Sesquiterpenoids and lignans from the roots of Valeriana officinalis L

Two new guaiane-type sesquiterpenoids, valerol A (1) and kessyl 3-acetate (2), together with nine known compounds, valeracetate (3), anismol A (4), orientalol C (5), spatulenol (6), 4α,10α-epoxyaromadendrane (7), (+)-8-hydroxypinoresinol (8), pinorespiol (9), pinoresinol 4-O-β-D-glucopyranoside (10), and 8-hydroxypinoresinol 4'-O-β-D-glucopyranoside (11) were isolated from the roots of Valeriana officinalis. The structures and relative configurations of 1 and 2 were elucidated on the basis of spectroscopic methods (1D- and 2D-NMR, MS, UV, and IR). These compounds were evaluated for inhibitory activity on acetylcholinesterase (AChE) and enhancing activity on nerve growth factor (NGF)-mediated neurite outgrowth in PC12 cells.     

Sesquiterpenoids of Torilis japonica fruit

From the methanolic extract of Torilis japonica D. C. fruit (Umbelliferae), two eudesmane-type sesquiterpenoids were isolated together with five previously described sesquiterpenoids. From the results of spectral analyses, they were characterized as 4(15)-eudesmene-1beta,5alpha-diol and 4alpha,15-epoxyeudesmane-1beta,6alpha-diol, respectively. The absolute stereostructures of these sesquiterpenoids were elucidated by the modified Mosher's method.     

Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells

A cycloartane-type triterpenoid (1), an aliphatic alcohol glycoside (2), an eudesmane-type sesquiterpenoid (3), and a guaiane-type sesquiterpenoid (4) were isolated from the resinous exudates of Commiphora opobalsamum along with six known sesquiterpenoids (5-10). Their structures were established by extensive analysis of their 1D and 2D NMR spectroscopic data and chemical methods. The isolated compounds 1-3 and 5-9 were tested against human prostate cancer cell PC 3 and LNCaP. Among them, 1 and 2 showed moderate antiproliferative effects on human prostate cancer cell lines with IC50 values ranging from 5.7 to 23.6 microM; they were also able to inhibit the expression of androgen receptor (AR) in LNCaP cells. The six sesquiterpenoids were inactive in the bioassays.     

Biotransformation of germacrane-type sesquiterpenoids by Aspergillus niger

Three germacrane-type sesquiterpenoids, (+)-germacrone-4,5-epoxide, germacrone and (+)-curdione were biotransformed by Aspergillus niger to give hydroxylated guaiane-type sesquiterpenoids together with allylic alcohols and spirolactone.     

Pinguisane and dimeric pinguisane-type sesquiterpenoids from the Japanese liverwort Porella acutifolia subsp. tosana

Two new pinguisane-type, three new Diels-Alder reaction-type dimeric pinguisane sesquiterpenoids and known sesqui and diterpenoids were isolated from the ether extract of the Japanese liverwort Porella acutifolia subsp. tosano. Their absolute stereostructures were established by a combination of extensive 2D-NMR, CD spectra, X-ray crystallographic analysis, modified Mosher's method and chemical correlation.     

Sesquiterpenoids from Saussurea laniceps and their chemotaxonomic significance

Twenty-five sesquiterpenoids including seventeen guaiane-type sesquiterpenoids and glucose glycosides (1–17), six eudesmane-type sesquiterpenoids (18–23), and two germacrane-type sesquiterpenoids (24 and 25) were isolated from the aerial parts of Saussurea laniceps Hand.-Mazz. Their structures were elucidated by spectroscopic methods and comparison with previously reported spectral data. Among them, compounds (6 and 8) are new, and seven compounds (2, 9, 12, 18–19, 22–23) are reported for the first time from the genus Saussurea. This paper deals with the isolation, structural elucidation and chemotaxonomic significance of these sesquiterpenoids from S. laniceps.     

Commiphoranes K−O,New Terpenoids from Resina Commiphora and Their Anti-Inflammatory Activities

Commiphorane K ( 1 ), a new dinorditerpenoid, commiphoranes L−N ( 2 – 4 ), three new germacrane-type sesquiterpenoids, and commiphorane O ( 5 ), one new guaiane-type sesquiterpenoid, were isolated from Resina Commiphora. Their structures were characterized by spectroscopic and computational methods. In particular, the structure of 4 was confirmed by X-ray crystallography. Compounds 2 – 5 were evaluated for their anti-inflammatory activities. The result shows that compound 2 suppresses lipopolysaccharide (LPS)-stimulated production of TNF-α in RAW264.7 cells in a dose-dependent manner.     

New Guaiane-Type Sesquiterpene and Norsesquiterpene from Alisma plantago-aquatica and Their Xanthine Oxidase Inhibitory Activity

A new sesquiterpene ( 1 ) and a new norsesquiterpene ( 2 ) belonging guaiane-type skeleton together with six known compounds ( 3 – 8 ) were isolated from the rhizomes of Alisma plantago-aquatica. Their structures were determined by HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Absolute configurations of new compounds were established by experimental and TD-DFT computational ECD spectra. Compounds 1 – 8 exhibited xanthine oxidase inhibitory activity with their IC₅₀ values in range of 9.4–66.7 μM. The sesquiterpenoids 1 – 5 displayed the inhibitory activity and hence they could be potential xanthine oxidase inhibitors from A. plantago-aquatica.     

Guaiane dimers from Xylopia vielana

From the leaves of Xylopia vielana (Annonaceae) two dimeric guaianes named vielanins D and E were isolated and structurally elucidated by mass and NMR spectroscopy. Vielanin D and E consist of bridged ring systems formally representing the Diels-Alder products from the hypothetical guaiane-type monomers. Due to a hemiketal function at C-8' both compounds occurred as epimeric mixtures.     

Effects of sesquiterpenes and triterpenes from the rhizome of Alisma orientale on nitric oxide production in lipopolysaccharide-activated macrophages: absolute stereostructures of alismaketones-B 23-acetate and -C 23-acetate

The methanolic extract from a Chinese herbal medicine, the rhizome of Alisma orientale, was found to exhibit inhibitory activity of nitric oxide (NO) production in lipopolysaccharide (LPS)activated macrophages. Novel triterpenes, alismaketones-B 23-acetate and -C 23-acetate, were isolated from the active extract together with eight sesquiterpenes and eighteen protostane-type triterpenes. The absolute stereostructures of new triterpenes were characterized on the basis of chemical and physicochemical evidence, which included the chemical correlations with known triterpenes. The guaiane-type sesquiterpenes (alismol, orientalols A and C) and protostane- and seco-protostane-types triterpenes (alisols C monoacetate, E-23-acetate, F, H, I, L-23-acetate, and M-23-acetate, alismaketones-B 23-acetate and -C 23-acetate, alismalactone 23-acetate, and 3-methylalismalactone 23-acetate) inhibited LPS-induced NO production (IC50 = 8.4-68 microM). Other triterpenes (alisols A, A monoacetate, B, B monoacetate, E, G, K-23-acetate, and N-23-acetate and 11-deoxyalisol B) also showed the potent inhibitory activity, but they showed cytotoxic effects more than 30 microM (MTT assay). In addition, alismol and alisol F were found to suppress iNOS induction.     

Sesquiterpenoids and steroids from gorgonian Echinogorgia sassapo reticulate

Three guaiane-type sesquiterpenoids (1−3) and five steroids with 3β-hydroxy-5-en-7-one moiety (4−8) were obtained from gorgonian Echinogorgia sassapo reticulata collected from the South China Sea. Among them, new compound 1 was identified as (1S,5S,8S)-8-methoxy-menelloide B by spectroscopic methods including IR, HRESIMS, 1D and 2D NMR, and ECD spectra. All compounds except for 3 were obtained for the first time from the genus Echinogorgia. The chemotaxonomic significance of these compounds was summarized.     

Guaiane- and aristolane-type sesquiterpenoids of Nardostachys chinensis roots

Two guaiane-type compounds, nardoguaianone J and K (1 and 2) and two aristolane-type compounds, kanshone F and G (3 and 4), were isolated from Nardostachys chinensis roots. The structures including the absolute configurations were elucidated by spectral means and by comparison of their CD spectra.     

Lanceocrepidiasides A-F, glucosides of guaiane-type sesquiterpene from Crepidiastrum lanceolatum

From the aerial parts of Crepidiastrum lanceolatum, six guaiane-type sesquiterpene glucosides, lanceocripidiasides A-F were isolated together with five known sesquiterpene glucosides, ixerin Y, crepidialanceosides A and B, and youngiasides A and D, two known megastigmane glucosides, icariside B1 and corchoionoside A, and benzyl 6'-O-beta-D-apiofuranosyl-beta-D-glucopyranoside. Structures were elucidated by spectroscopic analyses.     

Cytotoxic sesquiterpenoids from Winteraceae of Caledonian rainforest

One secobutanolide, two butanolides and six drimane sesquiterpenoids were isolated from the bark and leaves of Zygogynum pancheri and Zygogynum acsmithii (Winteraceae) along with six known drimanes, isodrimanial, 1β-O-p-methoxy-E-cinnamoyl-bemadienolide, 7-ketoisodrimenin, drimenin, polygodial and 1β-E-cinnamoyl-6α-hydroxypolygodial. Their structures were elucidated through analysis of spectroscopic data. Drimane sesquiterpenoids with a dialdehyde function exhibited significant inhibitory activities in the in vitro cytotoxic assays against KB, HL60 and HCT116 cancer cell lines.     

Strobilols A-D: four cadinane-type sesquiterpenes from the edible mushroom Strobilurus ohshimae

Four sesquiterpenoids--strobilols A (1), B (2), C (3), and D (4)--were isolated from the organic extracts of fruiting bodies of the edible mushroom Strobilurus ohshimae. Their structures were determined by spectroscopic methods. Compound 1 exhibited moderate activity against the brine shrimp Artemia salina. This paper is the first report on isolation of cadinane-type sesquiterpenoids from S. ohshimae.     

Sesquiterpenoids from Homalomena occulta affect osteoblast proliferation, differentiation and mineralization in vitro

Chemical investigation of rhizomes of Homalomena occulta (Lours) resulted in isolation and identification of two sesquiterpenoids (6,7), and one daucane ester 8, together with five known sesquiterpenoids, oplodiol, oplopanone, homalomenol C, bullatantriol, and 1beta,4beta,7alpha-trihydroxyeudesmane. Their structures were elucidated using 1D and 2D NMR spectroscopic and X-ray analyses. The chloroform extract of this plant and compounds 1-7 were tested in vitro for their activities in stimulating osteoblast (OB) proliferation, differentiation and mineralization. Compounds 1-4 had a stimulative effect on significantly proliferation and differentiation of culture osteoblasts, while the chloroform extract and 1 significantly stimulated mineralization of cultured osteoblasts in vitro.     

Illudalane sesquiterpenoids, echinolactones A and B, from a mycelial culture of Echinodontium japonicum

Illudalane sesquiterpenoids, echinolactones A and B, were isolated from the culture broth of the fungus Echinodontium japonicum, and their structures spectroscopically determined.     

ent-Verticillane-type diterpenoids from the Japanese liverwort Jackiella javanica

Three ent-verticillane diterpenoids and two ent-sesquiterpenoids were isolated from the Japanese liverwort Jackiella javanica Schiffn. together with five known ent-verticillane and three ent-kaurane diterpenoids, and three sesquiterpenoids. Five ent-verticillane epoxides were synthetically prepared from ent-verticillols action to clarify the absolute configuration of natural ent-9,10-epoxyverticillol. Their structures were established by extensive NMR spectroscopic and X-ray crystallographic analyses.     

Guaiane sesquiterpenes from Amoora rohituka

The petroleum ether extract of the stem bark of Amoora rohituka afforded two novel guaiane-derived sesquiterpenoids, 6beta,7beta-epoxyguai-4-en-3-one (1) and 6beta,7beta-epoxy-4beta,5-dihydroxyguaiane (2). The structures of 1 and 2 were determined by extensive NMR and MS analyses and by comparison of their spectral data with related compounds. The relative stereochemistry of the asymmetric centers in 1 and 2, except at C-5 of 2, were determined by selective 1D-NOESY experiments.     

Terpenoids from Tripterygium doianum (Celastraceae)

The extract of Tripterygium doianum (Celastraceae) afforded three triterpenoids [3beta-acetoxy-11-ursen-13alpha,30-olide, 25-chloro-24-hydroxytirucall-7-en-3-one and tirucall-7-en-3,24-dione], two sesquiterpenoids [5alpha-acetoxy-1beta,8alpha-bis-cinnamoyl-4alpha-hydroxydihydroagarofuran and 5alpha-acetoxy-1beta-benzoyl-8alpha-cinnamoyl-4alpha-hydroxydihydroagarofuran] and nine known triterpenoids. Their structures were established based on spectroscopic studies.