Three new lignans, longipedunins A-C, from Kadsura longipedunculata and their inhibitory activity against HIV-1 protease

Three new lignans, longipedunins A (1), B (2) and C (3), together with three known compounds, benzoyl-binankadsurin A (4), acetyl-binankadsurin A (5) and schisanlactone A (6), were isolated from Kadsura longipedunculata. Their structures and stereochemistry were determined by spectral and single-crystal X-ray analyses. Compounds 1 and 6 showed appreciable inhibitory activity against HIV-1 protease with IC50 values of 50 and 20 microM, respectively.     

New seco-dibenzocyclooctadiene lignans with nitric oxide production inhibitory activity from the roots of Kadsura longipedunculata

Four new seco-dibenzocyclooctadiene lignans,kadlongilignans A-D(1-4),consisting of a rare 6,7-seco-(1),two 15,16-seco-(2 and 3) and a 9,10-seco-dibenzocyclooctadiene(4) lignans,were isolated from the roots of Kadsura longipedunculata.Their structures were elucidated by spectroscopic analysis,including extensive NM R,MS and ECD(electronic circular dichroism) spectra.Compounds 3 and 4 exhibited potent inhibitory activities against NO(nitric oxide) production of LPS(lipopolysaccharide)-induced murine macrophages with the inhibition rates of 36.3% and 26.9%,respectively.     

Three new compounds from Sarcandra glabra

One new sesquiterpene lactone,1 α,8 α,9 α-trihydroxyeudesman-3(4),7(11)-dien-8 β,12-olide(1) and two new phenylpropanoidsubstituted catechin glycosides,glabraoside C(2) and glabraoside D(3) were isolated from the whole plant of Sarcandra glabra. Their structures were established by the analyses of spectral and chemical evidences.     

Kadlongilactones A and B, two novel triterpene dilactones from Kadsura longipedunculata possessing a unique skeleton

[structure: see text] Two novel triterpene dilactones with an unprecedented rearranged hexacyclic skeleton, kadlongilactones A (1) and B (2), have been isolated from the leaves and stems of Kadsura longipedunculata Finet et Gagnep (Schisandraceae). Their structures were established by comprehensive 1D and 2D NMR spectroscopic analysis, coupled with single-crystal X-ray crystallographic diffraction. Compounds 1 and 2 exerted significant inhibitory effects against human tumor K562 cells with IC(50) = 1.40 and 1.71 microg/mL, respectively.     

A new triterpenoid from Kadsura coccinea

<正>A new triterpenoid,possessing a lanost-9(11)-3-one skeleton,was isolated from the roots of Kadsura coccinea,based on the spectral analysis,its structure was elucidated as 3-hydroxy-12-acetoxycoccinic acid.     

Two new guaianolide-type sesquiterpenoids from Kadsura interior

Two new guaianolide-type sesquiterpenoids,4β,9β-dihydroxy-1α,5α-H-guaia-6,10(14)-dien(1) and 4β,9β,10α-trihydroxy-1α,5α-H-guaia-6-en(2),along with four known sesquiterpenoids(3a,3b,4 and 5),were isolated from Kadsura interior.Their structures and configurations were elucidated by spectroscopic methods including 2D-NMR and HR-MS techniques.Compounds 3a and 3b were obtained as a pair of enantiomers,and their structure and absolute configuration were established from their extensive NMR spectra and by single-crystal X-ray analysis.     

Three new compounds from the leaves of Acanthopanax senticosus Harms

<正>Three new compounds named(2E)-prenyl benzoate-4-O-α-L-arabinopyranosyl(1→6)β-D-glucopyranoside(1),7-methoxy-8- O-β-D-glucopyranosyl coumarin(2),and 3,4'-dihydroxy-3'-methoxy benzenepentanoic acid(3) were isolated from the leaves of Acanthopanax senticosus Harms.The structures of new compounds were determined by means of 2D NMR experiments and chemical methods.     

Four new nonaoxygenated C18 dibenzocylcooctadiene lignans from Kadsura philippinensis

Four new nona-oxygenated C18 dibenzocyclooctadiene lignans, kadsuphilins C-F (1-4), were isolated from the EtOAc soluble portion of the alcoholic extract of the aerial parts of Kadsura philippinensis. The structures of 1-4 were elucidated on the basis of extensive spectroscopic analyses, including 2D NMR (HMQC, HMBC, and NOESY) experiments, comparison of the spectral data with those of the related metabolites. The stereochemistries of the biphenyl and octadiene moieties were deduced from circular dichorism (CD) and the NOESY spectra, respectively. The in vitro antiplatelet aggregation activity of metabolites 1-4 also have been evaluated.     

Renchanglactone A, a new triterpenoid lactone from Kadsura renchangiana

From the stems of Kadsura rechangiana, a new triterpenoid lactone named renchanglactone A (1), was isolated together with four known triterpenoids, kadsulactone A, mawuweizic acid, ganwuweizic acid and kadsuric acid. Their structures were determined by spectroscopic methods including 2D-NMR techniques.     

Three minor new compounds from the aerial parts of Leonurus japonicus

Phytochemical investigation of the aerial parts of Leonurus japonicus led to the isolation of one new labdane diterpenoid, leojaponin D(1) and two new ionone derivatives, leojaponones A and B(2 and 3),together with seven known diterpenoids(4–10). Their structures were elucidated by extensive 1D and2 D NMR spectroscopic data and by comparison with data reported in the literature. Selected isolates were evaluated their effects on Jurkat IL2 secretion.     

Structural determination of seven new triterpenoids from Kadsura heteroclita by NMR techniques

Seven new triterpenoids, namely heteroclitalactones G-M (1-7), were isolated from the ethanol extract of the stems of Kadsura heteroclita. Structures of these compounds were characterized by extensive 1D and 2D NMR spectroscopic analyses.     

Lanostane-type triterpenoids from Kadsura coccinea

Systematic phytochemical investigation on the stems of Kadsura coccinea resulted in the isolation of eleven new lanostane-type triterpenoids, named kadcoccinones G–Q (1–11), together with two known structural analogues, kadpolysperin M (12) and abiesatrine D (13). Their structures were characterized on the basis of comprehensive spectroscopic methods, and the absolute configuration of 1 was ascertained by single-crystal X-ray diffraction. Structurally, compounds 1/2, 4/5, and 6/7 were three pairs of C-12 epimers, respectively. Additionally, compounds 1–11 were evaluated for their in vitro cytotoxicity against the human tumor HL-60, SMMC-772, A-549, MCF-7, SW-480, and HeLa cell lines using the MTS viability assay.     

Three New Cyclolanostane Triterpenoids from the Ethanol Extract of the Stems of Kadsura heteroclita

Three new cyclolanostane triterpenoids, 1 – 3 , were isolated from the EtOH extract of the stems of Kadsura heteroclita. Their structures and configurations were determined by extensive 1D‐ and 2D‐NMR spectroscopy, high‐resolution mass spectrometry (HR‐MS), and circular dichroism (CD) spectroscopy. The three new compounds are likely to be artificial products formed during the extraction process, and might be derived from schisanlactone E ( 4 ) and two related double‐bond isomers, respectively.     

Three new enanti­omerically pure ferrocenylphosphole compounds

The absolute configurations of three new enanti­omerically pure ferrocenylphosphole compounds, namely (2S,4S,S_Fc)‐4‐methoxy­methyl‐2‐[2‐(9‐thioxo‐9λ⁵‐phosphafluoren‐9‐yl)­ferro­cenyl]‐1,3‐dioxane, [Fe(C₅H₅)(C₂₃H₂₂O₃PS)], (III), (S_Fc)‐[2‐(9‐thioxo‐9λ⁵‐phosphafluoren‐9‐yl)ferrocenyl]methanol, [Fe(C₅H₅)(C₁₈H₁₄OPS)], (V), and (S_Fc)‐diphenyl[2‐(9‐thioxo‐9λ⁵‐phosphafluoren‐9‐yl]ferrocenylmethyl]phosphine, [Fe(C₅H₅)(C₃₀H₂₃P₂)], (VIII), have been unambiguously established. All three ligands contain a planar chiral ferrocene group, bearing a dibenzo­phos­phole and either a dioxane, a methanol or a diphenyl­phosphino­methane group on the same cyclopentadienyl. In compound (V), the occurrence of O—H⋯S and C—H⋯S hydrogen bonds results in the formation of a two‐dimensional network parallel to (001). The geometry of the ferrocene frameworks agrees with related reported structures.     

New Oxygenated Lignans from Kadsura philippinensis

Seven new oxygenated lignans, kadsuphilins G–M ( 1 – 7 , resp.), were isolated by chromatographic fractionation of an AcOEt extract of the aerial part of Kadsura philippinensis including four compounds with a dibenzocyclooctadiene skeleton, two with a bicyclooctane ring system, and one of 1,4‐biphenyldimethylbutane type. The structures of the isolated compounds were elucidated through extensive spectroscopic analyses, particularly 2D‐NMR experiments (HMQC, HMBC, and NOESY). The configuration of the chiral centers and the biphenyl moiety were determined by NOESY as well as CD spectroscopy, respectively.     

Kadsutherins A–C: Three New Dibenzocyclooctane Lignans from the Stems of Kadsura Species

Three new dibenzocyclooctane‐type lignans, kadsutherins A–C ( 1 – 3 ), were isolated from the stems of two Kadsura species. Their structures and configurations were elucidated by spectroscopic methods including 2D‐NMR and HR‐MS techniques. Kadsutherin C ( 3 ) is the first dibenzocyclooctane lignan without an oxygen‐containing substituent at C(2).     

Seven New Lignan Esters from Kadsura philippinensis

Five new oxygenated lignans with a dibenzocyclooctadiene skeleton, kadsuphilols P–T ( 1 – 5 ), and two new C₁₉ homolignans, kadsuphilols U and V ( 6 and 7 ), were isolated by chromatographic fractionation of an AcOEt extract of the stems of Kadsura philippinensis. The structures of the isolated metabolites were elucidated through extensive spectroscopic analysis including HR‐ESI‐MS and 2D‐NMR (HMQC, COSY, and HMBC). The configuration at the chiral centers and at the biphenyl moiety were determined by interpretation of NOESY and CD data, respectively.     

A new anti-HBeAg lignan, kadsumarin A, from Kadsura matsudai and Schizandra arisanensis.

A new C18 dibenzocyclooctadiene lignan, kadsumarin A (1) was isolated from Kadsura matsudai Hayata and Schizandra arisanensis Hayata. The anti-HBeAg test revealed that kadsumarin A had activity at a concentration of 40 micrograms/ml (= 90.1 microM). Its structural elucidation by spectral analysis was discussed in this note.     

Four New Dibenzocyclooctene Lignans from Kadsura renchangiana

Four new dibenzocyclooctene‐type lignans, named renchangianins A–D ( 1 – 4 ), were isolated from the stems of Kadsura renchangiana. Their structures and configurations were elucidated by spectroscopic methods, including 2D‐NMR techniques. Renchangianin D ( 4 ) possesses a spiro[dibenzocyclooctene‐6,2′‐oxirane] parent structure previously unknown in plants of the Schisandraceae family.