A new diacylated labdane diterpenoid from Andrographis wightiana

A new acylated labdane diterpenoid, 14-deoxy-3,19-diacetyl-11,12-didehydroandrographolide (1), together with three known labdane diterpenoids, wightionolide (2), andrographolide (3) and neoandrographolide (4), and three known flavones, echioidinin (5), skullcapflavone I 2'-methyl ether (6) and echioidin (7), were isolated from the whole plant of Andrographis wightiana. The structure of compound 1 was elucidated by 1D and extensive 2D-NMR spectral studies.     

A new labdane type diterpenoid from Trollius ledebouri

A new labdane type diterpenoid, (8alpha,13R)-epoxy-14-labden-6beta,7beta-diol-7-beta-D-(4'-acetyl) fucopyranoside, named ledebourene 1, was isolated from the flowers of Trollius ledebouri. The absolute stereostructure was elucidated on the basis of the spectroscopic analysis.     

New Octadecanoyl Diterpenoid Arabinoside from Conyza blinii

A new octadecanoyl diterpenoid glycoside,(E)-8α,15-dihydroxy-15-(3S-hydroxy-octadecanoyl)-13-labdene-8-O-α-L-arabinopyranoside(1),was isolated from the aerial parts of Conyza blinii,and the structure was identified on the basis of a detailed spectroscopic analysis,including 2D NMR spectrometry and HRESI-MS.     

Rapid characterization of triterpene saponins from Conyza blinii by liquid chromatography coupled with mass spectrometry

Conyza blinii Le'vl is a medicinal herb used for the treatment of inflammation in Chinese folk medicine. Its major bioactive constituents are triterpene saponins, most of which contain 6–8 sugar residues. In this report, electrospray ionization tandem mass spectrometry fragmentation behaviors of bisdesmosidic triterpene saponins (conyzasaponin A, B, and C) were studied in both positive and negative ion modes with an ion‐trap mass spectrometer. In full scan mass spectrometry, these saponins gave predominant [M–H]^? and [M+Na]⁺ ions, which determined the molecular weights. In tandem mass spectrometry (MSⁿ, n = 2–4), the [M–H]^? and [M+Na]⁺ ions yielded fragments [Y_0α–H]^? and [B_α+Na]⁺, which were diagnostic for the structures of the triterpene skeleton and sugar chains. The structural elucidation was approved by accurate mass data using IT‐TOF‐MS. An interpretation guideline based on MSⁿ (n = 2–4) diagnostic ions was proposed in order to elucidate the chemical structures of unknown triterpene saponins in C. blinii extract. The saponins in C. blinii were separated by liquid chromatography with a methanol/acetonitrile/water solvent system, and then analyzed by ion‐trap and IT‐TOF mass spectrometers. Based on the interpretation guideline, a total of 35 triterpenoid saponins were tentatively identified. Among them, 15 saponins had been previously reported, and the other 20 saponins were reported from Conyza species for the first time. This study indicates that LC/MS is a powerful technology for the rapid characterization of complicated saponins in herbal extracts. Copyright © 2010 John Wiley & Sons, Ltd.     

A new diterpenoid from Euphorbia helioscopia

<正>A new jatrophane-type diterpenoid,7β,14β,15β-triacetoxy-3β-benzoyloxy-9-oxojatropha-5E,11E-diene,named euphornin N was isolated from Euphorbia helioscopia L.The structure and relative stereochemistry of the new compound was elucidated by spectroscopic methods.     

Structure revision and synthesis of a novel labdane diterpenoid from Zingiber ottensii

The structure of ottensinin, a recently reported constituent of the medicinal plant Zingiber ottensii, was revised by re-evaluation of available NMR data from alpha-ylidenebutenolide 1 to gamma-pyrone 2, whose rearranged labdane skeleton is unprecedented. Structure 2 was proven by synthesis from (+)-sclareolide (nine steps, 27% overall yield) and was further validated by X-ray diffraction analysis of our synthetic sample. A plausible biosynthesis of 2 is proposed.     

A new ent-labdane diterpenoid from Andrographis paniculata

<正>A new ent-labdane diterpenoid,19-O-β-D-glucopyranosyl-ent-labda-8(17),13-dien-15,16,19-triol,together with six known ent-labdane diterpenoids,was isolated from the aerial parts of Andrographis paniculaia.The structure of the new compound was elucidated by extensive spectral analysis.     

A new macrocyclic diterpenoid from Anisomeles indica

Abstract

A new macrocyclic diterpenoid, 4β,5β-dihydroxyovatodiolide (1), together with twenty-two known compounds (2-23) were isolated from the MeOH extract of the dried aerial parts of Anisomeles indica (L.) O. Kuntze (Labiatae). The structure of 1 was established on the basis of spectral evidence. Phenylethanoids, acteoside (5) and isoacteoside (6) showed significant inhibitory to IL-2 secretion of with respect to phorbol myristate acetate and anti-CD28 monoclonal antibody co-stimulated activation of human peripheral blood T cells.     

A new ent-kaurane diterpenoid from Isodon japonica

<正>One new ent-kaurane diterpenoid,named maoyecrystal L was isolated from the EtOAc extract of the dried leaves of lsodon japonica.Its structure was established by various spectroscopic means and confirmed by X-ray crystallographic analysis.     

A new azorellane diterpenoid from Azorella madreporica

A new azorellane diterpenoid has been isolated and identified from the aerial parts of Azorella madreporica Clos. The structure of 1 was established by one- and two-dimensional NMR techniques.     

A new diterpenoid alkaloid from Aconitum hemsleyanum

Abstract

A new C₁₉-diterpenoid alkaloid named hemsleyaline (1), along with fourteen known alkaloids (2-15), were isolated from the roots of Aconitum hemsleyanum Pritz. (Ranunculaceae), a herbal medicine in southwest China. Their structures were established on the basis of extensive spectroscopic analyses. Compound 1 showed mild cholinesterase inhibitory effect with IC₅₀ value of 471?±?9?μM.     

A new guaiane diterpenoid from Euphorbia wallichii

A new guaiane-type diterpenoid, (1alpha,5beta,7alpha)-3,10(18),11-dictytriene-19-acid, was obtained from the roots of Euphorbia wallichii. This is the first isolation of guaiane diterpene from this genus of Euphorbia. The structure was elucidated by spectral methods. And the compound was tested for the cytotoxicities on the cancer cell line P-388 and A-549 in vitro.     

A new ent-kaurane diterpenoid from Ixora amplexicaulis

A new ent-kaurane diterpenoid, 6α,16α-dihyroxy-ent-kaurane (1), was isolated from the stems of Ixora amplexicaulis, together with (24R)-6β-hydroxy-24-ethyl-cholest-4-en-3-one (2), 7β-hydroxysitosterol (3), maslinic acid (4), 3,3′-bis(3,4-dihydro-4-hydroxy-6-methoxy-2H-1-benzopyran) (5) and protocatechuric acid (6). Their structures were established by extensive spectroscopic analysis, including 2D NMR techniques. Compounds 2–5 were isolated from the genus Ixora for the first time and 6 obtained originally from I. amplexicaulis.     

A new ent-abietane diterpenoid from Isodon macrophyllus

A new ent-abietane diterpenoid, named dayecrystal C, was isolated from the EtOAc extract of the dried leaves of Isodon macrophyllus. Its structure was determined on the basis of spectroscopic methods.     

A new labdane diterpene from the flowers of Solidago canadensis

A new labdane diterpene, 9alpha,16xi-dihydroxy-6-oxo-7,13-labdadien-15,16-olide (solicanolide, 1) and six known compounds identified as quercetin (2), 3-O-caffeoylquinic acid (3, neochlorogenic acid), 5-O-caffeoylquinic acid (4, chlorogenic acid), 4,5-di-O-caffeoylquinic acid (5), 3,5-di-O-caffeoylquinic acid (6) and 3,4-di-O-caffeoylquinic acid (7) were isolated from the flowers of Solidago canadensis. To our knowledge, compound 7 was isolated for the first time in S. canadensis. This work describes the isolation of compounds 1-7 and the structure elucidation of a new compound identified as compound 1. Solicanolide (1) showed cytotoxic activity against A549 (IC(50): 13+/-2 microM), DLD-1 (IC(50): 26+/-2 microM) and WS1 (IC(50): 17+/-1 microM) cell lines.     

A new ent-labdane diterpenoid lactone from Andrographis paniculata

<正>A new ent-labdane diterpenoid lactone was isolated from Andrographis paniculata.Its structure was identified on the basis of spectral data including 2D NMR.     

A new labdane diterpene from the rhizomes of Alpinia officinarum

A new labdane diterpene, (Z)-12,14-labdadien-15(16)-olide-17-oic acid (1), and a new natural cadinane sesquiterpene, 4-isopropyl-6-methyl-1-naphthalenemethanol (2), were isolated from the ethanolic extract of the rhizomes of Alpinia officinarum, together with three other products, galangin (3), kaempferol (4) and quercetin (5). Their structures were elucidated by using extensive spectroscopic methods. Compounds 1 and 2 showed no remarkable cytotoxic activity against HeLa and HepG2 cancer cell lines with IC₅₀>50 μg mL^? 1.