Bibenzyl and phenolic glycosides from Pterospermum heterophyllum

A new bibenzyl, heterophyllic acid (1), and three new phenolic glycosides, heterophylloside A–C (2–4), along with two known phenolic glycosides oldhamioside (5) and 6′-O-vanilloylisotachioside (6) were isolated from Pterospermum heterophyllum. The structures of these compounds were elucidated on the basis of 1D, 2D NMR, MS spectroscopic analysis, and chemical methods. Their cytotoxic activities against KB and MCF-7 cancer cell lines were evaluated. Compound 2 showed significant cytotoxic activities.     

Iridoids and lignans from Valeriana officinalis L. and their cytotoxic activities

Two new iridoids (1 and 2), one new lignan (3) together with one known iridoid (4) and twelve known lignans (5－16) were obtained from the roots of Valeriana officinalis L. (V. officinalis). The structures were determined using IR, MS, ¹D and ²D NMR spectroscopy and the absolute configurations of the new structures were deduced by ECD experiments. All of the isolated compounds were assayed for their cytotoxic activities against three tumour cell lines (A549, HCT116 and SW620) and the results showed that compounds 9 and 10 showed cytotoxicities against A549 cells, compounds 9 and 11 showed cytotoxicities against SW620 cells and compound 10 showed cytotoxicities against HCT116 cells.     

Novel cassane diterpenes from the seeds of Caesalpinia minax

Three new cassane diterpenes, sucutiniranes G (1), H (2) and I (3) were isolated from the seeds of Caesalpinia minax Hance. Their structures were elucidated by various spectroscopic techniques (UV, IR, MS, CD, 1D and 2D NMR). All compounds were evaluated for cytotoxic activities against MCF-7 and HepG-2 human cancer cell lines.     

Bioactive triterpenoids from twigs of Betula schmidtii

Investigation of the MeOH extract of Betula schmidtii twigs resulted in the isolation and identification of three new triterpenoids (1–3), along with ten known ones (4–13). The structures of new compounds (1–3) were elucidated by spectroscopic methods, including 1D, 2D NMR (¹H and ¹³C NMR, COSY, HSQC, HMBC, and NOESY), HR-MS, and chemical methods. All the isolated compounds were evaluated for their cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines. Compound 11 exhibited potent cytotoxic activities against four cell lines, and compounds 5 and 13 significantly induced nerve growth factor secretion in a C6 rat glioma cell line. Their anti-inflammatory effects were also assessed by measuring nitric oxide production in lipopolysaccharide–activated BV-2 cells. Compounds 7 and 12 displayed potent inhibition of nitric oxide production, without significant cell toxicity.     

Bioactive styryllactones,two new naphthoquinones and one new styryllactone,and other constituents from Goniothalamus scortechinii

Two new naphthoquinones, goniothalaminone A (1) and B (2), and a new styryllactone, (?)-8-epi-9-deoxygoniopypyrone acetate (12) together with one known naphthoquinone (3), one known indolequinone (4), one known 1-azaanthraquinone (5), six known styryllactones (6–11) and one known sesquiterpene (13) were isolated from the roots and leaves of Goniothalamus scortechinii. The structures of the new compounds were elucidated by spectroscopic analysis and of the known compounds by comparison of their physical, UV, IR, ¹H and ¹³C NMR data with those of published compounds. Antiplasmodial, antimycobacterial and cytotoxic activities of the styryllactones were evaluated. Compounds 6–10 exhibited cytotoxic against human cancer cell lines, KB, BC and NCI-H187 with IC₅₀ values ranging from 0.13 to 11.7 μg/ml.     

Cytotoxic quassinoids from Ailanthus altissima

Two new quassinoids, altissinol A (1) and B (7), together with 12 known quassinoids, were isolated from the 95% ethanol extract of the barks of Ailanthus altissima. The structures of the new compounds (1 and 7) were determined on the basis of the spectroscopic methods including UV, IR, HR-ESI-MS, 1D and 2D NMR. The cytotoxic potential of all isolates were evaluated in vitro against three human hepatoma cell lines. Quassinoids 1–7 displayed potent cytotoxic activities against human hepatoma Hep3B and HepG2 cell lines. Interestingly, compounds 2, 3, and 5 exhibited cytotoxic activity against multidrug resistance HepG2/ADM cell line with IC₅₀ value 4.3-fold more sensitive to Doxorubicin (DOX).     

Two new compounds from Trigonostemon heterophyllus

Phytochemical investigation on the stems of Trigonostemon heterophyllus led to the isolation of a new diterpene, trigonoheterene (1), and a new naphthoquinone, trigonoheterone (2), together with two known compounds, 3,4-seco-sonderianol, (3) and trigonochinene E, (4). Their structures were determined by spectroscopic techniques (UV, IR, MS, 1D and 2D NMR). All compounds were evaluated for cytotoxic activities and antibacterial activities.     

New ceramides and isoflavone from the Egyptian Iris germanica L. rhizomes

Two new ceramides, irisamides A (1) and B (2), together with a new isoflavone, iridin S (3) have been isolated from the MeOH extract of the rhizomes of Iris germanica L. (Iridaceae). Their structures were established by UV, IR, HRESIMS, 1D and 2D NMR experiments, in addition to comparison with literature data. The isolated compounds were tested for their cytotoxic activity against different cancer cell lines.     

Steroidal saponins with cytotoxic activities from the rhizomes of Anemarrhena asphodeloids Bge.

Two new steroidal saponins, named timosaponin R (1) and S (2), together with seven known compounds (3-9) were isolated from the rhizomes of Anemarrhena asphodeloides Bge. Their structures were elucidated on the basis of NMR spectroscopy and mass spectrometry. All the compounds were evaluated for cytotoxic activities against the four human cancer cell lines MCF7, SW480, HepG2 and SGC7901 in vitro. Compounds 7-9 showed moderate activities against all the cell lines.     

Cytotoxic indole diketopiperazines from the deep sea-derived fungus Acrostalagmus luteoalbus SCSIO F457

Two new indole diketopiperazines, namely luteoalbusins A–B (1–2), along with eight known ones (3–10), were isolated from the fungus Acrostalagmus luteoalbus SCSIO F457 originated from deep-sea sediment. Their structures were determined by 1D/2D NMR, MS, and CD data analyses. Each of these compounds was evaluated for their cytotoxic activities against SF-268, MCF-7, NCI-H460, and HepG-2 cell lines, and compounds 1–5 showed significant cytotoxicties against all four cancer cell lines. Moreover, new compounds 1 and 2 had more potent cytotoxicity than the other ones and cisplatin.     

Three new terpenoids from the Eupatorium chinense

Three new terpenoids compounds (1–3) were obtained from ethyl acetate fraction, which was yielded from Eupatorium chinense’s ethanol extract. Their structures were determined on the basis of 1D and 2D NMR spectroscopy, including ¹H-¹H COSY, HMBC, HSQC and NOESY experiments. All of the isolated compounds were tested in vitro for their cytotoxic activities against the HepG₂, HGC-27 and MDA-MB-231 cancer cell lines.     

The cytotoxicity of 8-O-4′ neolignans from the seeds of Crataegus pinnatifida

Nine new 8-O-4′ neolignans, named pinnatifidanin B I–IX (1–9), together with 9 known analogs (10–18) were isolated from the seeds of Crataegus pinnatifida. The structures of 1–18 were determined by spectroscopic methods, including 1D, 2D NMR, CD and HRESIMS analysis. Compounds 8–11, 17 and 18 displayed potent cytotoxic activities against human cancer cell lines, and most interestingly, none of the 6 compounds displayed inhibitory activity against human lung cell line (Mrc5). The 6 cytotoxic compounds are considered to be potential as antitumor agents, which could significantly inhibit the cancer cell growth in a dose-dependent manner and are probably safer than positive control drug.     

Tomensides A–D,new antiproliferative phenylpropanoid sucrose esters from Prunus tomentosa leaves

To search for novel cytotoxic constituents against cancer cells as lead structures for drug development, four new 3-phenylpropanoid-triacetyl sucrose esters, named tomensides A–D (1–4), and three known analogs (5–7) were isolated from the leaves of Prunus tomentosa. Their structures were elucidated by spectroscopic analyses (1D, 2D NMR, CD and HRESIMS). The cytotoxic activities of all isolates against four human cancer cell lines (MCF-7, A549, HeLa and HT-29) were assayed, and the results showed that these isolates displayed stronger inhibitory activities compared with positive control 5-fluorouracil. Tomenside A (1) was the most active compound with IC₅₀ values of 0.11–0.62 μM against the four tested cell lines. The structure–activity relationship (SAR) of the isolates was also discussed. The primary screening results indicated that these 3-phenylpropanoid-triacetyl sucrose esters might be valuable source for new potent anticancer drug candidates.     

Ecdysteroids from the flowers of Aerva javanica

Four new ecdysteroids (1–4), along with three known steroids, β-ecdysone (5), 5-β-2-deoxyintegristerone A (6) and 24-epi-makisterone A (7) (Fig. 1), were isolated from the methanolic extract of the flowers of Aerva javanica by using normal and reverse phase chromatography. The structures of the new compounds (1–4) were determined due to 1D (¹H and ¹³C), 2D NMR (HSQC, HMBC, COSY, NOESY) techniques and high resolution mass spectrometry (HREIMS). The known compounds (5–7) were characterized based on the 1D NMR spectroscopy and mass spectrometry and by comparison with the literature values. All isolates were evaluated for their inhibitory activities against enzymes acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and lipoxygenase (LOX).     

Steroidal saponins with cytotoxic activity from the rhizomes of Paris polyphylla var. yunnanensis

Two previously unreported spirostanol saponins, dianchonglouosides A and B (1 and 2), along with 7 known steroidal saponins (3–9) were isolated from the rhizomes of Paris polyphylla var. yunnanensis. Their structures were elucidated by extensive spectroscopic analysis (MS, 1D, and 2D NMR), and chemical methods. The cytotoxic activities of the isolated compounds 1–9 were also evaluated against two human cancer cell lines (HEK293 and HepG2). The results showed that compound 7 had the strongest cytotoxic activity against the two cancer cell lines with the IC₅₀ values of 0.6 and 0.9 μM, respectively.     

Cytotoxic prenylated xanthone and coumarin derivatives from Malaysian Mesua beccariana

Our recent research on the phytochemical constituents of the stem bark of Mesua beccariana gave one new xanthone, beccarixanthone T (1) and one new coumarin, beccamarin T (2) together with three known xanthones mesuarianone (3), mesuasinone (4), 1,5-dihydroxyxanthone (5) and four known terpenoids, friedelin (6), stigmasterol (7), beta-sitosterol (8) and gamma-sitosterol (9). The structures of these compounds were elucidated and determined using spectroscopic techniques such as NMR and MS. The cytotoxic activities of compounds 1-4 as well as the crude extracts were tested against two cancer cell lines, Hep G2 (liver cancer cell line) and HT-29 (colon cancer cell line) using MTT assays. Mesuarianone (3) gave a significant activity on the HT-29 cell line while mesuasinone (4) gave moderate activity against HT-29 cell line.     

Penicillivinacine,antimigratory diketopiperazine alkaloid from the marine-derived fungus Penicillium vinaceum

In the course of our ongoing search for biologically active compounds from marine-derived fungi, the organic extract of the marine-derived fungus Penicillium vinaceum species was investigated. Seven compounds including a new alkaloid with an unprecedented carbon skeleton, penicillivinacine (1) together with six previously reported ones were isolated. The known compounds were identified as indol-3-carbaldehyde (2), α-cyclopiazonic acid (3), terretrione A (4), brevianamide F (5), cyclo-d-Trp-l-pro (6) and citreoisocoumarin (7). Their structures were established by different spectroscopic data including 1D (¹H NMR and ¹³C NMR) and 2D NMR (COSY, HSQC, HMBC and NOESY) studies as well as high-resolution mass spectral data. The isolated compounds were evaluated for their antimigratory activity against the human breast cancer cell line MDA-MB-231 as well as antimicrobial activities against different pathogens. Compounds 1 and 4 displayed potent antimigratory activities against the highly metastatic triple negative human breast cancer cells MDA-MB-231 with IC₅₀ of 18.4 and 17.7 μM, respectively. Furthermore, compounds 1–7 showed different antimicrobial activities.     

Cytotoxic polyhydroxy serratene triterpenoids from Lycopodium complanatum

Phytochemical investigation of the 70% aqueous EtOH extract of Lycopodium complanatum led to six new polyhydroxy serratene triterpenoids (serrat A-F, 1–6), along with a known analogue (7). Their structures and configurations were elucidated by data analysis of HRESIMS, 1D and 2D NMR, in combination with comparisons of reported experimental spectroscopic data. All the isolates were evaluated cytotoxic activities against HepG2 cells, MCF-7 cells and series human lung cancer cell lines A549, Calu-6, NCI-H441, NCI-H226 and NCI-H1975. The results indicated that certain compounds inhibited proliferation of human cancer cells. Moreover, all compounds possessed selective cytotoxic activities on MCF-7 cells. Further, possible biosynthesis pathways of these compounds were proposed.     

Prenylated flavonol glycosides from Epimedium grandiflorum: Cytotoxicity and evaluation against inflammation and metabolic disorder

Two new prenylated flavonol glycosides, epimedigrandiosides A and B (1 and 2), and 28 previously known compounds including prenylated flavonol derivatives, flavonol glycoside, megastigmanes, phenyl alkanoids, sesquiterpenoid glycoside, lignan, and hexene glucoside were isolated from the methanol extract of Epimedium grandiflorum. Structure elucidation was achieved by means of spectroscopic and spectrometric techniques including 1D and 2D NMR and HRESIMS. The absolute configuration of sugars was determined by chemical methods Structure elucidation of 3‴-carbonyl-2″-β-l-quinovosyl icariin (19) was not previously described, so its ¹H and ¹³C NMR data were reported for the first time. The methanol extract and the isolated compounds were evaluated for their activity towards several targets related to inflammation and metabolic disorder including NF-κB, iNOS, PPARα and PPARγ. Moreover, their cytotoxic activity against four cancer cell lines (SK-MEL, KB, BT-549, SK-OV-3) and two noncancerous kidney cell lines (LLC-PK1 and Vero) were also evaluated.     

Illigerones A and B,two new long-chain secobutanolides from Illigera henryi W. W. Sm.

Two new long-chain secobutanolides, illigerones A (1) and B (2), together with five known compounds, actinodaphnine (3), cryptodorine (4), β-sitosterol (5), daucosterol (6), and stigmasterol (7) were isolated from Illigera henryi W. W. Sm. The structures of 1 and 2 were identified by HRESIMS, EIMS, 1D/2D NMR, and electronic circular dichroism (ECD) spectra. Compound 1 exhibited the moderate cytotoxic activities against five tumour cells. This is the first report of secobutanolides isolated from plants of Hernandiaceae.