Kurilosides A1, A2, C1, D,E and F—Triterpene Glycosides from the Far Eastern Sea Cucumber Thyonidium (= Duasmodactyla) kurilensis (Levin): Structures with Unusual Non-Holostane Aglycones and Cytotoxicities     

Alexandra S. Silchenko  Anatoly I. Kalinovsky  Sergey A. Avilov  Pelageya V. Andrijaschenko  Roman S. Popov  Pavel S. Dmitrenok  Ekaterina A. Chingizova  Vladimir I. Kalinin 《Marine drugs》2020,18(11)

Six new monosulfated triterpene tetra-, penta- and hexaosides, namely, the kurilosides A₁ (1), A₂ (2), C₁ (3), D (4), E (5) and F (6), as well as the known earlier kuriloside A (7), having unusual non-holostane aglycones without lactone, have been isolated from the sea cucumber Thyonidium (= Duasmodactyla) kurilensis (Levin) (Cucumariidae, Dendrochirotida), collected in the Sea of Okhotsk near Onekotan Island from a depth of 100 m. Structures of the glycosides were established by 2D NMR spectroscopy and HR-ESI mass spectrometry. Kurilosides of the groups A and E contain carbohydrate moieties with a rare architecture (a pentasaccharide branched by C(4) Xyl1), differing from each other in the second monosaccharide residue (quinovose or glucose, correspondingly); kurilosides of the group C are characterized by a unique tetrasaccharide branched by a C(4) Xyl1 sugar chain; and kurilosides of the groups D and F are hexaosides differing from each other in the presence of an O-methyl group in the fourth (terminal) sugar unit. All these glycosides contain a sulfate group at C-6 of the glucose residue attached to C-4 Xyl1 and the non-holostane aglycones have a 9(11) double bond and lack γ-lactone. The cytotoxic activities of compounds 1–7 against mouse neuroblastoma Neuro 2a, normal epithelial JB-6 cells and erythrocytes were studied. Kuriloside A₁ (1) was the most active compound in the series, demonstrating strong cytotoxicity against the erythrocytes and JB-6 cells and a moderate effect against Neuro 2a cells.  相似文献   

Six New Diterpene Glycosides from the Soft Coral Lemnalia bournei     

Xia Yan  Han Ouyang  Te Li  Yutong Shi  Bin Wu  Xiaojun Yan  Shan He 《Marine drugs》2021,19(6)

A chemical study on the extracts of soft coral Lemnalia bournei resulted in the isolation and identification of six new bicyclic diterpene glycosides including three new lemnaboursides E–G (1–3), and three new lemnadiolboursides A–C (4–6), along with three known lemnaboursides (7–9). Their structures were elucidated by detailed spectroscopic analysis, ECD analysis, chemical methods, and comparison with the literature data. Lemnadiolboursides A–C (4–6) contained a lemnal-1(10)-ene-7,12-diol moiety compared with the lemnaboursides. All these compounds were evaluated for antibacterial activity; cell growth inhibition of A549, Hela, HepG2, and CCRF-CEM cancer cell lines; and inhibition of LPS-induced NO production in RAW264.7 macrophages. The results indicated that compounds 1, 2, and 4–6 exhibited antibacterial activity against Staphylococcus aureus and Bacillus subtilis (MIC 4–16 μg/mL); compounds 1–9 displayed low cytotoxicity on the CCRF-CEM cell lines (IC₅₀ 10.44–27.40 µM); and compounds 1, 2, and 5 showed weak inhibition against LPS-induced NO production (IC₅₀ 21.56–28.06 μM).  相似文献   

海参皂苷的分离提取与生物活性   总被引：3，自引：0，他引：3  

苏永昌  刘淑集  吴成业 《福建水产》2008,(1):66-69

海参具有较高的营养价值和药用价值.海参皂苷具有抗肿瘤,抗菌等多种生物活性,具有重大的应用价值和广阔的应用前景.本文对海参皂苷的提取、分离纯化、分析方法及生物活性进行初步的介绍.  相似文献   

Yield components,light interception and marker compound accumulation of stevia (Stevia rebaudiana Bertoni) affected by planting material and plant density under western Himalayan conditions     

Rakesh Kumar  Saurabh Sharma  Swati Sood 《Archives of Agronomy and Soil Science》2013,59(12):1731-1745

A field experiment was conducted to study the effect of planting material and plant density on stevia (Stevia rebaudiana Bertoni) under western Himalayan conditions during 2011 and 2012. The experiment conducted in a split plot design consisted of two types of planting material (rooted slips and fresh seedlings) in the main plot and five inter- and intra-row spacing in subplots with three replications. Yield attributes and dry leaf biomass yield of stevia were not affected by the type of planting material; however, plant density significantly influenced the yield attributes and leaf and stem dry biomass. Although the wider spacing (60 × 45 cm) gave more leaves, higher leaf area index, higher leaf dry mass per plant as compared to closer spacing, it resulted in lower values of these attributes per unit area. Plants spaced in 30 × 30 cm accumulated 41.2% and 42.8% more total biomass than 60 × 45 cm. Steviol glycoside content did not change due to different planting materials and plant densities; however, closer plant spacing (30 × 30 cm) recorded 114.8% and 70.0% higher steviol glycoside accumulation compared to wider row spacing (60 × 45 cm) in 2011 and 2012, respectively.  相似文献   

In Vitro Anticancer and Cancer-Preventive Activity of New Triterpene Glycosides from the Far Eastern Starfish Solaster pacificus     

Timofey V. Malyarenko  Olesya S. Malyarenko  Alla A. Kicha  Anatoly I. Kalinovsky  Pavel S. Dmitrenok  Natalia V. Ivanchina 《Marine drugs》2022,20(3)

Sea stars or starfish (class Asteroidea) and holothurians or sea cucumbers (class Holothuroidea), belonging to the phylum Echinodermata (echinoderms), are characterized by different sets of glycosidic metabolites: the steroid type in starfish and the triterpene type in holothurians. However, herein we report the isolation of eight new triterpene glycosides, pacificusosides D–K (1–3, 5–9) along with the known cucumarioside D (4), from the alcoholic extract of the Far Eastern starfish Solaster pacificus. The isolated new compounds are closely related to the metabolites of sea cucumbers, and their structures of 1–3 and 5–9 were determined by extensive NMR and ESIMS techniques. Compounds 2, 5, and 8 have a new type of tetrasaccharide chain with a terminal non-methylated monosaccharide unit. Compounds 3, 6, and 9 contain another new type of tetrasaccharide chain, having 6-O-SO₃-Glc as one of the sugar units. The cytotoxic activity of 1–9 against non-cancerous mouse epidermal cells JB6 Cl41 and human melanoma cell lines SK-MEL-2, SK-MEL-28, and RPMI-7951 was determined by MTS assay. Compounds 1, 3, 4, 6, and 9 showed potent cytotoxicity against these cell lines, but the cancer selectivity (SI > 9) was observed only against the SK-MEL-2 cell line. Compounds 1, 3, 4, 6, and 9 at the non-toxic concentration of 0.1 μM significantly inhibited neoplastic cell transformation of JB6 Cl41 cells induced by chemical carcinogens (EGF, TPA) or ionizing radiation (X-rays and UVB). Moreover, compounds 1 and 4 at the non-toxic concentration of 0.1 µM possessed the highest inhibiting activity on colony formation among the investigated compounds and decreased the colonies number of SK-MEL-2 cells by 64% and 70%, respectively. Thus, triterpene glycosides 1 and 4 can be considered as prospective cancer-preventive and anticancer-compound leaders.  相似文献   

Cytotoxic and Apoptosis-Inducing Activity of Triterpene Glycosides from Holothuria scabra and Cucumaria frondosa against HepG2 Cells     

Juanjuan Wang  Hua Han  Xiangfeng Chen  Yanghua Yi  Hongxiang Sun 《Marine drugs》2014,12(8):4274-4290

The cytotoxic effects of thirteen triterpene glycosides from Holothuria scabra Jaeger and Cucumaria frondosa Gunnerus (Holothuroidea) against four human cell lines were detected and their cytotoxicity-structure relationships were established. The apoptosis-inducing activity of a more potent glycoside echinoside A (1) in HepG2 cells was further investigated by determining its effect on the morphology, mitochondrial transmembrane potential (Δψ_m) and mRNA expression levels of the apoptosis-related genes. The results showed that the number of glycosyl residues in sugar chains and the side chain of aglycone could affect their cytotoxicity towards tumor cells and selective cytotoxicity. 1 significantly inhibited cell viability and induced apoptosis in HepG2 cells. 1 also markedly decreased the Δψ_m and Bcl-2/Bax mRNA express ratio, and up-regulated the mRNA expression levels of Caspase-3, Caspase-8 and Caspase-9 in HepG2 cells. Therefore, 1 induced apoptosis in HepG2 cells through both intrinsic and extrinsic pathway. These findings could potentially promote the usage of these glycosides as leading compounds for developing new antitumor drugs.  相似文献   

Two new chalcone glycosides from the stems of Entada phaseoloides     

Zhao ZX  Jin J  Lin CZ  Zhu CC  Liu YM  Lin AH  Liu YX  Zhang L  Luo HF 《Fitoterapia》2011,82(7):1102-1105

Two new chalcone glycosides 4′-O-(6″-O-galloyl-β-d-glucopyranosyl)-2′,4-dihydroxychalcone (1) and 4′-O-(6″-O-galloyl-β-d-glucopyranosyl)-2′-hydroxy-4-methoxychalcone (2) together with one known chalcone glycoside 4′-O-β-d-glucopyranosyl-2′-hydroxy-4-methoxychalcone (3) were isolated from the stems of Entada phaseoloides. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis, including HSQC, HMBC, ¹H–¹H COSY, and chemical evidences. This is the first report of chalcone-type compounds isolated from the genus Entada.  相似文献   

小佛肚竹生氰糖苷合成关键酶CYP79家族同源基因的克隆和鉴定     

王月圆  刘向敏  周明兵  汤定钦 《浙江林学院学报》2012,29(4):510-515

生氰糖苷是由氰醇衍生物的羟基和D-葡萄糖缩合形成的糖苷,已在2 000多种植物中发现,分属于蕨类植物、裸子植物和被子植物的130个家族.生氰糖苷的主要生物学功能在于阻止食草动物和病原体对植物的侵害.通过反转录-聚合酶链式反应(RT-PCR)和cDNA末端快速扩增(RACE)技术从小佛肚竹Bambusa ventricosa幼笋中克隆到CYP79家族同源基因的cDNA全长,命名为BvCYP79.BvCYP79共有1 913个碱基对,翻译起始点为193碱基处,终止子位于1 752 bp,包含1个1 559 bp的完整编码区,开放阅读框共编码519个氨基酸.具有PERF和SFSTGRRGCIA保守结构域,属于典型的单子叶植物CYP79家族基因.生氰糖苷途径可能也存在于竹类植物,因而在食用笋的安全性评估上具有一定指导意义.  相似文献   

甜菊全生育期含甙量变化调查     

朱娟  肖辉  刘繁桂 《中国甜菜》2012,(2):55-56

试验结果表明,两个高RA型甜菊品种的含甙总量（TSG）和RA含量占TSG含量比重总趋势是均随着田间植株生长而递增,ST含量占TSG含量比重总趋势则是随田间植株生长而递减。守田3号TSG含量在80d时达最高,RA含量占TSG含量比重在130d时（现蕾期）达最高,ST含量占TSG含量比重在100d时降至最低。谱星1号TSG含量也在80d时达最高,RA含量占TSG含量比重、ST含量占TSG含量比重在100d时升至最高和降至最低。试验结果对于选择最佳收获期意义重大。  相似文献   

Effects of tripterygium glycosides combined with dexamethasone on TLRs/NF-κB signaling pathway in EAE rats     

XIE Fu-hua  XIONG Xu-ming  LIANG Bing  LIN Zhe-cong  ZHANG Shan-shan 《园艺学报》2012,28(11):1961-1965

AIM: To investigate the role of TLRs/NF-κB pathway in experimental allergic encephalomyelitis (EAE) rats treated with tripterygium glycosides (TG) + dexamethasone (DX). METHODS: Lewis rats were used in the study and divided into control group, EAE model group, therapy 1 group (EAE rats treated with DX) and therapy 2 group (EAE rats treated with DX+TG). The mean clinical score of the rats was determined. The expression of TLR4 and TLR9 at mRNA and protein levels was detected by the methods of real-time quantitative RT-PCR and immunohistochemistry. The protein level of NF-κB p65 was also measured. The levels of TNF-α, IL-1β and IL-6 were assayed by ELISA. RESULTS: The mean clinical scores at 5th, 16th and 20th day were lower in therapy 1 group and therapy 2 group than that in EAE model group. The mean clinical score in therapy 2 group was even lower than that in therapy 1 group. At the 16th day (the peaking period), the mRNA expression of TLR4 and TLR9 in therapy 1 group and therapy 2 group were obviously lower than that in EAE model group. The protein levels of TLR4, TLR9 and NF-κB p65 were also significantly lower in therapy 1 group and therapy 2 group than those in EAE model group at peak stage of EAE. The levels of TNF-α, IL-1β and IL-6 were lower in therapy1 group and therapy2 group than those in EAE model group. The significant differences of the mean clinical score, the mRNA expression of TLR4 and TLR9, the positive ratio of NF-κB p65 and the levels of TNF-α, IL-1β and IL-6 between therapy 1 group and therapy 2 group were found. The result of orthogonal factorial analysis of variance indicated that the difference of therapeutic effect between DX and DX+TG was significant (F=75.749, P<0.01). CONCLUSION: The TLRs/NF-κB pathway takes part in the pathological process of EAE. TG combined with DX alleviates the symptoms of EAE by suppressing inflammatory and immunological reactions of EAE.  相似文献