Two New Iridoid Glucosides from Clerodendrum serratum

Clerodendrumserratumcalledas"SanDuiJie"inChinese,isasmallshrubwithfragrantflowersfoundwidelyintheforestsofthesouthofChina.IthasbeenusedasafolkmedicineinYunnanfortreatmentofmanydiseasessuchashepatitisandmalaria.Inordertofindthebioactivecomponents,studiesonthechemicalconstituentsoftheleavesofClerodendrumserratum,collectedatLongLingofYunnanprovince,werecarriedout.Wehavereportedtwonewglycosidespreviously'.NoW,furtherinvestigationofglycosidesofthisplantresultedintwonewiridoidglucosides76coumar…     

Two New Iridoid Glucosides from Clerodendrum serratum

In our previous paper"', we have reported some constituents' from the extract of C.Serralum var. amplexghlium Moldenke. Further investigation on the same plant led tothe isolation of two new iridoid glucosides, serratoside A (l) and serratoside B (2). Inthis communication, we describe the structural elucidation of the two new compounds.Serratoside A (l) (Figure l) was obtained as brown gum. The positive FABMSestablished a molecular formula of C,,H,,O,. for I (m/z 505 IM l] ), which was…     

Two New Diterpenoid Glucosides from Clerodendrum serratum

WereportedsomeconstituentsfromtheplantofC.serrartumvar.amplexghliumMoldenkel.Furtherstudyontheaerialpadsoftheplainresultedintheisolationoftwonewlabdanetypediterpenoidglucosides,cleroserraosideA(l)andcleroserraosideB(2).InthispaperwedescribethestructIJralelucidationofthecompounds.CleroserrosideA(l),[a]:'-97.22(c0.289,MeOH),wasobtainedaswhiteamorphouspowders.Itexhibitedan[M-l],ionpeakatm/z481inthenegativeionFABMSindicatingitsmolecularweighttobe482.ThemolecularformulawasdeterminedasC,,H.,…     

A New Triterpenoid Saponin: Se-saponin A

In continuation of our studies on the constituents of Clerodendrum serratum var.amplexghlium Moldenke'-"', a new triterpenoid saponin, sc-saponin A (l), was isolated.To the best of our knowledge, it is the second instance oftriterpenoid saponin from theClerodendrum genus. This paper deals with the structural elucidation of the newcompound.Se-saponin A (l) an amorphous powder, gave positive Liebermann-Burchardreaction. It was deduced to have a molecular formula of C58H,,O,, by high resoluti…     

Two New C29 Sterols from Clerodendrum colebrookianum

Clerodendrum. colebrookianum Walp. is a traditional Chinese medicine, it possesses thefunctions of "expelling toxin by cooling, cooling blood to induce diuresis and purgingheat"', and has been used as a remedy for hypertension in india2. The chemicalinvestigation of this plant has been reported previously'-'. In continuation of our studieson the constituents of the plant, we examined the steroid constitllents of the title speciesand isolated two new C,, sterols, colebrin A (l) and colebrin B…     

苷类研究ⅩⅩⅥ: 苯丙素苷Eutigoside A的合成研究

首次报道了苯丙素苷类化合物EutigosideA,即1-O-[2-(4-羟基苯基)乙基]-6-O-(E)-香豆酰基-β-D-吡喃葡萄糖的全合成。从四乙酰溴代葡萄糖出发,经过成苷、脱乙酰基两步反应,制备了2-对烯丙氧基苯基-β-D-吡喃葡萄糖苷(3),采用酰氯法在低温下将对乙酰氧基肉桂酰基引入化合物3的葡萄糖6位,再经过脱烯丙基、脱乙酰基两步,便顺利地合成了天然苯丙素苷EutigosideA。以化合物3为原料,经过对葡萄糖4,6位亚苄基化、2,3位乙酰化、4,6位脱亚苄基、选择性6位乙酰化及4位引入对乙酰氧基肉桂酰基等五步反应,得到了保护的苯丙素苷(OsmanthusideA(10);但在NH~3/MeOH条件下脱乙酰基时,化合物10中的香豆酰基从葡萄糖的4位迁移至6位,最终又得到了EutigosideA。     

三对节中两个新环烯醚萜甙的研究

从三对节的叶子中分离得到４个化合物,经化学和光谱方法鉴定其为７－Ｏ－ｐ－Ｃｏｕｍａｒｏｙｌｏｘｙｕｇａｎｄｏｓｉｄｅ（１）,７－Ｏ－ｃｉｎｎａｍｏｙｌｏｘｙｕｇａｎｄｏｓｉｄｅ（２）,ａｃｔｅｏｓｉｄｅ（３）和ｍａｒｔｙｎｏｓｉｄｅ（４）,其中前两者是新环烯醚萜甙化合物,后两者为首次从该植物中获得的苯丙素甙类化合物。     

Calceolarioside A,a Phenylpropanoid Glycoside from Calceolaria spp., Displays Antinociceptive and Anti-Inflammatory Properties

Phenylpropanoid glycosides are a class of natural substances of plant origin with interesting biological activities and pharmacological properties. This study reports the antinociceptive and anti-inflammatory effects of calceolarioside A, a phenylpropanoid glycoside previously isolated from various Calceolaria species. In models of acute nociception induced by thermal stimuli, such as the hot plate and tail flick test, calceolarioside administered at doses of 1, 5, and 10 μg in the left cerebral ventricles did not modify the behavioral response of mice. In an inflammatory based persistent pain model as the formalin test, calceolarioside A at the high dose tested (100 μg/paw) reduced the licking activity induced by formalin by 35% in the first phase and by 75% in the second phase of the test. In carrageenan-induced thermal hyperalgesia, calceolarioside A (50 and 100 μg/paw) was able to significantly reverse thermal hyperalgesia induced by carrageenan. The anti-inflammatory activity of calceolarioside A was then assessed using the zymosan-induced paw edema model. Calceolarioside A (50 and 100 μg/paw) induced a significant reduction in the edema from 1 to 4 h after zymosan administration. Measuring IL-6, TNFα, and IL-1β pro-inflammatory cytokines released from LPS-stimulated THP-1 cells, calceolarioside A in a concentration-dependent manner reduced the release of these cytokines from THP-1 cells. Taken together, our results highlight, for the first time, the potential and selective anti-inflammatory properties of this natural-derived compound, prompting its rationale use for further investigations.     

A New Dihydroflavone Glycoside from Glycyrrhiza uralensis

A new dihydroflavone glycoside was isolated from the underground parts of Glycyrrhiza uralensis. Its structure was elucidated as 7-hydroxyl-4′-O-]3-D-(6″-O-α-hydroxylpropionyl) glucopyranosyl dihydroflavone by spectral methods.     

Chlorophytoside A, a New Labdane Diterpene Glycoside from Chlorophytum laxum

A new labdane-type diterpene glycoside 1 , chlorophytoside A, had been isolated from Chlorophytum laxum R.Br. The structure had been elucidated as (10S)-6α-hydroxylabda-8,13-dien-15,16-olide 3R-O-β-D-glucopyranoside on the basis of chemical and spectroscopic data.     

A new rearranged abietane diterpene from Clerodendrum inerme with antioxidant and cytotoxic activities

Eight compounds were isolated from the leaves of Clerodendrum inerme, including one new rearranged abietane diterpene, crolerodendrum B (1). Their structures were determined by means of spectroscopic methods including one-dimensional and two-dimensional nuclear magnetic resonance (1-D and 2-DNMR), high-resolution electrospray ionisation mass spectrometry (HR-ESI-MS) and circular dichroism (CD). The DPPH radical scavenging and cytotoxic activities of isolated compounds against MCF7 (breast), HCT116 (colon) and B16F10 (melanoma) cancer cell lines were evaluated. Compounds 1, 3 and 4 exhibited strong DPPH radical-scavenging effects (ED₅₀ values of 17.6 ± 2.1, 10.1 ± 0.8 and 11.3 ± 0.3 μM, respectively) and 4 showed strong cytotoxicity against the HCT116 cell line (IC₅₀ = 3.46 ± 0.01 μM).     

A New Bianthraqinonc Glycoside from Eremurus chinensis

Eremurus chinensis Fedtch has a wide distribution in the western part of China; it hasbeen used in Chinese folk medicine for the treatment of rheumatism and physicalweaknessl. Only few reports describe polysaccharides'-' rather than other chemicalconstituents from the genus Eremurus. We report here the isolation and structuralelucidation of a new bianthraquinone glycoside, 8-O- P -D-glucopyranosyl-2,7'-hi(l,8dihydroxy-3-methyl-9,10-anthraqu 1 from E. chinensis.The EtOAc soluble fraction ob…     

Lavandulifolioside: A New Phenylpropanoid Glycoside from Stachys lavandulifolia

A new phenlypropanoid glycoside has been isolated from the methanolic extract of the aerial parts of Stachys lavandulifolia (Lamiaceae), lavandulifolioside (1) . On the basis of chemical and spectral data the structure of the new compound 1 has been elucidated as β-(3,4-dihydroxyphenyl)ethyl O-α-L -arabinopyranosyl-(1→2)-α-L -rhamnopyranosyl-(1→3)-4-O-caffeoyl-β-D -glucopyranoside.     

Lagotoside: A New Phenylpropanoid Glycoside from Lagotis stolonifera

From the aerial parts of Lagotis stolonifera (Scrophulariaccae), a new phenylpropanoid glycoside, lagotoside ( 8 ), and the three known glycosides ehrenoside ( 5 ), verbascoside (= acteoside; 6 ), and plantamajoside ( 7 ) were isolated, together with the four known iridoid glucosides aucubin ( 1 ), catalpol( 2 ), globularin ( 4 ), and lythantosalin ( 3 ). The structure of the new compound 8 was elucidated on the basis of chemical and spectral data as 2-(3-hy-droxy-4-methoxyphenyl)ethyl O-[α-L -arabinopyranosyl-(1 → 2)]-O-[α-L -rhamnopyranosyl-(1 → 3)]-4-O-feruloyl-β-D -glucopyranoside.     

Paeonivayin, A New Monoterpene Glycoside from Paeonia delavayi

Paeoniarootbark,"Dan-Pi"inChinese,isoneofthemostimportantherbaldrugswhichhasbeenusedfortreatmentofmuscularspasm,chestpains,diarrhoea,bloodandliverdisordersaswellasageneralanalgesicintraditionalChinesemedicine.SignificantchemicalandpharmacologicalinvestigationshavebeenconductedonthedifferentspeciesofPaeonia'-',P.albifiora,P.anomala,P.lacli/loraandP.sloffflllicosa.Asoneofthemainsourcesof"Dan-Pi",theconstituentsofP.delayal'iFranch.havenotbeenstudied.Inthecourseofourstudyonpharmacologicallyac…     

A New Monoterpene Glycoside from Paeonia veitchii

The root cortex of Paeonia veitchii Lynch. is one of the most important crude drugs in Chinese traditional medicine. It is used as an analgesic, sedative, anti-inflammatory agent and a remedy for cardiovascular, extravasated blood1. The present paper deals with the structural elucidation of a new compound from this material. Compound 1, obtained as viscous oil, gave a quasi-molecular ion peak at m/z 521 [M-1]- in the negative FAB-MS, which was 42 amu greater than that of paeon…     

Dissectol A,A Novel Monoterpene Glycoside from Incarvillea dissectifoliola

Dissectol A,a novel monoterpene glycoside was isolated from the methanol part of the 95% EtOH extract of Incarvillea dissecfoliola and its structure was determined by 1D and 2D NMR data.     

A New Bibenzyl Glycoside from Dendrobium moniliforme

A new bibenzyl glycoside has been isolated from the stems of Dendrobium moniliforme (L.) Sw.(Orchidaceas).Its structure has been identified on the basis of spectroscopic and chemical methods.     

A New Monoterpene Glycoside from Swertia punicea

The plant Swerlia punicea Hemsl. (Gentianaceae), distributed in Southwest China, isused in Chinese medicine for acute bilious hepatitis and cholecystitis'. Previousinvestigations of this plant have led the isolation of various compounds'. In thisinvestigation, seven compounds were isolated tyom the whole plants of S. punicea,collected in E-Shan, Yunnan Province in July, 1997 and identified by P. Y. Bet inKunming institUte of Botany, Chinese Academy of Sciences, where the specimen isdep…     

A New Pregnane Glycoside from Fermented Leaves of Agave americana

A new minor pregane glycoside was isolated from the fermented leaves of Agave americana.Its structure was elucidated as (20S)-5α-pregnane-3β，20-diol 20-O-β-D-glucopyrano-side(1)by spectral methods.