A New Disulfated Triterpene Glycoside from the Sea Cucumber Mensamaria intercedens Lampert

A new disulfated triterpene glycoside named intercedenside B was isolated from the sea cucumber Memsamaria intercedens Lampert.The structure was deduced from the spectral data.     

Philinopsides A and B,Two New Sulfated Triterpene Glycosides from the Sea Cucumber Pentacta quadrangularis

Two new sulfated triterpene glycosides, philinopsides A ( 1 ) and B ( 2 ), were isolated from the sea cucumber Pentacta quadrangularis. Their structures were established by extensive spectral analysis (2D‐NMR and MS) and chemical evidence. Philinopside A ( 1 ) and B ( 2 ) showed significant cytotoxicity (ED₅₀ 0.75–3.50 μg/ml) against ten tumor cell lines. Compound 1 also significantly inhibited the proliferation, migration, and tube formation of human microvascular endothelial cells.     

Triterpene glycosides from the Vietnamese sea cucumber Holothuria edulis

Abstract

From the MeOH extract of the Vietnamese sea cucumber Holothuria edulis, eight triterpene glycosides (1–8), including one new compound namely holothurin A₅ (1), were isolated by using various chromatographic separations. Their structures were established by spectroscopic experiments including 1D, 2D NMR and HR-ESI-MS. Holothurin A₅ (1) has a hydroperoxy group at C-25. To the best of our knowledge, this is the first report of this group in triterpene saponins obtained from sea cucumbers to date. In addition, the in vitro cytotoxicity against five human cancer cell lines (HepG2, KB, LNCaP, MCF7 and SK-Mel2) of all isolated compounds was also evaluated using SRB assays.     

A new triterpene glycoside from sea cucumber Holothuria leucospilota

A new triterpene glycoside, leucospilotaside A, along with a known saponin, isolated from sea cucumber Holothuria leucospilota, and its structure was elucidated as 3β-O-[4-O-sodiumsulfate-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-holosta-22-ketone-9-en-17α,25α-diol (1) by extensive spectroscopic analysis and chemical methods. Leucospilotaside A (1) has a ketone carbonyl group (22) in the aglycon side chain.     

A New Cycloartane Triterpene Glycoside from Souliea vaginata

Souliea vaginata (Maxim.) Franch. (Ranunculaceae) is widely distributed in the southwest and northwest of China. It possesses anti-inflammatory analgesic functions as a well-known Chinese folk medicine. Its rhizomes or the whole plant are used to treat conjunctivitis, stomatitis, pharyngitis, enteritis, and diarrhea1. Previously, we have reported the isolation and structural elucidation of suolieasides A-C from the ethanol extract of the rhizomes of this plant2. In our further investigation…     

A New Cycloartane Triterpene Glycoside from Soufiea vaginata

A new cycloartane triterpene glycoside was isolated from the rhizome of Souliea vaginata. Its structure was established as 12-deacetyloxy-15α-hydroxy-23-epi-26-deoxyactein by spectroscopic and chemical methods.     

中药枸骨叶中三萜皂苷和黄酮苷类成分研究

A new triterpene glycoside, pomolic acid 3-O-6″-methyl-β-D-glucuronopyranosyl-（1→3）-α-L-arabino- pyranoside, and a new flavonol glycoside, quercetin 3-O-β-D-glucopyranosyl-（1→2）-α-L-arabinopyranoside together with three known triterpene saponins and two flavonol glycosides, were isolated from the leaves of Ilex cornuta. Their structures were established on the basis of spectroscopic analysis.     

Silviridoside: A New Triterpene Glycoside from Silene viridiflora with Promising Antioxidant and Enzyme Inhibitory Potential

A new triterpene glycoside, silviridoside, was isolated from the aerial parts of Silene viridiflora (Caryophyllaceae) using different chromatographic techniques. The structure of silviridoside was comprehensively elucidated as 3-O-β-D-galacturonopyranosyl-quillaic acid 28-O-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-fucopyranosyl ester by one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). Silviridoside showed promising antioxidant activity in different antioxidant assays such as 2,2-diphenyl-1-picrylhydrazyl (DPPH) (2.32 mg TE/g), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) (1.24 mg TE/g), cupric-reducing antioxidant capacity (CUPRAC) (9.59 mg TE/g), ferric-reducing antioxidant power (FRAP) (5.13 mg TE/g), phosphomolybdenum (PHD) (0.28 mmol TE/g), and metal-chelating (MCA) (6.62 mg EDTA/g) assays. It exhibited a good inhibitory potential on acetylcholinesterase (AChE) (2.52 mg GALAE/g), butyrylcholinesterase (BChE) (7.16 mg GALAE/g), α-amylase (0.19 mmol ACAE/g), α-glucosidase (1.21 mmol ACAE/g), and tyrosinase (38.83 mg KAE/g). An in silico evaluation of the pharmacodynamic, pharmacokinetic, and toxicity properties of silviridoside showed that the new compound exhibited reasonable pharmacodynamic and pharmacokinetic properties without any mutagenic effect, but slight toxicity. Thus, it could be concluded that silviridoside could act as a promising lead drug for pharmaceutical and nutraceutical developments to combat oxidative stress and various disorders, but a future optimization is necessary.     

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 Euphane-Type Triterpene from Melia Azedarach

ThefamilyMeliaceaeiswellknownforitslimonoidcomponentspossessinginsectantifeedantactivityandthosehighlyoxygenatedtriterpenesrelatedtotirucallol(euphanetypeskeleton)','.MeliaazedarachisaplantofthefamilyMeliaceae,distributedwidelyinChina'.Inordertofindnewlimonoidwithstronginsectantifeedantactivityandalsointerestinghighlyoxygenatedtriterpenes,westudiedsystematicallythechemicalcomponentsofMeliaazedarach.Inthispaper,wereportthestructureelucidationofanewtriterpene,namedazedarachicacid.Azedarachicac…     

A New Triterpene from Cynanchum forrestii

Cynanchum forrestii Schlechter (Asclepiadaceae) is widely distributed in Yunnan, Xizang, Gansu, Sichuan, Guizhou Provinces, etc. in China and its roots have been used as an antifebrile, diuretic and analgetic in China1. In the previous investigation, we i…     

The Isolation,Structure Elucidation and Bioactivity Study of Chilensosides A,A1, B,C, and D,Holostane Triterpene Di-, Tri- and Tetrasulfated Pentaosides from the Sea Cucumber Paracaudina chilensis (Caudinidae,Molpadida)

Five new triterpene (4,4,14-trimethylsterol) di-, tri- and tetrasulfated pentaosides, chilensosides A (1), A₁ (2), B (3), C (4), and D (5) were isolated from the Far-Eastern sea cucumber Paracaudina chilensis. The structures were established on the basis of extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The structural variability of the glycosides concerned the pentasaccharide chains. Their architecture was characterized by the upper semi-chain consisting of three sugar units and the bottom semi-chain of two sugars. Carbohydrate chains of compounds 2–5 differed in the quantity and positions of sulfate groups. The interesting structural features of the glycosides were: the presence of two sulfate groups at C-4 and C-6 of the same glucose residue in the upper semi-chain of 1, 2, 4, and 5 and the sulfation at C-3 of terminal glucose residue in the bottom semi-chain of 4 that makes its further elongation impossible. Chilensoside D (5) was the sixth tetrasulfated glycoside found in sea cucumbers. The architecture of the sugar chains of chilensosides A–D (1–5), the positions of sulfation, the quantity of sulfate groups, as well as the aglycone structures, demonstrate their similarity to the glycosides of the representatives of the order Dendrochirotida, confirming the phylogenetic closeness of the orders Molpadida and Dendrochirotida. The cytotoxic activities of the compounds 1–5 against human erythrocytes and some cancer cell lines are presented. Disulfated chilensosides A₁ (2) and B (3) and trisulfated chilensoside C (4) showed significant cytotoxic activity against human cancer cells.     

A New Phenylpropanoid Glycoside: Serratumoside A from Clerodendrum serratum

In the previous papers"', we have reported some chemical constituents fromClerodendrum serratum var. amplerghlium Moldenke. A continuation of our studies onthe same plant led to the isolation of a new phenylpropanoid, serratumoside A (l), whichis reported in this paper.Serratumoside A (l) with three known phenylpropanoid glycosides identified asacteoside', mwtinoside' and myricoside', respectively, were isolated from the Cserratum. Compound I was isolated as a brown amorphous powder, laly …     

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 Bianthraqinone Glycoside from Eremurus chinensis

A new bianthraquinone glycoside, 8-O-β-D-glucopyranosyl-2,7'-bi(1,8-dihydroxy-3-methyl-9,10-anthraquinonyl) 1 was isolated from Eremurus chinensis Fedtch. Its structure was established by spectroscopic techniques including 2D-NMR and chemical methods.     

A New Flavanone and a New Flavanone Glycoside from Scutellaria baicalensis

A new flavanone (2S)-5, 7, 2',5'-tetrahydroxy-flavanone 1 together with a new flavanone glycoside (2S)-5, 7, 2',5'-tetrahydroxy-flavanone 7-O-β-D-glucopyranoside 2, were isolated from the dry roots of Scutellaria baicalensis. Their structures were elucidated on the basis of spectroscopic data.     

A New Flavone Glycoside from Epimedium koreanum

Epimedium koreanum is widely distributed throughout the east-northern part of China. As a Chinese herbal medicine, its aerial parts are used as tonics, aphrodisiacs and antirheumatics. Constituents of Epimedium koreanum have been reported as flavonoids, n…     

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…     

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…