酸浆茎叶中的四甲基环己烯型单萜苷类化合物

目的研究茄科植物酸浆[Physalis alkekengiL.var.franchetii(Mast.)Makino]茎叶的化学成分。方法用体积分数为60%的乙醇水溶液加热回流提取,提取液浓缩后用水混悬,依次用环己烷、乙酸乙酯、正丁醇萃取;将正丁醇层通过聚酰胺柱色谱,Sephadex LH-20柱色谱、反相ODS开放柱色谱及反相制备HPLC等手段,共分离得到4个四甲基环己烯型单萜苷类(megastigmane glyco-sides)化合物;利用其理化性质和波谱学数据,鉴定化合物结构。结果分离得到4个四甲基环己烯型单萜苷类化合物,分别鉴定为(6S,9R)-长寿花糖苷[(6S,9R)-roseoside,1)]、(6S,9R)-长寿花糖苷[(6S,9S)-roseoside,2]、(6S,9R)-3-氧-α-紫罗兰醇-β-D-吡喃葡萄糖苷[(6R,9S)-3-oxo-α-ionol-β-D-glucopyranoside,3]、citroside A(4)。结论4个化合物均为首次从该属植物中分离得到。     

Chemical constituents from the fruit calyx of Physalis alkekengi var. francheti

In the present study, in order to investigate the chemical constituents of Physalis alkekengi L. var. franchetii (Mast.) Makino, the isolation of ingredients was performed by repeated chromatography on silica gel, Sephadex LH-20 and preparative HPLC. Their structures were identified based on 1D, 2D NMR, and mass spectral analysis. A total of 14 compounds were obtained, and their structures were identified as physalin P (1), 4,7-didehydroneophysalin B (2), physalin D (3), 5α-hydroxy-25,27-dihydro-7-dehydro-7-deoxyneophysalin A(4), 4,7-didehydrophysalin B (5), ursolic acid (6), wogonin (7), blumenol A (8), nobiletin (9), liquiritigenin (10), schizandrin (11), 5-hydroxymethylfurfural (12), 5-(hydroxymethyl)-2-(dimethoxymethyl)furan (13), 1-O-[3-O-2-methyl-5-(2,3,4-trimethyl)phenyl-2,3-pentanediol]-β-D-xylopyranosyl-(1→6)-β-D-galactopyranoside(14). Among them, compound 14 is a new compound. Compounds 7–11, 13 are isolated from Physalis alkekengi L. var. franchetii (Mast.) Makino for the first time.     

HPLC法测定锦灯笼中酸浆苦素类成分的含量

目的:建立测定锦灯笼药材中酸浆苦素类成分含量的方法。方法:采用高效液相色谱法。色谱柱为Cromasil C18(250mm×4.6mm,5μm),流动相为乙腈-0.1%磷酸(34∶66),检测波长为220nm。结果:4种酸浆苦素类成分均达到基线分离,而且各个成分均有较宽的线性范围和良好的线性关系。酸浆苦素A、酸浆苦素O、酸浆苦素L和酸浆苦素B的平均加样回收率分别为97.8%、98.7%、102.6%、103.3%,RSD分别为1.98%、2.20%、1.85%、1.39%(n=6)。结论:本法快速、灵敏、准确、可靠、重复性好,可同时测定锦灯笼药材中4种酸浆苦素类成分的含量,适用于锦灯笼药材的质量控制。     

酸浆中苦味素类化学成分的分离与结构鉴定

目的分离、鉴定酸浆中的苦味素类化学成分。方法采用大孔树脂、硅胶柱色谱分离纯化,经理化常数和谱学方法鉴定结构。结果分离鉴定了4个化合物,分别为酸浆苦味素A(1)、酸浆苦味素D(2)、酸浆苦味素P(3)、4,7二去氢7脱氧新苦味素L(4)。结论4,7二去氢7脱氧新苦味素L为新的天然产物。     

酸浆宿萼的化学成分

目的研究茄科植物酸浆宿萼(Physalis alkekengiL.var.franchetii(Mast.)Makino)的化学成分。方法用体积分数为80%的乙醇溶液对酸浆宿萼进行加热回流提取,回收乙醇,浓缩后用水混悬,依次用环己烷、乙酸乙酯萃取,取乙酸乙酯层经硅胶柱色谱,CHCl3MeOH混合溶剂做梯度洗脱;CHCl3MeOH体积比为100∶2、100∶6,洗脱部分以及萃取后的水层再次经硅胶柱色谱、Sephadex LH 20柱色谱、反相ODS开放柱色谱及RP HPLC等,共得到7个化合物;利用其理化性质和波谱学分析数据,鉴定化学结构。结果分离得到了7个化合物中4个为酸浆苦素类化合物,分别鉴定为酸浆苦素D(Ⅰ)、酸浆苦素L(Ⅱ)、酸浆苦素O(Ⅲ)、4,7二脱氢新酸浆苦素B(Ⅳ);3个黄酮类化合物,分别鉴定为木犀草素(Ⅴ)、商陆素(Ⅵ)、木犀草素7,4′二OβD葡萄糖苷(Ⅶ)。结论商陆素(Ⅵ)、木犀草素7,4′二OβD葡萄糖苷(Ⅶ)为首次从该植物中分离得到的2个已知化合物。     

酸浆宿萼的黄酮苷类化学成分

目的研究茄科植物酸浆(Physalis alkekengiL.var.francheti(Mast.)Makino)宿萼的化学成分。方法用体积分数为80%的乙醇溶液加热回流提取,回收乙醇,浓缩后用水混悬,依次用环己烷、乙酸乙酯、正丁醇萃取;将正丁醇层通过聚酰胺柱色谱,Sephadex LH-20柱色谱、反相ODS开放柱色谱及反相制备HPLC等手段,共分离得到5个黄酮苷类化合物;利用其理化性质和波谱学分析数据,鉴定化合物结构。结果分离得到的5个黄酮苷类化合物,分别鉴定为木犀草素-7-O-β-D-葡萄糖苷(1),木犀草素-4′-O-β-D-葡葡萄糖苷(2),槲皮素-3-O-β-D-葡葡萄糖苷(3),槲皮素-7,3-二-O-β-D-葡葡萄糖苷(4),木犀草素7,3′-二-O-β-D-葡葡萄糖苷(5)。结论木犀草素-4′-O-β-D-葡萄糖苷(2),槲皮素-3,7-二-O-β-D-葡萄糖苷(4),木犀草素7,3′-二-O-β-D-葡萄糖苷(5)为首次从该属植物中分离得到,槲皮素-3-O-β-D-葡萄糖苷(3)为首次从该植物中分离得到。     

RP—HPLC测定酸浆药材中3种有效成分的含量

目的:采用 RP-HPLC 建立同时测定酸浆药材中酸浆苦味素 A、酸浆苦味素 D 及木犀草素含量的方法。方法:分析柱采用 Diamonsil C_(18)(200 mm×4.6 mm,5 μm)色谱柱,流动相为甲醇-0.2%醋酸(45:55,v/v);流速:1.0 mL·min~(-1);检测波长:220 nm。结果:酸浆苦味素 A、酸浆苦味素 D 及木犀草素浓度分别在0.15～1.20 mg·mL~(-1)(r=0.9995),0.10～0.81 mg·mL~(-1)(r=0.9996),0.12～0.96 mg·mL~(-1)(r=0.9997)范围内与峰面积呈良好的线性关系,酸浆苦味素 A 平均回收率分别为95.9%,97.1%,103%;RSD 分别为2.0%,0.7%,1.4%。酸浆苦味素 D 的平均回收率分别为97.3%,101%,97.1%;RSD 分别为1.0%,1.9%,1.3%。木犀草素的平均回收率分别为97.8%,97.8%,97.7%;RSD 分别为0.4%,2.9%,0.5%。结论:采用 RP-HPLC 同时测定酸浆药材中酸浆苦味素 A、酸浆苦味素 D 及木犀草素3种成分的含量,该法简单、可靠,可作为控制酸浆药材质量的参考标准。     

Two sulfonate metabolites of physalin A in rats

1.?Physalin A is a bioactive withanolide isolated from the natural plant Physalis alkekengi var. franchetii (Solanaceae), a common traditional Chinese herbal medicine. This study aims to investigate the metabolites of physalin A in vivo.

2.?Two metabolites (M1 and M2) were characterized as sulfonate metabolites in the feces obtained from rats treated with physalin A orally at a dose of 15?mg/kg/day for 3 days, by application of a UPLC-Q/TOF-MS method. Furthermore, formation of the two sulfonate metabolites was verified by chemical synthesis and NMR, including ¹H NMR, ¹³C NMR and two-dimensional NMR. The structures of M1 and M2 were identified to be 3α-sulfo-2,25β,27-trihydrophysalin A and 3α,27-disulfo-2,25α-dihydrophysalin A, respectively.

3.?In summary, this study indicated that physalin A could be biotransformed to sulfonate metabolites with strong polarity, which contributed to the elimination of physalin A. A rare metabolic pathway has been revealed in this study.     

The structure of physalin T from Physalis alkekengi var. franchetti

A new steroidal constituent named physalin T (3) was isolated from the aqueous extract of Physalis alkekengi var. francheti. Based on 1H and 13C NMR spectral studies the structure was assigned as 2,3-dihydrophysalin D, i.e., 5alpha,6beta-dihydroxy-2,3,5,6-tetrahydrophysalin B, which is the first example of a natural physalin possessing a saturated ring A moiety. The structure was confirmed by the chemical transformation from the known physalin D (2) to physalin T.     

中药锦灯笼化学成分的分离与鉴定

目的研究中药锦灯笼(Physalis alkekengiL.var.franchetii(Mast.)Makino)的宿萼和果实的化学成分。方法采用乙醇提取,硅胶柱色谱分离纯化,根据理化性质和波谱数据鉴定结构。结果分离得到11个化合物,分别鉴定为4,7-二脱氢新酸浆苦素B(4,7-didehydroneophysalin B,1)、酸浆苦素D(physalin D,2)、酸浆苦素P(physalin P,3)、木犀草素(luteolin,4)、木犀草素-7-葡萄糖苷(lute-olin-7-O-glucoside,5)、3′,4′-二甲氧基杨梅皮素(3′,4′-dimethoxymyricetin,6)、柠檬酸二甲酯(1,5-dimethyl citrate,7)、5-羟甲基糠酸(5-hydroxymethylfuroic acid,8)、环(酪-亮)二肽(cyclo(tyrosine-amidocaproic)-bipeptide,9)、β-谷甾醇(β-sitosterol,10)、胡萝卜苷(daucosterol,11)。结论化合物6~9为首次从该植物中分离得到的已知化合物。     

Effects of polysaccharide from Physalis alkekengi var. francheti on liver injury and intestinal microflora in type-2 diabetic mice

Context: Diabetic liver injury is a serious diabetic complication. The alterations of intestinal microbiota play an important role in induction and promotion of liver injury progression. Physalis alkekengi L. var. francheti (Mast.) Makino (Solanaceae) has been used as a water decoction for treating diabetes.

Objective: To study the effects of a polysaccharide (PPSB) from Physalis alkekengi var. francheti on liver injury and intestinal microflora in type-2 diabetic mice.

Materials and methods: Streptozotocin (160?mg/kg) was injected i.p. for 3?days to build model. The diabetic mice were randomly divided into four groups together with control group (10 mice in each group). The doses of PPSB were 50 and 100?mg/kg, respectively. After 5 weeks administration, level of blood glucose, ALT and AST were measured. Alterations of intestinal microflora, and protein expression of TGF-β1, TNF-α and DCN were detected.

Results: Level of blood glucose decreased from (25.38?±?2.21) mmol/L to (18.01?±?2.53) mmol/L, ALT and AST decreased to (24.67?±?4.86) U/L and (30.84?±?7.50) U/L in PPSB-H group. Lactobacillus, Clostridium butyricum, and Bacteroides increased remarkably with increasing concentration of PPSB, but Enterobacter was inhibited. The relative expression of TGF-β1 and TNF-α decreased to (0.70?±?0.17) and (0.39?±?0.06), and the expression of DCN increased to (0.65?±?0.13).

Discussion and conclusions: Probiotics have been promoted by PPSB, and protein expressions have been modulated in the progression of liver injury. PPSB could be used as a natural agent for treating diabetic liver injury and intestinal microflora imbalance.     

锦灯笼中酸浆苦素类化学成分的研究

目的 研究锦灯笼95％乙醇提取物的石油醚、氯仿、醋酸乙酯萃取部位中化学成分.方法 利用硅胶柱色谱、反相ODS柱色谱、制备液相色谱等方法进行分离、纯化,根据化合物的理化性质和光谱数据鉴定其结构.结果 分离得到了7个化合物,经结构鉴定分别为酸浆苦素A(1)、酸浆苦素D(2)、酸浆苦素L(3)、酸浆苦素O(4)、木犀草素(5...     

A pair of 3-epimeric physalins from Physalis alkekengi L. var. franchetii

A pair of new 3-epimeric steroids possessing a rare 13,14-seco-16,24-cycloergostane skeleton, 3alpha-methoxy-2,3-dihydro-4,7-didehydrophysalin B (1), and 3beta-methoxy-2,3-dihydro-4,7-didehydrophysalin B (2) were isolated from the 60% EtOH extract of the stems and leaves of Physalis alkekengi L. var. franchetii. Their structures were characterized on the basis of spectral evidence.     

The potential antineoplastic acting constituents of Physalis alkekengi L. var franchetii Mast

In a continuing search for potent antineoplastic compounds in indigenous plants, a water extract of Physalis alkekengi L. var. franchetii Mast. fruits was shown to have reproducible antineoplastic activity against Ehrlich ascites carcinoma in mice. Systematic fractionation of the extract led to the isolation of citric acid as the major active principle.     

Structure of lasiansine from Aconitumnagarum var. lasiandrum

A new C₁₉-diterpenoid alkaloid, lasiansine (1), was isolated from the roots of Aconitu nagarum var. lasiandrum (Ranunculaceae) together with six known diterpenoid alkaloids. The structure of 1 was elucidated by spectral methods (¹H-NMR, ¹³C-NMR, 2D-NMR, HRMS, IR), and the ¹³C-NMR spectrum of 16-epipyroaconine (3) and the single-crystal X-ray analysis of its derivative (5) are reported for the first time.     

Structure of lasiansine from Aconitum nagarum var. lasiandrum

A new C₁₉-diterpenoid alkaloid, lasiansine (1), was isolated from the roots of Aconitu nagarum var. lasiandrum (Ranunculaceae) together with six known diterpenoid alkaloids. The structure of 1 was elucidated by spectral methods (¹H-NMR, ¹³C-NMR, 2D-NMR, HRMS, IR), and the ¹³C-NMR spectrum of 16-epipyroaconine (3) and the single-crystal X-ray analysis of its derivative (5) are reported for the first time.     

Sesquiterpenes from Artemisia giraldii var. longipedunculata

A phytochemical investigation on the aerial parts of Artemisia giraldii var. longipedunculata led to the isolation of 10 known sesquiterpenes, including12-hydroxy-α-cyperone (1), 1β,6α-dihydroxyeudesma-4(15)-ene (2), carainterol A (3), oplodiol (4),douglanin (5), 1α-hydroxyisodauc-4-en-15-al (6), 3α,6α-dihydroxybisabola-4,10-diene (7), 4α,5β-dihydroxybisabola-2,10-diene(8), opposit-4(15)-ene-1β,7-diol (9), and saniculamoid D (10), respectively. Their structures were elucidated by analysis of the MS and NMR spectroscopic data and comparison with the literature. All the isolates were obtained from A. giraldii var. longipedunculata for the first time, and five of them were obtained from the genus Artemisia for the first time. Additionally, the ¹³C NMR data of 1 were fully assigned based on the 2D NMR data for the first time.     

丰城鸡血藤黄酮类化合物的分离鉴定

目的对丰城鸡血藤Millettia nititavar.hirsutissima的化学成分进行研究。方法应用色谱技术分离纯化化合物,利用波谱技术确定化合物的结构。结果从丰城鸡血藤中分离鉴定了4个化合物,分别为甘草素(1),柚皮素(2),马卡因(3), 3R-牛角花酮(4)。结论化合物1和2为首次从本属植物中分离得到;3和4为首次从本植物中分离得到。     

丰城鸡血藤异黄酮类化合物的分离鉴定

为建立丰城鸡血藤质量控制方法提供对照品, 对其化学成分进行了研究, 从中分离鉴定了8个化合物, 分别为丰城鸡血藤异黄酮苷F (1), 芒柄花素 (2), 芒柄花苷 (3), 奥刀拉亭7-O-β-D-吡喃葡萄糖苷 (4), 澳白檀苷 (5), 阿夫罗摩辛 (6), 圆荚草双糖苷 (7) 和丰城鸡血藤异黄酮苷B (8)。化合物1为新化合物, 化合物3～5和7为首次从本属植物中分离得到, 2为首次从本植物中分离得到。