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Melicope quercifolia, a plant from the Rutaceae family, is known for its medicinal properties, especially in traditional herbal medicine. Flavonoids, bioactive compounds widely found in plants, are recognized for their antioxidant and cytotoxic effects, making them promising candidates for cancer therapy and combating oxidative stress. Two flavonols, pachypodol (1) and ternatin (2), were isolated from the stem bark of M, quercifolia. Compounds 1-2 were isolated and purified with column and planar radial chromatography. The structures of 1-2 were determined based on HRESI-MS data, UV, 1D, and 2D NMR spectra. Compound 1 showed high activity against HeLa cells (IC50 values 0.65 µg/mL), moderate against P-388 cells (IC50 values 2.45 µg/mL), and weak activity against (DPPH radical (IC50 values 254 µg/mL. [ABSTRACT FROM AUTHOR]

Abstract Acetophenones are naturally occurring phenolic compounds which have found in over 24 plant families and also fungi strains. They are exist in both free or glycosides form in nature. The biological activities of these compounds have been assayed and reported including cytotoxicity, antimicrobial, antimalarial, antioxidant and antityrosinase activities. Herein, we review the chemistry and biological activity of natural acetophenone derivatives that have been isolated and identified until January 2024. Taken together, it was reported 252 acetophenone derivatives in which the genera Melicope (69) and Acronychia (44) were the principal species as producers of acetophenones. Graphical Abstract

Acetophenones are naturally occurring phenolic compounds which have found in over 24 plant families and also fungi strains. They are exist in both free or glycosides form in nature. The biological activities of these compounds have been assayed and reported including cytotoxicity, antimicrobial, antimalarial, antioxidant and antityrosinase activities. Herein, we review the chemistry and biological activity of natural acetophenone derivatives that have been isolated and identified until January 2024. Taken together, it was reported 252 acetophenone derivatives in which the genera Melicope (69) and Acronychia (44) were the principal species as producers of acetophenones. [ABSTRACT FROM AUTHOR]

In the restoration of drained and degraded tropical peat swamp forest (PSF) it is not well understood whether fire suppression on its own is sufficient to facilitate regeneration, or if rewetting plays a key role. We attempt to answer this question in the Merang area, a 23,000-ha peatland located in South Sumatra province, Indonesia. As with more than 90 % of PSF in Southeast Asia, the area has been largely degraded by logging and drainage canals, along with multiple fires. It has been designated and managed as an ecosystem restoration area since 2016, by which time only a single 254 ha patch of original PSF habitat remained. However, scattered remnant PSF trees (< 1 % cover) occurred throughout the area, along with seedlings of pioneer woody species in a landscape otherwise dominated by sedges and ferns. Peatland rehabilitation began with installation of 84 box dams in 2017, followed by 212 peat compaction dams mainly between late 2019 and early 2020. Since installation of the latter, the average water table depth (WTD) has decreased by 20–120 cm. In parallel with reduced WTD and fire prevention, regrowth has been vigorous, with total cover of woody plants increasing by almost a third, from 28.6 % in 2016 to 39.4 % in 2021. At the same time, changes in normalised difference vegetation index (NDVI) indicate a doubling in increase of woody vegetation cover between 20172020 and 20202021. Reduced WTD supports the recovery of woody vegetation cover, but Principal Component Analysis (PCA) strongly suggests that fire history determines the species composition of regenerated woody pioneer vegetation. Melaleuca cajuputi dominates where fires have been most frequent (on average > 4 fires), while Macaranga pruinosa, Melicope glabra and Melicope lunu-ankenda dominate in regenerating areas that have experienced 12 fires. While fire suppression is essential to prevent further loss of vegetation, effective rewetting is required before woody vegetation can recover.

In the restoration of drained and degraded tropical peat swamp forest (PSF) it is not well understood whether fire suppression on its own is sufficient to facilitate regeneration, or if rewetting plays a key role. We attempt to answer this question in the Merang area, a 23,000-ha peatland located in South Sumatra province, Indonesia. As with more than 90 % of PSF in Southeast Asia, the area has been largely degraded by logging and drainage canals, along with multiple fires. It has been designated and managed as an ecosystem restoration area since 2016, by which time only a single 254 ha patch of original PSF habitat remained. However, scattered remnant PSF trees (< 1 % cover) occurred throughout the area, along with seedlings of pioneer woody species in a landscape otherwise dominated by sedges and ferns. Peatland rehabilitation began with installation of 84 box dams in 2017, followed by 212 peat compaction dams mainly between late 2019 and early 2020. Since installation of the latter, the average water table depth (WTD) has decreased by 20-120 cm. In parallel with reduced WTD and fire prevention, regrowth has been vigorous, with total cover of woody plants increasing by almost a third, from 28.6 % in 2016 to 39.4 % in 2021. At the same time, changes in normalised difference vegetation index (NDVI) indicate a doubling in increase of woody vegetation cover between 2017-2020 and 2020-2021. Reduced WTD supports the recovery of woody vegetation cover, but Principal Component Analysis (PCA) strongly suggests that fire history determines the species composition of regenerated woody pioneer vegetation. Melaleuca cajuputi dominates where fires have been most frequent (on average > 4 fires), while Macaranga pruinosa, Melicope glabra and Melicope lunu-ankenda dominate in regenerating areas that have experienced 1-2 fires. While fire suppression is essential to prevent further loss of vegetation, effective rewetting is required before woody vegetation can recover. [ABSTRACT FROM AUTHOR]

The data on 31 species of lichenicolous fungi (Abrothallus caerulescens, Arthonia phaeophysciae, Athelia arachnoidea, Cercidospora macrospora, Clypeococcum hypocenomycis, Cornutispora lichenicola, Erythricium aurantiacum, Heterocephalacria physciacearum, Intralichen christiansenii, Lichenochora obscuroides, Lichenoconium erodens, L. lecanorae, L. usneae, Lichenodiplis lecanorae, Lichenostigma cosmopolites, Lichenothelia convexa, L. scopularia, Marchandiomyces corallinus, Monodictys epilepraria, Muellerella pygmaea, M. erratica, Pronectria leptaleae, Pyrenochaeta xanthoriae, Sclerococcum sphaerale, Sphaerellothecium propinquellum, Stigmidium fuscatae, S. squamariae, S. xanthoparmeliarum, Taeniolella phaeophysciae, T. punctata, Xanthoriicola physciae) new to the Teteriv River Basin are provided. Further five species (Cercidospora crozalsiana, Lichenostigma epipolina, Lichenothelia tenuissima, Polysporina subfuscescens and Taeniolella beschiana) are new to Ukraine. Additional localities for all newly reported species are listed. [ABSTRACT FROM AUTHOR]

The genus Melicope, which consists of 230 species, stands out as the largest genus within the Rutaceae family. Melicope species are characterized by their evergreen nature and can range from shrubs to predominantly dioecious trees. The Melicope species have been utilized in traditional medicine to address a wide range of ailments, including fever, colds, cramps, and inflammation. These plants have gained significant attention due to their noteworthy ethnopharmacological and ethnomedicinal significance. Researchers have isolated numerous biologically active secondary metabolites from different Melicope species, which include polymethoxylated flavonoids, furanocoumarins, acetophenones, benzenoids, and quinolone alkaloids. These compounds exhibit diverse biological activities, such as antibacterial, antidiabetic, antifungal, and antiproliferative properties against human cancer cell lines. This review provides an update on the chemical constituents of the selected species of Melicope. The study also highlights the anticancer and cytotoxicity properties of the plant extracts and phytochemical constituents from Melicope species. Furthermore, the molecular mechanisms underlying the anticancer effects are elucidated. Overall, this review contributes to understanding the significant pharmacological potential of Melicope species and unlocking their chemical composition, emphasizing their relevance in the development of therapeutic agents, particularly in the field of cancer research., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)

Abstract 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 agent. [ABSTRACT FROM AUTHOR]

Oceanic islands are unique in their species composition, which is defined by arrival of colonizers via long distance dispersal followed by establishment of species followed in some cases by adaptive radiation. Evolutionary biologists identified traits facilitating successful colonization of islands as including polyploidy, self‐compatibility, herbaceousness and ability for long‐distance dispersal. Successful establishment and evolutionary diversification of lineages on islands often involves shifts to woodiness and shifts in methods of outcrossing as well as changes in dispersal ability. The genus Melicope colonized numerous archipelagos throughout the Pacific including the Hawaiian Islands, where the lineage comprises currently 54 endemic species and represents the largest radiation of woody plants on the islands. The wide distributional range of the genus illustrates its high dispersibility, most likely due to adaption to bird dispersal. Here we investigate ploidy in the genus using flow cytometry and chromosome counting. We find the genus to be paleopolyploid with 2n = 4x = 36, a ploidy level characterizing the entire subfamily Amyridoideae and dating back to at least the Palaeocene. Therefore Hawaiian Melicope have not undergone recent polyploidization prior to colonization of the islands. Thus Melicope retained colonization success while exhibiting a combination of traits that typically characterize well established island specialists while lacking some traits associated to successful colonizers. [ABSTRACT FROM AUTHOR]

The genus Melicope (Rutaceae) occurs on most Pacific archipelagos and is perfectly suited to study Pacific biogeography. The main goal was to infer the age, geographic origin and colonization patterns of Melicope and its relatives. We sequenced three nuclear and two plastid markers for 332 specimens that represent 164 species in 16 genera of Rutaceae. Phylogenetic reconstruction, molecular dating, ancestral area reconstruction and diversification analyses were carried out. The two main clades (Acronychia‐Melicope and Euodia) originated in Australasia and their crown ages are dated to the Miocene. Diversification rates differed among the subclades and were lowest in the Euodia lineage and highest in the Hawaiian Melicope lineage. The Malagasy and Mascarene species form a clade, which split from its SE Asian relatives in the Pliocene/Pleistocene. At least eight colonizations to the Pacific islands occurred. The timing of all colonizations except for the Hawaiian group is congruent with age of the island ages. Australia, New Guinea and New Caledonia have been the source of colonizations into the Pacific islands in the Melicope clade. Melicope shows high dispersability and has colonized remote archipelagos such as the Austral and Marquesas Islands each twice. Colonization of islands of the Hawaiian‐Emperor seamount chain likely predates the ages of the current main islands, and the initial colonization to Kaua'i occurred after the splitting of the Hawaiian lineage into two subclades. Wider ecological niches and adaptations to bird‐dispersal likely account for the much higher species richness in the Acronychia‐Melicope clade compared to the Euodia clade. [ABSTRACT FROM AUTHOR]

Platydesma, an endemic genus to the Hawaiian Islands containing four species, has long been considered of obscure origin. Recent molecular phylogenetic studies have unequivocally placed Platydesma within the widespread genus Melicope as sister to the rest of the Hawaiian species of Melicope. This makes submerging Platydesma into Melicope necessary. We make the necessary new combinations: Melicope cornuta (Hillebr.) Appelhans, K.R. Wood & W.L. Wagner, M. cornuta var. decurrens (B.C.Stone) Appelhans, K.R. Wood & W.L. Wagner, M. remyi (Sherff) Appelhans, K.R. Wood & W.L. Wagner, and M. rostrata (Hillebr.) Appelhans, K.R. Wood & W.L. Wagner. An additional species that has been recognized within Platydesma should now be recognized under its original name M. spathulata A. Gray. All Hawaiian species belong to Melicope section Pelea. Our molecular phylogenetic studies also showed that in addition to merging Platydesma into section Pelea, five species described from New Caledonia need to be excluded from the section in order to achieve monophyly of section Pelea. [ABSTRACT FROM AUTHOR]

Melicope stonei K.R. Wood, Appelhans & W.L. Wagner (section Pelea, Rutaceae), a new endemic tree species from Kaua'i, Hawaiian Islands, is described and illustrated with notes on its distribution, ecology, conservation status, and phylogenetic placement. The new species differs from its Hawaiian congeners by its unique combination of distinct carpels and ramiflorous inflorescences arising on stems below the leaves; plants monoecious; leaf blades (5-)8-30 × (4-)6-11 cm, with abaxial surface densely tomentose, especially along midribs; and very long petioles of up to 9 cm. Since its discovery in 1988, 94 individuals have been documented and are confined to a 1.5 km2 region of unique high canopy mesic forest. Melicope stonei represents a new Critically Endangered (CR) single island endemic species on Kaua'i. [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

tHGA, a geranyl acetophenone compound originally isolated from a local shrub called Melicope ptelefolia , has been previously reported to prevent ovalbumin-induced allergic airway inflammation in a murine model of allergic asthma by targeting cysteinyl leukotriene synthesis. Mast cells are immune effector cells involved in the pathogenesis of allergic diseases including asthma by releasing cysteinyl leukotrienes. The anti-asthmatic properties of tHGA could be attributed to its inhibitory effect on mast cell degranulation. As mast cell degranulation is an important event in allergic responses, this study aimed to investigate the anti-allergic effects of tHGA in cellular and animal models of IgE-mediated mast cell degranulation. For in vitro model of IgE-mediated mast cell degranulation, DNP-IgE-sensitized RBL-2H3 cells were pre-treated with tHGA before challenged with DNP-BSA to induce degranulation. For IgE-mediated passive systemic anaphylaxis, Sprague Dawley rats were sensitized by intraperitoneal injection of DNP-IgE before challenged with DNP-BSA. Both in vitro and in vivo models showed that tHGA significantly inhibited the release of preformed mediators (β-hexosaminidase and histamine) as well as de novo mediators (interleukin-4, tumour necrosis factor-α, prostaglandin D 2 and leukotriene C 4 ). Pre-treatment of tHGA also prevented IgE-challenged RBL-2H3 cells and peritoneal mast cells from undergoing morphological changes associated with mast cell degranulation. These findings indicate that tHGA possesses potent anti-allergic activity via attenuation of IgE-mediated mast cell degranulation and inhibition of IgE-mediated passive systemic anaphylaxis. Thus, tHGA may have the potential to be developed as a mast cell stabilizer for the treatment of allergic diseases in the future. [ABSTRACT FROM AUTHOR]

The demand of herbal medicine has been increasing for the purpose of reducing the side effects of modern medicine. Melicope ptelefolia ( M. ptelefolia ) is a local Malaysian plant claimed to have many benefits for health. This study was performed to evaluate the potential of M. ptelefolia root extract as anti-nociceptive and anti-inflammatory agents in rats. The anti-nociceptive activity of M. ptelefolia root extracts (50 and 100 mg/kg) was evaluated using acetic acid-induced writhing and tail immersion test, while the anti-inflammatory activity was studied using carrageenan-induced paw edema test. M. ptelefolia root extract significantly inhibited the pain stimulant in acetic acid-induced writhing test, however it did not exert any significant change in the tail immersion test. Nevertheless, the mean reaction time in tail immersion test of M. ptelefolia root extract increased as the doses of extract increased. Furthermore, M. ptelefolia root extract at both doses showed significant anti-inflammatory activity by reducing paw edema volume ( p < 0.05). In conclusion, methanol root extract of M. ptelefolia possesses anti-inflammatory effects and anti-nociceptive effects in rats. [ABSTRACT FROM AUTHOR]

Five acetophenones bearing spiroketal-hexofuranoside rings, one di- C -glycosidic acetophenone and two benzopyrans, along with 16 known compounds were isolated from the leaves of Melicope pteleifolia . Structures of all the isolates were elucidated using extensive spectroscopic methods, including 1D, 2D-NMR and HRESIMS. All the isolates were also evaluated for their neuraminidase inhibitory activities against H1N1, H9N2, wild-type H1N1 and oseltamivir-resistant H1N1 (H274Y mutation) virus strains. Of the isolates, tamarixetin 3-robinobioside was found to exhibit the strongest enzymatic inhibition (IC 50 24.93 ± 3.46, 23.19 ± 5.41, 26.67 ± 5.16 and 40.16 ± 4.50 μ M, respectively). Selected candidates, kaempferol 3-robinobioside, kaempferol 3- O - β - d -glucopyranosyl (1 → 2)- α - d -xylopyranoside and tamarixetin 3-robinobioside, also showed moderate reductions in H1N1-induced cytopathic effects on MDCK cells. [ABSTRACT FROM AUTHOR]

Melicope madagascariensis (Rutaceae) is an endemic plant species of Madagascar that was first classified as a member of the genus Euodia J. R. & G. Forst (Rutaceae) under the scientific name Euodia madagascariensis Baker. Based on morphological characteristics, Thomas Gordon Hartley taxonomically revised E. madagascariensis Baker to be M. madagascariensis (Baker) T.G. Hartley. Chemotaxonomical studies have long been used to help the identification and confirmation of taxonomical classification of plant species and botanicals. Aiming to find more evidences to support the taxonomical revision performed on E. madagascariensis, we carried out phytochemical investigation of two samples of the plant. Fractionation of the ethanol extracts prepared from two stem bark samples of M. madagascariensis (Baker) T.G. Hartley led to the isolation of seven known furoquinoline alkaloids 1- 7 and two known methoxyflavones 8 and 9. The presence of furoquinoline alkaloids and methoxyflavones in the title species is in agreement with its taxonomic transfer from Euodia to Melicope. Antiprotozoal evaluation of the isolated compounds showed that 6-methoxy-7-hydroxydictamnine (heliparvifoline, 3) showed weak antimalarial activity (IC = 35 µM) against the chloroquine-resistant strain Dd2 of Plasmodium falciparum. Skimmianine ( 4) displayed moderate cytotoxicity with IC value of 1.5 µM against HT-29 colon cancer cell line whereas 3,5-dihydroxy-3′,4′,7-trimethoxyflavone ( 9) was weakly active in the same assay (IC = 13.9 µM). Graphical Abstract: [ABSTRACT FROM AUTHOR]

Melicope oppenheimeri K.R. Wood, Appelhans & W.L. Wagner (section Pelea (A. Gray) Hook. f., Rutaceae), a rare endemic tree from West Maui, Hawaiian Islands, is described and illustrated with notes on its ecology, conservation, and phylogenetic placement. The new species differs from Hawaiian congeners by its carpels basally connate 1/5, narrowed into a strongly reflexed beak 10-15 mm long. It also differs in a combination of leaves with 7-10 pair of secondary veins; cymes to 3 cm long; peduncles 5-6.5 mm long; flowers perfect; capsules 4-9 × 40-52 mm; and a densely appressed short-sericeous ovary. Melicope oppenheimeri is known only from an isolated cliff-base plateau in upper Waihe'e Valley, West Maui. Its discovery brings the number of recognized Melicope J.R. Forst. & G. Forst. species in the Hawaiian Islands to 49. A table is included indicating the conservation status of Hawaiian Melicope and Platydesma H. Mann., which is nested within Melicope sect. Pelea. Melicope oppenheimeri falls into the IUCN Critically Endangered (CR) Red List category. [ABSTRACT FROM AUTHOR]

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 (1H 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 1H-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 1H-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. [ABSTRACT FROM AUTHOR]

The names Cissus frutescens and C. arborea have a long history of confusion. Cissus frutescens Blanco belongs to the genus Melicope (Rutaceae) and we herein correct a nomenclatural mistake made by T.G. Hartley in the revision of Melicope. The name Melicope confusa (Merr.) P.S. Liu was accepted for this taxon by Hartley. However, Cissus frutescens Blanco represents the earliest name for this entity and a new combination, Melicope frutescens (Blanco) Appelhans & J.Wen is herein proposed. Neotypification of Cissus arborea Blanco is also provided. [ABSTRACT FROM AUTHOR]

MelicolonesA (1) and B (2), a pair ofrearranged prenylated acetophenone epimers with an unusual 9-oxatricyclo[3.2.1.13,8]nonane core, were isolated from the leaves of Melicopeptelefolia.Further chiral high-performance liquid chromatographyresolution gave enantiomers (+)- and (−)-1, aswell as (+)- and (−)-2, respectively. The structuresand absolute configurations of the pure enantiomers were determinedby extensive spectroscopic data and single crystal X-ray diffraction.All the isolated enantiomers exhibited potent cell protecting activitiesagainst high glucose-induced oxidative stress in human vein endothelialcells. [ABSTRACT FROM AUTHOR]

We present the first detailed phylogenetic study of the genus Melicope , the largest genus of the Citrus family (Rutaceae). The phylogenetic analysis sampled about 50% of the 235 accepted species of Melicope as well as representatives of 26 related genera, most notably Acronychia and Euodia . The results based on five plastid and nuclear markers have revealed that Acronychia , Euodia and Melicope are each not monophyletic in their current circumscriptions and that several small genera mainly from Australia and New Caledonia need to be merged with one of the three genera to ensure monophyly at the generic level. The phylogenetic position of the drupaceous Acronychia in relation to Melicope , which has capsular or follicular fruits, remains unclear and Acronychia might be a separate genus or a part of Melicope . The seed coats of Melicope , Acronychia and related genera show adaptations to bird-dispersal, which might be regarded as key innovations for species radiations. Euodia and its relatives, which lack these adaptations, include only about 20 species while the Melicope – Acronychia group consists of about 340 species. The drupaceous genera Comptonella , Dutaillyea , Picrella and Sarcomelicope are nested within Melicope and need to be merged with Melicope . The expanded genus is a prime example of the artificial classification system of Engler, who defined Rutaceous subfamilies mainly based on gynoecial and fruit characters. [ABSTRACT FROM AUTHOR]

Melicope ( Rutaceae) is one of the largest plant genera on the Hawaiian Islands. We present here a detailed molecular phylogenetic analysis of the Hawaiian species of this genus and compare the results with the other genera of Hawaiian Rutaceae, Platydesma and Zanthoxylum. Four nuclear and two plastid markers were sequenced, with the goals of untangling phylogenetic relationships, inferring biogeographic events and comparing patterns of distribution among the three genera. Our results show that there were two colonization events ( Melicope + Platydesma, and Zanthoxylum) to the Hawaiian Islands, that Hawaiian Rutaceae have an Asian, Australian or Pacific origin and that there were two independent colonization events of Hawaiian Melicope lineages to the Marquesas Islands. The two most widely distributed Hawaiian Melicope spp. are not monophyletic and the current subgeneric classification of Hawaiian Melicope is highly artificial. On the Hawaiian Islands, Melicope and Zanthoxylum show contrasting biogeographic patterns, suggesting different patterns of dispersal. Melicope has a high percentage of single-island endemics suggesting low dispersal ability, whereas Zanthoxylum taxa tend to occur across multiple islands. © 2013 The Linnean Society of London, Botanical Journal of the Linnean Society, 2014, 174, 425-448. [ABSTRACT FROM AUTHOR]

A high performance liquid chromatography procedure for the quantitative determination of three marker benzene derivatives, 2,4,6-trihydroxy-3-prenyl acetophenone (tHPA) (1), 2,4,6-trihydroxy-3-geranyl acetophenone (tHGA) (2), and p-O-geranyl coumaric acid (GCA) (3), in the Melicope ptelefolia ethanolic leaf extracts, a medicinal herb obtained from a few locations of the Peninsula Malaysia, was described. The quantitative analysis was performed using high performance liquid chromatography-photodiode array detection on Xterra octadecylsiyl silica (ODS; 3.0 × 150 mm, 3.5 μm) column kept at 32°C, using gradient elution with acetonitrile and water containing 0.1% formic acid at a flow-rate of 1 ml/min with UV detection wavelength at 280 nm. All calibration curves showed good linearity (R2of 0.999 to 1.0000) within the concentrations range of 2.5 × 10−3to 0.1 mg/mL. The method was shown to be simple, sensitive, and reliable for qualitative and quantitative analysis of the marker compounds inM. ptelefolialeaf preparations. [ABSTRACT FROM AUTHOR]

Chemical investigation on the stem and root of Melicope pteleifolia afforded three new prenylated benzene metabolites as racemic mixtures, named pteleifolins A-C ( 1- 3, resp.). Their gross structures were elucidated on the basis of spectroscopic analysis, especially 2D-NMR experiments. An enantiomer resolution of (±)- 1 using chiral HPLC was performed, and the absolute configuration of the enantiomers were determined to be (+)-( S) - 1 and (−)-( R) - 1 by means of circular-dichroism analysis. [ABSTRACT FROM AUTHOR]

Abstract: Seven new diglycosidic constituents, named pteleifosides A–G (1–7), along with ten known glycosides, were isolated from the roots and rhizomes of Melicope pteleifolia (Champ. ex Benth.) T. Hartley. The structures of the isolated compounds were established on the basis of chemical and spectroscopic methods, mainly 1D and 2D NMR data and mass spectrometry. [Copyright &y& Elsevier]

Abstract: 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 =42.8μM). [Copyright &y& Elsevier]

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. [ABSTRACT FROM AUTHOR]

Abstract: Six novel quinolinone alkaloids bearing a phenylpropanoid or a coumarin moiety, named melicodenines C–H (1–6), two new cinnamyl alcohol derivatives, named melicodins A (7) and B (8), and a new coumarinolignan, named melicodin C (9), were isolated from the leaves of Melicope denhamii (Seem.) T. G. Hartley. Their structures were established by spectroscopic analyses including extensive 2D-NMR experiments. Compounds 1–5 and 9 possess a cyclobutane ring and are hypothetically produced by a [2+2] cycloaddition, whereas compound 6 is presumed to form through a Diels–Alder cycloaddition followed by the elimination of an acetone molecule. Ten quinolinone alkaloids (1–6, 10–13) and a coumarinolignan (9) were tested for anti-proliferative activity against DLD-1 human colon cancer cells. Melicodenine G (5) showed the most potent inhibitory activity, causing the induction of apoptosis with an IC 50 value of 9.4±0.3 μM. [Copyright &y& Elsevier]

Abstract: A bioassay-guided investigation of Melicope ptelefolia Champ ex Benth (Rutaceae) resulted in the identification of an acyphloroglucinol, 2,4,6-trihydroxy-3-geranylacetophenone or tHGA, as the active principle inhibiting soybean 15-LOX. The anti-inflammatory action was also demonstrated on human leukocytes, where the compound showed prominent inhibitory activity against human PBML 5-LOX, with an IC50 value of 0.42μM, very close to the effect produced by the commonly used standard, NDGA. The compound concentration-dependently inhibited 5-LOX product synthesis, specifically inhibiting cysteinyl leukotriene LTC4 with an IC50 value of 1.80μM, and showed no cell toxicity effects. The anti-inflammatory action does not seem to proceed via redox or metal chelating mechanism since the compound tested negative for these bioactivities. Further tests on cyclooxygenases indicated that the compound acts via a dual LOX/COX inhibitory mechanism, with greater selectivity for 5-LOX and COX-2 (IC50 value of 0.40μM). The molecular features that govern the 5-LOX inhibitory activity was thus explored using in silico docking experiments. The residues Ile 553 and Hie 252 were the most important residues in the interaction, each contributing significant energy values of −13.45 (electrostatic) and −5.40kcal/mol (electrostatic and Van der Waals), respectively. The hydroxyl group of the phloroglucinol core of the compound forms a 2.56Å hydrogen bond with the side chain of the carboxylate group of Ile 553. Both Ile 553 and Hie 252 are crucial amino acid residues which chelate with the metal ion in the active site. Distorting the geometry of these ligands could be the reason for the inhibition activity shown by tHGA. The molecular simulation studies supported the bioassay results and served as a good model for understanding the way tHGA binds in the active site of human 5-LOX enzyme. [Copyright &y& Elsevier]

Melicope ptelefolia (MP) is one of the alternative herbal resources which have a great potential to be marketed worldwide. Because of its exploratory nature, this study used qualitative research methodology, which is natural and highly interpretive in order to gain consumer insights. This preliminary qualitative study used an in-depth personal interview approach for data collection. Informants for this study were 30 regular consumers of MP, aged from 18 years old and above. From the findings, it is reported that MP had a slightly bitter taste, crunchy young leaves, pungent, and lemon-lime aroma. In terms of its physical characteristics, it is said that MP has trifoliate, green, thick, broad leaves and has small white and greenish lowers. Respondents have varying levels of awareness and knowledge regarding MP but most of them believed that medicinal products can be produced from this herb. Respondents also stressed the importance of scientific research to properly develop MP into medicinal products and turn it into alternative treatment that has commercial values in the market. [ABSTRACT FROM AUTHOR]

Abstract: 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-MS n ), 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, MS n and comparison with literature data. Kokusaginine (1) demonstrated in vitro activity on NO inhibition in murine peritoneal macrophages. [Copyright &y& Elsevier]

Melicope ptelefolia is a medicinal herb commonly used in Malaysia to treat fever, pain, wounds, and itches. The present study was conducted to evaluate the antinociceptive activity of the Melicope ptelefolia ethanolic extract (MPEE) using animal models of nociception. The antinociceptive activity of the extract was assessed using acetic acid-induced abdominal writhing, hot-plate, and formalin-induced paw licking tests. Oral administration of MPEE produced significant dose-dependent antinociceptive effects when tested in mice and rats using acetic acid-induced abdominal constriction test and on the second phase of the formalin-induced paw licking test, respectively. It was also demonstrated that MPEE had no effect on the response latency time to the heat stimulus in the thermal model of the hot-plate test. In addition, the antinociception produced by MPEE was not blocked by naloxone. Furthermore, oral administration of MPEE did not produce any effect in motor performance of the rota-rod test and in acute toxicity study no abnormal behaviors as well as mortality were observed up to a dose level of the extract of 5 g/kg. These results indicated that MPEE at all doses investigated which did not produce any sedative and toxic effects exerted pronounce antinociceptive activity that acts peripherally in experimental animals. [ABSTRACT FROM AUTHOR]

Three species of the anamorphic fungus Shrungabeeja were collected from tropical forests in Yunnan Province, southern China. S. melicopeae sp. nov. and S. begoniae sp. nov. are described and illustrated from specimens collected respectively on dead branches of Melicope triphylla and Begonia semperflorens. S. vadirajensis is recorded for the first time from China. A key to the three known species of Shrungabeeja is provided. [ABSTRACT FROM AUTHOR]

Abstract: The ethyl acetate extract of the leaves of Melicope vitiflora was separated by column chromatography and the resulting fractions tested for their bioactivity towards methicillin-resistant-Staphylococcus aureus (MRSA) and Micrococcus luteus (ML). The bioactive column chromatography fractions were further separated by preparative TLC and dereplication was carried out on them by first subjecting them to electrospray ionisation-ion trap mass spectrometry (ESI-MSn). The resulting molecular masses, their fragmentation patterns in addition to the chemnet database (www.chemnetbase.com) were used to aid in the structural elucidation of some of the compounds by permitting comparison with known structures of natural origin. Some molecular masses and the corresponding fragmentations were found that did not correlate with any known compounds thus revealing potentially novel natural products that could be investigated on a larger scale and could ultimately find application as new drugs against MRSA and other multi drug resistant microorganisms. Structures are also proposed for known compounds that have not been previously reported for M. vitiflora. [Copyright &y& Elsevier]

Aim Pacific biogeographical patterns in the widespread plant genus Melicope J.R. Forst. & G. Forst. (Rutaceae) were examined by generating phylogenetic hypotheses based on chloroplast and nuclear ribosomal sequence data. The aims of the study were to identify the number of colonization events of Melicope to the Hawaiian Islands and to reveal the relationship of Hawaiian Melicope to the Hawaiian endemic genus Platydesma H. Mann. The ultimate goal was to determine if the Hawaiian Islands served as a source area for the colonization of Polynesia. Location Nineteen accessions were sampled in this study, namely eight Melicope species from the Hawaiian Islands, four from the Marquesas Islands, one species each from Tahiti, Australia and Lord Howe Island, two Australian outgroups and two species of the Hawaiian endemic genus Platydesma. To place our results in a broader context, 19 sequences obtained from GenBank were included in an additional analysis, including samples from Australia, Papua New Guinea, New Zealand, Southeast Polynesia and Asia. Methods DNA sequences were generated across 19 accessions for one nuclear ribosomal and three chloroplast gene regions. Maximum parsimony analyses were conducted on separate and combined data sets, and a maximum likelihood analysis was conducted on the combined nuclear ribosomal and chloroplast data set. A broader nuclear ribosomal maximum parsimony analysis using sequences obtained from GenBank was also performed. Geographic areas were mapped onto the combined chloroplast and nuclear ribosomal tree, as well as onto the broader tree, using the parsimony criterion to determine the dispersal patterns. Results Phylogenetic analyses revealed that Platydesma is nested within Melicope and is sister to the Hawaiian members of Melicope. The Hawaiian Melicope + Platydesma lineage was a result of a single colonization event, probably from the Austral region. Finally, Marquesan Melicope descended from at least one, and possibly two, colonization events from the Hawaiian Islands. Main conclusions These data demonstrate a shifting paradigm of Pacific oceanic island biogeography, in which the patterns of long-distance dispersal and colonization in the Pacific are more dynamic than previously thought, and suggest that the Hawaiian Islands may act as a stepping stone for dispersal throughout the Pacific. [ABSTRACT FROM AUTHOR]

Twelve microsatellite loci were isolated and characterized for Melicope quadrilocularis, an insular endemic tree species of the Bonin Islands. The observed number of alleles at each locus ranged from 1 to 18. The range of expected heterozygosity was 0.0000-0.9445. The inter-specific applicability of these loci was evaluated by analyzing two other endemic species and one endemic variety of Melicope that are also distributed on the Bonin Islands. All primer pairs for the 12 loci tested successfully amplified the loci in all taxa, except for primers for four loci in M. nishimurae. [ABSTRACT FROM AUTHOR]

The article studies the phylogeny and the classification of Rutaceae subfamilies Rutoideae and Toddalioideae. According to the authors, the inferred phylogeny lends support to merging these two subfamilies established by Engler based on different fruit types. The authors add that cladistic results are congruents with the morphological and biochemical interpretations made by two previous authors.