A new dibenzofuran and other constituents from Ligularia caloxantha, a Chinese medicinal plant

A new dibenzofuran named 1,2,4-trimethyl-7,8-dimethoxy-dibenzofuran (1), together with seven known compounds, euparin (2), 2,5-diacetyl-6-hydroxy-benzofuran (3), 2-acetyl-5,6-dimethoxy-benzofuran (4), gummosogenin (5), lupeol (6), stigmasterol (7) and (E)-2,5-dihydroxy-cinnamic acid (8), were isolated from the roots of Ligularia caloxantha, a Chinese medicinal plant. The structures of the compounds were elucidated by spectroscopic methods.     

Two new olean-type triterpene fatty esters from Scorzonera mongolica

Two new triterpene fatty esters, 33-tetradecanoyl moradiol 1 and 3β-dodecanoyl moradiol 2, were isolated from Scorzonera mongolica. Their structures were elucidated as 3β-tetradecanoyloxy-28-hydroxylolean-18-ene and 3β-dodecanoyl-28-hydroxyl-olean-18-ene on the basis of IR, MS, ID NMR and extensive 2D NMR spectroscopic analyses.     

Sesquiterpenes, nortriterpenes and other constituents from Ligularia tongolensis

Two new eremophilane-type sesquiterpenes, 3beta-(2'-methylbutanoyloxy)-8betaH-eremophil-7(11)-ene-12,8alpha-(14,6alpha)-diolide (1) and 8betaH-eremophil-3,7(11)-diene-12,8alpha(14,6alpha)-diolide (2), and two new norursane-type triterpenes, 2alpha,3beta,19alpha-trihydroxy-28-norurs-12-ene (7) and 2alpha,3alpha,19alpha-trihydroxy-28-norurs-12-ene (8), were isolated from the roots of Ligularia tongolensis, together with nine known compounds. The structures of the new compounds were elucidated by spectroscopic methods.     

A new benzofuran derivative from Flemingia philippinensis Merr. et Rolfe

A new prenylated benzofuran derivative, named flemiphilippinone A, was isolated together with ten known flavonoids from the roots of Flemingia philippinensis. Flemiphilippinone A was identified as (2S,3aS)-5-(1-hydroxy-3-(4-methoxyphenyl)-propylidene)-2-(2-hydroxypropan-2-yl)-3a,7-bis(3-methylbut-2-en-1-yl)tetrahydrobenzofuran-4,6(2H,5H)-dione, and its structure was established by a combination of HR EIMS, 1H-NMR, 13C-NMR, HMQC, HMBC and NOESY spectra data.     

Isolation of a new natural kingiside aglucone derivative and other anti-inflammatory constituents from Syringa reticulata

Abstract

A new secoiridoid, (1R,5S,8S,9R)-1-methyl-kingiside aglucone (1), along with nine known compounds (2–10), were isolated from the ethanol extract of the stem bark of Syringa reticulata (Bl.) Hara. The structure of compound 1 was elucidated using HR-ESI-MS, 1D and 2D NMR spectroscopy. Compounds 1–10 were evaluated for their inhibitory activity against NO, TNF-α and IL-6 production. Compounds 1, 3, 5 and 7–10 significantly inhibited the levels of NO, TNF-α and IL-6 in LPS-induced RAW264.7 cells from concentrations of 3 to 30?μM.     

A new benzofuran derivative from the leaves of Ficus pumila L.

A new benzofuran derivative, pumiloside (1), together with seven known flavonoid glycosides, afzelin (2), astragalin (3), quercitrin (4), isoquercitrin (5), kaempferol 3-O-rutinoside (6), rutin (7) and kaempferol 3-O-sophoroside (8) were isolated from the leaves of Ficus pumila. Their structures were established by spectroscopic data and comparison with the literature values.     

A novel bieremophilanolide from Ligularia lapathifolia

A new bieremophilanolide was isolated from the roots and rhizomes of Ligularia lapathifolia. Its structure was established as 8,8'-bi-3beta-angeloyloxy-eremophil-7(11)-en-12,8alpha(14beta,6alpha)-diolide (1) by IR, MS, 1D, and 2D NMR experiments.     

Three new dimeric benzofuran derivatives from the roots of Ligularia stenocephala MATSUM. et KOIDZ

Three new dimeric benzofuran derivatives, ligulacephalins A (1), B (2) and C (3), were isolated from the roots of Ligularia stenocephala MATSUM. ET KOIDZ. (Compositae) together with three known compounds, 5,6-dimethoxy-2-isopropenylbenzofuran (4), euparin (5) and (R)-(-)-hydroxytremetone (6). The structures of the new compounds were determined by spectroscopic evidence. The chiral HPLC analysis demonstrated that 1-3 occurred as a racemate. The absolute configurations of each enantiomer from 1-3 were elucidated on the basis of circular dichroism (CD) data.     

A new derivative of triterpene with anti-melanoma B16 activity from Conyza Canadensis

<正>A new derivative of triterpene named Erigeronol 1 was isolated from the EtOH extract of the aerial part of Conyza canadensis together with 15 known compounds for the first time from this plant.The structure of Erigeronol 1 was elucidated as 3-O-(hydroxyacetyl) -23,28-dihydroxy-β-amyrin by hydrolysis and spectroscopic analysis.Erigeronol 1 showed potent cytotoxic activity with IC_(50) value of 7.77±0.47μg/mL against melanoma B16 determined by the 3-(4,5-dimethylthiazo-2-yl)-2,5-diphenyltetrazolium bromide(MTT) method.     

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).     

A new lignan and other constituents from Zanthoxylum armatum DC

A new lignan (1), named armatumin, along with 25 known compounds, was isolated from Zanthoxylum armatum. The structure of compound 1 was elucidated using spectroscopic methods. Compounds 7, 8, 11, 13, 16, 20 and 21 were first isolated from Z. armatum and compounds 14 and 19 were isolated for the first time from Rutaceae.     

A new lignan glycoside and other constituents from Cephalaria ambrosioides

A new lignan glycoside, 1,5-dihydroxy-2-(4"-beta-D-glucopyranosyloxy-3"-methoxyphenyl)-6-(4'-hydroxy-3'-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane, named ambrosidine ([structure: see text]), along with seven known compounds (four iridoids and three hydroxycinnamic esters) were isolated from the roots of Cephalaria ambrosioides. The structures of these compounds were determined by use of NMR and MS techniques and by chemical transformations. The cytotoxic activity of the novel compound [structure: see text] was evaluated against five human solid tumour cell lines.     

A new phenanthrene glycoside and other constituents from Dioscorea opposita

Phytochemical investigation of the rhizome of Dioscorea opposita has led to the isolation of a new phenanthrene glycoside, 3,4,6-trihydroxyphenanthrene-3-O-beta-D-glucopyranoside (1), and five known compounds, soyacerebroside I (2), adenosine (3), beta-sitosterol (4), palmitic acid (5) and palmitoyloleoylphosphatidylcholine (6). Their structures were determined by spectroscopic methods, including 1D- and 2D-NMR. Compounds 1-6 exhibited no antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis.     

A novel triterpene from Centella asiatica

A novel triterpene, 2alpha,3beta,20,23-tetrahydroxyurs-28-oic acid (1), was isolated from the aerial part of Centella asiatica. Its structure was elucidated by spectroscopic methods, including 2D-NMR spectra. It displayed no activity against Hela and A549 cell lines at concentrations of 10 and 30 microg/mL, respectively.     

A new triterpene and a saponin from Centella asiatica

A new triterpene and a saponin,named 2α,3β,23-trihydroxyurs-20-en-28-oic acid(1)and 2α,3β,23-trihydroxyurs-20-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester(2),have been isolated from the aerial part of Centella asiatica.Their structures were elucidated by spectral methods,including 2D-NMR spectra.     

A new fatty ester and a new triterpene from Skimmia laureola

Aerial parts of Skimmia laureola yielded a new fatty ester, (+)-skimmilaureol (1), and a new triterpene 16-29-dihydroxy, 20-ene cyclolaudenol (2). Five known compounds, namely, O-methyl-cyclolaudenol (3), (R)-7-methoxy-6-(3'-hydroxy-2'R-methoxy-3'-methyl butyl)coumarin (4), (+)-(S)-psi-ribalinine (5), (R)-(+)-ribalinine (6) and methyl isoplatydesmine (7), previously isolated from this plant were subjected to enzymatic bioassays for the first time. Compounds 3 and 4 were found to be prolyl endopeptidase inhibitors with IC(50) 8.21 +/- 0.407 and 39.63 +/- 1.502 microM, respectively, while compounds 5-7 were found to be acetyl-cholinesterase and butyryl-cholinesterase inhibitors with IC(50) 62.46 +/- 1.58, 153.31 +/- 1.9, 74.5 +/- 1.05 and 150.04 +/- 0.45, 12.99 +/- 0.31, 78.3 +/- 1.86 microM, respectively.     

Cimicifugadine from Cimicifuga foetida, a new class of triterpene alklaoids with novel reactivity

[structure: see text] An unprecedented triterpene alkaloid glycoside, designated cimicifugadine (1), with a pyridine ring incorporated to a cycloartane triterpenoid nucleus, was isolated from the roots of Cimicifuga foetida. Its structure was established on the basis of extensive spectroscopic measurements and chemical transformation with the absolute configuration at C-24 determined to be S by a modified Mosher method. It demonstrated a novel reactivity in mild acidic media whereby the cyclopropane ring is opened followed by the formation of two isomeric conjugated trienes.     

Micrandilactone A: a novel triterpene from Schisandra micrantha

[structure: see text] A novel nortriterpene, micrandilactone A, was isolated from the medicinal plant Schisandra micrantha. This is the first example of an unusual, natural, highly oxidized cycloartane skeleton with a biosynthetically modified eight-membered ring D isolated from the family Schisandraceae.