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 cadinane sesquiterpenoid from cultures of the Basidiomycete Panus conchatus

A new cadinane sesquiterpenoid, named panutorulon A (1), was isolated from cultures of the basidiomycete Panus conchatus. The new structure was elucidated by means of spectroscopic methods. Compound 1 was tested for its cytotoxicity against five human cancer cell lines and for its inhibitory activity against isozymes of 11β-hydroxysteroid dehydrogenases (11β-HSD).     

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 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.     

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 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).     

Two New Pentacyclic Triterpenes from Abelmoschus esculentus

Two new pentacyclic triterpenes, (3β,21β)‐19,21‐epoxylup‐20(29)‐en‐3‐yl acetate ( 1 ) and (3β)‐9,18‐dihydroxyolean‐12‐en‐3‐yl acetate ( 2 ), were isolated from Abelmoschus esculentus (L.) Moench . Their structures were determined on the basis of detailed analyses of their 1D‐ and 2D‐NMR‐spectroscopic and MS data.     

A new 5-alkylresorcinol glucoside derivative from Cybianthus magnus

One new 5-alkylresorcinol glucoside (1) was isolated from leaves of Cybianthus magnus, along with 12 known compounds, isolated from four plants belonging to Myrsinaceae family (2, 3 isolated from C. magnus; 4–7, 10 and 11 isolated from Myrsine latifolia; 4, 8 and 9 isolated from Myrsine sessiflora; 6, 7, 10, 12 and 13 isolated from Myrsine congesta). Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. So far, only nine 5-alkylresorcinol glucosides were isolated from leaves of Grevillea robusta. Since resorcinols are known to exhibit strong cytotoxic activity, compounds 1 and 2 were tested against cell lines 3T3, H460, DU145 and MCF-7 for cytotoxicity in vitro and compounds 3–13 were tested for their antileishmanial activity. Compound 2 displayed a strong cytotoxic activity with IC₅₀ values ranging between 22 and 100 μM for all tested cell lines. Compounds 3–13 were not active against Leishmania amazonensis amastigotes.     

A pair of humulane sesquiterpenoid enantiomers from Syringa pinnatifolia

Two humulane-type sesquiterpenoids, namely (+)-alashanoid I (1a) and (–)-alashanoid I (1b), were isolated as a pair of enantiomers from the peeled stems of Syringa pinnatifolia. Their structures were elucidated by extensive spectroscopic data (1?D and 2?D NMR, UV, and IR), and the absolute configurations were resolved by X-ray diffraction and experimental and calculated ECD data analysis.     

Colletotrichine A,a new sesquiterpenoid from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla

One new compound, Colletotrichine A (1), was produced by the fungal Colletotrichum gloeosporioides GT-7. The structure was established by 1D and 2D NMR spectra. Monoamine oxidase (MAO) and acetylcholinesterase (AChE) inhibitory activity of 1 was also evaluated. Compound 1 showed AChE-inhibiting activity with IC₅₀ value of 28 μg/mL.     

New sesquiterpenoid derivatives from Solanum septemlobum with cytotoxicities

Two new sesquiterpenoid derivatives, attributable to eudesmane-type (1–2, named septemlobin D and 11,12-O-isopropylidenesolajiangxin F), were isolated from the whole plant of Solanum septemlobum. Their structures were elucidated on the basis of integrated spectroscopic techniques, mainly HR-FAB-MS, 1D and 2D-NMR (¹H–¹H COSY, HMQC, HMBC and ROESY). In vitro, two sesquiterpenoid derivatives were found to show significant cytotoxicity against three cancer cell lines (P-388, HONE-1 and HT-29), and gave IC₅₀ values in the range of 3.0–7.3 μM.     

Roseosporol A,the first isolation of a novel sesquiterpenoid from Streptomyces roseosporus

A novel sesquiterpenoid, roseosporol A (1), together with 12 known compounds (2–13) were isolated from the ethyl acetate extract of Lsr2-deletion mutant strain of Streptomyces roseosporus. Their structures were determined by spectroscopic methods, including NMR, HRMS, UV, IR and ECD.     

A novel sesquiterpenoid from <Emphasis Type="Italic">Ecdysanthera rosea</Emphasis>

A novel sesquiterpenoid was isolated from the whole plant of Ecdysanthera rosea Hook. et Arn. Its structure was elucidated as tricyclo[5,3,1,0^2,4]-3-aldehyde-3,11-dimethyl-8-methanoic acid on the basis of spectral evidence (1D and 2D NMR) and was named ecdysanthblic acid. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 245–246, May–June, 2008.     

A new triterpenoid saponin and a diterpene glucoside from the seeds of Orychophragmus violaceus

One new triterpenoid saponin orychoside A (1) and one new diterpene glucoside orychoside B (12), together with eleven known compounds, were isolated from the seeds of Orychophragmus violaceus. The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The known compounds were identified by comparison with data reported in the literature. All compounds were tested for their cytotoxic activities against the HepG2 and A549 cell lines in vitro. The new compound 1 exhibited potent cytotoxicity against the two cell lines with IC₅₀ values of 7.13 and 8.77 μM, respectively. Compounds 2, 5, 8 and 9 were found to possess obvious cytotoxicity.     

Microporotriol,a new cadinane-type sesquiterpenoid from the cultures of the wood-decay fungus Microporus affinis HFG829

Abstract

A new cadinane-type sesquiterpenoid, microporotriol (1), together with four known compound, 5-methylresorcinol (2), (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (3), (22E,24R)-ergosta-5,7,22-trien-3β-ol (4), (22E,24R)-5α,8α-epidioxy-ergosta-6,22-dien-3β-ol (5), were isolated from the fermentation broth of the wood decaying fungus Microporus affinis HFG829. The structures of the compounds were established by extensive spectroscopic methods, including 1D & 2D NMR, along with HRMS spectroscopic analysis. The relative configuration of 1 was confirmed by NMR calculation. Compound 1 was evaluated for the cytotoxicity against five human cancer cell lines.     

Japonicones A-C: Three lindenane sesquiterpenoid dimers with a 12-membered ring core from Chloranthus japonicus

Japonicones A–C (1–3), three new dimeric lindenane-type sesquiterpenoids featuring a rare 12-membered ring framework, were isolated from the whole plants of Chloranthus japonicus Sieb. Their structures and absolute configurations were unequivocally established by a combination of spectroscopic data, ECD calculation, and X-ray crystallography. Compounds 1–3 were evaluated for their DNA Topoisomerase Ⅰ (Top1) inhibitory, cytotoxic, and antibacterial activities.     

Officinalioside,a new lignan glucoside from Borago officinalis L.

A new lignan glucoside, officinalioside (1), was isolated from n-BuOH fraction of the aerial parts of Borago officinalis L., together with four known compounds: actinidioionoside (2), roseoside (3), crotalionoside C (4) and kaempferol 3-O-β-D-galactopyranoside (5). The structure of the new compound was established by means of spectroscopic and chemical analyses. Compounds 1 and 2 showed a moderate DPPH radical scavenging activity (IC₅₀: 52.6 ± 1.70 and 41.3 ± 0.25 μM, respectively) comparable with that of the standard trolox (16.6 ± 2.2 μM) without any significant cytotoxicity towards human cell line A549 (IC₅₀ > 100 μM).     

Colletotrichine B,a new sesquiterpenoid from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla

One new compound, colletotrichine B (1), was produced by the fungal Colletotrichum gloeosporioides GT-7. The structure of 1 was elucidated on the basis of spectroscopic analysis and X-ray crystallographic analysis. Monoamine oxidase (MAO), acetylcholinesterase (AChE) and phosphoinositide 3-kinase (PI3Kα) inhibitory activity of 1 was also evaluated. Compound 1 showed only AChE inhibiting activity with IC₅₀ value of 38.0 ± 2.67 μg/mL.     

Polygonatone H,a new homoisoflavanone with cytotoxicity from Polygonatum Cyrtonema Hua.

A new homoisoflavonoid, (3R)-5,7-dihydroxy-6-methyl-3-(2′-hydroxy-4′-methoxybenzyl)-chroman-4-one (1), namely polygonatone H, in addition to fourteen known homoisoflavones (2–15) were isolated from the rhizome of Polygonatum Cyrtonema Hua. The structures were identified with the aid of 1D/2D NMR spectroscopic technologies. Compounds 2, 6, 8, 10, 11, 13, and 15 were isolated from P. Cyrtonema for the first time. Compound 1 showed cytotoxicities to human cancer cell lines with IC₅₀ values to comparable those of cisplatin.     

A new sesquiterpenoid from Saussurea lappa roots

A new sesquiterpenoid, 10α-methoxyartemisinic acid (1) was isolated from Saussurea lappa roots along with two known compounds, costunolide (2) and dehydrocostus lactone (3) by high-speed countercurrent chromatography with purities of 85, 95 and 98%, respectively. Their structures were determined on the basis of spectral data including 1D and 2D NMR and HREIMS.