Arylglycerol glucosides from Dracocephalum forrestii

Three new arylglycerol glucosides, threo-guaiacylglycerol 3-O-(6-O-p-hydroxybenzoyl)-β-D-glucopyranoside (1), threo-guaiacylglycerol 3-O-[6-O-(E)-p-coumaroyl]-β-D-glucopyranoside (2) and threo-guaiacylglycerol 3-O-[6-O-(Z)-p-coumaroyl]-β-D-glucopyranoside (3), together with seven known compounds were isolated from the whole plants of Dracocephalum forrestii and their structures were determined on the basis of spectroscopic evidences.     

Further flavonol and iridoid glycosides from Ajuga remota aerial parts

Five new iridoid glycosides characterised as 6-keto-8-acetylharpagide (1), 6,7-dehydro-8-acetylharpagide (2), 7,8-dehydroharpagide (3), 8-acetylharpagide-6-O-β-glucoside (4), harpagide-6-O-β-glucoside (5) together with three flavonol glycosides, myricetin 3-O-rutinoside-4'-O-rutinoside (6), myricetin 3-O-rutinoside-3'-O-rutinoside (7) and isorhamnetin 3-O-rutinoside-7-O-rutinoside-4'-O-β-glucoside (8) have been isolated from the aerial parts of Ajuga remota. Also isolated were two known compounds ajugarin IV and ajugarin V. Their structures were established using spectroscopic methods including UV, IR, FAB-MS, HR-MS, 1D and 2D NMR techniques.     

Isolation and identification of a novel flavonoid from Penthorum chinense P

A novel flavonoid, pinocembrin-7-O-[3'-O-galloyl-4',6'-hexahydroxydiphenoyl]-β-glucose (1) was isolated from the whole plant of Penthorum chinense P., along with four known compounds, pinocembrin-7-O-β-glucoside, quercitrin, quercetin-3-O-rhamnoside and gallic acid. The structures were established by spectroscopic analysis.     

Stilbene C-glucosides from Cissus repens

Four new stilbene C-glucosides, namely trans-3-O-methyl-resveratrol-2-C-β-glucoside (1), cis-3-O-methyl-resveratrol-2-C-β-glucoside (2), trans-3-O-methyl-resveratrol-2-(2-p-coumaric)-C-β-glucoside (cissuside A) (3), and trans-3-O-methyl-resveratrol-2-(3-p-coumaric)-C-β-glucoside (cissuside B) (4), were isolated from the aerial parts of Cissus repens, along with known trans-resveratrol (5), trans-resveratrol-2-C-β-glucoside (6) and cis-resveratrol-2-C-β-glucoside (7). Their structures were established by spectroscopic methods. Stilbene C-glucosides were found in the genus Cissus for the first time.     

基于指纹图谱和网络药理学的白花蛇舌草质量标志物预测分析

目的：基于指纹图谱和网络药理学方法,分析预测白花蛇舌草[Oldenlandia diffusa（Willd.） Roxb,ODWR]的质量标志物（quality markers,Q-Marker）。方法：利用HPLC建立ODWR指纹图谱,确认共有峰;通过对照品比对和HPLC-ESI-Q-TOF-MS对共有峰进行鉴定;运用网络药理学筛选和分析ODWR共有成分及炎症、肿瘤作用靶点和通路,构建"药物-成分-靶点-通路"网络,预测ODWR潜在Q-Marker;使用Auto Dock Vina软件对ODWR潜在的Q-Marker与关键靶点进行分子对接验证。结果：槲皮素-3-O-[2-O-（6-O-E-阿魏酰基）-β-D-吡喃葡糖苷]-β-D-吡喃半乳糖苷、（E/Z）-6-O-香豆酰鸡屎藤次苷甲酯、（E/Z）-6-O-阿魏酰鸡屎藤次苷甲酯成分为ODWR潜在的Q-Marker,主要通过作用于PIK3R1、NFKB1、HRAS等靶点,调控Pathways in cancer、Proteoglycans in cancer、Focal adhesion等信号通路,发挥抗炎、抗肿瘤等作用。结论：槲皮素-3-O-[2-O-（6-O-E-阿魏酰基）-β-D-吡喃葡糖苷]-β-D-吡喃半乳糖苷、（E/Z）-6-O-香豆酰鸡屎藤次苷甲酯、（E/Z）-6-O-阿魏酰鸡屎藤次苷甲酯成分可作为ODWR潜在Q-Marker。本研究为ODWR质量控制和评价提供参考,同时也为其抗炎、抗肿瘤活性成分及作用机制研究奠定基础。     

Blood-pressure lowering, positive chronotropy and inotropy by the Veratrum alkaloids germidine and germerine but negative chronotropy by veratridine in mice

Germidine and germerine, the Veratrum alkaloids lowered blood pressure accompanied with positive chronotropy and inotropy in mice. Germerine was more potent than germidine in both blood-pressure lowering and positive inotropy, whereas veratridine produced negative chronotropy and positive inotropy. An acyl group (an acetyl or a 2-methylbutyroyl group) at 3-O-R¹ position and a 2-methylbutyroyl group at 15-O-R² position in germine were important to produce the positive inotropy and chronotropy. The presence of a veratroyl group at 3-O-R¹ position and a free hydroxyl group at 15-O-R² position may be essential to produce the negative chronotropy by veratridine. The positive inotropy by germidine and veratridine may be due to TTX-resistant Na⁺ channel activation.     

A new cycloartane saponin from Cimicifuga acerina

A new cycloartane saponin along with two known compounds, cimigenol and cimigenol 3-O-β-D-xyloside, was isolated from the rhizomes of Cimicifuga acerina (Sieb. et Zucc.) Tanaka (Ranunculaceae). The structure of the new compound was elucidated as 3'-O-acetyl cimigenol 3-O-β-D-xyloside on the basis of chemical and spectral evidence.     

Sesquiterpene glucosides from anti-leukotriene B4 release fraction of Taraxacum officinale

Chemical examination of the MeOH extract of the root of Taraxacum officinale, which exhibited inhibitory activity on the formation of leukotriene B₄ from activated human neutrophils, has resulted in the isolation of 14-O-β-D-glucosyl-11,13-dihydro-taraxinic acid (1) and 14-O-β-D-glucosyl-taraxinic acid (2). The absolute stereostructure of 1 has been established by X-ray chrystallographic examination.     

The 6-derivative of beta-cyclodextrin with succinic acid: a new chiral selector for CD-EKC

6-O-Succinil-β-cyclodextrin (CDsuc6) was synthesized with very good yield by one pot synthesis and characterized by NMR spectroscopy and ESI-MS. It was used as a chiral selector in capillary electrophoresis to resolve catecholamine racemates, namely norepinephrine, epinephrine, terbutaline and norphenilephrine.

The CE experiments at pH 5.6 show very promising selector ability by 6-O-succinil-β-cyclodextrin for the chiral recognition of all the catecholamines tested, while at pH 9.2, only racemic terbutaline was successfully separated.     

Pyrrolizidine alkaloids from Cynoglossum furcatum

Two new pyrrolizidine alkaloids have been isolated from the roots of Cynoglossum furcatum. On the basis of chemical and spectroscopic evidence, structures of the compounds have been elucidated. They are lactodine (3), a monoster alkaloid and viridinatine (4), a pyrrolizidine diester alkaloid. The structure of lactodine is elucidated as 9-O-(-)lactyl heliotridine and viridinatine as 7-O-(-)viridifloryl echinatine.     

Glycosyl flavonoids from the roots and rhizomes of Asarum longerhizomatosum

Two new glycosyl flavonoids including a glycosyl aurone, together with six known flavonoids were isolated from the roots and rhizomes of Asarum longerhizomatosum. The structures of the two new compounds were elucidated as 4,6,4'-trihydroxy-aurone-4,6-di-O-β-D-glucopyranoside (7, caulesauroneside) and naringenin-7,4'-di-O-β-D-glucopyranoside (8, caulesnarinside). The six known flavonoids were identified as naringenin (1), naringenin-5-O-β-D-glucopyranoside (2), naringenin-7-O- β-D-glucopyranoside (3), chalcononaringenin-2'-O-β-D-glucopyranoside (4), naringenin-5,7-di-O-β-D-glucopyranoside (5), chalcononaringenin-2',4'-di-O-β-D-glucopyranoside (6), respectively. This is the first report of the isolation of aurones in the family Aristolochiaceae.     

Three new norlignans from Curculigo capitulata

From the ethanolic extract of the rhizomes of Curculigo capitulata have been isolated, and structurally elucidated by spectral evidences and chemical methods, three new norlignans, capituloside (1), a mixture of curculigenin (2) and isocurculigenin (3), along with four known compounds (4-7), a mixture of 1-O-methylcurculigine (4) and 1-O-methylisocurculigine (5) and a mixture of curculigine (6) and isocurculigine (7).     

Absolute configuration determination of angular dihydrocoumarins from Peucedanum praeruptorum

From Peucedanum praeruptorum, one new khellactone ester (3'R)-O-acetyl-(4'S)-O-angeloylkhellactone (3), as well as four known angular dihydropyranocoumarins (1, 2, 4, 5) have been isolated. On the basis of NMR spectra and X-ray crystallography, their structures were determined. We have elucidated their absolute configuration by either chiral separation of their alkaline hydrolysis products with Rp-18 HPLC eluted with 5% hydroxypropyl-β-cyclodextrin (β-HCD) or by measurement of their CD spectra. A general rule relating the position and absolute stereochemistry of the khellactone esters to the sign of their Cotton effects in CD curves is proposed.     

Direct scavenging of nitric oxide and superoxide by green tea

In the present study, we investigated the free radical scavenging effects of green tea extract and green tea tannin mixture and its components using a nitric oxide (NO) and superoxide (O₂⁻) generating system in vitro. Green tea extract showed direct scavenging activity against NO and O₂⁻ and green tea tannin mixture, at the same concentration, showed high scavenging activity. Comparison of the activities of seven pure compounds isolated from green tea tannin mixture showed that (−)-epigallocatechin 3-O-gallate (EGCg), (−)-gallocatechin 3-O-gallate (GCg) and (−)-epicatechin 3-O-gallate (ECg) had higher scavenging activities than (−)-epigallocatechin (EGC), (+)-gallocatechin (GC), (−)-epicatechin (EC) and (+)-catechin (C), showing the importance of the structure of flavan-3-ol linked to gallic acid for this activity. Among the gallate-free tannins, EGC and GC were more effective O₂⁻ scavengers than EC and C, indicating the O-trihydroxy structure in the B ring is an important determinant of such activity. However, this structure did not affect the NO scavenging activity. These findings confirm that green tea tannin has excellent antioxidant properties, which may be involved in the beneficial effect of this compound.     

Detection of new 7-O-acyl derivatives of diarrhetic shellfish poisoning toxins by liquid chromatography-mass spectrometry.

A novel method for the detection of acylated diarrhetic shellfish poisoning toxins is reported. Direct determination of these compounds is possible using high performance liquid chromatography coupled with ion-spray mass spectrometry. An extract, purified from the digestive glands of toxic mussels (Mytilus edulis) contaminated with okadaic acid, dinophysistoxin-1, and a recently reported analog, dinophysistoxin-2, was also shown to contain small amounts of dinophysistoxin-3, a mixture of 7-O-acyl ester derivatives of dinophysistoxin-1. In addition, acyl ester derivatives of okadaic acid and dinophysistoxin-2 were also detected by direct LC-MS analysis and confirmed by analysis of their hydrolysis products. This is the first report of the detection of other naturally occurring 7-O-acyl esters similar to dinophysistoxin-3.     

白英中两个新糖苷生物碱

对中药白英的生物碱类成分进行研究.采用ODS、硅胶柱层析和高效液相色谱相结合的方法对生物碱进行分离纯化.通过UHPLC-ESI-Q-TOF-MS、 1D和2D NMR鉴定了7个生物碱类化合物,分别为15β-ethoxy-(3β,5a,25R)-16,23-epoxy-23,24-imino-cholestan-16,2...     

A new iridoid diglycoside from Clerodendrum chinense

A new iridoid diglucoside, 5-O-β-glucopyranosyl-harpagide, has been isolated from the aerial part of Clerodendrum chinense together with three known iridoid glucosides and six known cyclohexylethanoids. Their structures have been determined by analyses of spectroscopic data.     

Chemical constituents from the stem of Embelia laeta

In the present study, we aimed to investigate the chemical constituents from Embelia laeta. The constituents were separated by various column chromatography, including silica gel, ODS gel, MCI gel, Sephadex LH-20, and semipreparative HPLC. Their structures were elucidated by spectroscopic means. A total of 13 compounds were isolated from E. laeta and identified as (6R,9R)-1-Oxo-α-ionol-9-O-β-D-goucopyranoside (1), (+)-Pinoresinol (2), Leptolepisol D (3), Kaempferol (4), Kaempferol-3-α-L-Ramnopyranoside (5), Kaempferol-3-β-D-(6-O-trans-p-coumaroyl) glucopyranoside (6), Bis(2-ethylhexyl) phthalate (7), 2-Benzenedicarboxylic diisobutyl ester (8), Caffeic acid methyl ester (9), Paldehyde (10), Coniferaldehyde (11), Caffeic acid (12) and 5-Hydroxymethyl furfural (13), respectively. All the compounds were isolated from E. laeta for the first time.     

Androechin, a new chalcone glucoside from Andrographis echioides

A new chalcone glucoside, androechin, and a known flavone glucoside, echioidinin 5-O-glucoside, were isolated from the whole plant of Andrographis echioides. Androechin was characterized as 2,2',6'-trihydroxy-4'-methoxychalcone 2'-O-β-D-glucopyranoside by spectral and chemical studies.     

Irritant contact dermatitis in humans from phorbol and related esters

Nine compounds, based on four biogenetically-related polycyclic diterpene skeletons, were subjected to open and closed patch testing on human volunteer subjects. The tigliane esters phorbol-12, 13, 20-triacetate, 12-O-2Z-4E-octadienoyl-4-deoxyphorbol-13-acetate and 12-O-tigloyl-4-deoxyphorbol-13-isobutyrate, in increasing order of potency, produced symptoms of toxicity in closed patch tests, with the dose of the most potent compound in this series being 0.5 μg in 5 μl acetone. Phorbol, a tigliane alcohol, was inactive in closed tests at a dose level of 50 μg/5 μl. The daphnane derivative, daphnetoxin, produced bullae and vesiculation in closed patch tests, but daphnetoxin-5,20-diacetate was devoid of these effects when applied at 10 times the dose of daphnetoxin. The ingenane compounds, ingenol-3,5,20-triacetate and 20-deoxy-16-hydroxyingenol-3,5,16-triacetate, and the lathyrane compound, ingol-3,7,8,12-tetraacetate, were obtained from the hydrolyzed, acetylated irritant latex of Euphorbia hermentiana. At the doses tested, ingenol-3,5,20-triacetate was the only compound derived from this plant to exhibit irritant activity in closed patch tests. In contrast, this compound is inactive as an irritant to the mouse ear at doses up to 250 μg/ear. Only three compounds, 12-O-2Z-4E-octadienoyl-4-deoxyphorbol-13-acetate, 12-O-tigloyl-4-deoxyphorbol-13-isobutyrate and daphnetoxin, produced dermatological toxicity in open patch tests at the doses used. Inflammatory signs and symptoms for several of the compounds under test persisted for over four days in open patch tests and for a week or more after application in closed patch testing.