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Two new phloroglucinol derivatives and five photosensitizing pheophorbides from Syzygium polyanthum leaves (Salam)

Har LW, Shaari K, Boon LH, Kamarulzaman FA, Ismail IS

Nat Prod Commun, 2012 Aug;7(8):1033-6.
PMID: 22978223

Two new phloroglucinol derivatives, identified as anthuminoate (1) and anthuminone (2), were isolated from the ichthyotoxic ethyl acetate fraction of Syzygium polyanthum leaves. In addition, bioassay-guided fractionation followed by dereplication of the photocytotoxic fraction of this plant part has resulted in the identification of five known pheophorbides as the bioactive constituents. The compounds were identified as pheophorbide-a, methyl pheophorbide-a, methyl hydroxypheophorbide-a, pheophorbide-b and hydroxypheophorbide-b. Inhibition of cell viability shown by the compounds ranged from 83.3 to 86.1% at a test concentration of 5 microg/mL. This shows that Syzygium polyanthum leaves are a potential new source in the studies of photocytotoxicity for photodynamic therapy.

Matched MeSH terms: Syzygium/chemistry*
Fulltext Antioxidant activity and phenolic content of Paederia foetida and Syzygium aqueum

Osman H, Rahim AA, Isa NM, Bakhir NM

Molecules, 2009;14(3):970-8.
PMID: 19305354 DOI: 10.3390/molecules14030970

The antioxidant activity of fresh and dried plant extracts of Paederia foetida and Syzygium aqueum were studied using beta-carotene bleaching and the 2,2'-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS) radical cation assay. The percentage of antioxidant activity for all extract samples using both assays was between 58 and 80%. The fresh samples of both plants had higher antioxidant activity than the dried samples. The results of the beta-carotene bleaching assay were correlated (R(2) = 0.9849) with those of the ABTS assay.

Matched MeSH terms: Syzygium/chemistry*
Lead contamination in Eugenia dyeriana herbal preparations from different commercial sources in Malaysia

Ang HH

Food Chem Toxicol, 2008 Jun;46(6):1969-75.
PMID: 18328612 DOI: 10.1016/j.fct.2008.01.037

The Drug Control Authority (DCA) of Malaysia implemented the phase three registration of traditional medicines on 1 January, 1992. A total of 100 products in various pharmaceutical dosage forms of a herbal preparation, containing Eugenia dyeriana, either single or combined preparations (more than one medicinal plant), were analyzed for the presence of lead contamination, using atomic absorption spectrophotometry. These samples were bought from different commercial sources in the Malaysian market, after performing a simple random sampling. Results showed that 22% of the above products failed to comply with the quality requirement for traditional medicines in Malaysia. Although this study showed that 78% of the products fully complied with the quality requirement for traditional medicines in Malaysia pertaining to lead, however, they cannot be assumed safe from lead contamination because of batch-to-batch inconsistency.

Matched MeSH terms: Syzygium/chemistry*
Fulltext Physiochemical and phytochemical properties of wax apple (Syzygium samarangense [Blume] Merrill & L. M. Perry var. Jambu Madu) as affected by growth regulator application

Moneruzzaman Khandaker M, Nasrulhaq Boyce A, Osman N, Sharif Hossain A

ScientificWorldJournal, 2012;2012:728613.
PMID: 22701370 DOI: 10.1100/2012/728613

This study represents the first paper of the effects of growth regulators on the physiochemical and phytochemical properties of the wax apple fruit, a widely cultivated fruit tree in southeast Asia. Net photosynthesis, sucrose phosphate synthase (SPS) activity, peel color, fruit firmness, juice content, pH value, total soluble solids (TSSs), and the sugar acid ratio were all significantly increased in growth regulators (PGRs) treated fruits. The application of gibberellin (GA(3)), naphthalene acetic acid (NAA), and 2,4-dichlorophenoxy acetic acid (2,4-D) significantly reduced titratable acidity and increased total sugar and carbohydrate content compared to the control. The 50 mg/L GA₃, 10 mg/L NAA, and 5 mg/L 2,4-D treatments produced the greatest increases in phenol and flavonoid content; vitamin C content was also higher for these treatments. PGR treatment significantly affected chlorophyll, anthocyanin, and carotene content and produced higher phenylalanine ammonia lyase (PAL) and antioxidant activity levels. There was a positive correlation between peel color and TSS and antioxidant activity and both phenol and flavonoid content and PAL activity and anthocyanin formation. A taste panel assessment was also performed, and the highest scores were given to fruits that had been treated with GA₃ or auxin. The study showed that application of 50 mg/L GA₃, 10 mg/L NAA, and 5 mg/L 2,4-D once a week from bud development to fruit maturation increased the physiochemical and phytochemical properties of wax apple fruits.

Matched MeSH terms: Syzygium/chemistry*
Fulltext Inhibition of quorum sensing-controlled virulence factor production in Pseudomonas aeruginosa PAO1 by Ayurveda spice clove (Syzygium aromaticum) bud extract

Krishnan T, Yin WF, Chan KG

Sensors (Basel), 2012;12(4):4016-30.
PMID: 22666015 DOI: 10.3390/s120404016

Quorum sensing controls the virulence determinants in most proteobacteria. In this work, the hexane, chloroform and methanol extracts of an Ayurveda spice, namely clove (Syzygium aromaticum), shown anti-quorum sensing activity. Hexane and methanol extracts of clove inhibited the response of C. violaceum CV026 to exogenously supplied N-hexanoylhomoserine lactone, in turn preventing violacein production. Chloroform and methanol extracts of clove significantly reduced bioluminescence production by E. coli [pSB1075] grown in the presence of N-(3-oxododecanoyl)-L-homoserine lactone. We demonstrated that clove extract inhibited quorum sensing-regulated phenotypes in Pseudomonas aeruginosa PA01, including expression of lecA::lux (by hexane extract), swarming (maximum inhibition by methanol extract), pyocyanin (maximum inhibition by hexane extract). This study shows that the presence of natural compounds that exhibit anti-quorum sensing activity in the clove extracts may be useful as the lead of anti-infective drugs.

Matched MeSH terms: Syzygium/chemistry*
Anticancer Potential of Syzygium Species: a Review

Chua LK, Lim CL, Ling APK, Chye SM, Koh RY

Plant Foods Hum Nutr, 2019 Mar;74(1):18-27.
PMID: 30535971 DOI: 10.1007/s11130-018-0704-z

Cancer is a preventable and treatable disease, however, the incidence rates are on the rise. Classical treatment modalities for cancer include surgery, radiotherapy and chemotherapy. However, these are associated with detrimental side effects such as nausea and emesis. Therefore, researchers currently vest interest in complementary and alternative medicines for cancer treatment and prevention. Plants such as Syzygium sp. are a common basis of complementary medicines due to its abundance of bioactive phytochemicals. Numerous natural compounds derived from Syzygium sp., such as phenolics, oleanolic acids, and betulinic acids, and dimethyl cardamonins, were reported to have anticancer effects. Many possess the ability to inhibit cell proliferation and induce apoptosis. In this review, we discuss the vast potential Syzygium sp. harbours as a source of anticancer natural compounds due to its abundance, easy acceptability, affordability and safety for regular consumption.

Matched MeSH terms: Syzygium/chemistry*
Fulltext A comparative study of conventional and supercritical fluid extraction methods for the recovery of secondary metabolites from Syzygium campanulatum Korth

Memon AH, Hamil MS, Laghari M, Rithwan F, Zhari S, Saeed MA, et al.

J Zhejiang Univ Sci B, 2016 Sep;17(9):683-982.
PMID: 27604860 DOI: 10.1631/jzus.B1600019

Syzygium campanulatum Korth is a plant, which is a rich source of secondary metabolites (especially flavanones, chalcone, and triterpenoids). In our present study, three conventional solvent extraction (CSE) techniques and supercritical fluid extraction (SFE) techniques were performed to achieve a maximum recovery of two flavanones, chalcone, and two triterpenoids from S. campanulatum leaves. Furthermore, a Box-Behnken design was constructed for the SFE technique using pressure, temperature, and particle size as independent variables, and yields of crude extract, individual and total secondary metabolites as the dependent variables. In the CSE procedure, twenty extracts were produced using ten different solvents and three techniques (maceration, soxhletion, and reflux). An enriched extract of five secondary metabolites was collected using n-hexane:methanol (1:1) soxhletion. Using food-grade ethanol as a modifier, the SFE methods produced a higher recovery (25.5%‒84.9%) of selected secondary metabolites as compared to the CSE techniques (0.92%‒66.00%).

Matched MeSH terms: Syzygium/chemistry*
Leucoxenols A and B, two new phenolics from Bornean medicinal plant Syzygium leucoxylon

Shamsudin KJ, Phan CS, Kulip J, Hatai K, Vairappan CS, Kamada T

J Asian Nat Prod Res, 2019 May;21(5):435-441.
PMID: 29502443 DOI: 10.1080/10286020.2018.1440391

The medicinal plant, Syzygium leucoxylon or commonly known as Obah found in North Borneo was considered as traditional medicine by local committee. Two new phenolics, leucoxenols A (1) and B (2) were isolated and identified as major secondary metabolites from the leaves of S. leucoxylon. Their chemical structures were elucidated based on spectroscopic data such as NMR and HRESIMS. Furthermore, these compounds were active against selected strains of fungi.

Matched MeSH terms: Syzygium/chemistry*
Fulltext Antibacterial Activity of Ethanolic Extract of Syzygium polyanthum L. (Salam) Leaves against Foodborne Pathogens and Application as Food Sanitizer

Ramli S, Radu S, Shaari K, Rukayadi Y

Biomed Res Int, 2017;2017:9024246.
PMID: 29410966 DOI: 10.1155/2017/9024246

The aim of this study was to determine antibacterial activity of S. polyanthum L. (salam) leaves extract foodborne pathogens. All the foodborne pathogens were inhibited after treating with extract in disk diffusion test with range 6.67 ± 0.58-9.67 ± 0.58 mm of inhibition zone. The range of MIC values was between 0.63 and 1.25 mg/mL whereas MBC values were in the range 0.63 mg/mL to 2.50 mg/mL. In time-kill curve, L. monocytogenes and P. aeruginosa were found completely killed after exposing to extract in 1 h incubation at 4x MIC. Four hours had been taken to completely kill E. coli, S. aureus, V. cholerae, and V. parahaemolyticus at 4x MIC. However, the population of K. pneumoniae, P. mirabilis, and S. typhimurium only reduced to 3 log CFU/mL. The treated cell showed cell rupture and leakage of the cell cytoplasm in SEM observation. The significant reduction of natural microflora in grapes fruit was started at 0.50% of extract at 5 min and this concentration also was parallel to sensory attributes acceptability where application of extract was accepted by the panellists until 5%. In conclusion, S. polyanthum extract exhibits antimicrobial activities and thus might be developed as natural sanitizer for washing raw food materials.

Matched MeSH terms: Syzygium/chemistry*
Syzygium aqueum leaf extract and its bioactive compounds enhances pre-adipocyte differentiation and 2-NBDG uptake in 3T3-L1 cells

Manaharan T, Ming CH, Palanisamy UD

Food Chem, 2013 Jan 15;136(2):354-63.
PMID: 23122070 DOI: 10.1016/j.foodchem.2012.08.056

The insulin-like and/or insulin-sensitising effects of Syzygium aqueum leaf extract and its six bioactive compounds; 4-hydroxybenzaldehyde, myricetin-3-O-rhamnoside, europetin-3-O-rhamnoside, phloretin, myrigalone-G and myrigalone-B were investigated in 3T3-L1 adipocytes. We observed that, S. aqueum leaf extract (0.04-5 μg/ml) and its six bioactive compounds (0.08-10 μM) at non-cytotoxic concentrations were effectively enhance adipogenesis, stimulate glucose uptake and increase adiponectin secretion in 3T3-L1 adipocytes. Clearly, the compounds myricetin-3-O-rhamnoside and europetin-3-O-rhamnoside showed insulin-like and insulin-sensitising effects on adipocytes from a concentration of 0.08 μM. These compounds were far better than rosiglitazone and the other isolated compounds in enhancing adipogenesis, stimulating 2-NBDG uptake and increasing adiponectin secretion at all the concentrations tested. These suggest the antidiabetic potential of S. aqueum leaf extract and its six bioactive compounds. However, further molecular interaction studies to explain the mechanisms of action are highly warranted.

Matched MeSH terms: Syzygium/chemistry*
Presence of calcium antagonist activity explains the use of Syzygium samarangense in diarrhoea

Ghayur MN, Gilani AH, Khan A, Amor EC, Villaseñor IM, Choudhary MI

Phytother Res, 2006 Jan;20(1):49-52.
PMID: 16397921

Syzygium samarangense (Family; Myrtaceae) or 'makopa', as it is commonly known, is native to Malaysia, some islands of Indonesia and to Far East in general. This study was undertaken to rationalize the use of this plant in hypermotility states of the gut. The hexane extract of S. samarangense (Ss.Hex) was found to dose-dependently (10-3000 microg/mL) relax the spontaneously contracting isolated rabbit jejunum. When tested for a possible calcium channel blocking (CCB) activity, the extract (10-1000 microg/mL) relaxed the high K+-induced contractions and also decreased the Ca++ dose-response curves in a dose-dependent manner (30-100 microg/mL), confirming the CCB activity. Four flavonoids isolated from the hexane extract were tested for a possible spasmolytic activity. All flavonoids, identified as: 2'-hydroxy-4',6'-dimethoxy-3'-methylchalcone (SS1), 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (SS2), 2',4'-dihydroxy-6'-methoxy-3'-methylchalcone (SS3) and 7-hydroxy-5-methoxy-6,8-dimethylflavanone (SS4), showed dose-dependent (10-1000 microg/mL) spasmolytic activity with SS2 being the most potent. These results indicate that the presence of compounds with spasmolytic and calcium antagonist activity may be responsible for the medicinal use of the plant in diarrhoea.

Matched MeSH terms: Syzygium/chemistry*
Fulltext Isolation, Characterization, Crystal Structure Elucidation of Two Flavanones and Simultaneous RP-HPLC Determination of Five Major Compounds from Syzygium campanulatum Korth

Memon AH, Ismail Z, Al-Suede FS, Aisha AF, Hamil MS, Saeed MA, et al.

Molecules, 2015;20(8):14212-33.
PMID: 26248073 DOI: 10.3390/molecules200814212

Two flavanones named (2S)-7-Hydroxy-5-methoxy-6,8-dimethyl flavanone (1), (S)-5,7-dihydroxy-6,8-dimethyl-flavanone (2), along with known chalcone, namely, (E)-2',4'- dihydroxy-6'-methoxy-3',5'-dimethylchalcone (3) and two triterpenoids, namely, betulinic and ursolic acids (4 and 5), were isolated from the leaves of Syzygium campanulatum Korth (Myrtaceae). The structures of compounds (1 and 2) were determined on the basis of UV-visible, FTIR, NMR spectroscopies and LC-EIMS analytical techniques. Furthermore, new, simple, precise, selective, accurate, highly sensitive, efficient and reproducible RP-HPLC method was developed and validated for the quantitative analysis of the compounds (1-5) from S. campanulatum plants of five different age. RP-HPLC method was validated in terms of specificity, linearity (r2 ≤ 0.999), precision (2.0% RSD), and recoveries (94.4%-105%). The LOD and LOQ of these compounds ranged from 0.13-0.38 and 0.10-2.23 μg·mL-1, OPEN ACCESS respectively. Anti-proliferative activity of isolated flavanones (1 and 2) and standardized extract of S. campanulatum was evaluated on human colon cancer (HCT 116) cell line. Compounds (1 and 2) and extract revealed potent and dose-dependent activity with IC50 67.6, 132.9 and 93.4 μg·mL-1, respectively. To the best of our knowledge, this is the first study on isolation, characterization, X-ray crystallographic analysis of compounds (1 and 2) and simultaneous RP-HPLC determination of five major compounds (1-5) from different age of S. campanulatum plants.

Matched MeSH terms: Syzygium/chemistry*
Fulltext Amelioration of high-fat diet-induced obesity and its associated complications by a myricetin derivative-rich fraction from Syzygium malaccense in C57BL/6J mice

Nallappan D, Chua KH, Ong KC, Chong CW, Teh CSJ, Palanisamy UD, et al.

Food Funct, 2021 Jul 05;12(13):5876-5891.
PMID: 34019055 DOI: 10.1039/d1fo00539a

Obesity is a driving factor in the onset of metabolic disorders. This study aims to investigate the effects of the myricetin derivative-rich fraction (MD) from Syzygium malaccense leaf extract on high-fat diet (HFD)-induced obesity and its associated complications and its influence on uncoupling protein-1 (UCP-1) and gut microbiota in C57BL/6J mice. Mice were randomly assigned into four groups (n = 6) and given a normal diet (ND) or high-fat diet (HFD) for 10 weeks to induce obesity. The HFD groups (continued with HFD) were administered 50 mg kg-1 MD (treatment), 50 mg kg-1 metformin (positive control) and normal saline (HFD and ND controls) daily for four weeks via oral gavage. The ten-week HFD-feeding resulted in hyperglycemia and elevated urinary oxidative indices. The subsequent MD administration caused significant weight reduction without appetite suppression and amelioration of insulin resistance, steatosis and dyslipidemia. Besides, MD significantly reduced lipid hydroperoxides and protein carbonyls in tissue homogenates and urine and elevated Trolox equivalent antioxidant capacity (TEAC), ferric reducing antioxidant power (FRAP) and reduced glutathione (GSH) and thus, alleviated oxidative stress. The weight reduction was correlated with downregulation of inflammatory markers and the increased UCP-1 level, suggesting weight loss plausibly through thermogenesis. The Akkermansia genus (reflects improved metabolic status) in the HFD50 group was more abundant than that in the HFD group while the non-enzymatic antioxidant markers were strongly associated with UCP-1. In conclusion, MD ameliorates obesity and its related complications possibly via the upregulation of UCP-1 and increased abundance of Akkermansia genus and is promising as a therapeutic agent in the treatment of obesity and its associated metabolic disorders.

Matched MeSH terms: Syzygium/chemistry*
Standardized extract of Syzygium aqueum: a safe cosmetic ingredient

Palanisamy UD, Ling LT, Manaharan T, Sivapalan V, Subramaniam T, Helme MH, et al.

Int J Cosmet Sci, 2011 Jun;33(3):269-75.
PMID: 21284663 DOI: 10.1111/j.1468-2494.2010.00637.x

Syzygium aqueum, a species in the Myrtaceae family, commonly called the water jambu is native to Malaysia and Indonesia. It is well documented as a medicinal plant, and various parts of the tree have been used in traditional medicine, for instance as an antibiotic. In this study, we show S. aqueum leaf extracts to have a significant composition of phenolic compounds, protective activity against free radicals as well as low pro-oxidant capability. Its ethanolic extract, in particular, is characterized by its excellent radical scavenging activity of EC(50) of 133 μg mL(-1) 1,1-diphenyl-2-picryl-hydrazyl (DPPH), 65 μg mL(-1) 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) and 71 μg mL(-1) (Galvinoxyl), low pro-oxidant capabilities and a phenolic content of 585-670 mg GAE g(-1) extract. The extract also displayed other activities, deeming it an ideal cosmetic ingredient. A substantial tyrosinase inhibition activity with an IC(50) of about 60 μg mL(-1) was observed. In addition, the extract was also found to have anti-cellulite activity tested for its ability to cause 98% activation of lipolysis of adipocytes (fat cells) at a concentration of 25 μg mL(-1). In addition, the extract was not cytotoxic to Vero cell lines up to a concentration of 600 μg mL(-1). Although various parts of this plant have been used in traditional medicine, this is the first time it has been shown to have cosmeceutical properties. Therefore, the use of this extract, alone or in combination with other active principles, is of interest to the cosmetic industry.

Matched MeSH terms: Syzygium/chemistry*
Fulltext Assessment of antioxidant capacity and cytotoxicity of selected Malaysian plants

Ling LT, Radhakrishnan AK, Subramaniam T, Cheng HM, Palanisamy UD

Molecules, 2010 Apr;15(4):2139-51.
PMID: 20428033 DOI: 10.3390/molecules15042139

Thirteen Malaysian plants; Artocarpus champeden, Azadirachta indica, Fragaria x ananassa, Garcinia mangostana, Lawsonia inermis, Mangifera indica, Nephelium lappaceum, Nephelium mutobile, Peltophorum pterocarpum, Psidium guajava and Syzygium aqueum, selected for their use in traditional medicine, were subjected to a variety of assays. Antioxidant capability, total phenolic content, elemental composition, as well as it cytotoxity to several cell lines of the aqueous and ethanolic extracts from different parts of these selected Malaysian plants were determined. In general, the ethanolic extracts were better free radical scavengers than the aqueous extracts and some of the tested extracts were even more potent than a commercial grape seed preparation. Similar results were seen in the lipid peroxidation inhibition studies. Our findings also showed a strong correlation of antioxidant activity with the total phenolic content. These extracts when tested for its heavy metals content, were found to be below permissible value for nutraceutical application. In addition, most of the extracts were found not cytotoxic to 3T3 and 4T1 cells at concentrations as high as 100 microg/mL. We conclude that although traditionally these plants are used in the aqueous form, its commercial preparation could be achieved using ethanol since a high total phenolic content and antioxidant activity is associated with this method of preparation.

Matched MeSH terms: Syzygium/chemistry
Fulltext Syzygium campanulatum korth methanolic extract inhibits angiogenesis and tumor growth in nude mice

Aisha AF, Ismail Z, Abu-Salah KM, Siddiqui JM, Ghafar G, Abdul Majid AM

BMC Complement Altern Med, 2013;13:168.
PMID: 23842450 DOI: 10.1186/1472-6882-13-168

Syzygium campanulatum Korth (Myrtaceae) is an evergreen shrub rich in phenolics, flavonoid antioxidants, and betulinic acid. This study sought to investigate antiangiogenic and anti-colon cancer effects of S.C. standardized methanolic extract.

Matched MeSH terms: Syzygium/chemistry*
Protective effect of myricetin derivatives from Syzygium malaccense against hydrogen peroxide-induced stress in ARPE-19 cells

Arumugam B, Palanisamy UD, Chua KH, Kuppusamy UR

Mol Vis, 2019;25:47-59.
PMID: 30820141

Purpose: Oxidative stress is implicated in the etiology of diabetes and its debilitating complications, such as diabetic retinopathy (DR). Various flavonoids have been reported to be useful in reducing DR progression. Myricetin derivatives (F2) isolated from leaf extract of Syzygium malaccense have the potential to serve as functional food as reported previously. The present study was performed with the aim of determining the antioxidant potential and protective effect of myricetin derivatives (F2) isolated from leaf extract of S. malaccense against glucose oxidase (GO)-induced hydrogen peroxide (H2O2) production that causes oxidative stress in ARPE-19 (RPE) cells.
Methods: Antioxidant properties were assessed through various radical (DPPH, ABTS, and nitric oxide) scavenging assays and determination of total phenolic content and ferric reducing antioxidant power level. ARPE-19 cells were preincubated with samples before the addition of GO (to generate H2O2). Cell viability, change in intracellular reactive oxygen species (ROS), H2O2 levels in cell culture supernatant, and gene expression were assessed.
Results: F2 showed higher antioxidant levels than the extract when assessed for radical scavenging activities and ferric reducing antioxidant power. F2 protected the ARPE-19 cells against GO-H2O2-induced oxidative stress by reducing the production of H2O2 and intracellular reactive oxygen species. This was achieved by the activation of nuclear factor erythroid 2-related factor 2 (Nrf2/NFE2L2) and superoxide dismutase (SOD2), as well as downregulation of nitric oxide producer (NOS2) at the transcriptional level.
Conclusions: The results showed that myricetin derivatives from S. malaccense have the capacity to exert considerable exogenous antioxidant activities and stimulate endogenous antioxidant activities. Therefore, these derivatives have excellent potential to be developed as therapeutic agents for managing DR.

Matched MeSH terms: Syzygium/chemistry*

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