A new sesquiterpenoid glycoside from Saussurea involucrata

Abstract

Saussurea involucrata, known for the abundant bioactive components, is a precious traditional Chinese medicine. In this study, a novel guaiane sesquiterpenoid glycoside named (1R, 5R, 6R, 7R, 8S, 11S)-11, 13-dihydrodehydrocostuslactone-8-O-6'-2''(E)-butenoyl-β-D-glucopyranoside (1), together with seven known compounds (2–8) were isolated from the dried aerial part of S. involucrata. Their structures were elucidated by spectroscopic and physico-chemical analyses. The antioxidant and anti-inflammatory activities of compound 1 were investigated. And compound 1 showed weak radical scavenging activity and low inhibitory activity on nitric oxide (NO) production.     

Structure-Based Molecular Networking for the Discovery of Anti-HBV Compounds from Saussurea lappa (Decne.) C.B Clarke

It is a crucial to find target compounds in natural product research. This study presents a concept of structure-guided isolation to find candidate active molecules from herbs. We establish a process of anti-viral sesquiterpene networking. An analysis of the networking suggested that new anti-HBV sesquiterpene may be attributable to eudesmane-, guaiane-, cadinane-, germacane- and bisabolane-type sesquiterpenes. In order to evaluate the efficiency of the structure-based molecular networking, ethanol extract of Saussurea lappa (Decne.) C.B Clarke was investigated, which led to the isolation of two guaiane-type (1 and 14), ten eudesmane-type (2–5 and 8–13), two chain (6 and 7) and one germacrane-type (15) sesquiterpenes, including seven new ones, lappaterpenes A–G (1–7), which are reported on herein. The absolute configurations of the new compounds were established by coupling constants, calculated ECD and ROESY correlations, as well as comparisons of optical rotation values with those of known compounds. The absolute configuration of compound 2 was further confirmed by X-ray diffraction. Compounds 1–15 were evaluated for their potency against hepatitis B virus. Compounds 4, 6, 7 and 9 showed effect on HBsAg with inhibition ratios of more than 40% at 30 μM concentrations. Compounds 14 and 15 inhibited HBsAg secretion with the values of IC₅₀ 0.73 ± 0.18 and 1.43 ± 0.54 μM, respectively. Structure-based molecular networking inspired the discovery of target compounds.     

A New Sesquiterpene from Saussurea parviflora

A new sesquiterpene:11,12,13-trihydroxy-4(15),7(8)-eudesmdien-9-one was isolated from Saussurea parviflora. The structure was elucidated on the basis of spectral evidence.     

A New Guaianolide from Saussurea macrota

A new guaianolide was isolated from Saussurea macrota.Its structure was elucidated by NMR spectroscopic and X-ray diffraction methods.     

A new sesquiterpene and other constituents from Saussurea lappa root

Five sesquiterpenes, dehydrocostus lactone (1), santamarine (5), beta-cyclocostunolide (6), 4alpha-hydroxy-4beta-methyldihydrocostol (7) and 10alpha-hydroxyl-artemisinic acid (9), along with four other compounds, beta-sitosterol (2), daucosterol (3), 5-hydroxymethyl-furaldehyde (4), and trans-syingin (8), were isolated and identified from the roots of Saussurea lappa (Compositae). Based on previous reports and our study, sesquiterpene derivatives are common and characteristic constituents of the genus Saussurea. Among the nine compounds obtained, 9 is a new sesquiterpene. It is an artemisinic acid derivative, whose structural skeleton has not been reported for Saussurea species before, but artemisinic acid is a common compound in another Compositae species, Artemisia annua. Dehydrocostus lactone (1) is present in high-content and is a possible bioprecursor of 10alpha-hydroxyartemisinic acid (9).     

Cytotoxic Principles from Saussurea Lappa and Corydalis Turtshaninovii f. Yanhusuo

Four protoberberine alkaloids, berberine, palmatine, dehydrocorydaline and coptisine were characterized as cytotoxic principles from the tuber of Corydalis turtshaninovii f. yanhusuo. On the other hand, dehydrocostus lactone and costunolide demonstrated cytotoxicity from the root of Saussurea lappa. Their structures were elucidated by spectral analyses.     

A new anti-diabetic sesquiterpenoid from Acorus calamus

A new sesquiterpenoid,1β,5α-guaiane-4β,10α-diol-6-one(1),was isolated from 70%EtOH extract of the rhizomes of Acorus calamus.The structure was determined on spectroscopic methods,especially 2D NMR techniques.The absolute configuration of 1 was confirmed by TDDFT quantum chemical calculation of its ECD spectrum.Compound 1 showed promising anti-diabetic activity on a insulin-mediated glucose consumption model of HepG2 cells.     

A new sesquiterpenoid from Polyalthia petelotii

A new sesquiterpenoid (?)-ethyl dihydrophaseate (1) was isolated from the stems and leaves of Polyalthia petelotii, together with two clerodane diterpenoids, 16α-hydroxycleroda-3,13(14)Z-dien-15,16-olide (2), 15-hydroxy-cis-ent-cleroda-3,13(E)-diene (3), a eudesmane sesquiterpenoid, eudesm-4(15)-ene-7α,11-diol (4), an aromatic aldehyde, vanillin (5), a bisisoquinolines alkaloid, spinosine (6) and an aporphine alkaloid, (?)-oliveroline-β-N-oxide (7). Their structures were established by extensive spectroscopic analysis, including 2D-NMR techniques. Compounds 3, 4 and 6 were isolated from the genus Polyalthia for the first time and the others obtained originally from P. petelotii. The isolates were assessed for their cytotoxicity against five human tumour lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that only 2 displayed weak inhibitory activity.     

A new chalcone from the aerial roots of Ficus microcarpa

A new flavonoid with chalcone skeleton was isolated from the dried aerial roots of Ficus microcarpa.The structure of the compound was elucidated on the basis of spectral methods including ID and 2D NMR.The new compound showed weak inhibitory effect on nitric oxide production and cytotoxicity against K562 and PC3 ceils.     

高速逆流色谱法分离制备鱼藤根中的2种鱼藤酮类化合物

建立了分离制备鱼藤根中2种鱼藤酮类化合物的高速逆流色谱法。以正己烷-乙酸乙酯-甲醇-水(体积比为7:0.25:5:3)为两相溶剂系统,上相为固定相,下相为流动相,在主机转速850 r/min、流速2.0 mL/min、检测波长254 nm条件下进行分离制备,从50 mg鱼藤根粗提物中得到了2种鱼藤酮类化合物,分别为6.4 mg纯度为96.60%的鱼藤酮和23.4 mg纯度为97.87%的鱼藤素。该方法为鱼藤酮类化合物的深入研究提供了物质基础。     

A New Sesquiterpene from Ligularia Songarica

ThechemicalstudiesofLigulariasongaricahavenotbeenreportedtillnow.Inourpreliminarystudyontherootsofthisplant,anewbisabolanesesquiterpenewasobtainedanditsstructurewasidentifiedasSp-acetoxy-40,8-diangeloyloxy-26,3p,;10,Ildiepoxy-bisabola-7(14)-ene1.,Com...     

Two new ionone glycosides from the roots of Rehmannia glutinosa Libosch.

Two new ionone glycosides, named frehmaglutoside G (1) and frehmaglutoside H (2), together with six known compounds, rehmapicroside (3), sec-hydroxyaeginetic acid (4), dihydroxy-β-ionone (5), trihydroxy-β-ionone (6), rehmaionoside A (7) and rehmaionoside C (8), were isolated from the 95% EtOH extract of the dried roots of Rehmannia glutinosa Libosch. Their structures were determined on the basis of extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, 1D and 2D NMR (¹H–¹H COSY, HSQC, HMBC and NOESY) methods. The absolute configurations were confirmed via the circular dichroism spectra.     

A new sesquiterpenoid quinone with cytotoxicity from Abelmoschus sagittifolius

A new sesquiterpenoid quinone, Acyl hibiscone B (1), together with five known compounds, (R)-lasiodiplodin (2), (R)-de-O-methyllasiodiplodin, (3) dibutyl phthalate (4), (R)-9-phenylnonan-2-ol (5) and hibiscone B (6), was obtained from the stem tuber of Abelmoschus sagittifolius. The structure of compound 1 was elucidated by analysing its ¹H and ¹³C NMR, ¹H–¹H COSY, HSQC, HMBC, NOESY and HR-ESI-MS values. Compound 1 showed significant cytotoxicity against Hela and HepG-2 human cancer cell lines.     

A new tremulane sesquiterpenoid from the fungus Irpex lacteus

A new tremulane sesquiterpenoid, named irlactam A (1), was isolated from cultures of the fungus Irpex lacteus. The new structure was elucidated by spectroscopic data analysis. The compound was tested for its cytotoxicities on HL-60, SMMC-7721, A-549, MCF-7, and SW480 cells and for its inhibitory activity against isozymes of 11β-hydroxysteroid dehydrogenases (11β-HSD).     

A new phenylpropanoid from the roots of Euphorbia nematocypha

A phytochemical investigation of the ethanolic extracts of the dried roots of Euphorbia nematocypha resulted in the isolation of a new phenylpropanoid, 16-O-caffeoyl-16-hydroxylhexadecanoic acid (1), together with 23 known compounds (2–24). Their structures were elucidated on the basis of spectroscopic data. Compound 1 was first to be isolated as a caffeic acyl long chain alkyl acid from the family Euphorbiaceae. The new isolated phenylpropanoid showed potent cytotoxic activities against the MCF-7 and HeLa cell lines.     

A new phenanthraquinone from the roots of Peucedanum praeruptorum

<正>A new compound,9,10-dihydrophenanthrinic acid,9,10-dione-3,4-methylenedioxy-8-methoxy(1) was isolated from the roots of Peucedanum praeruptorum Dunn on the basis of spectral evidences.     

A new cadinane sesquiterpenoid glucoside with cytotoxicity from Abelmoschus sagittifolius

A new cadinane sesquiterpenoid glucoside, 2β,7,3-trihydroxycalamenene 3-O-β-d-glucoside (1) together with six known compounds, N-(p-trans-coumaroyl)-N-methyl tyramine (2), Cleomiscosin A (3), 9,12,13-trihydroxy-10,15-heptadecadienoic acid (4), Cytochalasin B (5), Marmesinin (6) and N-(p-trans-coumaroyl) tyramine (7) were obtained from the stem bark of Abelmoschus sagittifolius. The new structure of compound 1 was elucidated by analysing its ¹H and ¹³C-NMR, ¹H-¹H COSY, HSQC, HMBC, NOESY and HR-ESI-MS spectra. Compounds 1–7 showed moderate cytotoxicity against Hela and HepG-2 human cancer cell lines.     

A new eudesmane sesquiterpene glycoside from Parepigynum funingense

A new eudesmane sesquiterpene glycoside,1α,6β-dihydroxy-5,10-bis-epi-eudesm-4(15)-ene-6-O-β-D-glucopyranoside(2), together with a known analogue compound,1α,6β-dihydroxy-5,10-bis-epi-eudesm-3-ene-6-O-β-D-glucopyranoside(1),were isolated from the roots of Parepigynumfuningense.The structure of 2 was determined by 1D and 2D NMR spectroscopy.Compound 1 was isolated from this plant for the first time.     

A new bisabolane sesquiterpenoid and a new abietane diterpenoid from Cephalotaxus sinensis

Phytochemical investigation of Cephalotaxus sinensis has led to the isolation of a new bisabolane sesquiterpenoid (1), a new abietane diterpenoid (2), and 13 known compounds (3–15). Their structures were elucidated by extensive spectroscopic analysis (MS, UV, IR, and NMR).     

A new sesquiterpene from Kalimeris integrifolia

A new sesquiterpene kalinturoside A (1), and 17 known compounds friedelan-3-ol (2), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (3), friedelin (4), syringaresinol (5), α-spinasterol (6), ciwujiatone (7), syringic acid (8), scopoletin (9), apocynin (10), 1-(3-hydroxy-4, 5-dimethoxyphenyl)ethan-1-one (11), apigenin (12), 5-hydroxymethylfurfural (13), stigmasterol-3-O-β-d-glucopy-ranoside (14), bidenoside C (15), citrusin (16), irioresinol A (17) and syringaresinol-4-O-β-d-glucopyranoside (18) were isolated from the herbs of Kalimeris integrifolia. The structures of these compounds were elucidated using spectroscopic techniques such as NMR and MS. All of the compounds were isolated from this genus for the first time.