Four new taraxastane-type triterpenoic acids from Cirsium setosum

Four new taraxastane-type triterpenoids acids 3β,22α-dihydroxy-20-taraxasten-30-oic acid (1), 3β-hydroxy-22-oxo-20-taraxasten-30-oic acid (2), 3-oxo-22α-hydroxy-20- taraxasten-30-oic acid (3), and 3β,19β-dihydroxy-20-taraxasten-30-oic acid (4) were isolated and characterized from Cirsium setosum (Willd.) MB. Their structures were determined by the combination of 1D and 2D NMR experiments (¹H-¹HCOSY, HSQC, HMBC and ROESY) and mass spectrometry. Compound 2 exhibited potent selective cytotoxicity against human ovarian cancer cell line A2780 with an IC₅₀ value of 3.9 μM.     

First total synthesis of a new phenylpropanoid glycoside: natural cytotoxic compound from Cirsium japonicum

Abstract

Phenylpropanoid glycoside compound 1, the natural anti-tumor compound isolated from the erial parts of Cirsium japonicum, was first totally synthesized using easily available materials in short, convenient route with overall yield of 13.9%.     

A new phenylpropanoid and a new isoflavone glycoside from Shenqi Fuzheng Injection

A new phenylpropanoid and a new isoflavone glycoside were isolated from Shenqi Fuzheng Injection. Their structures were elucidated as (αS)-α-ethenyl-4-hydroxy-3-methoxy-benzenemethanol (1) and calycosin 7-O-[α-d-glucopyranosyl (1 → 4)]-β-d-glucopyranoside (2) by means of spectroscopic methods including UV, IR, HR-ESI-MS, and NMR. The absolute configurations of 1 and 2 were confirmed by quantum chemical calculation and acid hydrolysis.     

Cytotoxic phenylpropanoid glycosides from Cirsium japonicum

Three new phenylpropanoid glycosides 1–3, along with nine known phenylpropanoid glycosides 4–12, were isolated from the aerial parts of Cirsium japonicum. The structures of isolated compounds were elucidated by chemical and spectroscopic methods. Compounds 1, 3, 6, 8, and 11 showed moderate cytotoxicities against MCF-7, U87, HCT116, and A549 cell lines with IC₅₀ values in the range of 1.35–11.32 μM. The known compounds 4–12 were obtained from this plant for the first time.     

Lugrandoside: a new phenylpropanoid glycoside from various digitalis species

A novel phenylpropanoid glycoside, lugrandoside, has been isolated from the caulinary leaves of DIGITALIS LUTEA L. and DIGITALIS GRANDIFLORA Miller. The structure of this compound has been elucidated on the basis of its chemical properties and spectral data as 3,4-dihydroxy-beta-phenylethoxy- O-beta- D-glucopyranosyl-(1-->6)-4- O-TRANS-caffeoyl-beta- D-glucopyranoside ( 1).     

小蓟中蒙花苷对照品的制备和鉴定

目的 研究从小蓟药材中制备蒙花苷对照品的制备方法和鉴定技术.方法 采用石油醚脱脂、碱溶解酸沉淀法对70％乙醇小蓟药材提取物进行分离纯化,通过UV、1H-NMR和13C-NMR进行结构鉴定,TLC和HPLC法对产品进行纯度检测.结果 从小蓟中分离、纯化得到蒙花苷对照品.经TLC法检查无杂质斑点,HPLC法检测质量分数达97％.结论 该方法制备的蒙花苷对照品符合中药化学对照品的相关要求,可作为小蓟药材及其制剂质量控制以及中药药效物质基础研究用的化学对照品.     

2'-O-acetylpoliumoside: a new phenylpropanoid glycoside from Orobanche ramosa.

A new phenylpropanoid glycoside, 2'-O-acetylpoliumoside, as well as two known compounds--acteoside and 2'-O-acetylacteoside--have been isolated from the aerial parts of Orobanche ramosa. The structures have been elucidated by spectroscopic methods and supported by chemical evidences.     

A phenylpropanoid glycoside with antioxidant activity from picria tel-ferae

A phytochemical study on Picria tel-ferae resulted in the isolation of a phenylpropanoid glycoside (1), which was reported for the first time from this plant. The structure of compound 1 was identified as 1-O-3,4-(dihydroxyphenyl)- ethyl-beta-D- apiofuranosyl- (1-->4)-alpha-L-rharmnopyranosyl- (1-->3)-4-O-caffeoyl- beta-D-glucopyranoside on the basis of spectroscopic analyses. In addition, it was found that 1 exhibited a remarkable inhibitory effect on lipid peroxidation initiated by either a free radical [AAPH; 2,2'-azobis-(2-amidinopropane)dihydrochloride] or generated hydroxyl radical (Fe2+/ascorbate). These findings, together with those of previous studies, suggest that P. tel-ferae possesses abundant phenylpropanoid glycosides, and the plant might be used beneficially in the treatment of oxidative stress-related human diseases.     

Ophiopojaponin D, a new phenylpropanoid glycoside fromOphiopogon Japonicus Ker-Gawl

A new phenolic glycoside, ophiopojaponin D (1), together with two known compounds, was isolated from the tubers of a famous traditional Chinese herb-Ophiopogon japonicus Ker-Gawl. The spectroscopic and chemical data revealed their structures to be 3-tetradecyloxy-4-hydroxy-allylbenzene-4-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside (1), 3, 4-dihydroxy-allylbenzene-4-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside (2) and L-pyroglutamic acid (3).     

HPCE法测定小蓟中咖啡酸含量

目的建立高效毛细管电泳法测定小蓟中咖啡酸的含量。方法采用石英毛细管柱,以硼砂溶液为缓冲液,运用电泳法测定小蓟中咖啡酸的含量。结果咖啡酸进样量在0.121~0.968μg范围内(r=0.999 0)线性关系良好,平均回收率为96.33%。结论本方法专属性强,灵敏度高,重复性好,可用于小蓟中咖啡酸的含量测定。     

A new irregular phenylpropanoid from Apollonias barbujana

In addition to the known compounds (+/-)-threo-guaiacylglycerol and the phenethyl alcohols, 3-methoxy-4-dihydroxyphenethyl alcohol and 3,4-dimethoxyphenethyl alcohol, a new irregular phenylpropanoid 2-(3-methoxy-4-hydroxyphenyl)-1,3-propanediol was isolated from the ethanolic extract of the leaves of Apollonias barbujana (Lauraceae). Their structures were elucidated on the basis of spectroscopic methods and chemical transformations.     

小蓟化学成分的分离与鉴定

目的对传统中药小蓟的化学成分进行分离与鉴定,为进一步开发利用小蓟提供科学依据。方法采用反复硅胶柱色谱法进行分离纯化,通过理化常数测定和波谱分析鉴定其化学结构。结果从小蓟提取物的氯仿层和乙酸乙酯层中分离得到9个化合物,即苜蓿素(tricin,1)、蒙花苷(linarin,2)、咖啡酸(caffeic acid,3)、香豆酸(courmaric acid,4)、丁二酸(succinic acid,5)、芹菜素(apigenin,6)、苜蓿素-7-O-β-D-葡萄糖(tricin-7-O-β-D-glucopyranoside,7)、β-谷甾醇(β-sitosterol,8)、β-胡萝卜苷(β-daucosterol,9)。结论化合物5、7为首次从蓟属植物中分离得到,化合物1、4为首次从小蓟中分离得到。     

小蓟化学成分的分离与鉴定

目的研究小蓟的化学成分。方法采用硅胶、凝胶、ODS柱色谱以及HPLC制备法对小蓟的乙醇提取物进行分离纯化,利用理化性质和波谱学手段鉴定其结构。结果从小蓟乙醇提取物中分离得到14个化合物,经鉴定分别为邻二苯酚(1,2-benzenediol,1)、反式对香豆酸葵酯(decyl transp-coumarate,2)、原儿茶醛(protocatechualdehye,3)、对羟基苯甲酸(p-hydroxybenzoic acid,4)、香草酸(vanillic acid,5)、刺槐素(ermanine,6)、岳桦素(acacetin,7)、马齿苋酰胺(oleracein E,8)、芹菜素(apigenin,9)、木犀草素(luteolin,10)、槲皮素(quercetin,11)、异山柰素-7-O-β-D-葡萄吡喃糖苷(isokaempferide-7-O-β-D-glucopyranoside,12)、高车前苷(homoplantaginin,13)和蒙花苷(linarin,14)。结论化合物1~4、7、8和13为首次从小蓟中分离得到。     

小蓟中挥发油成分的分析及其抑菌与止血作用的研究

目的 分析小蓟的花、叶和茎中挥发油的化学成分及其抑菌、止血作用.方法 采用超临界二氧化碳萃取,应用GC-MS法鉴定挥发油的化学成分,考察其体外抗菌、止血的活性.结果 共鉴定166个化合物,花的挥发油中主要有2-乙氧基-3-氯丁烷(16.68％)、二十八烷(12.96％)、甲苯(7.71％)等;叶的挥发油中主要有1,1-二乙氧基乙烷(18.90％)、二十八烷(13.13％)、2,3-丁二醇(13.00％)、二十五烷(10.00％)等;茎的挥发油中主要有甲氧基苯基肟(27.05％)、十六烷酸(14.48％)、3-癸炔-2-醇(12.84％)、仲丁基醚(11.05％)、十四烷酸(10.12％)等.花、叶和茎中不同萃取挥发油对特定病原菌有特殊抑菌效果,其MIC =0.031 mg·mL-1.茎的高剂量挥发油可明显缩短出血和凝血的时间.结论 花、叶和茎中挥发油的差异较大,含抑菌和止血成分.     

A new pregnane glycoside and a furostanol glycoside from Digitalis cariensis

Chemical investigation of the aerial parts of Digitalis cariensis Boiss. ex Jaub. & Spach resulted in the isolation of a new pregnane glycoside, cariensisoside (1) and a furostanol glycoside, uttroside A (2), along with the two known phenylethanoid glycosides, lugrandoside (3) and maxoside (4). On the basis of spectral (UV, IR, NMR, MS) and chemical methods, compounds 1 and 2 were identified as digifologenin-3-O-beta-glucopyranosyl-(1-->4)-beta-oleandropyranoside and 3-O-(beta-lycotetraosyl)-26-O-(beta-glucopyranosyl)-(25R)-22 alpha-methoxy-5-furostane-3 beta,26-diol, respectively.     

New sesquiterpenoid glycoside and phenylpropanoid glycosides from the tuber of Ophiopogon japonicus

A new sesquiterpenoid glycoside, cryptomeridiol 11-O-β-d-xylopyranosyl-(1→6)-β-d- glucopyranoside (1), two new phenylpropanoid glycosides, 3,4-dihydroxy-allylbenzene 3-O-β-d-glucopyranosyl-4-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (2), and 3,4,5-trihydroxy-allylbenzene 3-O-β-d-glucopyranosyl-4-O-β-d-glucopyranoside (3), along with four known phenylpropanoid glycosides (4–7), were isolated from the tuber of Ophiopogon japonicus. Compounds 4–7 were obtained from the genus Ophiopogon for the first time. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR and HR-ESI-MS.     

A new sterol glycoside from Securidaca inappendiculata

From the roots of Securidaca inappendiculata, one new sterol glycoside securisteroside (1) has been isolated, along with two known sterols, spinasterol (2) and 3-O-beta-D-glucopyranosyl-spinasterol (3). The new sterol was characterized by chemical and spectrometric methods, including EIMS, FABMS and one- and two-dimensional NMR experiments.