. and their chemotaxonomic significance

Phytochemical investigation of the roots of Sanguisorba officinalis L. led to the isolation of thirty-eight compounds, including seventeen triterpenoids (1–17), six monoterpenoid glycosides (18–23), six flavonoids (24–29), six phenols (30–35), two glycosides (36–37), and one lignan (38). The chemical structures of these compounds were elucidated on the basis of spectral data and by comparisons of spectroscopic data with reported values in the literature. Compounds 18, 29, and 36–37 were the first to be reported in the family Rosaceae, compounds 10, 12, 15, 27–28, and 38 were firstly identified from the genus Sanguisorba, and compound 11 was obtained from S. officinalis for the first time. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Two new penterpenoid saponins and a new diterpenoid glycoside from Hemsleya chinensis

Two new penterpenoid saponins, hemsloside-Ma4 (1) hemsloside-Ma5 (2), and a new diterpenoid glycoside, hemsloside-Ma6 (3), were isolated from the rhizomes of Hemsleya chinensis. By detailed analysis of the NMR spectra and chemical methods, the structures of new compounds were determined to be 3-O-β-l-arabinopyranosyl-(1 → 3)-O-(6′-methyl ester)-β-d-glucuropyranosyl-oleanolic acid-28-O-β-d-glucopyranosyl-(1 → 6)-O-β-d-glucopyranoside (1), 3-O-β-l-arabinopyranosyl-(1 → 3)-O-(6′-methyl ester)-β-d-glucuropyranosyl-oleanolic acid-28-O-β-d-xylopyranosyl-(1 → 6)-O-β-d-glucopy-ranoside (2), and 13ϵ-hydroxylabda-8(17), 14-dien-18-oic acid-18-O-α-l-rhamnopyranosyl-(1 → 2)-O-β-d-glucopyranosyl-(1 → 4)-O-α-l-rhamnopyranoside (3). Diterpenoid-type compound (3) was isolated from Hemsleya genus for the first time.     

胡桃楸胚性愈伤组织诱导与体细胞胚胎发生

胡桃楸是东北东部山地阔叶红松林的重要组成树种。因其被大量采伐,资源日趋枯竭。体细胞胚胎发生是快速繁殖和人工种子研制的基础,对遗传改良有重要意义。为探讨不同外植体、植物生长调节物质种类及配比对胡桃楸培养物的影响,建立了胡桃楸体胚发生及再生植株体系。结果表明:合子胚为外植体时最易形成胚性愈伤组织,外植体最佳取材时期为5～6月。胡桃楸胚性愈伤组织最适诱导为MS+1.0mg·mL-12,4-D+0.5mg·mL-16-BA;体细胞胚的诱导、发育和分化的适宜的培养基为附加蔗糖60g.L-1、水解酪蛋白700mg·mL-1时不添加任何生长调节物质的MS培养基。     

核桃楸种源选择试验及其环境因子的影响

收集13个核桃楸种源,在黑龙江省林口和兴隆两个试验点进行播种育苗,调查1年生苗木生长量,进行核桃楸种源选择试验。结果表明,不同种源核桃楸在两地播种后,苗高、基径生长量差异显著,适合林口地区的优良种源为绥阳、和龙、帽儿山和辉南种源;适合兴隆地区的优良种源为抚松、和龙、兴隆和绥阳种源。林口试验点核桃楸种子直径与1年生苗木基径生长量的相关系数达到了显著水平,可以作为反映基径生长量的指标,用线性函数模型来模拟核桃楸种子与苗木的生长情况的相关系数和拟合度相对较高。通过对13个种源地和2个试验点的主要环境因子差异与其1年生苗生长性状差异相关性分析,核桃楸不同种源1年生苗高与纬度和年平均气温等环境因子有一定相关性,且呈负相关,核桃楸种源可适当向北移栽。     

Chemical constituents from the bark of Juglans mandshurica Maxim. and their phenol oxidase inhibitory effects

Botanical insecticides investigation led to 21 compounds from the bark of Juglans mandshurica Maxim., in which, compounds 4, 10, 11, 13, 14 and 15 were isolated from Juglans genus for the first time. The inhibitory effect of dihydrokaempferol (6), naringenin (7) and rhoiptelol C (18) on phenol oxidase (PO) are 5–10 times more than arbutin, a well-known tyrosinase inhibitor. Thus, the selective and effective these inhibitors can be expected for using in the development of environment-friendly pesticide.     

核桃楸叶乙醇提取物杀虫活性及活性成分

采用常规提取法浸提核桃楸叶的杀虫活性成分.结果表明,核桃楸叶乙醇提取物和乙醇提取物氯仿萃取相对舞毒蛾幼虫和甘蓝夜蛾幼虫具有杀虫活性.施药5 d,药液浓度≥10g.L-1时,核桃楸叶乙醇提取物和氯仿萃取相对舞毒蛾幼虫和甘蓝夜蛾幼虫的触杀作用和胃毒作用的校正死亡率均超过50%.核桃楸叶乙醇提取物对舞毒蛾幼虫和甘蓝夜蛾幼虫的触杀作用和胃毒作用强于氯仿萃取相.采用气-质联用技术GC-MS分析核桃楸叶乙醇提取物中氯仿萃取相的化学组成和相对含量.结果表明:核桃楸叶乙醇提取物中氯仿萃取相的主要杀虫活性成分为相对含量最高的胡桃醌,即5-羟基-1,4-萘醌;其他杀虫活性成分可能为对称2,2’-亚甲基6-(1,1-二甲乙基)4-甲基双酚和2-甲氧基4-乙烯基苯酚.     

Chemical constituents of the rhizomes and roots of Gentiana scabra (Gentianaceae)

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Phenylpropanoids from Juglans mandshurica exhibit cytotoxicities on liver cancer cell lines through apoptosis induction

Three new phenylpropanoids (1–3) together with six known congeners (4–9) were isolated from the bark of Juglans mandshurica Maxim using anti-hepatoma activity as a guide. Their structures were determined by comprehensive NMR and HRESIMS spectroscopic data analyses. All the isolated compounds were evaluated for their growth inhibitory activities against two kinds of liver cancer cell lines (HepG2 and Hep3B). Among them, compound 4 showed moderate cytotoxic activities against HepG2 and Hep3B cell lines with IC₅₀ values of 58.58 and 69.87 μM. Compound 5 exhibited 50% cell death rate in HepG2 and Hep3B cell lines at 63.70 and 46.45 μM, respectively. Further observation of morphological changes and Western blot demonstrated that compounds 4 and 5 exhibited their cytotoxic activities through the induction of apoptosis. A structure-activity relationship study suggested that an α, β-unsaturated aldehyde might be the most important functional group.     

Two new rotenoids from the roots of Millettia speciosa

Two new rotenoids, named millettiaosas A–B (1–2), together with four known compounds were isolated from the roots of Millettia speciosa. Their structures were elucidated on the basis of spectroscopic analysis including 1D and 2D NMR techniques and HRESIMS. Evaluation of the two new compounds for cytotoxicity against four human cancer cell lines (MCF-7, HCT-116, A549 and HepG-2) showed moderate activities (10 μM < IC₅₀ < 26 μM).     

Phytochemical investigation on the roots of Juglans mandshurica and their chemotaxonomic significance

Phytochemical research of the roots of Juglans mandshurica Maxim. (Juglandaceae) verified 37 secondary metabolites, including thirteen diarylheptanoids (1–13), five naphthoquinones (14–18), five tetralones (19–23), three lignans (24–26), three phenols (27–29), two anthraquinones (30–31), two triterpenoids (32–33), two secoiridoids (34–35), one naphthalenyl glycoside (36), and one flavonoid (37). The chemical structures of these constituents were elucidated by NMR spectroscopy and compared with data from the literature. This is the first confirmation of the presence of ten compounds (6, 12, 16, 18, 24–26, 30, 32–33) isolated from the family Juglandaceae, two compounds (1 and 8) from the genus Juglans, and four compounds (27, 31, 34–35) from J. mandshurica. The isolation and chemotaxonomic significance of the metabolites from the roots of J. mandshurica were described in this study.     

胡桃楸不同营养器官 POD 同工酶的动态变化

对胡桃楸树根、树皮（茎皮）、枝皮、树枝（当年生枝条）、树叶5个营养器官过氧化物酶（POD）同工酶进行生长期动态测定比较,结果显示：胡桃楸POD同X-．酶表达具有发育阶段性和器官特异性;胡桃楸不同器官共有酶带B1,该酶带可能是胡桃属的特征性酶带;胡桃楸pod同工酶分析宜采用根、茎皮、枝皮部。试验结果为胡桃楸进一步食药用开发利用、引种栽培提供生化水平参考。     

Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis

Investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of five new oleanane-type triterpenoid saponins (1–5), together with seven known saponins (6–12). Their structures were determined by the extensive use of ¹D and ²D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1–12, prosapogenins 4a, 5a, 10a–12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines, including HepG2, HL-60, A549, HeLa and U87MG. The monodesmosidic saponins 6–8, 5a, 10a–12a and sapogenins SA, OA, HE exhibited cytotoxic activity toward all cancer cell lines, with IC₅₀ values ranging from 2.25 to 57.28 μM. Remarkably, the bisdesmosidic saponins 1–4 and 9 showed selective cytotoxicity against the U87MG cells.     

Two new glycosides and one new neolignan from the roots of Cynanchum stauntonii

Three new compounds including one C₂₁-steroidal glycoside, one methylglycoside, and one neolignan, named as Deoxyamplexicogenin A-3-O-yl-4-O-(4-O-α-l-cymaropyranosoyl-β-d-digitoxopyranosoyl)-β-d-canaropyranoside (1), Methyl-O-α-l-cymaropyranosoyl-(1 → 4)-β-D-digitoxopyranoside (2), and (+)-(7S, 8R, 7′E)-5-hydroxy-3, 5′-dimethoxy-4′, 7-epoxy-8, 3′-neolign-7′-ene-9, 9′-diol 9′-ethyl ether (3), respectively, were isolated from the roots of Cynanchum stauntonii. The structure elucidations were achieved by in-depth spectroscopic examination, mainly including the experiments and analyses of multiple 1D- and 2D-NMR and HRESIMS and CD analysis and qualitative chemical tests. Cytotoxicity activities of compounds 1–3 were evaluated against five tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780) in cell based assays where they were found to be inactive.     

核桃楸青果皮提取液对植物生长的影响

用核桃楸青果皮的氯仿、苯、正丁醇提取液,对萝卜、莴苣、稗草、马唐的发芽和生长的影响以及对黄瓜子叶叶绿素的形成的影响进行了试验。结果表明:氯仿、苯提取液抑制供试植物发芽和生长和叶绿素的形成,不同浓度的正丁醇提取液对供试植物显示抑制或促进作用。     

Coixlachryside A: A new lignan glycoside from the roots of Coix lachryma-jobi L. var. ma-yuen Stapf.

A new lignan glycoside, 1-[3,6-(4,4⿲-dihydroxy-3,3⿲-dimethoxy-δ-truxinyl)-β-fructofuranosyl]-α-glucopyranoside (1), named coixlachryside A, together with nine known simple phenolic compounds (3⿿11) were isolated from the roots of Coix lachryma-jobi var. ma-yuen using various chromatographic methods. Their chemical structures were determined based on the spectroscopic data interpretation, particularly circular dichroism (CD), 1D and 2D NMR data including HSQC and HMBC.     

Two new butanolides from the roots of Litsea acuminata

Two new butanolides, licunolides A (1) and B (2), were isolated from the roots of Litsea acuminata, together with three known compounds: isolancifolide (3), longifolin (4), and sesquirose furan (5). The structures of compounds 1 and 2 were determined by spectroscopic studies (IR, MS, 1D and 2D NMR) and chemical evidence. This is the first report of 4-hydroxy-5-methylbutanolides with a C₁₀-side chain from a natural source. Longifolin (4) and sesquirose furan (5) showed a significant cytotoxicity against HeLa cell lines in vitro.     

胡桃楸活性成分时空动态及抗肿瘤活性初步研究

采用超声波辅助提取方法,以胡桃楸为原料,在单因素实验的基础上研究一年内不同月份胡桃楸不同部位总黄酮、总酚的含量变化,同时对胡桃楸提取物体外抗肿瘤活性进行初步评价。结果显示,乙醇浓度60%,超声时间40 min,料液比1：20,提取温度30℃为最佳提取参数。在此条件下,不同采摘时期胡桃楸不同部位的总黄酮、总酚含量存在显著差异。5~7月份叶和小枝的总黄酮及总酚含量明显高于8~10月份,其中7月份叶的总黄酮总酚含量最高,分别为12.56±0.33和76.98±3.73 mg·g^-1,然而茎皮总黄酮、总酚含量随月份增加呈持续下降趋势。体外抗肿瘤研究表明胡桃楸叶提取物对人肝癌细胞SMMC-7721、人乳腺癌细胞MCF-7和人口腔表皮样癌细胞KB的增殖抑制作用,其中7月份胡桃楸叶提取物对人乳腺癌MCF-7细胞增殖抑制作用更明显,其IC₅₀值为0.24 mg·mL^-1。本研究为胡桃楸资源的合理开发及利用提供一定的理论基础。