Chemical constituents and cytotoxic activity from the wood-decaying fungus Xylaria sp. SWUF08-37

Abstract

A new cyclic pentapeptide, pentaminolarin (1), and a new cytochalasin, xylochalasin (2), along with thirteen known compounds (3–15) were isolated from the wood-decaying fungus Xylaria sp. SWUF08-37. The absolute configurations of 1 were determined by a combination of Marfey’s method and TDDFT ECD calculation and the absolute configurations of 2 were established by TDDFT ECD calculation. Compound 12 showed moderate cytotoxicity against HeLa (IC₅₀?=?19.60?µg/mL), HT29 (IC₅₀?=?17.31?µg/mL), HCT116 (IC₅₀?=?14.28?µg/mL), MCF-7 (IC₅₀?=?15.38?µg/mL), and Vero (IC₅₀?=?24.97?µg/mL) cell lines by MTT assay. Compounds 1 and 2 showed slight cytotoxicity against all tested cancer cell lines.     

Anti-inflammatory activity of saponins from roots of Impatiens parviflora DC.

Abstract

Two triterpene saponins (IPS-1, IPS-2) for the first time were isolated from the roots of Impatiens parviflora DC. (Balsaminaceae). Their anti-inflammatory activity was evaluated by means of two in vitro models: anti-hyaluronidase and anti-denaturation assays. Both saponins were shown to be potent hyaluronidase inhibitors that affect the enzyme in a dose-dependent manner. The anti-hyaluronidase effect of IPS-2 (IC₅₀?=?286.7?µg/mL) was higher than that of the reference drug: escin (IC₅₀?=?303.93?µg/mL). Both saponins protected bovine serum albumin from heat-induced denaturation in a dose-dependent manner. IPS-1 demonstrated higher anti-denaturation effect (IC₅₀?=?86.7?µg/ml) than IPS-2 (IC₅₀?=?109.76?µg/mL) or the standard drug: acetylsalicylic acid (IC₅₀?=?262.22?µg/mL). In conclusion, potent activity of IPS-1, IPS-2 in both in vitro assays shows that saponins from I. parviflora have anti-inflammatory activity. The obtained results allow to suggest that such compounds may be beneficial in inflammatory conditions, especially associated with excessive degradation of hyaluronic acid.     

Chemical composition,antioxidant and antiproliferative activities of essential oil from rhizome and leaves of Curcuma mutabilis Škorničk., M. Sabu & Prasanthk., endemic to Western Ghats of India

Abstract

Hydro-distilled essential oils, from fresh rhizomes and leaves of Curcuma mutabilis ?korni?k., M.Sabu & Prasanthk., characterized by GC–MS revealed the presence of thirty three and twenty three compounds therein respectively. Whilst estrone methyl ether (3-Methoxyestra-1,3,5(10)-trien-17-one) was the major component in rhizome oil (47.35%), sesquiterpene hydrocarbons predominated as the major group (63.92%) in leaf oil with a higher preponderance of β-caryophyllene (25.48%), β-farnesene (19.47%) and α-humulene (11.01%). Weak antioxidant activities observed in these oils determined by DPPH and ABTS methods were apparently influenced both by the oil composition and the assay conditions. Rhizome oil showed higher antiproliferative activity than leaf oil against leukemic K562 (IC₅₀-6.8µg/mL) and colorectal HCT116 (IC₅₀-8.5µg/mL) cancer cell lines. This first report reveals composition and biological activities of essential oils from C. mutabilis.     

Chemical characterization of constituents from Polygonatum cyrtonema Hua and their cytotoxic and antioxidant evaluation

Abstract

Twenty-four compounds were isolated from the roots of Polygonatum cyrtonema Hua, including a new octopamine dimer, named trans-bis(N-feruloyl)octopamine (1). The structure was established on the basis of spectroscopic and chemical methods. All the extracts and compounds were evaluated for cytotoxic and antioxidant activities by using MTT and chemiluminescence assay. The extracts showed activity against MCF-7 and HepG-2 cell lines from IC₅₀ 0.30 to 1.01 mg mL^?1. Compound 3 exhibited activity against HepG-2 cell lines with IC₅₀ 8.99?μM. Compound 7 exhibited activity against Hela cell lines with IC₅₀ 2.53?μM and BGC-823 cell lines with IC₅₀ 7.77?μM. Moreover, compound 7 showed antioxidant with IC₅₀ 12?µM compared to the positive control with IC₅₀ 77?µM. Compound 16 exhibited activity against HepG-2 cell lines with IC₅₀ 1.05?μM and MCF-7 cell lines with IC₅₀ 1.89?μM. These results indicated that this plant might be potential in natural medicine and healthy food.     

Antiglycation,antioxidant, and cytotoxic activities of Uvaria chamae root and essential oil composition

Abstract

Uvaria chamae (Annonaceae), is an essential oil bearing plant; the root is acclaimed as an effective remedy for folkloric diabetic therapy. The root extracts were evaluated for composition, antiglycation, antioxidant, and cytotoxicity. Flavonoids, cardiac glycosides, and tannins were relatively high in the alcohol extract; benzyl benzoate (23.3%), dimethoxy-p-cymene (14.2%), τ-cadinol (12.1%), and methyl thymol (8.7%) predominated the constituents identified by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The ethanol extract demonstrated significant antiglycation activity (IC₅₀, 1.12?mg/mL), and cytotoxicity to brine shrimp (LC₅₀, 25.01?µg/mL). The extract (IC₅₀, 8.0?µg/mL; absorbance 0.531, 100?µg/mL) also exhibited better antioxidant effects compared with the essential oil (IC₅₀, 50.0?µg/mL; absorbance 0.292, 100?µg/mL) using 2,2-diphenyl-1-picrylhydrazyl radical and ferric reducing power assays respectively. U. chamae root possess antiglycation effect, and may also reduce oxidative stress in patients with diabetes; its antiglycation effect, oil composition, and cytotoxicity are reported for the first time.

     

Reaction of 2-imino-2H-chromene-3-carboxamide with some phosphorus esters: Synthesis of some novel chromenes containing phosphorus heterocycles and phosphonate groups and their antioxidant and cytotoxicity properties

Abstract

Novel chromenyl α-aminophosphonic acid 4 and dialkyl chromenyl phosphonate 6 have been obtained. In addition, some novel types of chromene fused with phosphorus heterocycles such as chromeno[4,3-c][1,2]azaphospholes 5 and 7, chromeno[2,3-d][1,3,2]diazaphosphinine 8 and 1,2-oxaphosphinino[3,4-c]pyridine 10 have been synthesized. The methodology depended on treatment of 2-imino-2H-chromene-3-carboxamide (1) with some phosphorus esters. The synthesized compounds were evaluated for antioxidant and cytotoxic activities. Among the synthesized compounds, compound 5 exhibited the most antioxidant activity with IC₅₀ = 2.8?μg/mL in comparison with ascorbic acid as standard antioxidant. Also, compound 5 had significant cytotoxic effects against four cancer cell lines. Its IC₅₀ values ranged between 4.96 and 7.44?μg/mL in comparison to doxorubicin (IC₅₀ = 0.426–0.493?μg/mL).     

Rotenoid and isoflavone metabolites from an antioxidant seed extract of Dalbergia lanceolaria subsp. paniculata (roxb.) thoth

Abstract

A new rotenoid named 12-O-methylrotenolol along with five known rotenoid and isoflavone metabolites were isolated from the seeds of Dalbergia lanceolaria subsp. paniculata, collected from Egypt. The structures of these compounds were identified by physical and spectroscopic data measurements ([α]_D, UV, 1D- and 2D-NMR and MS). The methanol extract of the seeds exhibited strong antioxidant activity with IC₅₀ value 0.7?µg/µl against DPPH radical, in respect to quercetin as antioxidant reference (IC₅₀ 1.5?μM), while the tested compounds from this extract showed weak activities with IC₅₀ values ranged from 19.6 to 33.0?µM.     

New chemical constituents from the Piper betle Linn. (Piperaceae)

The phytochemical investigation of chloroform extract from Piper betle var. haldia, Piperaceae, leaves has resulted in the isolation of two new chemical constituents which were identified as 1-n-dodecanyloxy resorcinol (H1) and desmethylenesqualenyl deoxy-cepharadione-A (H4), on the basis of spectroscopic data 1D NMR (¹H and ¹³C) and 2D NMR (¹H-¹H COSY and HMBC) as well as ESI-MS, FT-IR and HR-ESI-MS analyses. Compounds H1 and H4 showed excellent antioxidant DPPH free radical scavenging activity with IC₅₀ values of 7.14 μg/mL and 8.08 μg/mL compared to ascorbic acid as a standard antioxidant drug with IC₅₀ value of 2.52 μg/mL, respectively. Evaluation of cytotoxic activity against human hepatoma cell line (PLC-PRF-5) showed moderate effect with the GI₅₀ values of 35.12 μg/mL for H1, 31.01 μg/mL for H4, compared to Doxorubicin^® as a standard cytotoxic drug with GI₅₀ value of 18.80 μg/mL.     

Two new bioactive triterpenoids from the roots of Colubrina asiatica

Abstract

Two new ceanothane triterpenes, 3,7-O,O-dibenzoyl ceanothic acid methylester (1) and 3-O-acetyl-7-O-benzoyl ceanothic acid methylester (2), along with nine known compounds (3–11), were isolated from the roots of Colubrina asiatica. The isolated compounds were identified by spectroscopic evidence. Compounds 1 and 2 showed antimalarial activity against Plasmodium falciparum with IC₅₀ values of 4.67 and 3.07?µg/mL, respectively. Compound 2 also showed antimycobacterial activity against Mycobacterium tuberculosis (MIC 6.25?µg/mL). In addition, compounds 1, 2, 10 and 11 showed cytotoxicity against three cancer cell lines (KB, NCI-H187 and MCF-7) with IC₅₀ values ranging from 8.32 to 46.72?µg/mL.     

Synthesis and in vitro anti-proliferative capabilities of steroidal thiazole and indole derivatives

Derivatives (1–15) of steroidal and indole class were synthesized using different strategies. These compounds were characterized by ¹H NMR spectroscopy and EI-MS, respectively. The synthetic derivatives were examined for their cytotoxic effects on human adenocarcinoma cells (HCT-116) using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and morphometric analysis. The cytotoxic effects of all the compounds were observed after 48 h treatment and it was found that out of fifteen, four compounds 1, 2, 3, and 14 showed inhibitory action on the cancer cells. We have calculated the IC₅₀ values for compounds 1, 2, 3, and 14 which were 22.50 µg/mL, 55.65 µg/mL, 21.35 µg/mL and 58.50 µg/mL, respectively. The compounds 3 (IC₅₀ = 21.35 µg/mL) and 1 (IC₅₀ = 22.50 µg/mL) showed highest inhibitory activities as compared to compounds 2 (IC₅₀ = 55.65 µg/mL) and 14 (IC₅₀ = 58.50 µg/mL). These results suggested that steroidal thiazole and indole derivatives are potent lead molecules having strong anti-cancer proliferative capabilities.     

In vitro cytotoxicity evaluation of thiourea derivatives bearing Salix sp. constituent against HK-1 cell lines

Abstract

In searching for drugs from natural product scaffolds has gained interest among researchers. In this study, a series of twelve halogenated thiourea (ATX 1-12) via chemical modification of aspirin (a natural product derivative) and evaluated for cytotoxic activity against nasopharyngeal carcinoma (NPC) cell lines, HK-1 via MTS-based colorimetric assay. The cytotoxicity studies demonstrated that halogens at meta position of ATX showed promising activity against HK-1 cells (IC₅₀ value ≤15?µM) in comparison to cisplatin, a positive cytotoxic drug (IC₅₀ value =8.9?±?1.9?µM). ATX 11, bearing iodine at meta position, showed robust cytotoxicity against HK-1 cells with an IC₅₀ value of 4.7?±?0.7?µM. Molecular docking interactions between ATX 11 and cyclooxygenase-2 demonstrated a robust binding affinity value of ?8.1?kcal/mol as compared to aspirin’s binding affinity value of ?6.4?kcal/mol. The findings represent a promising lead molecule from natural product with excellent cytotoxic activity against NPC cell lines.     

Perisomalien A,a new cytotoxic scalarane sesterterpene from the fruits of Periploca somaliensis

Abstract

The CHCl₃ fraction of MeOH extract of Periploca somaliensis (family Asclepiadaceae) fruits afforded a new scalarane sesterterpene, namely perisomalien A (1), along with lupeol acetate (2), β-amyrin (3), cycloart-23Z-ene-3β,25-diol (4), and β-sitosterol-3-O-β-D-glucopyranoside (5). Their chemical structures were established by various spectroscopic analyses, in addition to comparison with the formerly reported data. Moreover, the cytotoxic activity of these metabolites was assessed towards MCF-7, HepG2, and HCT-116 tumour cell lines using sulforhodamine B (SRB) assay. Compound 4 showed the most potent cytotoxic profile with IC₅₀ 9.0?µM towards MCF-7, compared to doxorubicin (IC₅₀ 0.18?µM). Also, 1 and 4 possessed the most potent effect towards HepG2 with IC₅₀s 26.7 and 25.9?μM, respectively. In addition, all tested compounds showed cytotoxic effects with IC₅₀ values ranging from 19.9 to 39.3?µM against HCT-116.     

Antimicrobial secondary metabolites of an endolichenic Aspergillus niger isolated from lichen thallus of Parmotrema ravum

Abstract

A new 6-benzyl-γ-pyrone (1), named aspergyllone was isolated from the culture filtrates of an endolichenic fungus Aspergillus niger Tiegh, obtained from lichen thallus Parmotrema ravum (Krog & Swinscow) Serus, collected in India. 1 was isolated for the first time from an endolichenic fungus together with six other known metabolites identified as aurasperones A (2) and D (3), asperpyrone A (4), fonsecinone A (5), carbonarone A (6) and pyrophen (7). The compounds were tested against a panel of human, plant, food borne and fish pathogens. Aspergyllone showed strong selective antifungal activity against Candida parapsilosis (Ashford) Langeron & Talice, with an IC₅₀ of 52?µg/mL. Aurasperone A and pyrophen showed moderate to strong antimicrobial activity inhibiting seven different test pathogens, being pyrophen active with IC₅₀ ranging from 35 to 97?µg/mL.

     

Carbazole-pyranocoumarin conjugate and two carbazole alkaloids from the stems of Clausena excavata

A carbazole-pyranocoumarin conjugate, carbazomarin B (1), and two carbazole alkaloids, 6-methoxymukonidine (2) and 2-hydroxy-3-methoxycarbazole (3), together with 27 known compounds (4–30), were isolated from the stems of Clausena excavata. Their structures have been elucidated by spectroscopic analyses. Compound 2 showed moderate cytotoxicity to HuCCA-1, MOLT-3 and HepG2 cancer cell lines with IC₅₀ values of 15.09–28.50 μg/mL, but none to A549 cell line. Heptaphylline (6) and nordentatin (23) were found to show moderate cytotoxic activity against HepG2 cell line with IC₅₀ values of 12.33 and 11.33, respectively, while clausine K (27) exhibited strong cytotoxicity with IC₅₀ value of 1.05 μg/mL, better than a standard drug (etoposide, IC₅₀ 13.40 μg/mL).     

In vitro and in silico study of Aloe vera leaf extract against human breast cancer

Abstract

Aloe vera leaf contains some bioactive compounds that have a strong binding affinity toward estrogen receptor as compared to standard drug tamoxifen. In this study, we have found that the IC₅₀ of Aloe vera leaf extract against breast cancer cell line (MCF-7) is 23?µg/mL which is much lower than the IC₅₀ (332?µg/mL) of Aloe vera leaf extract against non-cancerous cell line (NIH-3T3). We have also calculated the total concentration of phenolic acid (385.662?µg/mL), flavonoids (160.402?µg/mL) and alkaloids (276.754?µg/mL) in Aloe vera leaf extract. The free radical scavenging activity of Aloe vera leaf extract is 67% to 89% (at 50 to 300?µg/ml). Our virtual molecular docking study suggests that bioactive compounds like Aloe-emodin (?8.8?Kcal/mol), 7-hydroxy-2,5 dimethylchromone (?7.5?Kcal/mol), Beta-sitosterol (?7.3?Kcal/mol) etc. have a greater binding affinity toward estrogen alpha receptor as compared to standard drug Tamoxifen (?6.4?Kcal/mol).

     

New p-terphenyl and benzoquinone metabolites from the bioluminescent mushroom Neonothopanus nambi

Abstract

Two new p-terphenyls, neonambiterphenyls A and B (1–2), a new benzoquinone, neonambiquinone A (3), together with six known sesquiterpenes (4–9), were isolated from the bioluminescent mushroom Neonothopanus nambi PW3. The isolated compounds were identified by mass, IR and spectroscopic analyses (1D and 2D NMR). Compounds 1–3 and 5–7 showed cytotoxicity against cancer cell lines such as KB, NCI-H187 and MCF-7 with IC₅₀ values ranging from 1.45 to 49.31?µg/mL. In addition, compounds 1 and 5 showed cytotoxicity against Vero cells with IC₅₀ values of 38.72 and 32.90?µg/mL, respectively.     

Cytotoxic,antitumour-promoting and inhibition of protein denaturation effects of flavonoids,isolated from Potentilla evestita Th. Wolf

This study was designed to evaluate the isolated flavonoids (chrysin 1, and umbelliferone 2) from Potentilla evestita for cytotoxic, antitumour-promoting and inhibition of protein denaturation activities. The results showed marked cytotoxic effect of compounds 1 and 2 in brine shrimp cytotoxic assay at various concentrations with LD₅₀ of 34.5 and 31.8 mg/mL, respectively. In Epstein–Barr-virus early antigen activation assay, both compounds 1 and 2 illustrated significant antitumour-promoting effect with IC₅₀ values of 462 and 308 mol ratio/32 pmol TPA, respectively. The cytotoxic and antitumour-promoting effects of compounds were strongly supported by inhibition of protein denaturation activity with IC₅₀ of 119 and 112 μg/mL, respectively. In conclusion, both compounds possess strong cytotoxic, antitumour-promoting and inhibition of protein denaturation activities.     

In vitro solar protection factor,antioxidant activity,and stability of a topical formulation containing Benitaka grape (Vitis vinifera L.) peel extract

Abstract

A flavonoid enriched extract (FE) was obtained from grape peels, and in vitro SPF, antioxidant activity, and effects on cell viability of this extract were tested with the intent to develop a cosmetic product. A formulation was developed with the FE, and the stability of this mixture was evaluated in terms of pH, density, viscosity, and SPF (90-days). FE showed no cytotoxicity to human keratinocytes and an in vitro SPF of 18.56 (UV-spectrophotometry). Further, FE showed a UVA protection factor of 3.17?±?0.2, a critical wavelength of 318.0?±?0.1 and a UVA/UVB of 0.9. Antioxidant activity assays resulted in 92.08% and 86.85% of activity against DPPH and ABTS (IC₅₀ = 296.90?±?1.2?µg/mL and 643.13?±?0.9?µg/mL), respectively. Finally, SPF of formulation with FE was 12.45. Results from the in vitro SPF and product stability tests (especially storage under refrigeration), indicate that FE is a promising compound for use as an innovative sunscreen formulation.     

Synthesis,characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid

Three new ruthenium(II)-arene halido complexes, [(η⁶-p-cymene) RuX(L)] (1–3), were synthesized in a reaction of [(η⁶-p-cymene)RuX₂]₂ with 5-chloro-1H-benzimidazole-2-carboxylic acid (HL) in ethanol (X^– = Cl^– (1), Br^– (2), I^– (3)). The complexes were characterized by elemental analysis, mass spectrometry, IR, ¹H and ¹³C NMR spectroscopy. The cytotoxic activity of the ligand precursor and its ruthenium complexes was tested by MTT assay in human cancer cell lines: lung adenocarcinoma (A549), myelogenous leukemia (K562) as well as in one normal human fetal lung fibroblast cell line (MRC-5). The results show that ruthenium(II)-arene complexes possess enhanced cytotoxicity when compared to HL in the range of concentrations up to 300 µM. In terms of halido ligand substitution, cytotoxic activity toward A549 and K562 cell lines in 1–3 serie significantly increased (e.g., IC₅₀ values for K562: 1: 205.76 µM; 2: 174.77 µM; 3: 83.97 µM). All studied compounds were found to be ineffective toward MRC-5. Hydrolysis of 1–3 was followed by UV-vis spectroscopy at 25?°C, revealing ligand-substitution reactions at the Ru(II) center. Compounds 2 and 3 underwent rapid hydrolysis ranging from a few minutes for the aquation to ca. 20?min, confirming typical Ru-arene behavior in aqueous solutions.     

Design and synthesis of fluorescent symmetric bis-triazolylated-1,4-dihydropyridines as potent antibreast cancer agents

Herein, we report the synthesis of fluorescent 1,4-dihydropyridine-linked bis-triazoles (2a–2n) through Hantzsch synthesis by the condensation of o/m-chloro-substituted benzaldehyde, ethyl 3-oxo-4(prop-2-yn-1-yloxy)butanoate, and ammonium acetate in the presence of Ba(NO₃)₂ as a catalyst followed by the click reaction of resultant Hantzsch product (1) with various aromatic as well as aliphatic azides. All the synthesized compounds were well characterized by ¹H-NMR, ¹³C-NMR, FTIR, and HRMS spectral techniques. Antibreast cancer evaluation of all the synthesized derivatives revealed that the compounds 2f (IC₅₀?=?7?±?0.02?µM) and 2g (IC₅₀?=?5?±?0.03?µM) showed better anticancer activity (lower IC₅₀) than the standard drug tamoxifen (IC₅₀?=?11.2?±?0.01?µM) against breast carcinoma (MDA-MB-231) cell line. The synthesized compounds were also screened against normal human embryonic kidney (HEK-293) cell line and found to be nontoxic. The fluorescent nature and cytotoxicity assay of these newly synthesized hybrids recommend their utility in tumor cell imaging.