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  1. Fulltext Zerumbone Induces Apoptosis in Breast Cancer Cells by Targeting αvβ3 Integrin upon Co-Administration with TP5-iRGD Peptide
    E M Eid E, S Alanazi A, Koosha S, A Alrasheedy A, Azam F, M Taban I, et al.
    Molecules, 2019 Jul 13;24(14).
    PMID: 31337024 DOI: 10.3390/molecules24142554
    Cell-penetrating peptides (CPPs) are highly promising tools to deliver therapeutic molecules into tumours. αVβ3 integrins are cell-matrix adhesion receptors, and are considered as an attractive target for anticancer therapies owing to their roles in the process of metastasis and angiogenesis. Therefore, this study aims to assess the effect of co-administration of zerumbone (ZER) and ZERencapsulated in hydroxypropyl-β-cyclodextrin with TP5-iRGD peptide towards cell cytotoxicity, apoptosis induction, and proliferation of normal and cancerous breast cells utilizing in vitro assays, as well as to study the molecular docking of ZER in complex with TP5-iRGD peptide. Cell viability assay findings indicated that ZER and ZERencapsulated in hydroxypropyl-β-cyclodextrin (ZER-HPβCD) inhibited the growth of estrogen receptor positivebreast cancer cells (ER+ MCF-7) at 72 h treatment with an inhibitory concentration (IC)50 of 7.51 ± 0.2 and 5.08 ± 0.2 µg/mL, respectively, and inhibited the growth of triple negative breast cancer cells (MDA-MB-231) with an IC50 of 14.96 ± 1.52 µg/mL and 12.18 ± 0.7 µg/mL, respectively. On the other hand, TP5-iRGD peptide showed no significant cytotoxicity on both cancer and normal cells. Interestingly, co-administration of TP5-iRGD peptide in MCF-7 cells reduced the IC50 of ZER from 7.51 ± 0.2 µg/mL to 3.13 ± 0.7 µg/mL and reduced the IC50 of ZER-HPβCD from 5.08 ± 0.2 µg/mL to 0.49 ± 0.004 µg/mL, indicating that the co-administration enhances the potency and increases the efficacy of ZER and ZER-HPβCD compounds. Acridine orange (AO)/propidium iodide (PI) staining under fluorescence microscopy showed evidence of early apoptosis after 72 h from the co-administration of ZER or ZER-HPβCD with TP5-iRGD peptide in MCF-7 breast cancer cells. The findings of the computational modelling experiment provide novel insights into the ZER interaction with integrin αvβ3 in the presence of TP5-iRGD, and this could explain why ZER has better antitumor activities when co-administered with TP5-iRGD peptide.
    Matched MeSH terms: Sesquiterpenes/chemistry
  2. Fulltext Spectrofluorometric and molecular docking studies on the binding of curcumenol and curcumenone to human serum albumin
    Hamdi OA, Feroz SR, Shilpi JA, Anouar el H, Mukarram AK, Mohamad SB, et al.
    Int J Mol Sci, 2015;16(3):5180-93.
    PMID: 25756376 DOI: 10.3390/ijms16035180
    Curcumenol and curcumenone are two major constituents of the plants of medicinally important genus of Curcuma, and often govern the pharmacological effect of these plant extracts. These two compounds, isolated from C. zedoaria rhizomes were studied for their binding to human serum albumin (HSA) using the fluorescence quench titration method. Molecular docking was also performed to get a more detailed insight into their interaction with HSA at the binding site. Additions of these sesquiterpenes to HSA produced significant fluorescence quenching and blue shifts in the emission spectra of HSA. Analysis of the fluorescence data pointed toward moderate binding affinity between the ligands and HSA, with curcumenone showing a relatively higher binding constant (2.46 × 105 M-1) in comparison to curcumenol (1.97 × 104 M-1). Cluster analyses revealed that site I is the preferred binding site for both molecules with a minimum binding energy of -6.77 kcal·mol-1. However, binding of these two molecules to site II cannot be ruled out as the binding energies were found to be -5.72 and -5.74 kcal·mol-1 for curcumenol and curcumenone, respectively. The interactions of both ligands with HSA involved hydrophobic interactions as well as hydrogen bonding.
    Matched MeSH terms: Sesquiterpenes/chemistry
  3. Fulltext A Quantum Chemical and Statistical Study of Cytotoxic Activity of Compounds Isolated from Curcuma zedoaria
    Hamdi OA, Anouar el H, Shilpi JA, Trabolsy ZB, Zain SB, Zakaria NS, et al.
    Int J Mol Sci, 2015 Apr 27;16(5):9450-68.
    PMID: 25923077 DOI: 10.3390/ijms16059450
    A series of 21 compounds isolated from Curcuma zedoaria was subjected to cytotoxicity test against MCF7; Ca Ski; PC3 and HT-29 cancer cell lines; and a normal HUVEC cell line. To rationalize the structure-activity relationships of the isolated compounds; a set of electronic; steric and hydrophobic descriptors were calculated using density functional theory (DFT) method. Statistical analyses were carried out using simple and multiple linear regressions (SLR; MLR); principal component analysis (PCA); and hierarchical cluster analysis (HCA). SLR analyses showed that the cytotoxicity of the isolated compounds against a given cell line depend on certain descriptors; and the corresponding correlation coefficients (R2) vary from 0%-55%. MLR results revealed that the best models can be achieved with a limited number of specific descriptors applicable for compounds having a similar basic skeleton. Based on PCA; HCA and MLR analyses; active compounds were classified into subgroups; which was in agreement with the cell based cytotoxicity assay.
    Matched MeSH terms: Sesquiterpenes/chemistry
  4. Exploring the immunomodulatory and anticancer properties of zerumbone
    Haque MA, Jantan I, Arshad L, Bukhari SNA
    Food Funct, 2017 Oct 18;8(10):3410-3431.
    PMID: 28714500 DOI: 10.1039/c7fo00595d
    Plant-derived immunomodulators and anti-cancer agents have attracted a lot of interest from natural product scientists for their efficacy and safety and their significant contribution towards understanding targeted drug action and drug delivery mechanisms. Zerumbone, the main constituent of Zingiber zerumbet rhizomes, has been investigated for its wide-spectrum role in treating multitargeted diseases. The rhizomes have been used as food flavoring agents in various cuisines and in herbal medicine. Many in vivo and in vitro studies have provided evidence of zerumbone as a potent immunomodulator as well as a potential anti-cancer agent. This review is an interesting compilation of all those significant outcomes from investigations carried out to date to explore the immunomodulatory and anticancer properties of zerumbone. The ultimate objective of this comprehensive review is to provide updated information and a critical assessment on zerumbone including its chemistry and immunomodulating and anticancer properties, which may be of paramount importance to provide a new path for ensuing research to discover new agents to treat cancers and immune-related diseases. In addition, updated information on the toxicology of zerumbone has also been summarized to provide its safety profile.
    Matched MeSH terms: Sesquiterpenes/chemistry
  5. Fulltext Heterologous expression of cytotoxic sesquiterpenoids from the medicinal mushroom Lignosus rhinocerotis in yeast
    Yap HY, Muria-Gonzalez MJ, Kong BH, Stubbs KA, Tan CS, Ng ST, et al.
    Microb Cell Fact, 2017 Jun 12;16(1):103.
    PMID: 28606152 DOI: 10.1186/s12934-017-0713-x
    BACKGROUND: Genome mining facilitated by heterologous systems is an emerging approach to access the chemical diversity encoded in basidiomycete genomes. In this study, three sesquiterpene synthase genes, GME3634, GME3638, and GME9210, which were highly expressed in the sclerotium of the medicinal mushroom Lignosus rhinocerotis, were cloned and heterologously expressed in a yeast system.

    RESULTS: Metabolite profile analysis of the yeast culture extracts by GC-MS showed the production of several sesquiterpene alcohols (C15H26O), including cadinols and germacrene D-4-ol as major products. Other detected sesquiterpenes include selina-6-en-4-ol, β-elemene, β-cubebene, and cedrene. Two purified major compounds namely (+)-torreyol and α-cadinol synthesised by GME3638 and GME3634 respectively, are stereoisomers and their chemical structures were confirmed by 1H and 13C NMR. Phylogenetic analysis revealed that GME3638 and GME3634 are a pair of orthologues, and are grouped together with terpene synthases that synthesise cadinenes and related sesquiterpenes. (+)-Torreyol and α-cadinol were tested against a panel of human cancer cell lines and the latter was found to exhibit selective potent cytotoxicity in breast adenocarcinoma cells (MCF7) with IC50 value of 3.5 ± 0.58 μg/ml while α-cadinol is less active (IC50 = 18.0 ± 3.27 μg/ml).

    CONCLUSIONS: This demonstrates that yeast-based genome mining, guided by transcriptomics, is a promising approach for uncovering bioactive compounds from medicinal mushrooms.

    Matched MeSH terms: Sesquiterpenes/chemistry
  6. Fulltext Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities
    Chan WK, Tan LT, Chan KG, Lee LH, Goh BH
    Molecules, 2016 Apr 28;21(5).
    PMID: 27136520 DOI: 10.3390/molecules21050529
    Nerolidol (3,7,11-trimethyl-1,6,10-dodecatrien-3-ol) is a naturally occurring sesquiterpene alcohol that is present in various plants with a floral odor. It is synthesized as an intermediate in the production of (3E)-4,8-dimethy-1,3,7-nonatriene (DMNT), a herbivore-induced volatile that protects plants from herbivore damage. Chemically, nerolidol exists in two geometric isomers, a trans and a cis form. The usage of nerolidol is widespread across different industries. It has been widely used in cosmetics (e.g., shampoos and perfumes) and in non-cosmetic products (e.g., detergents and cleansers). In fact, U.S. Food and Drug Administration (FDA) has also permitted the use of nerolidol as a food flavoring agent. The fact that nerolidol is a common ingredient in many products has attracted researchers to explore more medicinal properties of nerolidol that may exert beneficial effect on human health. Therefore, the aim of this review is to compile and consolidate the data on the various pharmacological and biological activities displayed by nerolidol. Furthermore, this review also includes pharmacokinetic and toxicological studies of nerolidol. In summary, the various pharmacological and biological activities demonstrated in this review highlight the prospects of nerolidol as a promising chemical or drug candidate in the field of agriculture and medicine.
    Matched MeSH terms: Sesquiterpenes/chemistry*
  7. A Dimeric sesquiterpenoid from a Malaysian Meiogyne as a new inhibitor of Bcl-xL/BakBH3 domain peptide interaction
    Litaudon M, Bousserouel H, Awang K, Nosjean O, Martin MT, Dau ME, et al.
    J Nat Prod, 2009 Mar 27;72(3):480-3.
    PMID: 19161318 DOI: 10.1021/np8006292
    In an effort to find potent inhibitors of the antiapoptotic protein Bcl-xL, a systematic in vitro evaluation was undertaken on 1470 Malaysian plant extracts. The ethyl acetate extract obtained from the bark of Meiogyne cylindrocarpa was selected for its interaction with the Bcl-xL/Bak association. Bioassay-guided purification of this species led to the isolation of two new dimeric sesquiterpenoids (1 and 2) possessing an unprecedented substituted cis-decalin carbon skeleton. Meiogynin A (1) showed the strongest activity with a K(i) of 10.8 +/- 3.1 microM.
    Matched MeSH terms: Sesquiterpenes/chemistry
  8. Bioactive sesquiterpenes from Curcuma ochrorhiza and Curcuma heyneana
    Aspollah Sukari M, Wah TS, Saad SM, Rashid NY, Rahmani M, Lajis NH, et al.
    Nat Prod Res, 2010 May;24(9):838-45.
    PMID: 20461629 DOI: 10.1080/14786410903052951
    Curcuma ochrorhiza ('temu putih') and C. heyneana ('temu giring') are two Zingiberaceous species which are commonly used in traditional medicine in Malaysia and Indonesia. Phytochemical investigations on these Curcuma species have resulted in the isolation of six sesquiterpenes, namely zerumbone (1), furanodienone (2), zederone (3), oxycurcumenol epoxide (4), curcumenol (5) and isocurcumenol (6), along with phytosterols stigmasterol and alpha-sitosterol. Compounds 1 and 2 were obtained for the first time for C. ochrorhiza while 4 was new to C. heyneana. The hexane extract of C. ochrorhiza and sesquiterpenes 1 and 3 showed very strong cytotoxicity activity against T-acute lymphoblastic leukaemia cells (CEM-SS), with IC(50) values of 6.0, 0.6 and 1.6 microg mL(-1), respectively. Meanwhile, constituents from C. heyneana (4-6) demonstrated moderate inhibition against CEM-SS in cytotoxic assay, with IC(50) values of 11.9, 12.6 and 13.3 microg mL(-1), respectively. The crude extracts and sesquiterpenes isolated were moderately active against certain bacteria tested in antimicrobial screening.
    Matched MeSH terms: Sesquiterpenes/chemistry*
  9. Fulltext Biomedical properties of a natural dietary plant metabolite, zerumbone, in cancer therapy and chemoprevention trials
    Rahman HS, Rasedee A, Yeap SK, Othman HH, Chartrand MS, Namvar F, et al.
    Biomed Res Int, 2014;2014:920742.
    PMID: 25025076 DOI: 10.1155/2014/920742
    Zerumbone (ZER) is a naturally occurring dietary compound, present in many natural foods consumed today. The compound derived from several plant species of the Zingiberaceae family that has been found to possess multiple biomedical properties, such as antiproliferative, antioxidant, anti-inflammatory, and anticancer activities. However, evidence of efficacy is sparse, pointing to the need for a more systematic review for assessing scientific evidence to support therapeutic claims made for ZER and to identify future research needs. This review provides an updated overview of in vitro and in vivo investigations of ZER, its cancer chemopreventive properties, and mechanisms of action. Therapeutic effects of ZER were found to be scientifically plausible and could be explained partially by in vivo and in vitro pharmacological activities. Much of the research outlined in this paper will serve as a foundation to explain ZER anticancer bioactivity, which will open the door for the development of strategies in the treatment of malignancies using ZER.
    Matched MeSH terms: Sesquiterpenes/chemistry
  10. Fulltext Composition and Antibacterial Activity of the Essential Oils of Orthosiphon stamineus Benth and Ficus deltoidea Jack against Pathogenic Oral Bacteria
    Azizan N, Mohd Said S, Zainal Abidin Z, Jantan I
    Molecules, 2017 Dec 05;22(12).
    PMID: 29206142 DOI: 10.3390/molecules22122135
    In this study, the essential oils of Orthosiphon stamineus Benth and Ficus deltoidea Jack were evaluated for their antibacterial activity against invasive oral pathogens, namely Enterococcus faecalis, Streptococcus mutans, Streptococcus mitis, Streptococcus salivarius, Aggregatibacter actinomycetemcomitans, Porphyromonas gingivalis and Fusobacterium nucleatum. Chemical composition of the oils was analyzed using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The antibacterial activity of the oils and their major constituents were investigated using the broth microdilution method (minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC)). Susceptibility test, anti-adhesion, anti-biofilm, checkerboard and time-kill assays were also carried out. Physiological changes of the bacterial cells after exposure to the oils were observed under the field emission scanning electron microscope (FESEM). O. stamineus and F. deltoidea oils mainly consisted of sesquiterpenoids (44.6% and 60.9%, respectively), and β-caryophyllene was the most abundant compound in both oils (26.3% and 36.3%, respectively). Other compounds present in O. stamineus were α-humulene (5.1%) and eugenol (8.1%), while α-humulene (5.5%) and germacrene D (7.7%) were dominant in F. deltoidea. The oils of both plants showed moderate to strong inhibition against all tested bacteria with MIC and MBC values ranging 0.63-2.5 mg/mL. However, none showed any inhibition on monospecies biofilms. The time-kill assay showed that combination of both oils with amoxicillin at concentrations of 1× and 2× MIC values demonstrated additive antibacterial effect. The FESEM study showed that both oils produced significant alterations on the cells of Gram-negative bacteria as they became pleomorphic and lysed. In conclusion, the study indicated that the oils of O. stamineus and F. deltoidea possessed moderate to strong antibacterial properties against the seven strains pathogenic oral bacteria and may have caused disturbances of membrane structure or cell wall of the bacteria.
    Matched MeSH terms: Sesquiterpenes/chemistry
  11. Phytochemistry and biology of Loranthus parasiticus Merr, a commonly used herbal medicine
    Moghadamtousi SZ, Kamarudin MN, Chan CK, Goh BH, Kadir HA
    Am J Chin Med, 2014;42(1):23-35.
    PMID: 24467533 DOI: 10.1142/S0192415X14500025
    Loranthus parasiticus Merr (L. parasiticus) is a member of Loranthaceae family and is an important medicinal plant with a long history of Chinese traditional use. L. parasiticus, also known as Sang Ji Sheng (in Chinese), benalu teh (in Malay) and baso-kisei (in Japanese), is a semiparasitic plant, which is mostly distributed in the southern and southwestern regions of China. This review aims to provide a comprehensive overview of the ethnomedicinal use, phytochemistry and pharmacological activity of L. parasiticus and to highlight the needs for further investigation and greater global development of the plant's medicinal properties. To date, pharmacological studies have demonstrated significant biological activities, which support the traditional use of the plant as a neuroprotective, tranquilizing, anticancer, immunomodulatory, antiviral, diuretic and hypotensive agent. In addition, studies have identified antioxidative, antimutagenic, antiviral, antihepatotoxic and antinephrotoxic activity. The key bioactive constituents in L. parasiticus include coriaria lactone comprised of sesquiterpene lactones: coriamyrtin, tutin, corianin, and coriatin. In addition, two proanthocyanidins, namely, AC trimer and (+)-catechin, have been recently discovered as novel to L. parasiticus. L. parasiticus usefulness as a medicinal plant with current widespread traditional use warrants further research, clinical trials and product development to fully exploit its medicinal value.
    Matched MeSH terms: Sesquiterpenes/chemistry
  12. A novel caryophyllene type sesquiterpene lactone from Asparagus falcatus (Linn.); structure elucidation and anti-angiogenic activity on HUVECs
    Ghalib RM, Hashim R, Sulaiman O, Mehdi SH, Valkonen A, Rissanen K, et al.
    Eur J Med Chem, 2012 Jan;47(1):601-7.
    PMID: 22074984 DOI: 10.1016/j.ejmech.2011.10.037
    In this study the novel caryophyllene type sesquiterpene lactone (aspfalcolide) has been isolated from the leaves of Asparagus falcatus (Linn.) and characterized by IR, 1D NMR, 2D NMR, EI-MS, HR-ESI-MS and X-ray single crystal diffraction analysis. The aspfalcolide crystallizes in the orthorhombic space group P2(1)2(1)2(1) with a = 6.37360(10), b = 7.6890(2), c = 27.3281(6) Å, α = β = γ = 90(°) and Z = 4. One intermolecular O-H⋯O hydrogen bond enforces these natural molecules to form infinite chains through the crystal. Aspfalcolide was screened for its anti-angiogenic activity in human umbilical vein endothelial cells (HUVECs) and the result showed the remarkable inhibitory effect of aspfalcolide on the proliferation (IC(50) 1.82 μM), migration and tube formation of HUVECs.
    Matched MeSH terms: Sesquiterpenes/chemistry*
  13. Fulltext Binding mode analysis of zerumbone to key signal proteins in the tumor necrosis factor pathway
    Fatima A, Abdul AB, Abdullah R, Karjiban RA, Lee VS
    Int J Mol Sci, 2015 Jan 26;16(2):2747-66.
    PMID: 25629232 DOI: 10.3390/ijms16022747
    Breast cancer is the second most common cancer among women worldwide. Several signaling pathways have been implicated as causative and progression agents. The tumor necrosis factor (TNF) α protein plays a dual role in promoting and inhibiting cancer depending largely on the pathway initiated by the binding of the protein to its receptor. Zerumbone, an active constituent of Zingiber zerumbet, Smith, is known to act on the tumor necrosis factor pathway upregulating tumour necrosis factor related apoptosis inducing ligand (TRAIL) death receptors and inducing apoptosis in cancer cells. Zerumbone is a sesquiterpene that is able to penetrate into the hydrophobic pockets of proteins to exert its inhibiting activity with several proteins. We found a good binding with the tumor necrosis factor, kinase κB (IKKβ) and the Nuclear factor κB (NF-κB) component proteins along the TNF pathway. Our results suggest that zerumbone can exert its apoptotic activities by inhibiting the cytoplasmic proteins. It inhibits the IKKβ kinase that activates the NF-κB and also binds to the NF-κB complex in the TNF pathway. Blocking both proteins can lead to inhibition of cell proliferating proteins to be downregulated and possibly ultimate induction of apoptosis.
    Matched MeSH terms: Sesquiterpenes/chemistry
  14. Fulltext The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna
    Dahham SS, Tabana YM, Iqbal MA, Ahamed MB, Ezzat MO, Majid AS, et al.
    Molecules, 2015;20(7):11808-29.
    PMID: 26132906 DOI: 10.3390/molecules200711808
    The present study reports a bioassay-guided isolation of β-caryophyllene from the essential oil of Aquilaria crassna. The structure of β-caryophyllene was confirmed using FT-IR, NMR and MS. The antimicrobial effect of β-caryophyllene was examined using human pathogenic bacterial and fungal strains. Its anti-oxidant properties were evaluated by DPPH and FRAP scavenging assays. The cytotoxicity of β-caryophyllene was tested against seven human cancer cell lines. The corresponding selectivity index was determined by testing its cytotoxicity on normal cells. The effects of β-caryophyllene were studied on a series of in vitro antitumor-promoting assays using colon cancer cells. Results showed that β-caryophyllene demonstrated selective antibacterial activity against S. aureus (MIC 3 ± 1.0 µM) and more pronounced anti-fungal activity than kanamycin. β-Caryophyllene also displayed strong antioxidant effects. Additionally, β-caryophyllene exhibited selective anti-proliferative effects against colorectal cancer cells (IC50 19 µM). The results also showed that β-caryophyllene induces apoptosis via nuclear condensation and fragmentation pathways including disruption of mitochondrial membrane potential. Further, β-caryophyllene demonstrated potent inhibition against clonogenicity, migration, invasion and spheroid formation in colon cancer cells. These results prompt us to state that β-caryophyllene is the active principle responsible for the selective anticancer and antimicrobial activities of A. crassnia. β-Caryophyllene has great potential to be further developed as a promising chemotherapeutic agent against colorectal malignancies.
    Matched MeSH terms: Sesquiterpenes/chemistry
  15. Antibacterial activity of halogenated sesquiterpenes from Malaysian Laurencia spp
    Vairappan CS, Suzuki M, Ishii T, Okino T, Abe T, Masuda M
    Phytochemistry, 2008 Oct;69(13):2490-4.
    PMID: 18718619 DOI: 10.1016/j.phytochem.2008.06.015
    During our studies on Malaysian Laurencia species, brominated metabolites, tiomanene, acetylmajapolene B, and acetylmajapolene A were isolated from an unrecorded species collected at Pulau Tioman, Pahang along with known majapolene B and majapolene A. Acetylmajapolene A was a mixture of diastereomers as in the case of majapolene A. Tiomanene may be a plausible precursor for acetylmajapolenes B and A. In addition, three known halogenated sesquiterpenes and two known halogenated C(15) acetogenins were found from other two unrecorded species collected at Pulau Karah, Terengganu and Pulau Nyireh, Terengganu, respectively. Some of these halogenated metabolites showed moderate antibacterial activity against some marine bacteria.
    Matched MeSH terms: Sesquiterpenes/chemistry
  16. Metachromins X and Y from a marine sponge Spongia sp. and their effects on cell cycle progression
    Hitora Y, Takada K, Ise Y, Woo SP, Inoue S, Mori N, et al.
    Bioorg Med Chem, 2020 01 15;28(2):115233.
    PMID: 31848114 DOI: 10.1016/j.bmc.2019.115233
    New sesquiterpene quinones, metachromins X (1) and Y (2), together with the known metachromins C (3), J (4), and T (5), were isolated as inhibitors of cell cycle progression in the HeLa/Fucci2 cells. The structure of 1 was assigned by spectroscopic data and confirmed by a total synthesis. The planar structure of 2 was determined by interpretation of spectroscopic data, whereas its absolute configuration was analyzed by a combination of chiral HPLC and CD spectroscopy. Metachromins X (1) and C (3) arrested the cell cycle progression of HeLa/Fucci2 cells at S/G2/M phase.
    Matched MeSH terms: Sesquiterpenes/chemistry
  17. Chemical characterization of Goniothalamus macrophyllus and Goniothalamus malayanus leaves' essential oils
    Shakri NM, Salleh WMNHW, Khamis S, Mohamad Ali NA
    Z Naturforsch C J Biosci, 2020 Nov 26;75(11-12):485-488.
    PMID: 32966236 DOI: 10.1515/znc-2020-0090
    This study was aimed to investigate the chemical compositions of the essential oils from Goniothalamus macrophyllus and Goniothalamus malayanus growing in Malaysia. The essential oils were obtained by hydrodistillation and fully characterized by gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Analyses of the essential oils from G. macrophyllus and G. malayanus resulted in 93.6 and 95.4% of the total oils, respectively. The major components of G. macrophyllus oil were germacrene D (25.1%), bicyclogermacrene (11.6%), α-copaene (6.9%) and δ-cadinene (6.4%), whereas in G. malayanus oil bicyclogermacrene (43.9%), germacrene D (21.1%) and β-elemene (8.4%) were the most abundant components.
    Matched MeSH terms: Sesquiterpenes/chemistry
  18. Fulltext A Review of the Biomedical Applications of Zerumbone and the Techniques for Its Extraction from Ginger Rhizomes
    Kalantari K, Moniri M, Boroumand Moghaddam A, Abdul Rahim R, Bin Ariff A, Izadiyan Z, et al.
    Molecules, 2017 Sep 30;22(10).
    PMID: 28974019 DOI: 10.3390/molecules22101645
    Zerumbone (ZER) is a phytochemical isolated from the subtropical Zingiberaceae family and as a natural compound it has different biomedical properties such as antioxidant, anti-inflammatory anti-proliferative activity. ZER also has effects on angiogenesis and acts as an antitumor drug in the treatment of cancer, showing selective toxicity toward various cancer cell lines. Several techniques also have been established for extraction of ZER from the rhizomes of ginger. This review paper is an overview of recent research about different extraction methods and their efficiencies, in vivo and vitro investigations of ZER and also its prominent chemopreventive properties and treatment mechanisms. Most of the studies mentioned in this review paper may be useful use as a knowledge summary to explain ZER extraction and anticancer activities, which will show a way for the development of strategies in the treatment of malignancies using ZER.
    Matched MeSH terms: Sesquiterpenes/chemistry*
  19. Composition of the essential oils of three Malaysian Xylopia species (Annonaceae)
    Shakri NM, Salleh WMNHW, Khamis S, Mohamad Ali NA, Nadri MH
    Z Naturforsch C J Biosci, 2020 Nov 26;75(11-12):479-484.
    PMID: 32960782 DOI: 10.1515/znc-2020-0096
    The rich and diversified Malaysian flora represents an excellent resource of new chemical structures with biological activities. The genus Xylopia L. includes aromatic plants that have both nutritional and medicinal uses. This study aims to contribute with information about the volatile components of three Xylopia species essential oils: Xylopia frutescens, Xylopia ferruginea, and Xylopia magna. In this study, essential oils were extracted from the leaves by a hydrodistillation process. The identification of the essential oil components was performed by gas chromatography (GC-FID) and gas chromatography-coupled mass spectrometry (GC-MS). The major components of the essential oils from X. frutescens were bicyclogermacrene (22.8%), germacrene D (14.2%), elemol (12.8%), and guaiol (12.8%), whereas components of the essential oils from X. magna were germacrene D (35.9%), bicyclogermacrene (22.8%), and spathulenol (11.1%). The X. ferruginea oil was dominated by bicyclogermacrene (23.6%), elemol (13.7%), guaiol (13.4%), and germacrene D (12.3%).
    Matched MeSH terms: Sesquiterpenes/chemistry
  20. Fulltext Identification of small molecule inhibitors of p27(Kip1) ubiquitination by high-throughput screening
    Ooi LC, Watanabe N, Futamura Y, Sulaiman SF, Darah I, Osada H
    Cancer Sci, 2013 Nov;104(11):1461-7.
    PMID: 23910095 DOI: 10.1111/cas.12246
    Dysregulation of p27(Kip1) due to proteolysis that involves the ubiquitin ligase (SCF) complex with S-phase kinase-associated protein 2 (Skp2) as the substrate-recognition component (SCF(Skp2)) frequently results in tumorigenesis. In this report, we developed a high-throughput screening system to identify small-molecule inhibitors of p27(Kip1) degradation. This system was established by tagging Skp2 with fluorescent monomeric Azami Green (mAG) and CDK subunit 1 (Cks1) (mAGSkp2-Cks1) to bind to p27(Kip1) phosphopeptides. We identified two compounds that inhibited the interaction between mAGSkp2-Cks1 and p27(Kip1): linichlorin A and gentian violet. Further studies have shown that the compounds inhibit the ubiquitination of p27(Kip1) in vitro as well as p27(Kip1) degradation in HeLa cells. Notably, both compounds exhibited preferential antiproliferative activity against HeLa and tsFT210 cells compared with NIH3T3 cells and delayed the G1 phase progression in tsFT210 cells. Our approach indicates a potential strategy for restoring p27(Kip1) levels in human cancers.
    Matched MeSH terms: Sesquiterpenes/chemistry
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