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Lamduan (Melodorum fruticosum Lour.), a native Thai fruit represents an underutilized source of valuable phytochemicals. This study investigates opportunities towards its application in foods. Lamduan anthocyanin-rich extract was encapsulated by maltodextrin dextrose equivalent 20 (MD20) and arabic gum (AG) applied at various ratios. Encapsulation efficiency exceeded 97.9%. All encapsulates showed high solubility (>80%), low moisture content (>3.17 g/100 g DW), and water activity (>0.314 ± 0.002). The highest anthocyanin content (33.84 ± 1.34 mg C3G E/100 g DW) had MD20:AG 60:40 encapsulate. All encapsulates had crystalline-mixed amorphous structures. The crystalline phase increased with a higher AG ratio. Fourier transform infrared spectroscopy (FT-IR) revealed a broken glass structure and shriveled surfaces. The finest particles had MD20:AG 80:20 encapsulate. The MD20:AG 60:40 encapsulate was incorporated into gummy jellies used as a model food at 10 g/kg, 20 g/kg or 30 g/kg, replacing artificial colorant. Shelf-life storage of jellies (25 °C and 35 °C; 8 weeks) showed a gradual decrease in anthocyanin contents and antioxidant capacities in all treatments. The anthocyanin degradation rate was inversely proportional to anthocyanin content. Incorporation of encapsulated lamduan extract into jellies resulted in an attractive red color and enhanced antioxidant capacity, and demonstrated potential utilization of lamduan by the food industry.

Melodamide A, a phenolic amide from the leaves of Melodorum fruticosum Lour., has previously shown pronounced anti‐inflammatory activity. In order to rapidly isolate larger quantities for biological testing, a fast, one‐step isolation method by centrifugal partition chromatography was developed within this study. Fractionation of the dichloromethane extract was performed with a two‐phase solvent system consisting of n‐hexane, ethyl acetate, methanol, and water (3:7:5:5, v/v), leading to the isolation of melodamide A with a purity of >90% and a yield of 6.7 w% within 32 min. The developed method can also be used in dual mode for the enrichment of further constituents like flavonoids or chalcones. In order to support the centrifugal partition chromatography method development, additionally, a high‐performance liquid chromatography method was established and validated to determine quantities of melodamide A in plant material and crude extracts. Analysis of M. fruticosum leaves and a dichloromethane extract obtained from this plant material showed a total melodamide A content of 0.19 ± 0.008 and 8.9 ± 0.249 w%, respectively.

A hitherto unreported member of γ-alkylidenebutenolides in Melodorum fruticosum (Annonaceae), (4E)-6-benzoyloxy-7-hydroxy-2,4-heptadiene-4-olide, named as isofruticosinol (4) was isolated from the methanol extract of flowers, along with the known related butenolides, namely, the (4Z)-isomer (3) of 4, melodrinol (1), and its (4E)-isomer (2). To unambiguously determine the absolute configuration at the C-6 position in these butenolides, the first total syntheses of both enantiomers of 2–4 were achieved over 6–7 steps from commercially available D- or L-ribose (D- and L-5). Using the same protocol, both enantiomers of 1 were also synthesized. Based on chiral HPLC analysis of all synthetic compounds (S- and R-1–4), all naturally occurring butenolides were assigned as partial racemic mixtures with respect to the chiral center at C-6 (enantiomeric ratio, 6S/6R = ∼83/17). Furthermore, the melanogenesis inhibitory activities of S- and R-1–4 were evaluated, with all shown to be potent inhibitors with IC50 values i...

In an initial screening, the dichloromethane extract from the leaves of Melodorum fruticosum showed distinct inhibitory effects on the release of interleukin‐8 (IL‐8) in human neutrophils. Therefore, the aim of the present study was the phytochemical and pharmacological investigation of this extract, to better understand which compounds might be responsible for the anti‐inflammatory effect. Phytochemical analysis led to the isolation of 12 known compounds and two new natural products, 5‐hydroxy‐6‐(2‐hydroxybenzyl)‐4′,7‐dimethoxyflavanone (13) and 2′,4′‐dihydroxy‐3′‐(2‐hydroxybenzyl)‐4,6′‐dimethoxychalcone (14). The influence of the isolated compounds on the production and release of the pro‐inflammatory factors IL‐8, tumor necrosis factor alpha (TNF‐α), reactive oxygen species (ROS), and adhesion molecules (CD62L and CD11b) in human neutrophils was evaluated. Three constituents, melodamide A, 2′,4′‐dihydroxy‐4,6′‐dimethoxychalcone, and 2′,6′‐dihydroxy‐4′‐methoxychalcone, showed significant inhibition of IL‐8 release (IC50=6.6, 8.6, and 11.6 μm, respectively) and TNF‐α production (IC50=4.5, 13.3, and 6.2 μm, respectively).

Fifty-two strains of endophytic fungi were isolated from flowers of the medicinal plant Melodorum fruticosum. Seven genera were identified including Alternaria, Aspergillus, Colletotrichum, Diaporthe, Fusarium, Greeneria and Nigrospora. All strains were cultured for 30 days and further macerated in ethyl acetate solvent for 3 days. The obtained fungal extracts were examined for antibacterial activity using agar disc diffusion against nine pathogenic bacteria: Staphylococcus aureus, Bacillus subtilis, B. cereus, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Shigella flexneri, Vibrio cholerae and V. parahaemolyticus. Forty-three fungal extracts exhibited antibacterial activity against at least one tested pathogen. The antioxidant properties of all extracts were also investigated by DPPH scavenging assay. Sixteen extracts displayed high antioxidant capacity (IC50 ranging from 10 to 50 µg/mL) when compared to the gallic acid and trolox standards (IC50 of 12.46 and 2.55 µg/mL, respectively). The crude extracts of Diaporthe sp. MFLUCC16-0682 and Diaporthe sp. MFLUCC16-0693 exhibited notable antibacterial and antioxidant activities. Analysis of chemical composition using gas chromatography-mass spectrometry suggested that the observed antibacterial activity of the two Diaporthe spp. was possibly due to the presence of abienol, 4-methoxy stilbene, phenethyl cinnamate and 2Z,6Z-farnesal, while their potential antioxidant activity could be attributed to phenolic compounds, such as benzene acetaldehyde, benzyl benzoate, salicylaldehyde, benzoin and benzyl cinnamate. The results suggest that the genus Diaporthe is a potential source of metabolites that can be used in a variety of applications.

Klaivanolide is an antiparasitic natural product isolated from Uvaria klaineana, whose structure was originally assigned as a seven-membered lactone ring. Attempts towards the total synthesis of klaivanolide led us to revise its original structural assignment based on both experimental evidence and spectroscopic data. The isolated compound was revealed to be a known molecule, acetylmelodorinol, originally isolated from Melodorum fruticosum. Vibrational circular dichroism simulation of the reassigned structure was also performed to reinvestigate our previous studies on the determination of the absolute configuration of klaivanolide.

0009-3130/11/4702-0292 2011 Springer Science+Business Media, Inc. Program of Applied Chemistry, School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand, fax: +66 53 916776, e-mail: patcharee_pri@mfu.ac.th. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 264–266, March–April, 2011. Original article submitted October 28, 2009. Chemistry of Natural Compounds, Vol. 47, No. 2, May, 2011 [Russian original No. 2, March–April, 2011]

Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 µM. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.

This research presents the chemical composition antifungal and antioxidant activities of essential oils and various extracts from Melodorum fruticosum flowers. The essential oil composition of M. fruticosum flowers were investigated by GC-MS with 88 identified volatile constituents. Phenyl butanone, linalool, benzyl alcohol, alpha-cadinol, globulol and viridiflorol were found to be the major components, respectively. The dichloromethane extract played a major role as a remarkable fungicide according to their inhibition action against all tested pathogens followed by hexane extract, essential oil and methanol extract, respectively, along with their respective MIC values ranging from 125 to 1000 microg/ml. The dichloromethane extracts were also evaluated to be superior to all extracts tested with an IC(50) value of 87.6 microg/ml whereas other extracts showed their IC(50) values ranging from 100.13 to 194.50 microg/ml.

From leaves and branches of Melodorum fruticosum , five butenolides have been isolated: (4 Z )-6-acetoxy-7-benzoyloxy-2,4-heptadien-4-olide, (4 E )-6-acetoxy-7-benzoyloxy-2,4-heptadien-4-olide, (4 Z )-7-benzoyloxy-6-hydroxy-2,4-heptadien-4-olide, (4 E )-7-benzoyloxy-6-hydroxy-2,4-heptadien-4-olide and (4 Z )-6-benzoyloxy-7-hydroxy-2,4-heptadien-4-olide. In addition, two known flavonoids (chrysin, pinocembrin) and benzoic acid were isolated. All butenolides showed cytotoxic activities in several tumour cell lines. The structures of the isolated compounds were elucidated by spectroscopic methods.

By guiding fractionation with brine shrimp lethality, three novel compounds, with cytotoxic activities against human tumor cell lines, have been isolated from the bark of Melodorum fruticosum Lour.(Annonaccae). These compounds have benzoyl moieties in common with a c7 dienone or lactone terminal which appears to arise from a heptose or the equivalents. They were named melodienone, isomelodienone, and acetylmelodorinol.

The bark of Melodorum fruticosum was examined for bioactive constituents. Fractionation and isolation were guided by the brine shrimp lethality bioassay, leading to the isolation of several bioactive constituents which were identified as dichamanetin, pinocembrin, polycarpol, benzylbenzoate, and stigmasterol/sitosterol. Further bioassays (cytotoxicities, antitumour and plant growth regulating) were performed with these agents.

Chemical investigation of the CH2Cl2 and MeOH crude extracts of the roots of Melodorum fruticosum Lour. led to the isolation of 15 known compounds, of which 5, 10, and 12-15 are reported for the first time from this plant. In addition, melodorinol (7) was derivatized to afford six new (7a-7d and 7f-7g) analogues and one known compound (7e). Their structures were identified on the basic of spectroscopic data. Most of them were evaluated for their cytotoxicity against KB, HeLa, MCF-7 and HepG-2 cell lines. Compounds 4 and 7b were the most potent to all cell lines.

Three oxidized heptenes, 7-benzoyloxy-6-oxo-2,4Z-heptadiene-1,4-olide, [7-benzoyloxy-4-hydroxy-1-methoxy-2E,4Z-heptadiene-1,6-dione] and 7-benzoyloxy-6-oxo-2,4E-heptadiene-1,4-olide, were isolated from flowers of Melodorum fruticosum. Their structures were determined by spectral data analysis. The first two compounds exhibited moderate cytotoxicity against a panel of human tumor cell lines, whereas the third was inactive.

The essential oils obtained by hydrodistillation from the leaves of five species of Annonaceace grown in Vietnam were analyzed by gas chromatography (GC) coupled with mass spectrometry (GC/MS). The main constituents of Artabotrys hongkongensis Hance were the sesquiterpenes spathulenol (13.1%), β-caryophyllene (6.6%), γ-elemene (6.3%) and δ-cadinene (6.3%). β-Caryophyllene (12.1%), bicycloelemene (11.2%) and bicyclogermacrene (11.6%) were the predominant components of the oil of Melodorum fruticosum Lour, whereas the oil of Polyalthia longifolia var. pendula Hort was comprised mainly of β-caryophyllene (30.0%), α-zingiberene (21.7%), aromadendrene (15.2%) and β-selinene (9.1%). The main constituents of Fissistigma maclurei Merr. were germacrene D (26.1%), α-terpinene (8.2%), spathulenol (10.0%), and bicyclogermacrene (6.6%), while α-santalene (14.3%), β-caryophyllene (6.3%), terpinen-4-ol (6.3%), caryophyllene oxide (5.7%), trans-α-bergamotene (5.3%) and allo-ocimene (5.3%) were identified in significant quantity from Fissistigma rufinerve (Hook.f. & Thomson) Merr.

An unified approach to the construction of the seven carbon atom framework of the title compounds, having a γ-oxoacrylate moiety as common structural feature, utilizing an intermolecular [3+2] cycloaddition of the nitrile oxide generated from a malic acid derived C-4 aldehyde fragment with methyl acrylate, is described.

Four additional new bioactive heptenes, melodorinol [2], homomelodienone [4], 7-hydroxy-6-hydromelodienone [5], and homoisomelodienone [7] have been isolated from Melodorum fruticosum. These compounds were slightly to significantly cytotoxic to human tumor cell lines. Their structures have been determined by comparison of their 1H-nmr, 13C-nmr, and mass spectral data with those of prototype compounds (acetylmelodorinol [1], melodienone 3, and isomelodienone [6]).

The antifungal activity of hexane, dichloromethane and methanol extracts of 45 Thai plants were in vitro screened against plant phytopathogenic fungi ( Alternaria porri , Colletotrichum gloeosporioides , Fusarium oxysporum and Phytophthora parasitica ). Seven extracts strongly inhibited the mycelial growth of fungi. The plant extracts with highest antifungal activity were Limnophila aromatic , Eupatorium odoratum , Melodorum fruticosum and Alpinia galanga with 70%, 58%, 74% and 100% inhibition, respectively. The potent dichloromethane extract from M. fruticosum flowers was separated using bioassay guided against P. parasitica . Eight compounds: 1-hexacosanol ( 1 ), 5-hydroxy-7-methoxyflavone ( 2 ), β -sitosterol ( 3 ), melodorinone B ( 4 ), benzoic acid ( 5 ), chrysin ( 6 ), melodorinol ( 7 ) and melodorinone A ( 8 ) could be isolated. Among the isolated compounds, benzoic acid ( 5 ) and melodorinol ( 7 ) exhibited strong activity against mycelial growth of P. parasitica at 100% and 93% inhibition with the half maximal inhibitory concentration (IC 50 ) values of 108 μg/mL and 130 μg/mL, respectively. This plant could be exploited for eco-friendly management control of plant diseases.