New bioactive triterpenoid from Oldenlandia cantonensis How

A new pentacyclic triterpenoid, urs-12-en-29α-oic acid-3β-ol (1), was obtained from the ethanol extract of Chinese herb Oldenlandia cantonensis How. The structure was elucidated by spectroscopy methods, including nuclear magnetic resonance (NMR) (1D and 2D), infrared spectroscopy (IR), and mass spectrometry (MS). 1 exhibited significant inhibitory activity against the human DNA topoisomerase I (hTopo I), the cancer cell lines BEL-7402 and MCG-803, with the IC₅₀ values 12.0, 6.5, and 8.0 μg/mL, respectively. The volatile oil, the fraction of petroleum ether: EtOAc = 20:1 (V/V) on Si gel chromatography, was also quantitatively analyzed by gas chromatography mass spectrometry (GC-MS). As a result, 60 compounds were identified. Among them, the long chain aliphatics, terpenes and steroids, as the representative structure type, were found with percentages of 36.16%, 6.42% and 9.28%, respectively. Translated from Chinese Journal of Applied Chemistry, 2006, 23(8): 871–874 [译自: 应用化学]     

Further constituents from Rhododendron lepidotum L.

<正>A unusual flavone glycoside named Shamimarin(1) and a new compound Acetoxy-8-methyl-chromen-2H-one(2) were isolated from aerial parts of Rhododendron lepidotum L.along with four known coumarins daphnin(3),daphnetin 8-O-β-D-glucopyrano-side (4),daphnetin(5) and umbelliferone(6).The structural elucidations were based on analyses of chemical and spectroscopic data by including ID and 2D NMR analyses.     

A new sulfated triterpenoid from the bark of Zygophyllum fabago L.

<正>A new sulfated triterpenoid,3β,24-dihydroxyurs-20-ene-24-O-sulphonyl-28-oic acid(fabagoin.1) was isolated from the barks of Zygophyllum fabago L.Its structure was elucidated on the basis of spectroscopic data.     

Three new oleanane-type triterpenoid saponins from the seeds of Celosia cristata L.

Phytochemical investigation of the 1-butanol soluble fraction of 60% ethanol extract of the seeds of Celosia cristata L. led to the identification of three new oleanane-type triterpenoid saponins. Using ¹D and ²D NMR experiment methods, ESI-MS analysis and acid hydrolysis, their structures were identified as 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl]-2β-hydroxy-oleanolic acid-28-O-β-D-glucopyranoside (1), 3-O-[β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl]-2β, 23-dihydroxy-oleanolic acid-28-O-β-D-glucopyranoside (2) and 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl]-2-hydroxyl-medicagenic acid-28-O-β-D-glucopyranosyide (3), respectively.     

Saxifraganoids A and B,two novel cucurbitane triterpenoid glycosides from Saxifraga umbellulata var. pectinata

Two novel cucurbitane triterpenoid glycosides, named saxifraganoids A (1) and B (2), were isolated from Saxifraga umbellulata var. pectinata. Their structures including absolute configurations were elucidated based on the analysis of spectroscopic data (1D, 2D NMR and HRMS), and single-crystal X-ray diffraction. Compound 1 represents the first example of cucurbitane triterpenoid with a Δ¹⁷⁽²⁰⁾, and compound 2 contained an unusual N-acetylglucosamine at C-16. The protective effects against liver injury induced by carbon tetrachloride (CCl₄) in the human embryonic-liver L-02 cells of these two compounds were evaluated.     

Rhododendron molle G. Don Extract Induces Apoptosis and Inhibits Migration in Human Colorectal Cancer Cells and Potential Anticancer Components Analysis

Rhododendron molle G. Don is one example of traditional Chinese medicine with important medicinal value. In this study, the effects of methanol extract of R. molle leaves (RLE) on colorectal cancer HT-29 cells and its potential molecular mechanism were investigated. MTT analysis showed that RLE could significantly inhibit the cell viability and migration of HT-29 cells in a concentration-dependent manner. Cell cycle analyses via flow cytometer suggested that RLE induced DNA fragmentation, indicative of apoptosis, and arrest at the S phase in HT-29 cells. Quantitative real-time PCR (qRT-PCR) analysis showed that RLE could upregulate the mRNA expression of p53 and p21 in HT-29 cells, which would result in HT-29 cells being blocked in S phase. Meanwhile, RLE could upregulate the expression of Bax, and downregulate the expression of Bcl-2, which would induce cell apoptosis. Further western blot analysis showed that the protein expression changes of Bax and P53 were basically consistent with the results of qRT-PCR. In addition, GC-MS analysis detected 17 potential anticancer components in R. molle. These results indicate that R. molle has significant anticancer activity, which provides some useful information for further study and clinical application for R. molle.     

Antibacterial activity of a triterpenoid saponin from the stems of Caesalpinia pulcherrima Linn.

A new compound 1 was isolated from the methanolic extract of the stems of the Caesalpinia pulcherrima Linn. along with a reported compound (2) 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester. The new compound 1 has m.p. 272–274°C, m.f. C₄₆H₇₄O₁₇, [M]⁺ m/z 898. It was characterised as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-β-D- xylopyranosyl ester by various colour reactions, chemical degradations and spectral analyses. Antibacterial activity of compound 1 was screened against various Gram-positive and Gram-negative bacteria and showed significant results.     

Structure of ulososide A,a new triterpenoid glycoside from theUlosa sp. sponge

A new triterpenoid glycoside, (20S,22S,23R,24S)-3,22,23-trihydroxy-3-O-[O-(-D-glucuronopyranosyl)-(16)-(-D-glucopyranosyl)]-14-nor-24-methyllanost-8(9)-en-31-oic acid (ulososide A), has been isolated from the sponge Ulosa sp. and characterized.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1326–1329, July, 1994.     

Two new complex triterpenoid saponins from Gledistsia dolavayi Franch.

Two new triterpenoid saponins, gledistside A ( 1 ) and gledistside B ( 2 ), isolated from the fruits of Gledistsia dolavayi Franch., were characterized as the 3,28‐O‐bisdesmoside of echinocystic acid acylated with monoterpene carboxylic acids. On the basis of spectroscopic and chemical evidence, their structures were elucidated as 3‐O‐β‐D ‐xylopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl‐28‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→4)‐[β‐D ‐galactopyranosyl‐(1→2)]‐α‐L ‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2,6‐dimethyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D ‐glucopyranosylechinocystic acid ( 1 ) and 3‐O‐β‐D ‐xylopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl‐28‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→4)‐[β‐D ‐galactopyranosyl‐(1→2)]‐α‐L ‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2‐hydroxymethyl‐6‐methyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D ‐glucopyranosylechinocystic acid ( 2 ). The complete ¹H and ¹³C assignments of saponins 1 and 2 were achieved on the basis of 2D NMR spectra including HMQC‐TOCSY, TOCSY, ¹H–¹H COSY, HMBC, ROESY and HMQC spectra. Copyright © 2002 John Wiley & Sons, Ltd.     

Polysciosides J and K,two new oleanane-type triterpenoid saponins from the leaves of Polyscias fruticosa (L.) harms. cultivating in An Giang Province,Viet Nam

Abstract

For the first time, the phytochemical constituents of the leaves of Polyscias fruticosa (L.) Harms. cultivating in An Giang Province, Viet Nam were investigated and led to purify two new oleanane-type triterpenoid saponins, named polyscioside J (1) and polyscioside K (2) together with two known saponins, ladyginoside A (3) and chikusetsusaponin IVa (4) using variously chromatographic methods. Saponin (4) was reported for the first time from this species. Their structures were verified by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and compared with previous literatures.     

A bioactive new protostane-type triterpenoid from Alisma plantago-aquatica subsp. orientale (Sam.) Sam.

A new protostane-type triterpenoid, 5β,29-dihydroxy alisol A (1) was isolated from Alisma plantago-aquatica subsp. orientale (Sam.) Sam. as well as 12-deoxyphorbol-13α-pentadecanoate (2). We first report the presence of compound 2 in the genus Alisma. Their structures were established on the basis of 1D and 2D NMR, and HRESIMS spectroscopic analyses. All the isolated compounds were assayed for their inhibitory effects against human carboxylesterase 2 (HCE-2). Compounds 1 and 2 displayed inhibitory activities against HCE-2 with IC₅₀ values of 29.2 and 4.6 μM, respectively. The interaction mechanisms of HCE-2 with compounds 1 and 2 were investigated by molecular docking, respectively.     

Comparative analysis of essential oil compositions from leaves and stems of Rhododendron adamsii, R. aureum, and R. dauricum

Chemical compositions of essential oils (EO) from leaves and stems of Rhododendron adamsii, R. aureum, and R. dauricum were studied by GC/MS. The analysis demonstrated that the EO of these plants contained mainly mono-and diterpene hydrocarbons. A large amount of alkanes was also found in the EO of R. aureum. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 344–347, July–August, 2006.     

Two new dammarane triterpenoids from Kageneckia angustifolia D. Don

Two new dammarane triterpenoids, 20R,21-epoxydammar-24-ene-3,23-dione and 20R,21-epoxy-3beta-hydroxydammar-24-ene-23-one have been isolated from the aerial parts of Kageneckia angustifolia D. Don, Rosaceae, along with the previously reported triterpenoids oleanolic acid and 3beta-(beta-D-glucosyloxy)-16alpha,23alpha-epoxycucurbita-5,24-dien-11-one and the phenolic prunasin. The structures of these compounds were established by MS, 1D- and 2D-NMR experiments, and the structure of the new compounds were confirmed by X-ray diffraction analysis.     

Two antidiabetic constituents from Roylea cinerea (D.Don) Baill.

Two antidiabetic compounds named 4-methoxybenzo[b]azet-2(1H)-one (1) and 3β-hydroxy-35-(cyclohexyl-5′-propan-7′-one)-33-ethyl-34-methyl-bacteriohop-16-ene (2) together with stigmasterol and β-sitosterol were isolated from the aerial part of Roylea cinerea (D.Don) Baill. The structures of these compounds were elucidated by advanced spectroscopic methods, including two-dimensional NMR and MS techniques. These compounds were evaluated for their antidiabetic efficacy using in vitro and in vivo methods. Both compounds (1 and 2) showed a significant decline in blood glucose level of alloxan-induced diabetic rats at 10 mg/kg, p.o. when compared with glibenclamide at a similar dose. The in vitro studies revealed that compound 1 reduced α-amylase and α-glucosidase by 83.0 and 78.5%, respectively, whereas compound 2 reduced the same by 58.2 and 58.4%, respectively, at 100 μM. The present study supports the role of R. cinerea in Ayurvedic medicine for diabetes.     

Interaction effects on cytochrome P450 both in vitro and in vivo studies by two major bioactive xanthones from Halenia elliptica D. Don

The major components, 1‐hydroxy‐2,3,5‐trimethoxy‐xanthone (HM‐1) and 1,5‐dihydroxy‐2,3‐dimethoxy‐xanthone (HM‐5) isolated from Halenia elliptica D. Don (Gentianaceae), could cause vasodilatation in rat coronary artery with different mechanisms. In this work, high‐performance liquid chromatography coupled to ion trap time‐of‐flight mass spectrometry (LCMS‐IT‐TOF) was used to clarify the metabolic pathways, and CYP450 isoform involvement of HM‐1 and HM‐5 were also studied in rat. At the same time, in vivo inhibition effects of HM‐1 and ethyl acetate extracts from origin herb were studied. Three metabolites of HM‐5 were found in rat liver microsomes (RLMs); demethylation and hydroxylation were the major phase I metabolic reactions for HM‐5. Multiple CYP450s were involved in metabolism of HM‐1 and HM‐5. The inhibition study showed that HM‐5 inhibited Cyp1a2, 2c6 and 2d2 in RLMs. HM‐1 inhibited activities of Cyp1a2, Cyp2c6 and Cyp3a2. In vivo experiment demonstrated that both HM‐1 and ethyl acetate extracts could inhibit Cyp3a2 in rats. In conclusion, the metabolism of xanthones from the origin herb involved multiple CYP450 isoforms; in vitro, metabolism of HM‐5 was similar to that of its parent drug HM‐1, but their inhibition effects upon CYP450s were different; in vivo, Cyp3a2 could be inhibited by HM‐1 and ethyl acetate extracts.     

Three new phenanthrenes from Cremastra appendiculata (D. Don) Makino

Three new phenanthrenes,along with one known phenanthrene,were isolated from the ethanolic extract of the tubers of Cremastra appendiculata(D.Don) Makino.Their structures were elucidated on the basis of extensive spectroscopic analysis.Compounds 1-4 were tested for in vitro cytotoxic activities against human lung(A549),colon(HCT-116),liver(HepG2),and breast(MCF-7 and MDA-MB-231) cancer cell lines.     

A phenolic glycoside from Fagopyrum dibotrys (D.Don) Hara

A new phenolic constituent along with five known compounds were isolated from Fagopyrum dibotrys(D.Don)Hara.The new compound was characterized as 1,3-dimethoxy-2-O-β-xylo-pyranosyl-5-O-β-glucopyranosyl-benzene,by spectroscopic analysis and enzymatic hydrolysis.     

Lobarioid A,unusual antibacterial depsidone possessing an eight-membered diether ring from the edible lichen Lobaria sp.

Lobarioid A (1), an unusual depsidone possessing an eight-membered diether ring, was isolated from the edible lichen Lobaria sp. Its structure was elucidated by extensive NMR, MS, IR and single-crystal X-ray diffraction analyses. Compound 1 exhibited antibacterial activity against three strains of gram-positive bacteria.     

Potential bioactive secondary metabolites of Actinomycetes sp. isolated from rocky soils of the heritage village Rijal Alma,Saudi Arabia

The present study was designed to discover novel secondary antibiotic metabolites from Actinomycetes species from the soil of Rijal Almaa, Saudi Arabia. A laboratory-scale benchtop fermentation was utilized for the demonstration of antibiotics from the soil actinomycetes. Fourier transform-infrared spectroscopy (FT-IR) spectroscopy analysis of the fermented product (FP) was carried out, which showed unique fingerprint regions indicating the presence of phenolic hydroxyl groups, aliphatic compounds, carboxylic groups, esters, isothiocyanate, etc. GC-MS analysis of the FP depicted the unique structures of secondary metabolites, such as cyclononasiloxane octadecamethyl, cercosporin, ethyl iso-allocholate, octadecane, 3-ethyl-5-(2-ethylbutyl), dasycarpidan-1-methanol (acetate), heptadecane, 9-hexyl-, phthalic acid-butyl, and octadecane, 3-ethyl-5-(2-ethylbutyl). The TGA analysis showed the thermal stability of FP and the initial weight loss in FP was observed at 277.29 °C. The ¹H NMR and ¹³C NMR spectra of FP analysis demonstrated the various characteristic peaks presence of secondary metabolites. The XRD analysis at 2θ revealed distinct particles based on specific diffraction peaks. A set of six human bacterial pathogens, namely, the Gram-positive bacteria Staphylococcus aureus (S. aureus), Streptococcus pyogenes (S. pyogenes), and Bacillus subtilis (B. subtilis) and Gram-negative bacteria Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa), and Klebsiella pneumoniae (K. pneumoniae), were utilized for screening. The FP exhibited promising antibacterial effects against both Gram-positive and Gram-negative bacterial organisms. The antibacterial spectrum of activity was greater for E. coli and B. subtilis than for K. pneumoniae.     

Fascioquinols A-F: bioactive meroterpenes from a deep-water southern Australian marine sponge, Fasciospongia sp.

Chemical investigation of a southern Australian deep-water marine sponge, Fasciospongia sp., returned the new meroterpene sulfate fascioquinol A (1) together with a series of acid mediated hydrolysis/cyclization products, fascioquinols B (2), C (3) and D (4), and strongylophorine-22 (5). Additional co-metabolites include the new meroterpenes fascioquinol E (6) and fascioquinol F (8), together with the known sponge metabolite geranylgeranyl 1,4-hydroquinone (7). Structures were assigned to 1-8 on the basis of detailed spectroscopic analysis, chemical interconversion, mechanistic and biosynthetic considerations, and literature comparisons. The known 1,4-hydroquinone 7 was identified as the dominant cytotoxic principle in the Fasciospongia sp. extract, with selective inhibitory activity against gastric adenocarcinoma (AGS, IC₅₀ 8 μM) and neuroblastoma (SH-SY5Y, IC₅₀ 4 μM) cell lines. By contrast, while the fascioquinols displayed little or no inhibitory activity towards human cell lines, 1 and 2 displayed promising Gram-positive selective antibacterial activity towards Staphylococcus aureus (IC₅₀ 0.9-2.5 μM) and Bacillus subtilis (IC₅₀ 0.3-7.0 μM).