New bioactive macrocyclic diterpenoids from Jatropha multifida

Two new macrocyclic diterpenoids, multifidanol (1) and multifidenol (2) along with several known compounds have been isolated from the stem of Jatropha multifida. The structures of the new compounds were established from the extensive studies of their 1D and 2D NMR spectra. The cytotoxic and antimicrobial activities of these two constituents were examined.     

neo-Clerodane diterpenoids from Scutellaria barbata with cytotoxic activities

Three neo-clerodane diterpenoids, named barbatins A-C (1-3), and the neo-clerodane diterpenoid nicotinyl ester, named scutebarbatine B (4), were isolated from the whole plant of Scutellaria barbata D. Don. Their structures were elucidated by spectroscopic analyses (UV, IR, HRFAB-MS, 1D NMR and 2D NMR). In vitro, compounds 1-4 showed significant cytotoxic activities against three human cancer lines, namely, HONE-1 nasopharyngeal, KB oral epidermoid carcinoma, and HT29 colorectal carcinoma cells, with IC50 values in the range 3.5-8.1 microM.     

Cucurbitacins from Bacopa monnieri

Four cucurbitacins, bacobitacin A-D (1-4) as well as, a known cytotoxic, cucurbitacin E (5) together with three known phenylethanoid glycosides, monnieraside I, III and plantioside B were isolated form the aerial part of Bacopa monnieri. Their structures were elucidated on the basis of extensive spectroscopic investigations (1D, 2D NMR and ESI-QTOF-MS/MS). This is the first report on the characterization of cucurbitacins in B. monnieri.     

Four illudane sesquiterpenes from Coprinopsis episcopalis

Four new illudane derivatives with antibiotic and cytotoxic properties, illudins I (1), I(2) (2), J (3) and J(2) (4), have been isolated from the fungus Coprinopsis episcopalis (syn. Coprinus episcopalis). These sesquiterpenes are stereoisomers, and their relative structures have been determined taking into consideration 2D NMR data.     

New pregnane glycosides from Caralluma dalzielii

Twenty-seven new pregnane glycosides were isolated from the whole plant of Caralluma dalzielii, and their structures elucidated from extensive 2D NMR analysis as well as ESI-MS experiments. All isolated compounds were tested for their antiproliferative activity on J774.A1, HEK-293, and WEHI-164 cell lines. Moderate to high potency of cytotoxicities were found in almost all tested compounds, confirming the significant cytotoxic activity of pregnane glycosides.     

Purine-containing cucurbitane triterpenoids from Cucurbita pepo cv dayangua

Phytochemical investigation of the fruits of Cucurbita pepo cv dayangua led to the isolation of cucurbitaglycosides A (1) and B (2). This is the first report of cucurbitane triterpenoids with a purine unit. Their structures were elucidated mainly based on interpretation of HRESIMS results, as well as 1D and 2D NMR spectra. Cucurbitaglycosides A and B showed cytotoxic activity against the human epithelial carcinoma cell line HeLa with IC50 of 17.2 and 28.4 microg/mL, respectively.     

Cytotoxic triterpenes from the twigs of Celtis philippinensis

Two triterpene esters, 3beta-trans-sinapoyloxylup-20(29)-en-28-ol (1) and 3beta-trans-feruloyloxy-16 beta-hydroxylup-20(29)-ene (2), were isolated as cytotoxic constituents from the chloroform-soluble extract of the twigs of Celtis philippinensis, along with five known triterpenes, 3beta-O-(E)-feruloylbetulin (3), 3beta-O-(E)-coumaroylbetulin (4), betulin (5), 20-epibryonolic acid (6), and ursolic acid (7). The structures of 1 and 2 were assigned from their 1D and 2D NMR spectroscopic data. All isolates were evaluated for cytotoxicity against several human cancer cell lines.     

Alkylated benzoquinones from Iris kumaonensis

Six novel alkylated p-Benzoquinones irisoquin (A-F) (1-2, 4-7) together with a known cytotoxic quinone, irisoquin (3) along with three known isoflavones, tectoregenin, iristectorin and irigenin were isolated from the rhizomes of Iris kumaonensis and characterized. The structures of compounds 1-2, 4-7 were confirmed by extensive spectroscopic analysis, IR, MS, HRMS, GC, GC-MS, 1D (1H, 13C, NOE) and 2D (HMQC and HMBC) NMR and comparison with literature data of known compounds.     

Steroidal glycosides from the underground parts of Trillium erectum and their cytotoxic activity

Six steroidal glycosides, along with 14 known compounds, were isolated from the underground parts of Trillium erectum L. (Liliaceae). The structures of 1-6 were determined on the basis of extensive spectroscopic analysis, including two-dimensional (2D) NMR data, and a few chemical transformations. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells.     

Spirostanol saponins from the rhizomes of Tacca chantrieri and their cytotoxic activity

The rhizomes of Tacca chantrieri have been analysed for steroidal saponin constituents, resulting in the isolation of four new spirostanol saponins (1-4), along with one known saponin (5); their structures were elucidated on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells.     

Hericenols A-D and a chromanone from submerged cultures of a Stereum species

Extracts of submerged cultures of a Stereum species afforded four new pentasubstituted phenolic compounds, named hericenols A, B, C, and D (1-4), 6-hydroxymethyl-2,2-dimethylchroman-4-one (5) and the known erinapyrone C. Hericenol A (1) showed weak antimicrobial activity while hericenol C (3) was weakly cytotoxic. The structures of the metabolites were determined by spectroscopic techniques.     

Acylated farnesyl diglycosides from Guioa crenulata

Chemical investigation of the methanol extract of the leaves of Caledonian Guioa crenulata led to the isolation and characterisation of four farnesyl diglycosides, crenulatosides A, B, C and D, along with three known flavonol glycosides and one known trimeric proanthocyanidin possessing a doubly linked structure. The structures of these compounds were determined on the basis of spectroscopic studies and chemical evidence. The ethanol and ethyl acetate extracts of the leaves exhibited no cytotoxic activity and no inhibition of acetylcholinesterase.     

Indole and carbazole alkaloids from Glycosmis montana with weak anti-HIV and cytotoxic activities

A diprenylated indole, (E)-3-(3-hydroxymethyl-2-butenyl)-7-(3-methyl-2-butenyl)-1H-indole (1), and six known carbazole alkaloids were isolated from the twigs and leaves of Glycosmis montana Pierre (Rutaceae). Their structures were determined on the basis of analysis of spectral evidence including 1D and 2D NMR and MS. The alkaloids (1-3) exhibited weak to moderate take in vitro inhibitory activity against HIV replication in C8166 cells, and they (as well as carbalexine A and B) had cytotoxic activity against the human leukaemia cell line CCRF-CEM.     

Albizosides D and E, two new cytotoxic triterpene saponins from Albizia chinensis

Two oleanane-type triterpene saponins, named albizosides D and E (1 and 2), together with a known compound, Julibroside J₈ (3), were isolated from the stem bark of Albizia chinensis. The structures of compounds 1 and 2 were established by 1D, 2D NMR experiments, and chemical methods, and they showed moderate cytotoxic activity against a small panel of human tumor cell lines.     

Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent

Spinal-Z, a methanolic mixture of dried powdered seeds of Peganum harmala Linn. and leaf of Dracocephalum kotschyii Boiss. is an Iranian ethno-medical remedy. It has been used for the treatment of various types of cancer for many years. To evaluate the use of Spinal-Z in treatment of cancer, we examined its effects against a panel of malignant cell lines and tumors induced in mice. The in vitro antiproliferative activities of Spinal-Z, the seed extract of P. harmala and the leaf extract of D. kotschyii were determined using the MTT assay. The concentration of the agent required to inhibit cell growth by 50% (IC50) was estimated. In addition, the anti-tumor activities of the remedy and its constituents were investigated. Viability of cells treated with Spinal-Z and its components decreased in a dose dependent manner. Spinal-Z and its components showed cytotoxic effects against all cell lines tested. The leaf extract of D. kotschyii showed a greater preferential cytotoxic effect than the seed extract of P. harmala and Spinal-Z, on all cell lines tested. Harmine showed cytotoxicity against HL60 and K562 cell lines. This could explain the cytotoxic effect of P. harmala on these cells. The leaf extract of D. kotschyii was able to inhibit tumor proliferation in mice. The active ingredient in the leaf extract of D. kotschyii appears to be a flavone identified as xanthomicrol. Xanthomicrol was able to inhibit proliferation of a number of malignant cells. The cytotoxic effects of xanthomicrol were more selective towards malignant cells than doxorubicin.     

Miscellaneous terpenoid constituents of Abies nephrolepis and their moderate cytotoxic activities

Three monoterpenoids and two triterpenoids were isolated from Abiesnephrolepis together with 53 known terpenoids. The structures of the compounds were established by 1D and 2D NMR spectroscopy. The absolute configuration of 3-hydroxycamphane-2-carboxylic acid was established as (1S,2R,3S,4R) by Cu-Kα X-ray crystallography. All 58 isolates were tested for cytotoxic activity against four tumor cells viz. A549 (human lung adenocarcinoma), Colo205 (colon adenocarcinoma), QGY-7703 (human hepatoma) and THP-1 (human monocytic leukemia). α-Cadinol exhibited the best effects on A549, Colo205 and QGY-7703 with IC₅₀ values of 8.6, 8.1 and 4.6 μg/mL, respectively.     

Asperpyrone D and other metabolites of the plant-associated fungal strain Aspergillus tubingensis

Bioactivity-guided fractionation of a cytotoxic extract of Aspergillus tubingensis, a fungal strain occurring in the rhizosphere of the Sonoran desert plant, Fallugia paradoxa, afforded a dimeric naphtho-gamma-pyrone asperpyrone D, nine known naphtho-gamma-pyrones, funalenone, and the cytotoxic cyclic penta-peptide, malformin A1.     

9,10-seco-9,19-Cyclolanostane arabinosides from the roots of Actaea podocarpa

Seven 9,10-seco-9,19-cyclolanostane arabinosides, named podocarpasides A-G (1-7), were isolated from the roots of Actaea podocarpa DC., a species closely related to black cohosh (a well known dietary supplement). Their structures were determined with the help of spectroscopic data including extensive 2D NMR spectroscopy. The isolates were found inactive, when tested for cytotoxic, estrogenic, and antioxidant activities in cell based assays. They were also tested for anticomplement activity against the classical pathway of complement system and only podocarpaside C (3) inhibited modest complement activity with an IC50 value of 200 microM.     

Gerronemins A-F, cytotoxic biscatechols from a Gerronema species

The gerronemins A-F (1-6) were isolated as the cytotoxic components of an extract of a Gerronema species detected in a screening for new cytotoxic metabolites from basidiomycetes. Their structures were elucidated by spectroscopic techniques, and they are composed of a C12-C16 alkane or alkene substituted at both ends by 2,3-dihydroxyphenyl groups. The gerronemins blocked the inducible expression of a hCOX-2 and iNOS promoter driven reporter gene with IC50-values of 1-5 microg/ml. In addition, cytotoxic activities were observed which were due the inhibition of cellular macromolecular syntheses.     

A sugar ester and an iridoid glycoside from Scrophularia ningpoensis

From cytotoxic extracts of the roots of Scrophularia ningpoensis Hemsl. (Scrophulariaceae) a new sugar ester, ningposide D (3-O-acetyl-2-O-p-methoxycinnamoyl-alpha(beta)-L-rhamnopyranose) (1) and a new iridoid glycoside, scrophuloside B4 (6-O-(2'-O-acetyl-3'-O-cinnamoyl-4'-O-p-methoxycinnamoyl-alpha-L-rhamnopyranosyl) catalpol) (2) along with known compounds: oleanonic acid (3), ursolonic acid (4), cinnamic acid (5), 3-hydroxy-4-methoxy benzoic acid (6), 5-(hydroxymethyl)-2-furfural (7) and beta-sitosterol (8) were isolated. The structures of the new compounds were elucidated by spectral data (1, 2D NMR, EI, HRESI-MS and MS/MS). Oleanonic acid (3) and ursolonic acid (4) were found to be cytotoxic against a series of human cancer cell lines with IC50=4.6, 15.5 microM on MCF7; 4.2, 14.5 microM on K562; 14.8, 44.4 microM on Bowes; 24.9, 43.6 microM on T24S; 61.3, 151.5 microM on A549, respectively. Beta-sitosterol (8) inhibited Bowes cells growth at IC50=36.5 microM. Scrophuloside B4 (2) showed activity on K562 and Bowes cells at IC50=44.6, 90.2 microM, respectively.