Six secoiridoid glucosides from Adina racemosa

Six novel secoiridoid glucosides, adinosides A (1), B (2), C (3), D (4), E (5), and grandifloroside 11-methyl ester (6) were isolated, together with 27 known compounds, from the dried leaves, flowers, and twigs of Adina racemosa. The structures of the new compounds were determined by spectroscopic (NMR, MS) and chemical means.     

Triterpene glycosides from Cimicifuga racemosa

Eight new triterpene glycosides named cimiracemosides A-H, respectively, and eight known triterpene glycosides were isolated from the rhizome extracts of black cohosh (Cimicifuga racemosa). The new compounds were determined by spectral data to be 21-hydroxycimigenol-3-O-alpha-L-arabinopyranoside (1), 21-hydroxycimigenol-3-O-beta-D-xylopyranoside (2), cimigenol-3-O-alpha-L-arabinopyranoside (3), 12beta-acetoxycimigenol-3-O-alpha-L-arabinopyranoside (4), 24-acetylisodahurinol-3-O-beta-D-xylopyranoside (5), 20(S),22(R), 23(S),24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3be ta,23, 24-trihydroxy-9,19-cycloanost-7-ene-3-O-beta-D-xylopyranoside (6), 20(S),22(R),23(S),24(R)-16beta:23;22:25-diepoxy-12beta -acetoxy-3beta, 23,24-trihydroxy-9,19-cycloanost-7-en-3-O-alpha-L-arabinopyrano side (7), and 20(S),22(R),23(S), 24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3beta,23, 24-trihydroxy-9,19-cycloanostane-3-O-beta-D-xylopyranoside (8).     

Flavonoid glycosides from Rhazya orientalis

Six new flavonoid glycosides, quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (1), quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (2), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (3), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (4), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-cis-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (5), and isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-feruloyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (6), were isolated from the dried aerial parts of Rhazya orientalis. The structures of 1-6 were determined by spectroscopic and chemical means.     

山香圆叶中黄酮苷类成分及其抗炎活性研究

应用大孔树脂、聚酰胺、Sephadex LH-20,HPLC等各种色谱技术对山香圆叶95％乙醇提取物经乙酸乙酯萃取后的水部位进行分离纯化,分离得到8个黄酮苷类化合物,采用NMR等谱学方法分别鉴定为:野漆树苷(1),女贞苷(2),刺槐素-7-O-[β-D-吡喃葡萄糖基-(1→6)-α-L-吡喃鼠李糖基-(1→2)]-β-D-吡喃葡萄糖苷(3),刺槐素-7-O-[α-L-吡喃鼠李糖基(1→6)-o-L-吡喃鼠李糖基-(1→2)]-β-D-吡喃葡萄糖苷(密蒙花新苷,4),木犀草素-7-O-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖苷(5),金圣草素-7-O-α-L-吡喃鼠李糖基-(1→2)β-D-吡喃葡萄糖苷(6),刺槐素-7-O-α-L-吡喃鼠李糖基-(1→2)β-D-吡喃葡萄糖苷(蒙花苷,7),芹菜素6,8-二-C-β-D-吡喃葡萄糖苷(8).其中化合物3～8为首次从该植物中分离获得.采用脂多糖(LPS)刺激RAM264.7巨噬细胞炎症模型对分离得到的化合物进行抗炎活性评价,结果表明化合物2,3在1x10-5 mol.L-1浓度下,对LPS刺激RAW264.7细胞NO生成的抑制率分别为33.7％和23.8％,提示化合物2,3具有较弱的抗炎活性.     

点地梅中的黄酮苷成分

目的:对点地梅的化学成分进行研究.方法:运用多种色谱方法进行分离纯化,根据理化性质和波谱数据鉴定化合物的结构.结果:从点地梅95％乙醇提取物的正丁醇萃取部分中分离得到10个化合物,分别签定为山柰酚3-O-(3-O-乙酰基)-α-L-吡喃鼠李糖苷(1),山柰酚3-O-(2-O-乙酰基)-α-L-吡喃鼠李糖苷(2),山柰酚7-O-α-L-吡喃鼠李糖苷(3),山柰酚3-O-α-L-吡喃鼠李糖苷(4),山奈酚3-O-β-D-吡喃葡萄糖苷(5),山奈酚3-O-(3 -O-乙酰基)-α-L-吡喃鼠李糖基-7-O-α-L-吡喃鼠李糖苷(6),山奈酚3-O-(4-O-乙酰基)-α-L-吡喃鼠李糖基-7-O-α-L-吡喃鼠李糖苷(7),槲皮素3-O-α-L-吡喃鼠李糖苷(8),槲皮素3-O-β-D-吡喃葡萄糖苷(9),杨梅素3-O-β-D-吡喃葡萄糖苷(10).结论:所有化合物均为首次从该植物中分离得到.     

Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities

Three new sesquiterpenes, (2R,3S,5R)-2,3-epoxy-6,9-humuladien-5-ol-8-one (1), (2R,3R,5R)-2,3-epoxy-6,9-humuladien-5-ol-8-one (2), and (5R)-2,6,9-humulatrien-5-ol-8-one (3), and two new flavonol glycosides, kaempferol-3-O-(2,3-di-O-acetyl-alpha-l-rhamnopyranoside) (4) and kaempferol-3-O-(2,3,4-tri-O-acetyl-alpha-l-rhamnopyranoside) (5), were isolated from the EtOAc-soluble fraction of the water extract of Zingiber aromaticum, along with 13 known compounds (6-18). The structures of the isolated compounds were elucidated on the basis of spectroscopic and chemical analyses. The isolated compounds were tested for their inhibitory activity on the metabolism mediated by CYP3A4 or CYP2D6 using [N-methyl-(14)C]erythromycin or [O-methyl-(14)C]dextromethorphan as a substrate, respectively. Kaempferol-3-O-(2,3,4-tri-O-acetyl-alpha-l-rhamnopyranoside) (5) showed the most potent inhibitory activity (IC(50), 14.4 microM) on the metabolism mediated by CYP3A4, and kaempferol-3-O-methyl ether (14) inhibited CYP2D6 most potently (IC(50), 4.63 microM).     

Flavonoid glycosides from the stem bark of Margaritaria discoidea demonstrate antibacterial and free radical scavenging activities

One new flavonoid glycoside, along with three known flavonoid glycosides were isolated from the stem bark of Margaritaria discoidea, which is traditionally used in the management of wounds and skin infections in Ghana. The new flavonoid glycoside was elucidated as hydroxygenkwanin‐8‐C‐[α‐rhamnopyranosyl‐(1 → 6)]‐β‐glucopyranoside (1) on the basis of spectroscopic analysis. The isolated compounds demonstrated free‐radical scavenging as well as some level of antibacterial activities. Microorganisms including Staphylococcus aureus are implicated in inhibiting or delaying wound healing. Therefore, any agent capable of reducing or eliminating the microbial load present in a wound as well as decreasing the levels of reactive oxygen species may facilitate the healing process. These findings therefore provide some support to the ethnopharmacological usage of the plant in the management of wounds. Copyright © 2013 John Wiley & Sons, Ltd.     

Flavonoid, iridoid, and lignan glycosides from Putoria calabrica

From the aerial parts of Putoria calabrica, two new flavonol triglycosides were isolated and their structures were elucidated as quercetin-3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside]-7-O-beta-D-glucopyranoside (1, calabricoside A) and quercetin-3-O-[4' "-O-caffeoyl-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside]-7-O-beta-D-glucopyranoside (2, calabricoside B). Additionally, seven iridoid and three lignan glycosides were isolated and characterized. Radical scavenging activities of all compounds were determined by quantifying their effects on luminol-enhanced chemiluminescence in formyl-methionyl-leucyl-phenylalanine (FMLP) stimulated human polymorphonuclear neutrophils (PMNs). Calabricoside A and B showed strong radical scavenging activity with IC(50) values of 0.25 and 0.3 microM, respectively.     

Cimiracemosides I-P,new 9,19-cyclolanostane triterpene glycosides from Cimicifuga racemosa

Eight new and 13 known triterpene glycosides, along with the known compounds glyceryl-1-palmitate and daucosterol-6'-linoleate were isolated from the roots/rhizomes of Cimicifuga racemosa. The new compounds, designated as cimiracemosides I-P (1, 3-9), were determined by spectral analysis to be 7-dehydro-23-epi-12,26-dideoxyacteol-3-O-beta-D-xylopyranoside (1), 12-O-acetyl-25-anhydrocimigenol-3-O-alpha-L-arabinopyranoside (3), 12-O-acetyl-25-anhydrocimigenol-3-O-beta-D-xylopyranoside (4), 4',23-O-diacetylshengmanol-3-O-beta-D-xylopyranoside (5), 4',23-O-diacetylshengmanol-3-O-alpha-L-arabinopyranoside (6), 23-epi-acetylacteol-3-O-alpha-L-arabinopyranoside (7), 4'-O-acetyl-26-deoxyactein (8), and 16beta:23;24:25-diepoxy-12beta-O-acetyl-3beta-hydroxy-9,19-cyclolanost-23,26-olide-O- beta-D-xylopyranoside (9).     

Neocimicigenosides A and B, cycloartane glycosides from the rhizomes of Cimicifuga racemosa and their effects on CRF-stimulated ACTH secretion from AtT-20 cells

Two new cycloartane glycosides, named neocimicigenosides A (1) and B (2), were isolated from the rhizomes of Cimicifuga racemosa. The structures of 1 and 2 were determined on the basis of extensive spectroscopic analysis and enzymatic hydrolysis followed by chromatographic and spectroscopic analyses to be (16S,23R,24S)-24-acetoxy-16,23:16,25-diepoxy-15alpha-hydroxycycloartan-3beta-yl alpha-L-arabinopyranoside (1) and (16S,23R,24S)-24-acetoxy-16,23:16,25-diepoxy-15alpha-hydroxycycloartan-3beta-yl beta-D-xylopyranoside (2), respectively. Neocimicigenosides A and B enhanced CRF-stimulated ACTH secretion from AtT-20 cells.     

Phenylpropanoids from Daphne feddei and their inhibitory activities against NO production

Chemical examination of the methanolic extract from the stem bark of Daphne feddei led to the isolation of five new phenylpropanoids, 4,4'-dihydroxy-3,3'-dimethoxy-9-butoxy-9,9'-epoxylignan (1), 4,4'-dihydroxy-3,3'-dimethoxy-9-ethoxy-9,9'-epoxylignan (2), daphneresinol (3), armaosigenin (4), and isocubebin (5), together with 33 known phenylpropanoids. All 38 compounds were isolated for the first time from D. feddei. All compounds were tested for inhibitory activity against LPS-induced NO production in RAW 264.7 macrophages. Compounds 2, 8, 9, 12, 13, and 15 showed potent inhibitory activities against the production of NO with IC(50) values of 0.091, 0.047, 0.005, 0.088, 0.004, and 0.074 μM/mL, respectively.     

Cucurbitane glycosides from the fruits of Siraitia gros venorii and their inhibitory effects on Epstein-Barr virus activation

Six new cucurbitane glycosides, mogroside II B (2), 11-deoxymogroside III (4), 7-oxomogroside II E (5), 7-oxomogroside V (6), 11-oxomogroside II A1 (7), and 11-oxomogroside IV A (8), and two known but new naturally occurring cucurbitane glycosides, mogroside II A1 (1) and mogroside III A2 (3), were isolated from an ethanol extract of the fruits of Siraitia grosvenorii. Upon evaluation of compounds 1-8 for inhibitory effects against the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA), all compounds exhibited inhibitory effects with IC50 values of 346-400 mol ratio/32 pmol TPA. In addition, compounds 1-8 showed weak inhibitory effects on activation of (+/-)-(E)-methyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor.     

八角莲愈伤组织中黄酮苷类化学成分研究

综合运用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、制备薄层色谱和制备型HPLC等多种色谱技术对八角莲愈伤组织的化学成分进行分离纯化,并采用UV,IR,MS和NMR等波谱技术鉴定化合物的结构。从八角莲愈伤组织的95%乙醇提取物中共分离得到7个黄酮苷类化合物,分别鉴定为山柰酚-3-O-[6″-(3''-甲氧基)-丙二酰基]-β-D-吡喃葡萄糖苷(1),山柰酚-3-O-(6″-O-乙酰基)-β-D-吡喃葡萄糖苷(2),山柰素-3-O-β-D-吡喃葡萄糖苷(3),山柰酚-3-O-β-D-吡喃葡萄糖苷(4),异槲皮苷(5),槲皮素-4'-O-β-D-吡喃葡萄糖苷(6)和山柰酚-3-O-(6″-O-丙二酸单酰基)-β-D-吡喃葡萄糖苷(7)。以上化合物均为首次从八角莲愈伤组织中分离得到,其中化合物1,2,3,6和7为首次从八角莲植物材料中分离得到,化合物1是一个新化合物。     

Radical scavenging and angiotensin converting enzyme inhibitory activities of standardized extracts of Ficus racemosa stem bark

The present study evaluated the radical scavenging and angiotensin converting enzyme (ACE) inhibitory activity of cold and hot aqueous extracts of Ficus racemosa (Moraceae) stem bark. The extracts were standardized using HPLC. Radical scavenging activity was determined using 1,1‐diphenyl‐2‐picrylhydrazyl radical and angiotensin converting enzyme inhibitory activity using rabbit lung and partially purified porcine kidney ACE. HPLC profiles of cold aqueous extract (FRC) showed the presence of bergenin, an isocoumarin, while hot aqueous extract (FRH) was found to contain ferulic acid, kaempferol and coumarin in addition to bergenin. FRH showed significantly higher (p ≤ 0.01) radical scavenging activity than FRC and butylated hydroxytoluene (BHT), consequently resulting in a significantly lower (p ≤ 0.01) IC₅₀ value than FRC and BHT. Both the extracts exhibited a dose dependent inhibition of porcine kidney and rabbit lung ACE. FRH showed significantly higher (p ≤ 0.01) activity than FRC with lower IC₅₀ values of 1.36 and 1.91 μg/mL respectively, for porcine kidney and rabbit lung ACE, compared with those of FRC (128 and 291 μg/mL). Further, a significant correlation (r = 0.893; p ≤ 0.05) was observed between radical scavenging activity and ACE‐inhibitory activity. This is the first report on the ACE‐inhibitory activity of F. racemosa stem bark suggesting its potential to be utilized as a therapeutic alternative for hypertension. Copyright © 2010 John Wiley & Sons, Ltd.     

Triterpenoids and a sterol from the stem-bark of Styrax japonica and their protein tyrosine phosphatase 1B inhibitory activities

Five pentacyclic triterpenoids (1-5) and a sterol (6) were isolated from the stem-bark of Styrax japonica. The six compounds, 1-6, were determined to be 3beta-acetoxy-28-hydroxyolean-12-ene (1), 3beta-acetoxyolean-12-en-28-acid (2), 3beta-acetoxyolean-12-en-28-aldehyde (3), 3beta-acetoxy-17beta-hydroxy-28-norolean-12-ene (4), taraxerol (5) and stigmasterol (6), respectively, by spectroscopic means, including the 2D-NMR technique. Compound 4 is a newly discovered natural compound. The protein tyrosine phosphatase 1B (PTP1B) inhibitory activities of the isolated compounds (1-6) were determined in vitro. Among the isolated compounds, 3beta-acetoxyolean-12-en-28-acid (2) and 3beta-acetoxyolean-12-en-28-aldehyde (3) had the most potent inhibitory PTP1B activity, with IC50 values of 7.8 and 9.3 microm, respectively.     

黑果悬钩子化学成分及其PTP1B抑制活性的研究

目的研究黑果悬钩子Rubus caesius茎叶的化学成分及其对蛋白酪氨酸磷酸酶1B(PTP1B)的抑制活性。方法利用硅胶柱色谱、Sephadex LH-20柱色谱、半制备液相等色谱方法进行分离纯化,根据核磁共振波谱鉴定化合物结构,利用酶标仪测定不同萃取部位和单体化合物的PTP1B抑制活性。结果从黑果悬钩子茎的醋酸乙酯部位分离得到5个化合物,分别鉴定为柚皮苷(1)、芹菜素-7-O-β-D-吡喃葡萄糖苷(2)、异槲皮苷(3)、金丝桃苷(4)、(-)-表儿茶素3-O-没食子酸(5);从叶的醋酸乙酯部位分离得到2个化合物,分别鉴定为类叶升麻苷(6)、鞣花酸(7)。结论所有化合物均为首次从黑果悬钩子中分离得到。不同的萃取部位均有一定的PTP1B抑制活性,化合物6表现出较好的PTP1B抑制活性,IC_(50)为(27.41±0.61)μg/m L,推测该化合物可能是叶的醋酸乙酯部位中主要活性成分。     

麦芽蛋白质组成分析及其酶解物ACE抑制活性

目的分析麦芽蛋白质组成,并研究其清蛋白、球蛋白、醇溶蛋白及谷蛋白4类组分酶解产物的血管紧张素转化酶(ACE)抑制活性。方法采用顺序抽提法依次提取清蛋白、球蛋白、醇溶蛋白及谷蛋白4类组分,并采用凯氏定氮法及SDS-PAGE电泳进行定量和定性分析;各蛋白组分用胃蛋白酶水解,经超滤(截留分子量3 kD)后收集滤液,获得小分子肽组分,RP-HPLC法进行ACE抑制活性评价。结果麦芽总蛋白含有量为10.27%,其中清蛋白、球蛋白、醇溶蛋白及谷蛋白分别占总蛋白含有量的24.70%、9.25%、20.09%和33.30%。清蛋白酶解产物(小于等于3 kD)对ACE具有最高的抑制活性,在质量浓度0.01 mg/mL下的抑制率为33.28%。相反,谷蛋白酶解产物(小于等于3 kD)对ACE具有一定的促进活性,同一质量浓度下的抑制率为-10.50%。结论麦芽清蛋白含有量较为丰富,其多肽组分具有明确的体外ACE抑制活性,可进一步开发降压活性成分。     

白术中新桉叶烷倍半萜类成分及其SREBPs抑制活性

采用正相硅胶、Sephadex LH-20、ODS、HPLC等色谱手段,对中药白术的化学成分进行研究,从白术干燥根茎95％乙醇提取物中分离得到3个倍半萜类化合物,并根据波谱数据和理化性质对其结构进行鉴定,分别鉴定为2个桉叶烷倍半萜(7Z)-8β,13-diacetoxy-eudesma-4(15),7(11)-dien...     

水杨梅化学成分的研究

从水杨梅根中分得８个成分，经光谱和化学方法鉴定为：ｑｕｉｎｏｖｉｃ ａｃｉｄ（Ｉ），３－ｏｘｏ－ｕｒｓ－１２－ｅｎｅ－２７，２８－ｄｉｏｉｃ ａｃｉｄ（Ⅱ），ｑｉｎｏｖｉｃ ａｃｉｄ－３β－Ｏ－β－Ｄ－ｇｌｕｃｏｐｙｒａｎｏｓｉｄｅ（Ⅲ），ｑｕｉｎｏｖｉｃ ａｃｉｄ－３－β－Ｏ－α－Ｌ－ｒｈａｍｎｏｐｙｒａｎｏｓｉｄｅ（Ⅳ），ｎｏｒｅｕｇｅｎｉｎ（Ⅴ），７－Ｏ－β－Ｄ－ｇｌｕｃｏｓｙｌ－ｎｏｒｅｕ