A New Cardenolide and Two New Pregnane Glycosides from the Root Barks of Periploca sepium

A new cardenolide and two new pregnane glycosides, periplogenin 3‐[O‐β‐glucopyranosyl‐(1→4)‐β‐sarmentopyranoside] ( 1 ), (3β,20S)‐pregn‐5‐ene‐3,17,20‐triol 20‐[O‐β‐glucopyranosyl‐(1→6)‐O‐glucopyranosyl‐(1→4)‐β‐canaropyranoside] ( 2 ), and (3β,14β,17α)‐3,14,17‐trihydroxy‐21‐methoxypregn‐5‐en‐20‐one 3‐[O‐β‐oleandropyranosyl‐(1→4)‐O‐β‐cymaropyranosyl‐(1→4)‐β‐cymaropyranoside] ( 3 ), were isolated from the root barks of Periploca sepium Bge , together with seven related known compounds, periplogenin, xysmalogenin, (3β,20S)‐pregn‐5‐ene‐3,17,20‐triol, (3β,14β,17α)‐3,14,17‐trihydroxy‐21‐methoxypregn‐5‐en‐20‐one, (3β,20S)‐pregn‐5‐ene‐3,20‐diol 3‐β‐glucopyranoside 20‐β‐glucopyranoside, (3β,20S)‐pregn‐5‐ene‐3,20‐diol 3‐[O‐2‐O‐acetyl‐β‐digitalopyranosyl‐(1→4)‐β‐cymaropyranoside] 20‐[O‐β‐glucopyranosyl‐(1→6)‐O‐β‐glucopyranosyl‐(1→2)‐β‐digitalopyranoside], and (3β,20S)‐ pregn‐5‐ene‐3,20‐diol 20‐[O‐β‐glucopyranosyl‐(1→6)‐β‐glucopyranoside]. Their structures were elucidated on the basis of spectroscopic analyses.     

Five New Pregnane Glycosides from the Root Barks of Periploca sepium

Five new pregnane glycosides, perisepiumosides A–E ( 1 – 5 , resp.), along with the seven known constituents 6 – 12 , were isolated from the root barks of Periploca sepium Bge . (Asclepiadaceae), a traditional Chinese medicine used for the treatment of rheumatoid arthritis and wounds. Their structures were characterized on the basis of spectroscopic analyses.     

Perisomalien A,a new cytotoxic scalarane sesterterpene from the fruits of Periploca somaliensis

Abstract

The CHCl₃ fraction of MeOH extract of Periploca somaliensis (family Asclepiadaceae) fruits afforded a new scalarane sesterterpene, namely perisomalien A (1), along with lupeol acetate (2), β-amyrin (3), cycloart-23Z-ene-3β,25-diol (4), and β-sitosterol-3-O-β-D-glucopyranoside (5). Their chemical structures were established by various spectroscopic analyses, in addition to comparison with the formerly reported data. Moreover, the cytotoxic activity of these metabolites was assessed towards MCF-7, HepG2, and HCT-116 tumour cell lines using sulforhodamine B (SRB) assay. Compound 4 showed the most potent cytotoxic profile with IC₅₀ 9.0?µM towards MCF-7, compared to doxorubicin (IC₅₀ 0.18?µM). Also, 1 and 4 possessed the most potent effect towards HepG2 with IC₅₀s 26.7 and 25.9?μM, respectively. In addition, all tested compounds showed cytotoxic effects with IC₅₀ values ranging from 19.9 to 39.3?µM against HCT-116.     

Periplocain A,a New Naphthalene Derivative from Periploca aphylla Growing in Saudi Arabia

Periplocain A ( 2 ), a new naphthalene derivative together with four known compounds: 2‐ethylhexyl benzoate ( 1 ), quercetin‐3‐O‐α‐l ‐rhamnopyranoside ( 3 ), quercetin‐3‐O‐β‐d ‐glucopyranoside ( 4 ), and quercetin‐3‐(6‐O‐α‐l ‐rhamnopyranosyl‐β‐d ‐glucopyranoside) ( 5 ) were isolated from the AcOEt fraction of the aerial parts of Periploca aphylla (Asclepiadaceae). Their structures were established by multiple spectroscopic methods in addition to HR‐ESI‐MS and by comparison with literature data.     

Three New Pregnane Alkaloids from Veratrum taliense

Three new alkaloids, 3‐O‐acetylveralkamine ( 1 ), veralkamine 3‐(β‐D ‐glucopyranoside) ( 2 ), and 6,7‐epoxyverdine ( 3 ), together with five known alkaloids, veramitaline, veralkamine ( 4 ), angeloylzygadenine, veratroylzygadenine, and veramiline 3‐(β‐D ‐glucopyranoside), were isolated from the whole plants of Veratrum taliense. Their structures were elucidated on the basis of spectroscopic analysis, and the NMR data of veralkamine ( 4 ) are given for the first time. In addition, the cytotoxic activities of all isolated compounds, except for veramitaline, were tested.     

A New Diarylheptanoid from the Barks of Betula platyphylla

Chemistry of Natural Compounds - A new diarylheptanoid, 3,4-dihydroxy-1,7-bis(4′ ,4′′-dihydroxyphenyl)-heptane (1), was isolated from the ethyl acetate extract of Betula...     

A New Abietane Diterpenoid from the Barks of Taxus yunnanensis

Along with the major constituents taxoids, some non-taxane diterpenoids have also been isolated1. During the course of our phytochemical investigation on the bark of Taxus yunnanensis. Cheng et L. K. Fu, a new abietane diterpenoid, taxayunnin (1), and the known taxamairin C (2)2, were isolated. The structure elucidation of taxayunnin 1 was established by spectral analysis.Taxayunnin 1, pale yellow needles, mp 215oC, showed a molecular ion peak at m/z 346 [M+] in its EI mass spectrum, which…     

Optimized microwave‐assistant extraction combined ultrasonic pretreatment of flavonoids from Periploca forrestii Schltr. and evaluation of its anti‐allergic activity

Microwave extraction combined ultrasonic pretreatment of flavonoids from Periploca forrestii Schltr. was investigated in this study, extraction process was first performed in an ultrasonic cleaner, then treated by microwave irradiation. The optimum ultrasonic time of 25 min was selected by single‐factor experiments. A response surface methodology has been used to obtain a mathematical model that describes the process and analyzes the significant parameters ethanol concentration 59.92%, liquid to raw materials ratio 21.24 mL/g, microwave radiation time 209.53 s, and microwave power 274.14 w. In these optimum conditions, the yield of flavonoids from P. forrestii (TFPF) could be up to 9.11 ± 0.08%, which was increased by 14.30 and 19.86% compared microwave extraction and ultrasonic extraction, respectively. In vitro suppress hyaluronidase experimentation showed that TFPF purified using polyamide exhibited good anti‐hyaluronidase ability with IC₅₀ value of 1.033 mg/mL, possessing certain anti‐antiallergic and potential application prospect in pharmaceutical production of treating inflammation and other related fields.     

Two New C21 Steroidal Glycosides from the Stems of Marsdenia tenacissima

Two new pregnane glycosides, (3β,5α,12β,14β,17α)‐3‐(β‐cymaropyranosyloxy)‐8,14,17,20‐tetrahydroxypregnan‐12‐yl benzoate ( 1 ) and (3β,5α,12β,14β,17α)‐3‐(β‐cymaropyranosyloxy)‐8,14,17,20‐tetrahydroxypregnan‐12‐yl cinnamate ( 2 ) were isolated from the stems of Marsdenia tenacissima. The structures and relative configurations of the new compounds were elucidated by spectroscopic methods, including mass spectrometry and NMR spectroscopy.     

A New Pregnane Glycoside from Dioscorea collettii var. hypoglauca

Morphologicaldeformationsofthemyceliaorconidiaofmicroorganismssuchascurling,swelling,hyper-divergence,beadformationandinhibitionofgermination,areofteninducedinthepresenceofbioactivesubstances".AnewscreeningbioassaymethodfordetectingthedeformationofmyceliagerminatedfromconidiaofPyriculartaoryzaeP-2bwasfirstdevelopedforthequantitativeapplicationtoscreeningantifungalandantineoplasticagentsbyH.Kobayashi'.Thisbioassayisquick,easytoperform,andhasbeenefficientlyusedinthepreliminaryscreeningofantineo…     

A new triterpene and protective effect of Periploca somaliensis Browicz fruits against CCl4-induced injury on human hepatoma cell line (Huh7)

The potential hepatoprotective effect of the methanolic extract of Periploca somaliensis Browicz fruits, its different fractions (n-hexane, chloroform and n-butanol) and the major isolated compound ursolic acid was evaluated using the human hepatoma cell line (Huh7) based on the changes in the activity of aspartate aminotransferase, alanine transaminase, glutathione and superoxide dismutase. Each sample was tested at three different concentrations (1000, 100 and 10 μg/mL). All tested samples exhibited a potent concentration-independent cytoprotective effect relative to silymarin as a reference standard. Chromatographic fractionation of the chloroform-soluble fraction of the methanol extract of P. somaliensis Browicz fruits afforded two known triterpenes, namely ursolic acid, and 11α,12α-epoxy-3β-hydroxy-olean-13β,28-olide, and a newly discovered one, namely 3β-hydroxy-urs-11-en-13β,28-olide. The structures of the isolated compounds were elucidated by the analysis of 1D and 2D NMR spectral data.     

New Diarylheptanoid from the Barks of Alnus japonica Steudel

A new diarylheptanoid glycoside, 1,7-bis-（3,4-dihydroxyphenyl）-5-hydroxyheptane- 3-O-β-D-xylopyranoside （1）, together with nine known diarylheptanoids （2-10） were isolated from the fresh bark of Alnus japonica which is a species of the genus Alnus species, growing throughout Korea.     

A New Megastigmane Palmitate and a New Oleanane Triterpenoid from Aster yomena Makino

A new megastigmane palmitate, 9‐oxomegastigm‐5(13)‐ene‐2β‐palmitate ( 1 ), and a new oleanane triterpenoid, (3β)‐3,23,28‐trihydroxyolean‐12‐en‐11‐one ( 2 ), together with three known oleanane‐type triterpenoids, β‐amyrin ( 3 ), erythrodiol ( 4 ), and (3β)‐olean‐12‐ene‐3,23,28‐triol ( 5 ), were isolated from the aerial parts of Aster yomena (Asteraceae). Their structures were identified based on 1D‐ and 2D‐NMR analysis, including ¹H,¹H‐COSY, HSQC, HMBC, and NOESY techniques.     

Four New Taxoids from the Barks of Taxus yunnanensis

The ongoing study of our previous work1-4 led to the isolation of four new taxoids from the barks of Taxus yunnanensis. One of them belonged to a paclitaxel analogue named 7-xylosyl-taxol D, the others were 11(15?1)-abeotaxoids with an opened D-ring system, named taxuyunnanines P-R respectively. Their structures were determined by means of spectral method s including 1D and 2D NMR spectroscopy.7-Xylosyl-taxol D (1), white powder, has a molecular formula, C49H61NO18, from its positive HR…     

Two New Limonoids from the Root Bark of Chinese Medicinal Plant Dictamnus dasycarpus

Two new limonoids, kihadanin C ( 1 ) and 23‐methoxydasylactone A ( 2 ), together with seven related known ones, 3 – 9 , were isolated from the root bark of the plant Dictamnus dasycarpus. The structures of the new compounds were elucidated on the basis of extensive analyses of their spectroscopic data (1D‐ and 2D‐NMR, MS) and by comparison of their NMR data with those reported in the literature. To the best of our knowledge, 1 presents the first example of A,D‐seco limonoid with an unusual 3,4‐dihydroxy‐2,5‐dimethoxytetrahydrofuran moiety as ring E. In the bioassay in vitro, 7 showed moderate antibacterial activity against Staphylococcus aureus, while 8 and 9 displayed neuroprotective activities against H₂O₂‐induced injury in SH‐SY5Y cells.     

Complete 1H and 13C NMR assignments of four new oligosaccharides and two new glycosides from Periploca forrestii

Four new oligosaccharides (1–4), one new pregnane glycoside (5), and one new cardiac glycoside (6) were isolated from the roots of Periploca forrestii Schltr. (Asclepiadaceae), a traditional Chinese medicine used for the treatment of rheumatoid arthritis and wounds. Their structures were characterized on the basis of extensive analysis of NMR (¹H, ¹³C NMR, ¹H‐¹H COSY, HSQC, HMBC, TOCSY and ROESY) spectra. Copyright © 2009 John Wiley & Sons, Ltd.     

Taiwanin H,A New Lignan from the Barks of Taiwania Cryptomerioides Hayata

A new lignan, taiwanin H, has been isolated from the barks of Taiwania cryptomerioides Hayata and elucidated as formula ( 6a ) by chemical and physical evidence.     

A New Glycine Derivative and a New Indole Alkaloid from the Fermentation Broth of the Plant Endophytic Fungus Pestalotiopsis podocarpi Isolated from the Chinese Podocarpaceae Plant Podocarpus macrophyllus

A new glycine derivative, podocarpiamide ( 1 ), a new indole alkaloid, 1‐methoxy‐1H‐indol‐3‐ethanol ( 2 ), together with two known compounds, 1‐methoxy‐1H‐indole‐3‐acetic acid ( 3 ) and methyl 1‐methoxy‐1H‐indole‐3‐acetate ( 4 ), were isolated from the fermentation broth of the plant endophytic fungus Pestalotiopsis podocarpi. Their structures were elucidated by extensive spectroscopic analysis including 1D‐ and 2D‐NMR (HSQC, HMBC, and COSY) and MS experiments. Compound 1 has an interesting unusual carbamic acid structure.