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Melicope incana is one of the plant species that belongs to family Rutaceae. Melicope produces phenolic compounds, including alkaloids, acylphloroglucinol, flavonoids, and coumarins. This study aims to isolate the acyl phloroglucinol derivatives found in M. incana seeds. Extraction of acylphloroglucinol derivatives with methanol using the maceration method at room temperature. Separation and purification using a combination of gravity column chromatography, and radial chromatography. Two acylphloroglucinol compounds have been isolated, namely 3'-geranyl-2',4',6'-trihydroxy acetophenone ( 1 ) and 3'-isoprenyl-2',4',6'-trihydroxy acetophenone ( 2 ). The structure of the two compounds was determined based on UV, IR, 1D, and 2D NMR spectroscopic analysis. Anticancer activity of compounds 1-2 against breast cancer cells MCF-7 showed IC 50 values of 48.98 and 4.30 µg /mL, respectively.

Two furoquinoline alkaloids, leptanoine C (1) and haplopine-3,3´-dimethylallyl ether (2) were isolated from the leaves of Melicope moluccana. The chemical structure of both compounds was determined based on spectroscopic data, including UV, IR, HR-ESI-MS, 1D, and 2D NMR spectral data. The antimalarial activity of compounds 1-2 against Plasmodium falciparum 3D7 showing their IC50 values are 0.18 ppm and 2.28 µg/mL, respectively.

(±)-Melipatulinones A–C (1–3), three unique enantiomeric pairs of lignan–phloroglucinol hybrids along with the biogenetically related compound melipatulignan A (4), were isolated from the leaves of Melicope patulinervia. Melipatulinones A (1) and B (2) share a novel spiro[hydrobenzofuran-2,3′-furan] 5/5/6 tricyclic ring system, while melipatulinone C (3) features an unprecedented spiro[cyclopenta[b]hydrofuran-2,3′-furan] 5/5/5 tricyclic framework. Their structures were determined by spectroscopic methods, electronic circular dichroism (ECD) calculations, and X-ray diffraction. Compounds 1–3 exhibited a pancreatic lipase inhibitory effect.

(±)-Patulignans A–C (1–3), three unique pairs of lignan enantiomers were isolated from the leaves of Melicope patulinervia. Patulignan A (1) possesses an unprecedented dimethyloxonane moiety in nature, meanwhile patulignans B (2) and C (3) are epimers carrying a novel dimethyl-1,6-dioxaspiro[4.5]decane skeleton. Their structures were established by spectroscopy methods and electronic circular dichroism (ECD) calculations. Compounds 1–3 showed significant inhibitory activity against α-glucosidase.

© 2020 American Society for Biochemistry and Molecular Biology Inc.. All rights reserved. Cyclic peptides are reported to have antibacterial, antifungal, and other bioactivities. Orbitides are a class of cyclic peptides that are small, head-to-tail cyclized, composed of proteinogenic amino acids and lack disulfide bonds; they are also known in several genera of the plant family Rutaceae. Melicope xanthoxyloides is the Australian rain forest tree of the Rutaceae family in which evolidine, the first plant cyclic peptide, was discovered. Evolidine (cyclo-SFLPVNL) has subsequently been all but forgotten in the academic literature, so to redress this we used tandem MS and de novo transcriptomics to rediscover evolidine and decipher its biosynthetic origin from a short precursor just 48 residues in length. We also identified another six M. xanthoxyloides orbitides using the same techniques. These peptides have atypically diverse C termini consisting of residues not recognized by either of the known proteases plants use to macrocyclize peptides, suggesting new cyclizing enzymes await discovery. We examined the structure of two of the novel orbitides by NMR, finding one had a definable structure, whereas the other did not. Mining RNA-seq and whole genome sequencing data from other species of the Rutaceae family revealed that a large and diverse family of peptides is encoded by similar sequences across the family and demonstrates how powerful de novo transcriptomics can be at accelerating the discovery of new peptide families.

Five new prenylated acetophenones, melicoptelins A-E (1–5), along with one known congener (6) were isolated from the roots of Melicope ptelefolia. Among them, compounds 2a/2b, 3a/3b, and 4a/4b were obtained as inseparable interconverting mixtures of keto and enol tautomers. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D, 2D NMR and HRESIMS. Compouds 2a/2b, 4a/4b and 5 exhibit protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC50 values of 34.4, 55.2 and 66.6 μM, respectively.

The present study describes the antioxidant effect, glucose uptake activity and cytotoxicity of Melicope lunu-ankenda (ML) leaf extract using cell lines. Results of the study revealed that 60% ethanolic ML extract demonstrated the highest antioxidant activity with total phenolics and flavonoid contents of 354 mg GAE/g DW and 313 mg rutin equivalent (RE)/g DW, respectively. Ferric reducing antioxidant power (FRAP) was found to be 294.3 mM Fe (II) /g. The study showed that, ML leaf extract stimulated fluorescent d-glucose analog 2-[N-(7-nitrobenz-2-oxa-1, 3-diazol-4-yl) amino]-2-deoxy-d-glucose (2-NBDG) uptakes by both 3t3-L1 adipocytes and HepG2 hepatocarcinoma cells, showing significant increase in a dose dependent way. Interestingly, cytotoxic activity of the extract conducted against 3t3-L1 adipocytes and HepG2 using the 3-(4, 5-Dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide (MTT) assay, showed high activity against HepG2 hepatocarcinoma cells with IC 50 of 20.33 ± 1.5 μg/mL and 13.7 ± 2.1 μg/mL after exposure of 48 h and 72 h, respectively. However, ML extract was inactive against 3t3-L1 cell line with IC 50 values of 93 ± 3 μg/mL and 81 ± 2 μg/mL. The results ascertained the significance of ML as a medicinal plant with prodigious applications as an anti-diabetic as well as anti-cancer agents.

Background Type 2 diabetes mellitus (T2DM) is a metabolic disorder characterized by continuous hyperglycemia associated with insulin resistance and /or reduced insulin secretion. There is an emerging trend regarding the use of medicinal plants for the treatment of diabetes mellitus. Melicope lunu-ankenda (ML) is one of the Melicope species belonging to the family Rutaceae. In traditional medicines, its leaves and flowers are known to exhibit prodigious health benefits. The present study aimed at investigating anti-diabetic effect of Melicope lunu-ankenda (ML) leaves extract. Methods In this study, anti-diabetic effect of ML extract is investigated in vivo to evaluate the biochemical changes, potential serum biomarkers and alterations in metabolic pathways pertaining to the treatment of HFD/STZ induced diabetic rats with ML extract using 1H NMR based metabolomics approach. Type 2 diabetic rats were treated with different doses (200 and 400 mg/kg BW) of Melicope lunu-ankenda leaf extract for 8 weeks, and serum samples were examined for clinical biochemistry. The metabolomics study of serum was also carried out using 1H NMR spectroscopy in combination with multivariate data analysis to explore differentiating serum metabolites and altered metabolic pathways. Results The ML leaf extract (400 mg/kg BW) treatment significantly increased insulin level and insulin sensitivity of obese diabetic rats, with concomitant decrease in glucose level and insulin resistance. Significant reduction in total triglyceride, cholesterol and low density lipoprotein was also observed after treatment. Interestingly, there was a significant increase in high density lipoprotein of the treated rats. A decrease in renal injury markers and activities of liver enzymes was also observed. Moreover, metabolomics studies clearly demonstrated that, ML extract significantly ameliorated the disturbance in glucose metabolism, tricarboxylic acid cycle, lipid metabolism, and amino acid metabolism. Conclusion ML leaf extract exhibits potent antidiabetic properties, hence could be a useful and affordable alternative option for the management of T2DM.

A study of the chemical constituents obtained from twigs of Melicope lunu-ankenda (Gaertn.) T.G. Hartley (Rutaceae) led to the isolation and structure elucidation of two new coumarins, 7-(4-hydroxy-3-methylbutanoxy) coumarin and 7-(3-methyl-4-carboxybutanoxy) coumarin methyl ester, named melilunumarin A ( 1 ) and melilunumarin B ( 2 ), respectively. A new benzaldehyde derivative, 3,4-dihydro-3,4-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carboxaldehyde, named melilunumane ( 6 ), was also isolated and characterized, as well as five previously reported compounds, 6-deoxyhaplopinol ( 3 ), marmesin ( 4 ), umbelliferone ( 5 ), kokusaginine ( 7 ) and evolitrin ( 8 ). Among the five isolated coumarins, melilunumarin A ( 1 ), 6-deoxyhaplopinol ( 3 ) and marmesin ( 4 ) exhibited significant inhibitory activity towards Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoylphorbol 13-acetate in Raji cells.

Plant natural compounds have great potential as alternative medicines for preventing and treating diseases. Melicope lunu-ankenda is one Melicope species (family Rutaceae), which is widely used in traditional medicine, consumed as a salad and a food seasoning. Consumption of different parts of this plant has been reported to exert different biological activities such as antioxidant and anti-inflammatory qualities, resulting in a protective effect against several health disorders including neurodegenerative diseases. Various secondary metabolites such as phenolic acid derivatives, flavonoids, coumarins and alkaloids, isolated from the M. lunu-ankenda plant, were demonstrated to have neuroprotective activities and also exert many other beneficial biological effects. A number of studies have revealed different neuroprotective mechanisms for these secondary metabolites. This review summarizes the most significant and recent studies for neuroprotective activity of M. lunu-ankenda major secondary metabolites in neurodegenerative diseases.

Two new prenylated acetophenone derivatives racemates, meliviticines A ( 1 ) and B ( 2 ) with unprecedented rearranged skeletons, were isolated from Melicope viticina . Subsequent chiral resolution led to the separation of two pairs of enantiomers, (±)-meliviticines A ( 1a / 1b ) and (±)-meliviticines B ( 2a / 2b ). Their structures including absolute configurations were elucidated by extensive spectroscopic data, electronic circular dichroism analysis, and X-ray crystallography. A plausible biosynthetic pathway of 1 and 2 , involving ring cleavage and rearrangement of the prenylated acetophenone backbone was proposed. All the isolates showed moderate antimicrobial activities with MIC values of 25–50 μ g/mL against several bacterial and fungal strains.

A synthesis-inspired chemical investigation of the leaves of Melicope ptelefolia led to the isolation of evodialones A–D (1–4), four rearranged acetophenone stereoisomers possessing a prenylated acylcyclopentenone skeleton with three stereogenic carbons. Evodialones C and D (3 and 4) are new minor constituents. The chiral-phase HPLC resolution gave (+)-1–4 and (−)-1–4, eight enantiomers forming a complete stereoisomer library. Their absolute configurations were elucidated via extensive spectroscopic data and a modified Mosher’s method. The relationship between the chiral structures and their NMR and ECD data is discussed. Compounds (±)-1, -2, and -4 have significant protective effects on high-glucose-induced oxidative stress in human vein endothelial cells.

Melicope belahe (Baill.) T.G. Hartley (Rutaceae) is an endemic species to Madagascar. The chemical composition of leaf essential oil is reported for the first time. A sample was extracted by hydrodistillation and analysis was carried out by combination of chromatographic (GC), spectroscopic and spectrometric (MS, 13C NMR) techniques. In total, 56 compounds have been identified. The chemical composition was dominated by α-pinene (42.6%) followed by linalool (6.2%) and (E)-β-caryophyllene (5.2%).

Diabetes mellitus is normally characterized by chronic hyperglycemia associated with disturbances in the fat, carbohydrate, and protein metabolism. There is an increasing trend of using natural products instead of synthetic agents as alternative therapy for disorders due to their fewer side effects. In this study, antidiabetic and antioxidant activities of different Melicope lunu-ankenda (ML) ethanolic extracts were evaluated using inhibition of α-glucosidase and 2,2-diphenyl-l-picrylhydrazyl (DPPH) radicals scavenging activity, respectively; whereas, proton nuclear magnetic resonance ((1) H NMR) and ultra-high performance liquid chromatography-tandem mass spectrometric (UHPLC-MS/MS) techniques were used for metabolite profiling of ML leaf extracts at different concentrations of ethanol and water. Sixty percent of ethanolic ML extract showed highest inhibitory effect against α-glucosidase enzyme (IC50 of 37 μg/mL) and DPPH scavenging activity (IC50 of 48 μg/mL). Antidiabetic effect of ML extracts was also evaluated in vivo and it was found that the high doses (400 mg/Kg BW) of ML extract exhibited high suppression in fasting blood glucose level by 62.75%. The metabolites responsible for variation among ML samples with variable ethanolic levels have been evaluated successfully using (1) H-NMR-based metabolomics. The principal component analysis (PCA) and partial least squares(PLS) analysis scores depicted clear and distinct separations into 4 clusters representing the 4 ethanolic concentrations by PC1 and PC2, with an eigenvalue of 69.9%. Various (1) H-NMR chemical shifts related to the metabolites responsible for sample difference were also ascribed. The main bioactive compounds identified attributing toward the separation included: isorhamnetin, skimmianine, scopoletin, and melicarpinone. Hence, ML may be used as promising medicinal plant for the development of new functional foods, new generation antidiabetic drugs, as a single entity phytomedicine or in combinational therapy.

Four new lignans, patulinones A−D (1–4) and three new acetophenone derivatives, patulinones E−G (5–7) were isolated from the leaves of Melicope patulinervia. Their structures were elucidated on the basis of the interpretation of HR-ESIMS, NMR, CD data. All the isolated compounds were evaluated for α-glucosidase inhibitory activity. Of the isolates, compound 4 was found to exhibit the strongest inhibition against α-glucosidase with IC50 value of 6.02 ± 0.46 μM.

Meliquercifolins A (1), and B (2), two new coumarins are bearing an acetophenone derivative were isolated from the leaves of Melicope quercifolia along with three known compounds, melicodenines E (3), F (4) and I (5). Structures of two new compounds were identified based on spectroscopic analyses (UV, HR-ESI-MS, 1 D and 2 D NMR). Cytotoxic activities of compounds (1–5) towards three human cancer cells (HeLa, MCF-7, P-388), compounds 1, 4 and 5 showed very potent activity against Hela cells with IC50 values 2.6; 0.8; 1.1 μM, respectively.

The increasing number of prevalence infertility cases is becoming a major public health problem in developing countries due to changes in diet and lifestyle. Melicope ptelefolia is known for its health benefit as a sex enhancing effect among the Malays folk however there is no clinical data to prove it until these days. The main aim of the present study is to identify the effects of Melicope ptelifolia Aqueous extract (MPAE) on Sperm Parameters and Testosterone Level . A total of 30 male Sprague Dawley rats were divided equally into five different groups. MPAE was given by orally gavage for 28 days at a dose of 100mg/kg, 200 mg/kg and 500 mg/kg body weight to the animals of group II (n=6), III (n=6) and IV (n=6), respectively. The animals of group I (control, n=6) had distilled water and group V had sildenafil citrate. Results were analyzed using one way ANOVA test and the data were significant at p

Compost teas were proved to be used as effective biocontrol agent owing to their ability to inhibit plant diseases. In this experiment, aerated compost tea (ACT) and molasses aerated compost tea (MACT) sourced from oil palm compost were assessed to suppress against fungal pathogen namely, Grammothele lineata (KX532185) that causes leaf spot on Melicope ptelefolia leaf. Characterization of both aerated compost teas for physiochemical and microbiological analysis was carried out. All different concentrations (15%, 25%, 30%, and 40% v/v) of ACT and MACT significantly retarded the mycelial growth of Grammothele lineata in the range of 14.5–77.8% and 12.7–75.9%, respectively. The highest inhibition over Grammothele lineata was obtained by both compost teas at concentration of 40% (v/v) resulted with 12% and 14% growth only, respectively. Peroxidase (PO) and polyphenol oxidase (PPO) activities peaked 2–4 days after Grammothele lineata fungal suspension (5 × 105 conidia/mL) challenged on fortified leaf disks. Besides, in Melicope ptelefolia leaf fortified with both compost teas, peroxidase (PO) reached the highest (245.05 IU min−1 g−1 fresh weight) after 7 days, whereas polyphenol oxidase (PPO) recorded the highest at 91.3 IU min−1 g−1 fresh weight after 4 days upon challenged by Grammothele lineata suspension (5 × 105 conidia/mL). Our result showed that the defense enzyme properties play a significant role in contributing disease resistance against phytopathogen attack.

This article aims to provide detailed information on Malaysian plants used for treating inflammation. An extensive search on electronic databases including PubMed, Google Scholar, Scopus, and ScienceDirect and conference papers was done to find relevant articles on anti-inflammatory activity of Malaysian medicinal plants. The keyword search terms used were “inflammation,” “Malaysia,” “medicinal plants,” “mechanisms,” “in vitro,” and “in vivo.” As a result, 96 articles on anti-inflammatory activity of Malaysian medicinal plants were found and further reviewed. Forty-six (46) plants (in vitro) and 30 plants (in vivo) have been identified to possess anti-inflammatory activity where two plants,Melicope ptelefolia(Tenggek burung) andPortulaca oleracea(Gelang pasir), were reported to have the strongest anti-inflammatory activity of more than 90% at a concentration of 250 µg/ml. It was showed that the activity was mainly due to the occurrence of diverse naturally occurring phytochemicals from diverse groups such as flavonoids, coumarins, alkaloids, steroids, benzophenone, triterpenoids, curcuminoids, and cinnamic acid. Hence, this current review is a detailed discussion on the potential of Malaysian medicinal plants as an anti-inflammatory agent from the previous studies. However, further investigation on the possible underlying mechanisms and isolation of active compounds still remains to be investigated.

Melicolones A (1) and B (2), a pair of rearranged prenylated acetophenone epimers with an unusual 9-oxatricyclo[3.2.1.1(3,8)]nonane core, were isolated from the leaves of Melicope ptelefolia. Further chiral high-performance liquid chromatography resolution gave enantiomers (+)- and (-)-1, as well as (+)- and (-)-2, respectively. The structures and absolute configurations of the pure enantiomers were determined by extensive spectroscopic data and single crystal X-ray diffraction. All the isolated enantiomers exhibited potent cell protecting activities against high glucose-induced oxidative stress in human vein endothelial cells.

Melicolones C–K (1–9), nine acetophenone derivatives with three unprecedented architectures, were characterized from the leaves of Melicope ptelefolia. Among them, melicolone C (1) was a novel acetophenone analogue possessing a highly rearranged spiro skeleton. Melicolones D-F (2–4) were three novel acetophenone congeners bearing unusual octalactone ring. Melicolones G-K (5–9) were five new prenylated acetophenone derivatives featuring a 9-oxatricyclo [3.2.1.13, 8]nonane core. Their structures were established by extensive spectroscopic analysis and ECD spectra. These different structures were presumably derived from the same precursor via three major biosynthetic pathways. Compounds 5–9 exerted moderate effects to reverse multidrug-resistance in MCF-7/ADR cells with reversal fold values ranging from 6.2 to 13.3.

Malaysian is among the most diverse plant resource country in the world especially with its richesnest flora and fauna. It has about 12,000 species of flowering plants of which about 1,300 species were said to be medicinal plant and have been investigated for their therapeutic potential. Spies have been known to be a valuable source of bioactive compound which are being used to treat various diseases and improved health for a thousand years ago. The beneficial health effects of medicinal plants come from polyphenols group which is often attributed to their potent antioxidant activities. This paper reviews the antioxidant potential of selected plants from Malaysia as Persicaria hydropiper, Cosmos caudatus and Melicopeptelefolia based on reported from several researchers.

Four novel geminally dialkylated, non-aromatic acetophenone derivatives 1–4 were isolated from Melicope coodeana. The compounds, related to hop bitter acids, were named Coodeanones A–C, where Coodeanone B was found in both E and Z configuration of the 6′‴–7′‴ double bond. Antibacterial, antifungal and antimalarial activities of the acetophenone derivaties were investigated, and Coodeanone C (4) was found to have activity toward Plasmodium falciparum (malaria) (IC50 = 42.8 μM).

Quorum sensing regulates bacterial virulence determinants, therefore making it an interesting target to attenuate pathogens. In this work, we screened edible, endemic plants in Malaysia for anti-quorum sensing properties. Extracts from Melicope lunu-ankenda (Gaertn.) T. G. Hartley, a Malay garden salad, inhibited response of Chromobacterium violaceum CV026 to N-hexanoylhomoserine lactone, thus interfering with violacein production; reduced bioluminescence expression of E. coli [pSB401], disrupted pyocyanin synthesis, swarming motility and expression of lecA::lux of Pseudomonas aeruginosa PAO1. Although the chemical nature of the anti-QS compounds from M. lunu-ankenda is currently unknown, this study proves that endemic Malaysian plants could serve as leads in the search for anti-quorum sensing compounds.

The ‘Ulam’, a traditional Malay dish, are plants that can be eaten raw, as a form of local salad. The shoots and young leaves of Melicope ptelefolia are among the popular species, believed to be high in nutritional and medicinal values. The metabolomic fingerprinting analysis of the ethanolic extracts of leaves of M. ptelefolia was carried out using 1 H Nuclear Magnetic Resonance (NMR) spectroscopy and multivariate data analysis in order to differentiate young and mature leaves and to evaluate the variation of their chemical composition. Principle component analysis (PCA) of the 1 H NMR spectra showed a clear discrimination between the young and mature leaves extracts by PC3 and PC4. The compounds responsible for the differentiation were identified by comparison of 1 H NMR chemical shifts and qualitative HPLC. The young leaves were found to be richer in fatty acids and the levels of the three marker compounds, p - O -geranylcoumaric acid, 2,4,6-trihydroxy-3-geranylacetophenone and 2,4,6-trihydroxy-3-prenylacetophenone, were clearly higher. The mature leaves contain higher levels of sugars and glycosidic components.

A new quinolone alkaloid, melimoluccanin (1) along with two known alkaloids, leptanoine C (2) and 7-O-isoprenyl-γ-fagarin (3) were isolated from the leaves of Melicope moluccana T.G. Hartley. Structures all of compounds were elucidated using spectroscopic methods such as UV, IR, HRESIMS, 1D and 2D NMR. Compounds 1-3 were evaluated for their cytotoxicity against P-388 cells and for antimalaria activity using giemsa methods. The cytotoxic data of compounds 1-3 showed IC50 of 0.63; 5.85 and 2.09 μg/mL, respectively. The antiplasmodial activity of compound 1-3 showed IC50 value of 4.28; 2,28 and 0.18 μg/mL, respectively. Based on the data, it can be concluded that compound 1 has high activity against P-388 cells and compound 3 is potential as antimalaria.

Solvent–solvent fractionation of the methanolic extract of the popular Malay traditional vegetable “tenggek burung” (Melicope ptelefolia), followed by nitric oxide inhibition assay on RAW 264.7 cells revealed that the most active components reside mainly in hexane and dichloromethane fractions. Online profiling of the nitric oxide (NO) inhibitive fractions of the tenggek burung using liquid chromatography coupled diode array detection and electrospray ion-trap tandem mass spectroscopy (LC–DAD–ESI-MSn), has identified seven constituents. The compounds were identified as kokusaginine (1), compound 2, [kokusagine, (2a) or 5-methoxymaculine (2b)], 2,4,6-trihydroxy-3-prenylacetophenone (3), 2,4,6-trihydroxy-3-geranylacetophenone (4), 2,4,6-trihydroxy-3-geranylgeranylacetophenone (5), 3-[4-O-(3,7-dimethyl-2,6-octadienyl)phenyl]-2-propenoic acid (6) and 2,4,6-trihydroxy-3-farnesylgeranylacetophenone (7). The identity of compounds 1, 4 and 6 were unequivocally confirmed by isolation and spectroscopic evidences, other constituents are tentatively identified, based on their UV, MS, MSn and comparison with literature data. Kokusaginine (1) demonstrated in vitro activity on NO inhibition in murine peritoneal macrophages.

The leaves of Melicope ptelefolia (Rutaceae) afforded a new acetophenone named 2,4,6-trihydroxy-3-geranylacetophenone. The structure of the compound was established by mass and NMR spectroscopy.

The steam distilled leaf oil of the two species of Melicope (M. contermina and M. polybotrya) indigenous to Lord Howe Island have been examined by GC and GC/MS. Melicope contermina gave an oil in which the major components were limonene (33%) and elemol (23%). The oil yield was 0.1%. Melicope polybotrya gave a leaf oil in which the major components were geijerene (41%), pregeijerene (38%) and limonene (9%). The oil yield in this case was 0.6–1% based on fresh leaves.

Leaf extracts of Melicope lunu-ankenda were chemically studied and found to contain mixtures of hydrocarbons and squalene, fatty acids and esters. A geranylated coumaric acid was isolated as the major compound. The crude dichloromethane and methanol extracts of the leaves were found to be strongly larvicidal with LC50 values below 20 microg mL(-1). This is a first isolation of p-O-geranylcoumaric acid from this plant.

The leaf oils of the 14 Australian species of the genera Euodia and Melicope have been analyzed by GC and GC/MS. Euodia hylandii produced a leaf oil that was dominated by sesquiterpenes, with spathulenol (12–20%) as the major component. Euodia pubifolia gave a primarily sesquiterpenic oil with the major component being spathulenol (18.3%). Melicope affinis produced a sesquiterpenic oil in which the major components were the hydrocarbons bicyclogermacrene (7–18%) and (β-bisabolene (t-9%). Melicope bonwickii gave an oil in which sesquiterpenes predominated; zierone (0.3–3%) and three further suspected isomers (A, B each 5–10% and C 13–20%) were the principal components. The leaf oil of M. broadbentiana was, in most cases, dominated by monoterpenes. The major components detected were α-pinene (21–76%) and limonene (0.6–28%). Melicope elleryana gave a leaf oil which was dominated by zierone (26–42%) and the chromenes, allo-evodione (4–10%) and evodione (10–22%). Melicope fellii produced a sesquiterpe...

A phytochemical study of Melicope patulinervia gave a new flavone 7-(3-methyl-but-2-enyloxy)-5-hydroxy-3,6,8-trimethoxy-3’,4'-methylenedioxyflavone and three known flavones, melibentin, 5-hydroxy-3,7,8-trimethoxy-3’,4'-methylenedioxyflavone, 5-hydroxy-3,6,7,8-tetrameth-oxy-3’,4'-methylenedioxyflavone. Their structures were elucidated on the basis of spectroscopic analysis combined with chemical methods. The antifungal activities of the isolated compounds were evaluated against four plant pathogenic fungi species.

4-Methoxy-3-(3-methylbut-2-en-1-yl)-7-[(3-methylbut-2-en-1-yl)oxy]quinolin-2(1H)-one (1) was isolated from the leaves of Melicope moluccana T.G. Hartley. The chemical structure of 1 was elucidated using mainly UV, IR, HRESIMS, 1D and 2D-NMR spectroscopy.

Two novel compounds, the lignan, (+)-2- (3,4-dimethoxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo [3,3,0]octane, and the coumarin, (+)-7-(3-methyl-4-carboxybutanoxy)umbelliferone methyl ester, have been isolated from the aerialparts of Melicope hayesii . The known compounds, eudesmin, kobusin, N - p -coumaroyltyramine, N -methyl-2-pyrrolidinone, umbelliferone and 7- (3-methylbut-2-enoxy)umbelliferone were alsoobtained. Their structures were determined by extensive NMR studies.

The investigation of the leaves of Melicope ptelefolia (Rutaceae) afforded, besides N-methylflindersine, two new bisquinolinone alkaloids named melicobisquinolinone A and B. Their structures were established by MS and NMR spectroscopy, especially NOE and HMBC experiments.

Investigation of leaves of Melicope ptelefolia afforded 18 2,2-dimethyl-2H-1-benzopyrans, consisting of 14 new members, including one benzodipyran and four known compounds. Their structures were established by mass and NMR spectroscopy, especially NOE and HMBC experiments. © 1997 Elsevier Science Ltd. All rights reserved

The leaf oil from Melicope melanophloia C.T. White indicates that it exists in three chemical forms. One form contains methyl chavicol (5–13%) and methyl eugenol (51–67%) as major compounds; a second form is entirely terpenoid with α-pinene (34–37%), myrcene, α-phellandrene, limonene and 1,8-cineole (4–12%) as major compounds; while a third chemotype contains limonene (1–8%), (Z)-β-ocimene (12–18%) and (E)-β-ocimene (23–56%) as major compounds. This third form also contains 2-hydroxy-4,6-dimethoxyacetophenone (4–6%). The oil yield from all chemotypes was in the range 0.1–0.9%.

Octandrenolone and five novel related dimethylpyran acetophenones have been isolated from the chloroform extract of roots of Melicope erromangensis and identified by spectroscopic studies and chemical correlations as O-methyloctandrenolone, (+)-trans-3‴,4‴-dihydro-3‴,4‴-dihydroxy-O-methyloctandrenolone, (+)-trans- 3″,4″-dihydro-3″,4″-dihydroxy-O-methyloctandrenolone, and trans-3″,4″-dihydro-3″,4″-dihydroxyoctandrenolone. In addition, four known quinolines and three known flavones have been isolated.

Melicope patulinervia (Merr. and Chun) Huang is the rare and endangered plant in the Hainan Province, China. In the purpose of exploring the value of its exploitation and utilization, this study was conceived to evaluate the antimicrobial, antioxidant activities and the active ingredients of this plant. Spectrophotometry was the basis for the determinations of total phenol and total flavonoids. Meanwhile, the antioxidant activities of the different parts, different solvents extracts of M. patulinervia were measured by 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) methods. Seven plant pathogenic fungi species were used to assay for antimicrobial activity of the extracts of this plant. The results showed that 70% methanol extracts of the leaves had higher level of total flavonoids, with a content of 41.3194±0.071 mg·g-1. But it was strange that the contents of total phenol of the extracts of the plant were significantly less than that of total flavonoids. The antioxidant activities of the different parts, different solvents extracts of M. patulinervia were all weak. The leaf extract showed antimicrobial activity against 4 of the plant of pathogenic fungi species, especially Oxytetracycline hydrochloride. Key words: Melicope patulinervia (Merr. and Chun) Huang, active ingredients, antimicrobial activity, antioxidant activity.

Melicope stipitata has yielded six acetophenone derivatives; acronylin, evodionol methyl ether, evodionol and three novel compounds. The latter were identified as 5-acetyl-6-hydroxy-2-(2-hydroxyisopropyl)-4-methoxybenzofuran (furostipitol), (rel)-(±)-6-acetyl-3,4-dihydro-4α-ethoxy-3β-hydroxy-5,7-dimethoxy-2,2-dimethyl-2H-1-benzopyran (3-hydroxydihydropyranostipitol-4-ethyl ether) and (rel)-(±)-6-acetyl-3,4-dihydro-3β,4α-dihydroxy-5,7-dimethoxy-2,2-dimethyl-2H-1-benzopyran (3,4-dihydroxydihydropyranostipitol). 5-Acetyl-6-hydroxy-2-(2-hydroxyisopropyl)-4-methoxybenzofuran was isolated together with a small quantity of another compound, tentatively identified as its dihydrofuran analogue, namely, 5-acetyl-2,3-dihydro-6-hydroxy-2-(2-hydroxyisopropyl)-4-methoxy benzofuran. The 1 H NMR spectra of 3,4-dihydroxydihydropyranostipitol in different solvents is discussed. In addition, the furocoumarins, bergapten, phellopterin, isoimperatorin andisopimpinellin, the angular pyranocoumarin, seselin, the 8-prenylated coumarins, osthol, peroxyauraptenol and osthenon, the biscoumarin, phebalin, the lignan, sesamin, and the triterpene, isobaurenol, were obtained.

One of the products obtained from the fruit of the indigenous Australian tree Melicope ellyrana has been confirmed as the flavonoid pachypodol (4,5′-di­hydroxy-3,3′,7-tri­methoxy­flavone), C18H16O7. This compound is similar to a number of the flavonones from the same species with the exception of the reduced side chain. The usual intramolecular hydrogen bonding between the hydroxy and the adjacent carbonyl or methoxy substituent groups is found, together with intermolecular hydrogen bonding between one of these hydroxy groups and a methoxy O atom [O⋯O 2.875 (4) A], giving an infinite chain.

Investigation of leaves of Melicope ptelefolia afforded 18 2,2-dimethyl-2H-1-benzopyrans, consisting of 14 new members, including one benzodipyran and four known compounds. Their structures were established by mass and NMR spectroscopy, especially NOE and HMBC experiments. © 1997 Elsevier Science Ltd. All rights reserved

The investigation of the leaves of Melicope ptelefolia (Rutaceae) afforded, besides N-methylflindersine, two new bisquinolinone alkaloids named melicobisquinolinone A and B. Their structures were established by MS and NMR spectroscopy, especially NOE and HMBC experiments.

The crystal structure determinations of two crystalline components of the hexane extract of the fruit of the indigenous Australian tree Melicope ellyrana have shown them to be polymorphs of the same compound, namely the flavonoid 4′,5-di­hydroxy-3,3′,8-tri­methoxy-7-(3-methyl­but-2-enyl­oxy)­flavone [systematic name: 5-hydroxy-2-(4-hydroxy-3-methoxy­phenyl)-3,8-di­methoxy-7-(3-methyl­but-2-enyl­oxy)-4H-1-benzo­pyran-4-one], C23H24O8. The two polymorphs, one monoclinic (polymorph A) and the other triclinic (polymorph B), show significant conformational differences, particularly in the enyl­oxy side chain, while only one (polymorph A) shows intermolecular hydrogen bonding.

Aim of the study Melicope lunu-ankenda (Gaertn.) T.G. Hartley is used in Indian traditional medicine for fever, improving complexion and as a tonic. Previous studies have isolated fungicidal, antifeedant, anti-inflammatory and immunomodulatory compounds from Melicope lunu-ankenda . This study is aimed at the isolation and biological activity screening of potential molecules from the volatile oils and extracts of Melicope lunu-ankenda in the light of traditional applications. Materials and methods Volatile oil of Melicope lunu-ankenda leaves was isolated by hydrodistillation, characterized by GC–FID, GC–MS, LRI determination, Co-GC and database searches. Major chromene-type compounds in Melicope lunu-ankenda leaf oil, evodione and leptonol, were isolated by preparative TLC and characterized by UV–Vis, IR, 1H-, 13C-, 13C-DEPT NMR and EIMS. They were also isolated from the petroleum ether and acetone extracts of the leaves of Melicope lunu-ankenda by column chromatography in petroleum ether–ethyl acetate. Their contents in leaf oil, leaf and inflorescence extracts were estimated by HPTLC. Antipyretic (Baker's yeast-induced fever test), analgesic (acetic acid-induced writhing, tail immersion assays), anti-inflammatory (carrageenan-induced paw edema) and in vitro antioxidant (DPPH radical, superoxide radical scavenging) activities of evodione and leptonol were tested. Results and conclusions Gas chromatographic analyses found 50.7% monoterpene hydrocarbons, 0.4% oxygenated monoterpenes, 3.2% sesquiterpene hydrocarbons, 0.7% oxygenated sesquiterpenes and 43.7% chromene-type compounds in Melicope lunu-ankenda leaf oil, with evodione (20.2%) and leptonol (22.5%) as its two major constituents. HPTLC estimations in the petroleum ether, acetone extracts (leaf, inflorescence) and leaf oil found evodione 1.0% (dr. wt., leaf), 1.1% (inflorescence), 0.04% (fr. wt. leaves, leaf oil), and leptonol 0.3% (leaf), 0.3% (inflorescence) and 0.04% (leaf oil). Leptonol (200 mg/kg) showed good antipyretic activity. DPPH radical scavenging assay found moderate activity for leptonol (68.7%, 500 μM), whereas evodione showed near-zero activity. A very similar trend was found in superoxide radical scavenging activity of leptonol (64.5%) and evodione (10.3%), both at 100 μg/ml. Evodione and leptonol showed moderate analgesic activities in acetic acid-induced writhing and tail immersion assays. Moderate anti-inflammatory activity was found for both evodione (59.4%) and leptonol (49.0%) at 100 mg/kg. Ethnopharmacological relevance Biological activities of evodione and leptonol isolated from Melicope lunu-ankenda justify its traditional uses as a remedy for fever, inflammation and as a tonic.

The leaves of Melicopte ptelefolia afforded two new 2,2–dimethyl–2H–1–benzopyran dimers named 5,5’–dimethoxy–alloagerasanin and melifolin. Their structures were established by NMR spectroscopy, especially NOE and HMBC. © 1998 Published by Elsevier Science Ltd. All rights reserved.

A new acetophenone derivative, melicopone, along with twenty-nine known compounds has been isolated from the root wood of Melicope semecarpifolia. The structure of this new compound was determined using spectral analyses. The compound oxynitidine isolated in this study adds the Melicope genus to the benzo[c]phenanthridine-containing members chemotaxonomically. Three isolates were cytotoxic in P-388 and HT-29 cell lines, and anti-platelet aggregation activities were shown for 10 known compounds.

Three new natural products, 3,8-dimethoxy-5,7-dihydroxy-3',4'-methylenedioxyflavone, 3,6,8-trimethoxy-5,7-dihydroxy-3',4'-methylenedioxyflavone and 3,6,8,3',4'-pentamethoxy-5,7-dihydroxyflavone were isolated from Melicope coodeana syn. Euodia simplex (Rutaceae) along with 3,6,3'-trimethoxy-5,7,4'-trihydroxyflavone and 3,3'-dimethoxy-5,7,4'-trihydroxyflavone. The structural assignments are based on (1)H and (13)C NMR data, including discussion of the chemical shifts of C-2 in 3,5-dihydroxy- and 3-methoxy-5-hydroxyflavones. The presence of highly methoxylated and methylenedioxyflavones is characteristic of the genus Melicope, and the present findings support the recent transfer of Euodia simplex to Melicope.