Cytotoxic activity of steroidal glycosides from solanum plants

Since some Solanum-genera plants have traditionally been used as anti-cancer and anti-herpes agents from olden times, we examined the cytotoxic activity of typical steroidal glycosides with the framework of spirostane, furostane, spirosolane, and pregnane obtained from Solanum plants. Among these steroidal glycosides, the spirostanol glycosides having a beta-lycotetraosyl moiety were the most effective against PC-12 and HCT-116 cell lines. The potency of activity was observed to be decreased in the order of spirostane, furostane, spirosolane, and pregnane type steroid glycosides. It was also suggested that the activity depend on the kind of oligosaccharide moiety and aglycone moiety.     

Anti-herpes virus activity of Solanum steroidal glycosides

Since some Solanum-genus plants have traditionally been used for anti-cancer and anti-herpes agents from olden times, we examined anti-herpes simplex virus type 1 (HSV-1) activity of typical steroidal glycosides with the frameworks of spirostane (including nuatigenin glycoside), furostane, solasodane, tomatidane and ergostane (including dimer) obtained from Solanum plants. Among these steroidal glycosides, the spirostanol glycosides were most effective. An inclination was observed for the potency of activity to decrease in the order of spirostane, tomatidane, ergostane, solasodane, nuatigenin type, dimer of ergostane and furostane. It was also suggested that the activity depends on the kind of oligosacchride moiety.     

Content variations of the tomato saponin esculeoside A in various processed tomatoes

A tomato saponin, esculeoside A, may be metabolized into various steroidal hormones such as pregnane derivatives that are expected to exhibit various bioactivities in the body, such as anti-osteoporosis, anti-menopausal disorder and anti-tumor actions. Therefore, we attempted to examine the esculeoside A contents of fresh tomatoes, tomatoes boiled in water, tomatoes heated using a microwave oven, freeze-dried tomatoes, and commercially available processed tomato products contained in plastic bottles and cans, in order to develop a health food.     

Structural requirement of spirostanol glycosides for rat uterine contractility and mode of their synergism

Objectives Total steroidal saponins extracted from the rhizome of Paris polyphylla (TSSP) have been used in China for the treatment of abnormal uterine bleeding. The aim of this study was to analyse the structure–activity relationship of steroidal saponins purified from P. polyphylla Sm. var. yunnanensis on rat myometrial contractions, and investigate the synergism among themselves as well as with known inherent agonists, such as Prostaglandin F_2α (PGF‐2α). Methods In this study, 22 steroidal saponins purified from TSSP were screened for their contractile activity in isolated uterine strips from estrogen‐primed rats. Key findings It was shown that spirostanol glycosides exhibited inducible or inhibitory activity in rat uterine contraction based on the difference of their structures, which was not only attributed in part to the number, the length and the position of sugar side chains attached by a glycoside, but also related to the structure of the aglycone. Furthermore, synergistic actions were observed among pennogenin or diosgenin glycosides as well as with the known inherent agonist PGF‐2α, indicating they may share, at least in part, similar pathways with PGF‐2α in stimulating myometrial contractions. Finally, the contractile response of rat myometrium to spirostanol glycosides was significantly enhanced with advancing pregnancy. Conclusions Together, these data support the possibility that some spirostanol glycosides may represent a new type of contractile agonist for the uterus and their synergism may be responsible for the therapeutic effect of TSSP on abnormal uterine bleeding.     

Three new aromatic glycosides from the ripe fruit of cherry tomato

Three new aromatic glycosides were isolated from the ripe fruit of cherry tomato [Lycopersicon esculentum var. cerasiforme (Dunal) Alef. (Solanaceae)] along with six known aromatic glycosides and one known steroidal alkaloid glycoside. Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.     

Chromone and flavonol glycosides from <Emphasis Type="Italic">Delphinium hybridum</Emphasis> cv. “Belladonna Casablanca”

One new chromone and six known flavonol glycosides were isolated from the stems and leaves of Delphinium hybridum cv. “Belladonna Casablanca” (Ranunculaceae). The new chromone glycoside was elucidated as 2-methyl-chromone-5,7-diol 7-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (1). The six known flavonol glycosides were designated as compounds 2–5, being kaempferol-type glycosides, and compounds 6 and 7, being quercetin-type glycosides. The structures of these glycosides were determined by two-dimensional nuclear magnetic resonance (2D NMR) spectroscopic analysis and chemical evidence.     

Two new pregnane glycosides from soft coral Cladiella krempfi

Two new pregnane-type steroidal glycosides, pregna-5,20-dien-3-O-alpha-fucopyranoside (1) and pregna-20-en-3-O-alpha-fucopyranoiside (2), along with two known pregnane derivatives, were isolated from the soft coral Cladiella krempfi. Their structures were determined by spectroscopic data analysis.     

湖北山麦冬化学成分的研究

从湖北山麦冬(Liriope spicata Lout(Thunb).var.prolifera Y.T.Ma)块根的醇提物中分得四种甾体甙类化合物,根据化学性质和波谱(IR,¹HNMR,¹³CNMR,EI-MS,FAB-MR)分析,确定甙Ⅰ为以β-谷甾醇为主、豆甾醇为次的混合甾醇的β-D-吡喃葡萄糖甙;甙Ⅱ为25(S)-鲁斯可皂甙元1-O-β-D-吡喃夫糖3-O-α-L-吡喃鼠李糖甙;甙Ⅲ为25(S)-鲁斯可皂甙元1-O-α-L-吡喃鼠李糖基(1→2)-β-D-吡喃木糖甙;甙Ⅳ为25(S)-鲁斯可皂甙元1-O-[α-L-吡喃鼠李糖基(1→2)](β-D-吡喃木糖基(1→3)]-β-D-吡喃夫糖甙,其中甙Ⅲ和甙Ⅳ为新的甾体皂甙。     

10批栀子中环烯醚萜苷类成分含量测定

目的 测定不同产地的10批栀子药材中栀子苷、京尼平龙胆二糖苷及总环烯醚萜苷含量。方法 采用HPLC测定栀子苷、京尼平龙胆二糖苷含量;采用紫外分光光度法测定总环烯醚萜苷含量。结果 江西产栀子中环烯醚萜苷类成分含量高。结论 不同产地栀子药材中环烯醚萜苷类成分含量有所差别。     

New lignan glycosides from Justicia procumbens

Four new lignan glycosides (1–4), named procumbenosides I, K, L, and M, together with cleistanthin B (5) reported for the first time in the genus Justicia, and 5 other known arylnaphthalene lignan glycosides (6–10) were isolated from the whole plant of Justicia procumbens. The structures of the new compounds were elucidated by extensive one-dimensional (1D) and two-dimensional (2D) NMR experiments and mass spectrometry. Procumbenoside M (4) was a rare sesquilignan glycoside never previously reported in the species of Justicia. The paper also provided insight into the conformational equilibria existing in the lignan glycosides of the plant.     

Resin glycosides from the leaves and stems of <Emphasis Type="Italic">Ipomoea digitata</Emphasis>

Alkaline hydrolysis of the ether-soluble resin glycoside (jalapin) fraction of the leaves and stems of Ipomoea digitata L. (Convolvulaceae) gave six organic acids, isobutyric, (S)-2-methylbutyric, tiglic, n-decanoic, n-dodecanoic, and cinnamic acids, and two glycosidic acids, quamoclinic acid A and operculinic acid A. Further, a new genuine resin glycoside, named digitatajalapin I, was isolated from the jalapin fraction, along with three known resin glycosides. Their structures have been determined on the basis of chemical and spectroscopic data.     

Steroid compounds from <Emphasis Type="Italic">Yucca gloriosa</Emphasis> L. introduced into Georgia and their applications

A plantation of Yucca gloriosa L. (mound-lily yucca) was created in eastern Georgia as a source of the sapogenin tigogenin and for raw material for the synthesis of steroidal hormone preparations of the 5α series. Leaves drying on the lower tier of the living plant contained only spirostanol glycosides. The dominant components of yuccaloesides A, B, and C were extracted from these, along with the new compound 3-O-α-L-rhamnopyranoside(1→4)-O-β-D-xylopyranosyl(1→3)-O-[β-D-glucopyranosyl(1→2)]-O-β-D-gluc opyranosyl(1→4)-O-β-D-galactopyranosyl 25R,5α-spirostan-3β-ol. Total glycosides from leaves drying on living plants were used to prepare a potential antimycotic substance for external application, Gloriofucin. Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 43, No. 1, pp. 27–29, January, 2009.     

何首乌中二苯乙烯苷的药效学和药动学研究进展

二苯乙烯苷类成分是何首乌中的特有成分,具有广泛的药理学活性.本文综述了二苯乙烯苷(2,3,5,4’-四羟基二苯乙烯-2-O-β-D-葡萄糖苷)在抗氧化、心血管系统、中枢神经系统和抗肿瘤等药效学方面的作用,探讨了其可能的作用机制及应用前景.同时对其吸收和代谢等药动学方面的最新研究进展进行了总结,以期为进一步深入研究二苯乙烯苷类成分的药学特点和药物研发方向提供思路.     

Two new maltol glycosides and cyanogenic glycosides from <Emphasis Type="Italic">Elsholtzia rugulosa</Emphasis> Hemsl.

Two new maltol glycosides, maltol 6′-O-β-d-apiofuranosyl-β-d-glucopyranoside and maltol 6′-O-(5-O-p-coumaroyl)-β-d-apiofuranosyl-β-d-glucopyranoside, were isolated from Elsholtzia rugulosa Hemsl. along with 11 known compounds including prunasin and amygdalin. The structures were determined on the basis of spectroscopic and chemical evidence. This is the second example of isolation of cyanogenic glycosides from Lamiaceous plants.     

江苏地产白首乌 C21甾体苷对高血脂大鼠血脂调节和肝脏保护作用研究

目地研究江苏地产白首乌 C21甾体苷对实验性高脂血症大鼠的血脂调节作用和肝脏保护作用。方法建立实验性高脂血症大鼠模型,成模大鼠分别给予白首乌 C21甾体苷（20、40 mg·kg －1）、阿托伐他汀钙10 mg·kg －1和1％羧甲基纤维素钠溶液灌胃,每日1次,连续给药2周,同时设正常对照组。实验结束比较体质量变化,计算肝脏系数;检测给药后血清总胆固醇（TC）、总甘油三酯（TG）、低密度脂蛋白胆固醇（LDL-C）和高密度脂蛋白胆固醇（HDL-C）含量,并行大鼠肝脏病理学检查。结果给药1周后,阳性对照组和白首乌 C21甾体苷给药组,能够有效控制高脂血症模型大鼠肝脏系数,降低血清 TC、TG 和LDL-C 的含量,其中白首乌 C21甾体苷高剂量组升高血清 HDL-C 的含量与模型组比较有显著差异,病理学切片显示各用药组能改善肝脏脂肪变性。结论白首乌 C21甾体苷具有良好的调节血脂作用,改善肝脏脂肪变性。     

Monoterpene glycosides from Paeonia veitchii

The EtOH extract of the roots of Paeonia veitchii afforded two new monoterpene glycosides paeonidanin I (1) and paeonidanin J (2), and a new dimeric monoterpene glycoside paeonidanin K (3). Their structures were elucidated on the basis of spectroscopic means and hydrolysis products.     

Structural Requirements for Alkylglycoside-Type Renal Targeting Vector

Purpose. We have previously shown Glc-S-C7-Me (octyl -D-thioglucoside) exhibits renal targeting potential in vivo in addition to its specific binding to the renal membrane fraction in vitro. Thus, 'alkylglycoside' is considered to be a novel targeting vector for the kidney (1,2). The present study is designed to clarify the structural requirements for alkylglycoside as a renal targeting vector. Methods. Inhibitory effects of various sugars and glycosides on ³H-Glc-S-C7-Me binding to the kidney membrane fraction were evaluated by a centrifugation method. Results. As far as the sugar moiety is concerned, no other sugars except D-aldohexose and D-aldohexose derivatives (containing F, S, and N) showed greater inhibition than D-glucose. Therefore, octylthio derivatives of various D-aldohexose were prepared and their inhibitory effects were investigated. The following findings were obtained: Equatorial OH at 4 position is essential; OH at 2 position can have either orientation or be deleted. As far as the alkyl moiety is concerned, the length, branching and electrical environment in the region of the glycoside bond are important; aromatic structures can substitute for the alkyl portion; the preferred glycoside bonding atom is as follows: S > NH> O. Conclusions. The structural requirements for the renal targeting vector have been identified to be as follows: a hydrophobic group (alkyl chain or aromatic ring) should be introduced to a sugar (D-glucose, D-mannose, or 2-deoxy-D-glucose) via a -glycoside binding atom (S > NH > O).     

Pregnane glycosides from the stems of Marsdenia tenacissima

Four new pregnane glycosides, named marstenacissides A (1), B (2), C (3), and D (4), have been isolated from the stems of Marsdenia tenacissima. Their structures were established on the basis of chemical and spectral methods.     

Anti-acetylcholinesterase and anti-amnesic activities of a pregnane glycoside, cynatroside B, from Cynanchum atratum

We previously reported that seven pregnane glycosides including cynatroside B isolated from the roots of Cynanchum atratum significantly inhibited acetylcholinesterase (AChE) activity. In the present study, we have characterized the mode of AChE inhibition of cynatroside B, the most potent of these isolated pregnane glycoside inhibitors. We have also examined the anti-amnesic activity of cynatroside B. Cynatroside B inhibited AChE activity in a dose-dependent manner and its IC50 value was 3.6 microM. The mode of AChE inhibition by cynatroside B was reversible and non-competitive in nature. Moreover, cynatroside B (1.0 mg/kg body weight i.p.) significantly ameliorated memory impairments induced in mice by scopolamine (1.0 mg/kg body weight s.c.) as measured in the passive avoidance and the Morris water maze tests. We suggest, therefore, that cynatroside B has both anti-AChE and anti-amnesic activities that may ultimately hold significant therapeutic value in alleviating certain memory impairments observed in Alzheimer's disease.     

New steroidal glycosides from the rhizome of Anemarrhena asphodeloides

Two new steroidal saponins, timosaponin X (1) and timosaponin Y (2), and one new pregnane glycoside, timopregnane B (3), were isolated from the rhizomes of Anemarrhena asphodeloides, as well as three known compounds 25S-timosaponin BII (4), protodesgalactotigonin (5), and timosaponin BII-a (6) isolated from this plant for the first time. By the detailed analysis of 1D, 2D NMR, MS spectra, and chemical evidences, the structures of new compounds were elucidated as 26-O-β-d-glucopyranosyl-(25S)-5β-22-methoxy-furost-3β,26-diol 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranoside (1), 5β-pseudo-spirost-3β,15α,23α-triol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (2), (5β,17α)-Δ¹⁶⁽¹⁷⁾-20-one-pregn-2β,3β-diol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (3).