New Steroidal Glycosides from Rhizomes of Clintonia udensis

A total of 10 steroidal glycosides, together with three new spirostanol glycosides (6–8), a new furostanol glycoside (9), and a new cholestane glycoside (10), were isolated from the rhizomes of Clintonia udensis (Liliaceae). The structures of the new compounds were determined on the basis of extensive spectroscopic analyses, including 2-D nuclear magnetic resonance (NMR) data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. The isolated glycosides were evaluated for their cytotoxic activity against HL-60 leukemia cells. Spirostanol glycosides 1 and 2, and furostanol glycoside 4 showed cytotoxic activity with IC₅₀ values of 3.2±0.02, 2.2±0.12, and 2.2±0.06 μg/ml, respectively. Neither the spirostanol and furostanol saponins with a hydroxy group at C-1 (6 and 9) and C-12 (7 and 8) nor cholestane glycosides (5 and 10) exhibited apparent cytotoxic activity at a sample concentration of 10 μg/ml.     

Cytotoxic Activity of New Phenolic Compounds from Vietnamese Caesalpinia sappan

Two new phenolic compounds, caesalpiniaphenols G–H (1 and 2), were isolated from Vietnamese Caesalpinia sappan heartwood. The chemical structures were established mainly by extensive spectroscopic studies and chemical evidence. Compounds 1 and 2 showed potent inhibitory activity against HL-60 cancer cell lines with respective IC₅₀ values of 16.7 and 22.5 µg/mL. Treating HL-60 cells with various concentrations of 1 resulted in growth inhibition and the induction of apoptosis.     

Two New Eudesmane-Type Sesquiterpene from Clonostachys sp. Y6-1and Their Cytotoxic Activity

Two undescribed eudesmane-type sesquiterpenoids together with four known compounds were isolated from Clonostachys sp. Y6-1 associated. Their chemical structures were unambiguously determined by NMR, mass spectrometry, and ¹³C-NMR calculation as well as DP4+ probability analyses. The absolute configurations of compounds 1 and 2 were determined by ECD calculation and X-ray single-crystal diffraction methods. Furthermore, all isolates were evaluated for in vitro cytotoxic activities against MCF-7, HCT-116, MDA-MB-231, and SW620 cancer cells. Among them, bioactivity evaluation of compound 5 revealed that weak activity (IC₅₀=66.55±0.82 μM) against SW620.     

Glycosides from Roots of Cyathula officinalis Kuan

Abstract: To search for new and bioactive compounds from traditional Chinese medicines, a new glycoside, 3-O-[α- L -rhamnopyranosyl-(1→3)-( n -butyl-β- D -glucopyranosiduronate)]-28-O-β- D -glucopyranosyloleanolic acid ( 1 ), was isolated from the roots of Cyathula officinalis Kuan, along with 3-O-(methyl-β- D -glucopyranosiduronate)-28-O-β- D -glucopyranosyl oleanolic acid ( 2 ), 3-O-β- D -glucopyranosyl oleanolic acid ( 3 ), 3-O-β- D -glucuronopyranosyl oleanolic acid ( 4 ), 3-O-[β- L -rhamnopyranosyl-(1→3)-(β- D -glucuronopyranosyl)] oleanolic acid ( 5 ), 3-O-(β- D -glucuronopyranosyl)-28-O-β- D -glucopyranosyl oleanolic acid ( 6 ), 28-O-β- D -glucuronopyranosyl-(1→4)-β- D -glucopyranosyl hederagenin ( 7 ), 3-O-[β- L -rhamnopyranosyl-(1→3)-β- D -glucuronopyranosyl]-28-O-β- D -glucopyranosyl oleanolic acid ( 8 ), and 3-O-[β- D -glucopyranosyl-(1→2)-α- L -rhamnopyranosyl-(1→3)-β- D -glucuronopyranosyl]-28-O-β- D -glucopyranosyl oleanolic acid ( 9 ). The structures of these compounds were determined based on spectral and chemical evidence. The 50 per cent growth-inhibiting (GI₅₀) of compounds 1 and 5 against MDA-MB-231 (a human breast cancer cell line) was 3.44 × 10^-4 and 4.66 × 10^-4 mol/L, respectively.
(Managing editor: Wei WANG)     

Glycosides from Roots of Cyathula officinalis Kuan

To search for new and bioactive compounds from traditional Chinese medicines, a new glycoside,3-O-[α-L-rhamnopyranosyl-(l-→3)-(n-butyl-β-D-glucopyranosiduronate)]-28-O-β-D-glucopyranosyl oleanolic acid (1), was isolated from the roots of Cyathula officinalis Kuan, along with 3-O-(methyl-β-D-glucopyranosiduronate)-28-O-β-D-glucopyranosyl oleanolic acid (2), 3-O-β-D-glucopyranosyl oleanolic acid (3), 3-O-β-D-glucuronopyranosyl oleanolic acid (4), 3-O-[α-L-rhamnopyranosyl-(l→3)-(β-D-glucuronopyranosyl)] oleanolic acid (5), 3-O-(β-D-glucuronopyranosyl)-28-O-β-D-glucopyranosyl oleanolic acid (6), 28-O-β-D-glucuronopyranosyl-(1→4)-β-D-glucopyranosyl hederagenin (7), 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl]-28-O-β-D-glucopyranosyl oleanolic acid (8), and 3-O-[β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl]-28-O-β-D-glucopyranosyl oleanolic acid (9). The structures of these compounds were determined based on spectral and chemical evidence. The 50 per cent growth-inhibiting (GI50) of compounds 1 and 5 against MDA-MB-231(a human breast cancer cell line) was 3.44 × 10-4 and 4.66 × 10-4 mol/L, respectively.     

Flavonoids from Seeds of Camellia semiserrata Chi. and Their Estrogenic Activity

Two new flavonol glycosides and three known flavonoids were isolated from seeds of Camellia semiserrata Chi. The structures of these new flavonol glycosides were established as kaempferol 3-O-[(2'''',3'''',4''''-triacetyl)-α-L-rhamnopyranosyl(1→3)(2''',4'''-diacetyl)-α-L-rhamnopyranosyl (1→6)-β-D-glucopyranoside] and kaempferol 3-O-[(3'''',4''''-diacetyl)-α-L-rhamnopyranosyl(1→3)(2''',4'''-diacetyl)-α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside] by spectroscopic methods. The estrogenic activity of these compounds was investigated by a recombinant yeast screening assay.     

Diterpenoids from Euphorbia neriifolia and Their Related Anti‐HIV and Cytotoxic Activity

Fifteen diterpenoids ( 1 – 15 ), including three undescribed ones with ent‐atisane skeleton, eupnerias G–I ( 1 – 3 ), were obtained from Euphorbia neriifolia. Compounds 1 – 3 were established through comprehensive spectroscopic analysis. Compounds 4 and 5 exhibited obvious anti‐HIV‐1 effect, and their EC₅₀ were 6.6±3.2 and 6.4±2.5 μg mL^?1, respectively. Compound 6 exhibited moderate cytotoxicity on HepG2 and HepG2/Adr cells with IC₅₀ at 13.70 and 15.57 μm , respectively. In addition, compound 15 exhibited significant cytotoxicity on HepG2 cell lines (IC₅₀=0.01 μm ), while it did not show any cytotoxicity against HepG2/Adr cell lines.     

Ultrastructural evidence for a dual function of the phloem and programmed cell death in the floral nectary of Digitalis purpurea

BACKGROUND AND AIMS: The floral nectary of Digitalis purpurea is a transitory organ with stomatal exudation of nectar. In this type of nectary, the nectar is thought to be transported to the exterior via intercellular ducts that traverse the nectariferous tissue. The latter is also traversed by a ramified system of phloem strands from which prenectar sugar is most probably unloaded. The aims of this study were to provide some of the basic information needed to evaluate the possible mechanism involved in nectar secretion and to discover the fate of the nectary. METHODS: The ultrastructure of the nectary was investigated at different stages of development by analysis of a series of ultrathin (7 x 10(-8) m) sections 7 x 10(-7) m apart from one another. Proportions of the cells typical of the nectary were documented by 3D-reconstruction and morphometry. KEY RESULTS: The phloem consisted of variably shaped sieve elements and companion cells which, as a rule, were more voluminous than the sieve elements. Direct contact between the phloem strands and intercellular ducts was observed. In contrast to the phloem, which remained structurally intact beyond the secretory phase, the nectariferous tissue exhibited degenerative changes reminiscent of programmed cell death (PCD), which started as early as the onset of secretion and progressed in a cascade-like fashion until final cell death occurred in the exhausted nectary. Hallmarks of PCD were: increased vacuolation; increase in electron opacity of individual cells; progressive incorporation of plasmatic components into the vacuole reminiscent of autophagy; degradation of plastids starting with hydrolysis of starch; deformation of the nucleus and gradual disappearance of chromatin; loss of tonoplast integrity and subsequent autolysis of the rest of cellular debris. Degeneration of the cells occurred against a background of increasing cell size. CONCLUSIONS: The cytological and anatomical evidence presented here, and calculations of the solute fluxes necessary for accumulation of starch and for the production of nectar support the view that: (a) in the foxgloves' nectary, apoplastic phloem unloading dominates, at least during exudation of nectar; (b) the obsolete nectary may be dismantled by PCD; and (c) at least the products of late nectary degradation are loaded via the apoplast into the unchanged phloem and exported to sinks elsewhere in the plant for reallocation.     

Two New Chromone Glycosides from the Roots of Saposhnikovia divaricata

Five chromone glycosides were isolated from the water‐soluble portions of 70% EtOH extract of the roots of Saposhnikovia divaricata, including two new chromone glycosides 1 and 2 . The structures of the chromone glycosides were identified as (3′S)‐3′‐O‐β‐d ‐apiofuranosyl‐(1 → 6)‐β‐d ‐glucopyranosylhamaudol ( 1 ), (2′S)‐4′‐O‐β‐d ‐apiofuranosyl‐(1 → 6)‐β‐d ‐glucopyranosylvisamminol ( 2 ), 3′‐O‐glucopyranosylhamaudol ( 3 ), 4′‐O‐β‐d ‐glucopyranosylvisamminol ( 4 ), and 4′‐O‐β‐d ‐glucopyranosyl‐5‐O‐methylvisamminol ( 5 ) on the basis of extensive spectroscopic methods, and the absolute configurations of the new compounds were elucidated by the electronic circular dichroism (ECD) calculation and acid hydrolysis. The cytotoxic activities of the glycosides 1 – 5 against three human cancer cell lines (PC‐3, SK‐OV‐3, and H460) were evaluated. The result showed that compounds 1 – 5 had weak cytotoxic activities against the human cancer cell lines with IC₅₀ values in the range of 48.54 ± 0.80 – 94.25 ± 1.45 μm .     

Spatio‐Temporal Variation of Alkaloids in Annona purpurea and the Associated Influence on Their Antifungal Activity

Annona purpurea grows in the areas of low elevation in deciduous forests of Mexico, those areas have marked rainy and dry seasons. This species produces more than 30 bioactive alkaloids that could have potential in the control of phytopathogens. This research provides data on the variation of the content and number of alkaloids during an annual cycle and the associated inhibitory potential of the compounds against three phytopathogenic fungi. For one year, alkaloidal extracts of stems and leaves were obtained every two months. The extract profiles were determined by gas chromatography with tandem mass spectrometry and their antifungal activity was examined in vitro. The alkaloids, annomontine and oxopurpureine, obtained from the roots and leaves, respectively, were also evaluated individually. The yields, profiles and activities of the extracts, as well as the abundance of annomontine and oxopurpureine in the extracts, were contrasted with the seasonality and phenological phases of the plant. The data indicate that the alkaloid content was higher at the height of the dry season. High yields also occurred during flowering. The strongest inhibitory effect was obtained from the root extracts during the last month of dry season. This finding seems to be explained by the higher chemodiversity of alkaloids in extracts from this season. Annomontine and oxopurpureine inhibited all three phytopathogens; however, they were not solely responsible for the activity of A. purpurea.     

Steroidal glycosides from the bulbs of Bessera elegans and their cytotoxic activities

Examination of the bulbs of Bessera elegans (Liliaceae) led to isolation of nine new and five known steroidal glycosides. The structures of the nine compounds were determined based on the results of spectroscopic analysis, including two-dimensional NMR, and hydrolysis followed by chromatographic and spectroscopic analysis. The isolated compounds and derivatives were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and TIG-3 normal human diploid fibroblasts. One compound, the pseudo-furostanol glycoside, induced apoptosis in HL-60 and A549 cells in a time-dependent manner and cell-cycle arrest at the G0/G1 phase in A549 cells.     

Isolation and Characterization of a Novel Antitumor Substance,Renastacarcin

A new antitumor substance designated renastacarcin has been isolated from the cultured broth of Streptomyces violascens by means of DEAE-cellulose and Sephadex G-100 column chromatography. The homogeneity of renastacarcin was confirmed by electrophoreses on a polyacrylamide gel and a cellulose acetate membrane as well as by ultracentrifugal analysis. A sedimentation coefficient at 55,430 rpm was found to be 2.12S and the molecular weight was calculated to be 34,500.     

Tetranorlanostane and Lanostane Triterpenoids with Cytotoxic Activity from the Epidermis of Poria cocos

Two unprecedented tetranorlanostane triterpenoids, poricolides A ( 1 ) and B ( 2 ), and two new lanostane triterpenoids, 3β-acetoxy-24-methyllanosta-8,16,24(31)-trien-21-oic acid ( 3 ) and 3β-acetoxylanosta-7,9(11),16,23-tetraen-21-oic acid ( 4 ), were isolated from the epidermis of Poria cocos. The structures of 1–4 were determined via analysis of ¹H-, ¹³C-, and 2D-NMR, and HR-ESI-MS data, and the absolute configurations of 1 and 3 were established by single-crystal X-ray diffraction analysis. Compounds 1 and 2 were the first report of tetranorlanostane triterpenoid having a δ-lactone ring at C(17). Compounds 3 and 4 were rare lanostane triterpenoids having a double bond between C(16) and C(17). Compounds 1–4 exhibited potent antiproliferative effects against A549, SMMC-7721, MCF-7, and SW480 cancer cell lines with IC₅₀ values from 16.19±0.38 to 27.74±1.12 μM.     

Restoration of cardenolide-synthesis in redifferentiated shoots from callus cultures of Digitalis purpurea

No cardenolide was detected in cultured cells and roots of root forming callus of Digitalis purpurea under such conditions as addition of auxins, varied sugar concentration of the medium and illumination. Cardenolides such as digitoxin and purpurea glycoside A were found in leaves from the regenerated shoot from callus cultures. The manifestation of cardenolide-synthesizing potentiality seems to be closely related to some process of leaf development.     

新疆胀果甘草总黄酮的细胞毒活性研究

为了探讨新疆胀果甘草总黄酮(general flavonoids,GFs)对宫颈癌细胞的细胞毒活性,自制备胀果甘草GFs,通过离子阱喷雾式质谱技术分析,建立GFs组分的指纹图谱;并且对SiHa宫颈癌细胞进行GFs药物干预,应用MTT法和流式细胞技术分别鉴定细胞活力和细胞凋亡率。获得了新疆胀果甘草GFs组分的特征性指纹图谱,提取物中GFs含量可达35.40%;发现在0～500μg/mL GFs浓度范围内,GFs药物干预引起细胞活力梯度性下降,其MTT法检出的最低值为12%;在0～1000μg/mL GFs浓度范围内,GFs诱导的细胞凋亡率呈现梯度性上升趋势,其流式细胞仪检出的最高值为78%。结果表明新疆胀果甘草GFs具有较强的细胞毒活性,能够抑制宫颈癌细胞生长与活力,并诱导细胞凋亡。     

藏药砂生槐种子提取物抑菌和细胞毒活性的初步研究

砂生槐是我国西藏高原一种特有植物,是一种极为宝贵的药用植物资源.我们首次从砂生槐种子中获得氯仿、95%乙醇、75%乙醇和水提取物,用琼脂扩散实验测定其抑菌活性和用MTT法测定其对肿瘤细胞的细胞毒效应,表明氯仿提取物和95%乙醇提取物具有广谱的抑菌活性,抑菌活性较强的是氯仿提取物.各种提取物显示出浓度依赖性的细胞毒效应,氯仿、95%乙醇、75%乙醇和水提取物对胃癌SGC-7901细胞系的LC50分别是4.5、1.4、1.9和41.7 mg/mL,抑制胃癌SGC-7901细胞增殖作用较强的成分是砂生槐种子95%乙醇提取物.这一发现为开发砂生槐这一宝贵植物资源的药用价值提供了重要的依据.     

米碎花的酚苷类化合物及其鼻咽癌细胞毒活性

为了解米碎花(Eurya chinensis)的化学成分及其生物活性,运用多种色谱技术从其乙醇提取物分离得到11个化合物,并对化合物进行体外抗鼻咽癌细胞增殖活性评价。经波谱数据分析,分别为异落新妇苷(1)、3,5,7-三羟基色原酮-3-O-α-L-鼠李糖苷(2)、1-O-反式-桂皮酰基-β-D-葡萄糖(3)、1-O-(4-羟基苯乙基)-6-O-反式-桂皮酰基-β-D-葡萄糖(4)、eutigoside D (5)、1-O-(3,4-二羟基苯乙基)-6-O-反式-香豆酰基-β-D-葡萄糖(6)、eutigoside A (7)、1-O-(4-羟基苯乙基)-6-O-反式-咖啡酰基-β-D-葡萄糖(8)、grayanoside A (9)、1-O-(4-羟基苯乙基)-6-O-(4-羟基苯甲酰基)-β-D-葡萄糖(10)、3-O-β-D-葡萄糖基-4-羟基-苄基苯甲酸酯(11)。其中,化合物4为首次从天然来源获得,化合物2～4和8～11均为首次从该属植物中分离得到。MTT法表明,化合物10具有中等抑制5-8F细胞增殖活性。     

太子参细胞毒活性部位HPLC谱效关系分析

采用MTT法观察太子参提取物对人胃癌MGC80-3、人结肠癌RKO和人肝癌HepG2细胞的抑制作用;运用TLC法检识太子参的环肽类化合物;分析太子参有效部位HPLC指纹图谱与细胞毒活性的谱效关系。结果表明,太子参乙酸乙酯部位对MGC80-3、RKO细胞具有抑制作用,进一步分离得到的组分G对三种肿瘤细胞均具有明显抑制作用,并比较两者的TLC和HPLC图谱,可知太子参有效部位的细胞毒活性是各特征峰成分共同作用的结果,并可能与环肽类化合物有关。     

Eleven New Triterpenoid Glycosides from the Roots of Ilex asprella

Asprellosides A‐K, nine new ursane‐type triterpenoid glycosides ( 1 – 9 ), and two new oleanane‐type triterpenoid glycosides ( 10 and 11 ), including six rare sulfated triterpenoid glycosides, were isolated from the roots of Ilex asprella. Their structures were determined on the basis of comprehensive spectroscopic analysis and chemical methods. Among these compounds, asprelloside B ( 2 ) and asprelloside C ( 3 ) are the first examples of triterpenoid glycosides bearing a rare 3,4‐O‐disulfo‐xylopyranosyl residue. All the saponins isolated showed no significant effects against respiratory syncytial virus (RSV) and lipopolysaccharide‐induced nitric oxide production in Raw264.7 macrophages.     

Two New Cytotoxic Disulfated Holostane Glycosides from the Sea Cucumber Pentacta quadrangularis

Two new disulfated triterpene glycosides, pentactasides B and C ( 1 and 2 , resp.), were isolated from the sea cucumber Pentacta quadrangularis collected from the South China Sea. Their structures were elucidated by extensive spectral analysis (2D‐NMR and MS) and chemical methods. The compounds 1 and 2 possess the same tetrasaccharide moieties with two sulfated groups, but are different in the side chains of the triterpene aglycone. Pentactasides B and C ( 1 and 2 , resp.) showed significant cytotoxicities (IC₅₀ 0.09–2.30 μM ) against different human tumor cell lines.