Novel Coumarin Glycosides from Daphne oleoides

`Dimeric' coumarin glycoside 1 and `trimeric' coumarin fucosides 2 and 3 were isolated from Daphne oleoides. Their structures were established by means of different spectroscopic techniques, including 2D‐NMR spectroscopy.     

Phytochemistry of Daphne oleoides

Genus Daphne belongs to the Thymelaeaceae family and consists of 70 species. Its various species exist in Europe, Philippine Islands, temperate and subtropical Asia, North Africa, Australia and Pacific. In Pakistan, Daphne is represented by three species. Our focused Daphne oleoides is widely found in diverse climatic conditions from northern cold to central hot regions which creates a rich diversity and novelty in biosynthetic levels of its chemical constituents and hence is a great opportunity. Daphne oeloides is a proven rich source of a variety of unique and interesting nature-made skeletons with a wide range of therapeutic properties. D. oleoides possesses effective therapeutic properties, therefore, has been used in herbal medicines and is still being used to treat various diseases. The modern research by various groups, including ourselves, has resulted in the isolation of a number of natural molecules including some novel tris- and bis- coumarins, daphnane diterpenoids and lignoids. Therefore, due to novelty and richness of the nature-made molecules, and their therapeutic potential combined with our significant work on D. oleoides, this report covers chemical constituents isolated from D. oleoides. The pharmacological activities of the isolated compounds and use of this species in folk medicine have also been reviewed.     

Daphwazirin, biscoumarin glycopyranoside from Daphne oleoides

Daphwazirin, a new biscoumarin glycoside (1), along with four known compounds (2), (3), (4) and (5) has been isolated from the roots of Daphne oleoides. Its chemical structure is established as 7-hydroxy-8-[2-oxo-2H-1-benzopyran-7'-(O-alpha-L-rhamnosyl)-6'-yl]-2H-1-benzopyran-2-one through spectroscopic techniques and chemical analysis.     

Dimeric Coumarin and Phenylpropanoids from Clausena lenis

A new dimeric coumarin, diseselin B ( 1 ), and three new phenylpropanoids, lenisin A–C ( 2 – 4 ), together with eight known O‐terpenoidal coumarins, were isolated from the aerial part of Clausena lenis. Lenisin A ( 2 ) was also isolated from the aerial part of C. excavata. The structures were elucidated on the basis of 1D‐ and 2D‐NMR experiments (HMQC, HMBC, and ¹H,¹H‐COSY).     

Preparative Isolation and Purification of Two Phenylpropanoids from Daphne giraldii Nitsche by HSCCC

Preparative high-speed counter-current chromatography (HSCCC) was successfully applied to purify phenylpropanoids from the stem and root bark of Daphne giraldii Nitsche, a traditional Chinese medicine. Their structures were identified on the basis of ¹H NMR and ¹³C NMR technology. The two-phase solvent system composed of n -hexane–ethyl acetate–methanol–water (2: 3: 0.5: 4, v/v/v/v) was selected for HSCCC. A total of 8.0 mg woonenoside XI (1) and 18.0 mg daphnetin (2) were obtained in one-step separation from 200 mg of the crude extract with purity of 96.0 and 99.1%, respectively, as determined by LC. And the major compound (2) showed antithrombotic activity in vitro.     

A New Dimeric Secoiridoid Glycoside from the Leaves of Olea ferruginea Royle

A new dimeric secoiridoid glycoside, trivially named oleferrugine B ( 1 ), has been isolated from the AcOEt‐soluble part of the MeOH extract of leaves of Olea ferruginea Royle . The structure of the isolated compound was established on the basis of ESI‐MS fragmentation patterns, and 1D‐ and 2D‐NMR techniques, including ¹H‐ and ¹³C‐NMR, HSQC, ¹H,¹H‐COSY, HMBC, and NOESY experiments, and by comparison with literature data.     

Phenylpropanoids from Umbilicus pendulinus

Phytochemical investigation of the leaves of Umbilicus pendulinus afforded in addition to 2-O-caffeoyl malate, isoquercitrin and Z-venusol, the new isomer E-venusol. Special NMR experiments were carried out to elucidate the configuration of the two latter compounds.     

Dapholidins A – C,New Isomeric Biisoflavonoids From Daphne oleoides

Three new isomeric biisoflavonoids, dapholidins A–C ( 1 – 3 , resp.), have been isolated from the AcOEt‐soluble fraction of the MeOH‐soluble extract of the roots of Daphne oleoides, along with the known compounds daphwazirin ( 4 ), daphnetin 8‐O‐β‐D ‐glucopyranoside ( 5 ), daphnin ( 6 ), daphneticin 4″‐O‐β‐D ‐glucopyranoside ( 7 ), and 6,7‐dihydroxy‐3‐methoxy‐8‐[2‐oxo‐2H‐1‐benzopyran‐7‐(O‐β‐D ‐glucopyranosyl)‐8‐yl]‐2H‐1‐benzopyran‐2‐one ( 8 ). The structures of the new compounds were determined by spectroscopic analyses, including 1D‐ and 2D‐NMR.     

A Flavonol Glycoside from Smilax glabra

A new flavonol glycoside,named neosmitibin was isolated the rhizome of Smilax glabra. Its structure and absolute configuration were elucidated on the basis of spectroscopic studies.     

A New Daphnane Diterpene from Daphne tangutica

Daphne tangutica Maxim., a shrub of Thymelaeaceae family, meanly grows in northwest area of China at altitude of 1500-4000 m. The root barks of this plant are utilized as a traditional Tibetan medicine for releasing pain, curing rheumatism and as an abort…     

A new coumarin glycoside from Daphne giraldii

A new coumarin glycoside was isolated from the ethanol extract of the barks of stem of Daphne giraldii Nitsche. Its structure was defined as daphnetin 8-O-b-D-glucopyranosyl-(1→6)-b-D-glucopyranoside on the basis of spectral evidences.     

A New Glycoside from Erigeron Breviscapus

1Er!'geronbreviscapuS(Van)Hand-Mazzisaperennialherb,whichgrowsabundantlyinYunnanandGuangxiprovincesofChina.Manyerigerosideshavebeenfoundpreviouslyinthisplant'-'.WereportheretheisolationandstructuralelucidationofanewconstituenterigesideIIfromthebutanol-solublefractionofE.breviscapus.TheEtOHextractoftheplantwaspartitionedwithpetroleumether,EtOAcandn-BuOH.Then--BuOHfractionwasfurtherfractionatedbysilicagelchromatographyandHPLCtoafford1.l,mp.148--149"C,FAB-MSm/zf436[M] ,475[M K] .El…     

A New Compound from Daphne giraldii Nitsche

Daphne giraldii Nitsche (Thymelaeaceae) is widely distributed in Shanxi, Gansu, Sichuan and Ningxia provinces of China. According to the modern research, it showed the activity against inflammatory, pain, cancer and so on1. Herein we report the identifica…     

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.     

A New Triterpenoid Glycoside from Dichotomanthes tristaniaecarpa

Dichotomanthes tristaniaecarp ( Kurz.) belongs to the family Rosaceae. Its root bark is used as Chinese folk medicine for treatment of flu, cough, sore throat and nosebleed. Chemical constituents of this species have not been reported previously. Compound 1 was obtained as colorless needles, mp. 213-215 °C. The molecular formula was determined as C36H58O11 by its negative-ion FAB MS ([M]- at m/z 665) and 13C NMR DEPT spectrum. The analysis of 13C NMR spectrum showed 30 signals for …