Soft coral, Sinularia sp. had been proven to inherit promising anti-cancer properties against variety of cancer. Current study, Sinularia sp. extract was introduced to Hepatocellular carcinoma (Hep 3B). Cell viability assay indicated the extract exhibit a dose and time dependent cytotoxicity. LC50 exhibited the lowest at 72 h post treatment estimated as 45.3 µg/mL. Morphological alterations including nuclear condensation, cytoplasm shrinkage and deformed cellular shape in treated Hep 3B were observable. Chemometric analysis revealed hydrophobic metabolites were significantly altered. Elevated vitamin D and derivatives tend to up-regulation Ca2+ and ROS subsequently triggering apoptosis. Dysregulated glycerolipids may suggest that they were biotransformed to compensate the needs of phospholipids during cell damage. Perturbation of sphingolipids, ceramide and carbohydrate-conjugated ceramides species increased the release of pro-apoptotic components reside within mitochondria and promote programmed cell death in treated Hep 3B. To conclude, MS-based metabolomics enabled the characterization of Sinularia sp. extract-induced cell death.
An undescribed conjugated sesquiterpene, amelicarin (1), together with nine known compounds (2-10) were isolated for the first time from Melicope latifolia. Their structures were elucidated by extensive NMR spectroscopic and mass spectrometric methods. The conjugated sesquiterpene possesses a unique 6/6/9/4-ring fused tetracyclic skeleton. The proposed biosynthesis pathway of 1 consist of three reactions steps: (1) polyketide formation, (2) cyclisation and (3) addition to form the conjugated sesquiterpenoid as final metabolite. Out of the ten isolated metabolites, amelicarin (1) showed activity against 4 cancerous cell lines namely SK-MEL skin cancer, KB oral cancer, BT-549 breast cancer, and SK-OV-3 ovarian cancer with IC50 values between 15 and 25 µg/mL.
A new chromanone acid, namely caloteysmannic acid (1), along with three known compounds, calolongic acid (2), isocalolongic acid (3) and stigmasterol (4) were isolated from the stem bark of Calophyllum teysmannii. All these compounds were evaluated for their cytotoxic and antioxidant activities in the MTT and DPPH assays, respectively. The structure of compound 1 was determined by means of spectroscopic methods including 1D and 2D NMR experiments as well as HR-EIMS spectrometry. The stereochemical assignment of compound 1 was done based on the NMR results and X-ray crystallographic analysis. The preliminary assay results revealed that all the test compounds displayed potent inhibitory activity against HeLa cancer cell line, in particular with compound 1 which exhibited the highest cytotoxic activity comparable to the positive control used, cisplatin. However, no significant antioxidant activity was observed for all the test compounds in the DPPH radical scavenging capacity assay.
A concise synthesis of the 1,4-diarylbutanoid-phenethylamine alkaloids, schwarzinicines A (1) and B (2), recently isolated from Ficus schwarzii, is reported. Key steps include a Claisen condensation to assemble the 1,4-diaryl-2-butanone intermediate, followed by a reductive amination to furnish the core skeleton of the target compounds. The overall synthetic yields of 1 and 2 were 9.1% and 3.5%, respectively. Synthetic (-)-1, (+)-1 and (±)-1 exhibited comparable vasorelaxation as natural schwarzinicine A on rat isolated aortic rings, suggesting that the observed vasorelaxant effects were not influenced by the chirality at C-2.
This review describes the morphological, phytochemical and pharmacological properties of Cinnamomum subavenium (Lauraceae). The plant grows wild in southern Mainland China, Burma, Cambodia, Taiwan, Malaysia and Indonesia. This plant is recorded as having long been used to treat carcinomatous swelling, stomach ache, chest pain, abdominal pain, hernia, diarrhoea, rheumatism, nausea and vomiting. This article enumerates an overview of phytochemical and pharmacological aspects that is useful to researchers for further exploration for the necessary development of this potential herb.
Investigation on the leaves of Melicope bonwickii (F.Muell.) T.Hartley (Rutaceae) afforded a new 7-(2'-hydroxy-3'-chloroprenyloxy)-4-methoxyfuroquinoline (1) together with the known 7-(2',3'-epoxyprenyloxy)-4-methoxyfuroquinoline (2), evellerine (3) kokusaginine (4) and an amide aurantiamide acetate (5). Compounds 1 and 2 showed significant activity against cervical cell lines (Hela).
Ipomoea carnea Jacq. is an important folklore medicinal plant, assessed for its underexplored biological potential. Antioxidant, cytotoxic, antiproliferative and polyphenolic profile of whole plant was evaluated using various techniques. Maximum extract recovery (29% w/w), phenolic [13.54 ± 0.27 μg GAE/mg dry weight (DW)] and flavonoid (2.11 ± 0.10 μg QE /mg DW) content were recorded in methanol-distilled water (1:1) flower extract. HPLC-DAD analysis quantified substantial amount of six different polyphenols ranging from 0.081 to 37.95 μg/mg extract. Maximum total antioxidant and reducing potential were documented in methanol-distilled water and acetone-distilled water flower extracts (42.62 ± 0.47 and 24.38 ± 0.39 μg AAE/mg DW) respectively. Ethanol-chloroform root extract manifested highest free radical scavenging (IC50 of 61.22 μg/mL) while 94.64% of the extracts showed cytotoxicity against brine shrimps. Ethanol leaf extract exhibited remarkable activity against THP-1 cell line (IC50 = 8 ± 0.05 μg/mL) and protein kinases (31 mm phenotype bald zone).
A new alkylated coumarin derivative, hexapetarin (1) along with three other xanthones, trapezifolixanthone (2), cudraxanthone G (3) and 1,3,7-trihydroxy-2,4-di (3-methyl-2-butenyl)xanthone (4), and four common triterpenoids, friedelin (5), stigmasterol (6), beta-sitosterol (7) and gamma-sitosterol (8) were isolated from the stem bark of Mesua hexapetala (Clusiaceae), a plant, native to Malaysia. The structures of these compounds were elucidated and determined using spectroscopic techniques such as NMR and MS. Anti-inflammatory activity assay indicated hexapetarin (1) to possess moderate anti-inflammatory activity, while 1,3,7-trihydroxy-2,4-di (3-methyl-2-butenyl)xanthone (4) gave very good activity.
Pure β-mangostin (1) was isolated from the stem bark of Garcinia mangostana L. One monoacetate (2) and five O-alkylated β-mangostin derivatives (3-7) were synthesised from β-mangostin. The structures of these compounds were elucidated and determined using spectroscopic techniques such as 1D NMR and MS. The cytotoxicities and anti-inflammatory activities of these five compounds against RAW cell 264.7 were tested. The structural-activity relationship studies indicated that β-mangostin showed a significant activity against the LPS-induced RAW cell 264.7, while the acetyl- as well as the O-alkyl- β-mangostin derivatives did not give good activity. Naturally occurring β-mangostin demonstrated comparatively better anti-inflammatory activity than its synthetic counterparts.
Species from the Genus Calophyllum are rich source for bioactive phenolic compounds such as coumarins and xanthones. Phytochemical study carried out on the plant, Calophyllum macrocarpum has led to the isolation of three known prenylated xanthones, ananixanthone (1), trapezifolixanthone (2) and 8-deoxygartanin (3) with two common triterpenoids, stigmasterol (4), and friedelin (5). The structures of these compounds were identified and determined using spectroscopic techniques such as NMR and MS. The cytotoxic activities of compounds 1 and 2 as well as the extracts were tested against HeLa Chang liver and HEK-293 cell lines. Compound 1 exhibited appreciable cytotoxicity with the IC50 value of 11.08 ± 3.09 µM against HeLa Chang liver cell line and moderate cytotoxicity against HEK-293 cell line while compound 2 showed limited toxicity against these two cell lines.
The antioxidant activities of crude extract fractions using Hexane, Chloroform, Ethyl Acetate, Butanol and Water of Clematis orientalis and Clematis ispahanica were investigated. 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay and the ferric reducing/antioxidant potential (FRAP) were used to evaluate the antioxidant capacity. The total phenolics were found to be 4.37-9.38 and 1.32-11.37 mg gallic acid equivalents (GAE)/g in different fractions for C. orientalis and C. ispahanica, respectively. The ethyl acetate fraction of C. orientalis and chloroform fraction of C. ispahanica showed the highest DPPH and FRAP activities at a concentration of 300 μg/mL. The predominant phenolic compounds identified by HPLC in C. orientalis were Resorcinol (603.5 μg/g DW) in chloroform fraction and Ellagic acid (811.7 μg/g DW) in chloroform fraction of C. ispahanica.
Two naturally occurring xanthones, ananixanthone (1) and β-mangostin (2), were isolated using column chromatographic method from the n-hexane and methanol extracts of Calophyllum teysmannii, respectively. The major constituent, ananixanthone (1), was subjected to structural modifications via acetylation, methylation and benzylation yielding four new xanthone derivatives, ananixanthone monoacetate (3), ananixanthone diacetate (4), 5-methoxyananixanthone (5) and 5-O-benzylananixanthone (6). Compound 1 together with its four new derivatives were subjected to MTT assay against three cancer cell lines; SNU-1, K562 and LS174T. The results indicated that the parent compound has greater cytotoxicity capabilities against SNU-1 and K562 cell lines with IC50 values of 8.97 ± 0.11 and 2.96 ± 0.06 μg/mL, respectively. Compound 5 on the other hand exhibited better cytotoxicity against LS174T cell line with an IC50 value of 5.76 ± 1.07 μg/mL.
Two new non-halogenated sesquiterpenes, snakeol (1) and snakediol (2) were isolated together with 9 known sesquiterpenes such as (R,Z)-33-dimethyl-5-methylene-4-(3-methylpenta-24-dien-1-yl)cyclohex-1-ene (3), palisol (4), pacifigorgiol (5), palisadin D (6), palisadin A (7), palisadin B (8), 5-acetoxypalisadin B (9), debromolaurinterol (10) and α-bromocuparane (11) from the red algae Laurencia snackeyi. The structures of two new metabolites were determined from their spectroscopic data (IR, 1D and 2D NMR and MS). Compounds 1, 2, 10 and 11 showed strong antibacterial activity against selected human clinical bacterial pathogens.
Three new halogenated tricyclic sesquiterpenes, omphalaurediol (1), rhodolaurenones B (2) and C (3) were isolated together with nine known haloganated sesquiterpenes such as rhodolaurenone A (4), rhodolaureol (5), isorhodolaureol (6), (-)-laurencenone D (7), elatol (8), (+)-deschloroelatol (9), cartilagineol (10), (+)-laurencenone B (11) and 2-chloro-3-hydroxy-α-chamigren-9-one (12) from a population of Bornean red algae Laurencia majuscula. The structures of three new metabolites were determined based on their spectroscopic data (IR, 1D and 2D NMR, and MS). These compounds showed antibacterial activity against three human pathogenic bacteria (Escherichia coli, Salmonella typhi and Vibrio cholera).
The objective of this study was to compare the antioxidant activity and cytotoxicity of Durio zibethinus M. (Durian) leaf extract from two extraction methods. Ultrasound-assisted extraction and Accelerated-solvent extraction were used to produce crude extract. The results revealed that UAE achieved 3× higher in total phenolic content in the leaf extract compared to ASE. DPPH radical scavenging activity was 4.6× higher in leaf extract from ASE. No significant differences reported in ferric reducing power, and total flavonoid content of the leaf extract between the two methods. Cytotoxicity via MTT assay demonstrated no significant differences in cell viability upon exposure to the leaf extract from both methods. This suggested that they were appropriate in producing Durio zibethinus M. leaf extract for end use application in food related product. Both ensured similar level of safety in Durio zibethinus M. leaf extract as a new potential ingredient for the food industry.
A handful of bioactive compounds from plants have been reported to possess platelet-activating factor (PAF) antagonist activity. However, their mode of action is not well understood. Selected bioactive compounds that exhibit PAF antagonist activity and synthetic PAF antagonists were subjected to docking simulations using the MOE 2007.09 software package. The docking study of PAF antagonists was carried out on the PAF receptor (PAFR) protein which involves in various pathological responses mediated by PAF. The docking results revealed that amentoflavone (3) showed good interactions with the PAFR model where the flavone and phenolic moieties were mostly involved in these interactions. Knowledge on PAF antagonists' interactions with the PAFR model is a useful screening tool of potential PAF antagonists prior to performing PAF inhibitory assay.
One new sesquiterpene dilactone, coccinine (1) and one new β-carboline alkaloid, daibucarboline F (2) together with 10 known compounds; linderane (3), linderalactone (4), pseudoneolinderane (5), linderanlide C (6), linderanine A (7), epicatechin (8), (-)-taxifolin (9), astilbin (10), L-quercitrin (11) and afzelin (12) were isolated from the stems and leaves of Neolitsea cassia (L.) Kosterm (Lauraceae). The structures of (1 and 2) were established by extensive spectroscopic methods and the known compounds were identified by comparisons with data reported in literature. The relative stereochemistry of compound (1) was assigned by X-ray diffraction analysis with Cu-Kα irradiation. Compounds (3-8) and (10) were evaluated for their α-glucosidase enzymatic inhibitory activity. Compounds (4-6), (8) and (10) exhibited inhibition towards α-glucosidase enzymatic activity with IC50 values ranging from 12.10 to 96.77 μM. This is the first report on the isolation of phytochemicals from N. cassia and their bioactivities.
Hydrodistillation of the fresh stem and leaf of Neolitsea kedahense Gamble, collected from Gunung Jerai, Malaysia followed by the GC-FID and GC-MS analysis revealed the detection of a total of 47 constituents of which 28 (86.4%) from the stem and 31 (96.4%) constituents from the leaf. δ-Cadinene (17.4%), 1-epi-cubenol (11.8%), cyperotundone (9.0%), cis-cadin-4-en-7-ol (7.7%), τ-cadinol (7.1%) and α-cadinol (7.1%) were the principle constituents in the stem oil, whereas β-caryophyllene (18.9%), bicyclogermacrene (18.6%) and trans-muurola-4(14),5-diene (9.8%) were the major constituents in the leaf oil. Among the identified constituents, three constituents namely 7-epi-α-selinene, junenol and cis-cadin-4-en-7-ol have not been found previously from Neolitsea oils. The stem and leaf oils were screened for their α-glucosidase inhibitory and antibacterial activities. Both oils displayed potential α-glucosidase inhibitory activity, while the stem oil possessed weak antibacterial activity against Bacillus subtilis.
The chemical compositions, in vitro and in silico anti-dengue activity of the essential oils of the rhizomes of Curcuma longa Linn., C. aeruginosa Roxb., and C. xanthorrhiza Roxb. had been investigated. The C. longa oil was mainly composed of ar-turmerone (54.0%) and curlone (17.7%), while the C. aeruginosa oil was rich in curzerenone (23.4%), 1,8-cineole (21.2%), and camphor (7.1%). Xanthorrhizol (21.6%), β-curcumene (19.5%), ar-curcumene (14.2%), and camphor (9.2%) were the major compounds in the C. xanthorrhiza oil. Among the oils, the C. longa oil was found to be the most active NSB-NS3 protease inhibitor (IC50 1.98 μg/mL). PLS biplot disclosed that the essential oils were classified into three separated clusters based on their characteristic chemical compositions, with C. longa positioned closest to the in vitro anti-dengue activity. Four compounds from the C. longa oil have both hydrogen and hydrophobic bonds that could be responsible for the DENV-2 NS2B-NS3 inhibitory effect.
Garcinia species are reported to possess antimicrobial, anti-inflammatory, anticancer, anti-HIV and anti-Alzheimer's activities. This study aimed to investigate the in vitro cholinesterase enzyme inhibitory activities of garcihombronane C (1), garcihombronane F (2), garcihombronane I (3), garcihombronane N (4), friedelin (5), clerosterol (6), spinasterol glucoside (7) and 3β-hydroxy lup-12,20(29)-diene (8) isolated from Garcinia hombroniana, and to perform molecular docking simulation to get insight into the binding interactions of the ligands and enzymes. The cholinesterase inhibitory activities were evaluated using acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. In this study, compound 4 displayed the highest concentration-dependent inhibition of both AChE and BChE. Docking studies exhibited that compound 4 binds through hydrogen bonds to amino acid residues of AChE and BChE. The calculated docking and binding energies also supported the in vitro inhibitory profiles of IC50. In conclusion, garcihombronanes C, F, I and N (1-4) exhibited dual and moderate inhibitory activities against AChE and BChE.