Two new diarylheptanoids isolated from the roots of Juglans mandshurica

Two new diarylheptanoids, ( ? )-threo-3′,4″-epoxy-1-(4-hydroxyphenyl)-7-(3-methoxyphenyl)heptan-2,3-diol (1) and (1α,3β,5α,6α)-1,5-epoxy-3,6-dihydroxy-1,7-bis(3-methoxy-4-hydroxy-phenyl)-heptane (2), along with one known diarylheptanoid, rhoiptelol B (3), were isolated from the roots of Juglans mandshurica. The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR including ¹H–¹H COSY, HMQC, HMBC and NOESY spectroscopic methods.     

Secondary metabolites isolated from the fungus <Emphasis Type="Italic">Biscogniauxia cylindrospora</Emphasis> BCRC 33717

One new dihydroisocoumarin, (3S)-5-hydroxy-8-O-methylmellein (1), as well as nine known compounds, 5-formylmellein (2), mellein-5-carboxylic acid (3), 5-hydroxymethylmellein (4), 3β-hydroxystigmast-5- en-7-one (5), N-trans-feruloyltyramine (6), N-cis-feruloyltyramine (7), vanillic acid (8), methyl paraben (9), and syringaldehyde (10), were isolated from the n-BuOH-soluble fraction of the 70% EtOH extract of rice fermented with the endophytic fungus Biscogniauxia cylindrospora (BCRC 33717). Their structures were elucidated by 1D and 2D NMR spectroscopy together with HR-ESI-MS analysis and comparison of the spectroscopic data with those reported for structurally related compounds.     

An isoindole alkaloid from Portulaca oleracea L.

A novel isoindole alkaloid named oleraisoindole (1), together with six known compounds, 7′-ethoxy-trans-feruloyltyramine (2), N-trans-feruloyltyramine (3), N-trans-feruloyl-3-methoxytyramine (4), N-trans-p-coumaroyltyramine (5) aurantiamide (6) and ferulic acid methyl ester (7) were isolated from Portulaca oleracea L. Compounds 2 and 7 were isolated for the first time from this plant. Compound 1 was identified using spectroscopic methods including HR-ESI-TOF-MS, 1D-NMR, 2D-NMR. It was tested in a nitric oxide (NO) inhibition assay and was shown to inhibit NO production in RAW 264.7 cells induced by LPS.     

Three new acyltyramines from Anisodus luridus Link et Otto (Solanaceae)

Three new acyltyramines, N-[2-(4-hydroxyphenyl)ethyl]hentriacontanamide (1), N-[2-(4-hydroxyphenyl)ethyl]nonacosanamide (2) and N-[2-(4-hydroxyphenyl)ethyl]heneicosanamide (3) have been isolated from n-hexane extract of leaves of Anisodus luridus (Solanaceae). Successive extraction of defatted leaves of A. luridus with methanol afforded a residue on removal of solvent under reduced pressure. Residue was partitioned by means of chloroform and n-butanol. Chromatographic resolution of n-BuOH extract afforded six known compounds, apigenin (4), luteolin (5), quercetin (6), quercetin 3-O-α-l-rhamnoside (7), kaempferol 3-O-α-rhamnoside (8) and quercetin 3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (9). The structures of the isolated compounds were assigned with the help of spectroscopic techniques. This is the first report of isolation of these compounds from this plant.     

A new diarylheptanoid and a new diarylheptanoid glycoside isolated from the roots of Juglans mandshurica and their anti-inflammatory activities

A new diarylheptanoid, (2S,3S,5S)-2,3,5-trihydroxy-1,7-bis(4-hydroxy- 3-methoxyphenyl)heptane (1), and a new diarylheptanoid glycoside, (2S,3S,5S)-2,3-dihydroxy-5-O-β-d-xylopyranosyl-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptane (2), together with three known compounds, rhoiptelol C (3), rhoiptelol B (4) and 3′,4″-epoxy-2-O-β-d-glucopyanosyl-1-(4-hydroxyphenyl)- 7-(3-methoxyphenyl)heptan-3-one (5) were isolated from the roots of Juglans mandshurica (Juglandaceae). The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Compounds 1–5 were assayed for their inhibitory effects on the production of NO, TNF-α and IL-6 in LPS-stimulated RAW264.7 cells.     

A new cerebrogalactoside from <Emphasis Type="Italic">Juglans mandshurica</Emphasis>

A new cerebrogalactoside, Juglans cerebroside A (1), together with five known compounds, quercetin-3-O-β-D-galactopyranoside (2), myricetin-3-O-β-D-galactopyranoside (3), 2″E-quercetin-3-O-β-D-(6″″-O-[3″(4′″-hydroxyphenyl) propylene acyl]) glucopyranoside (4), gallic acid (5), and 2-methyl-1-hexadecanol (6) were isolated from the leaves of Juglans mandshurica Maxim. The structures of these compounds were determined by 1D, 2D NMR, and MS techniques.     

Two new quercetin glycoside derivatives from the fruits of Gardenia jasminoides var. radicans

Two new quercetin glycoside derivatives named quercetin-3-O-[2-O-trans-caffeoyl-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside] (1) and quercetin-3-O-[2-O-trans-caffeoyl-β-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside] (2) along with three known flavonoids, 5-hydroxy-6,7,3′,4′,5′-pentamethoxyflavone (3), 5,7-dihydroxy-8-methoxyflavone (4) and kaempferol 3-O-β-d-glucopyranoside (5), were isolated from the fruits of Gardenia jasminoides var. radicans. The structures of the new compounds were determined by means of extensive spectroscopic analysis (1D, 2D NMR and HR-ESI-MS), glycoside hydrolysis and sugar HPLC analysis after derivatisation. This is the first report on the isolation of a pair of compounds with α or β-l-rhamnopyranosyl configuration from plant and the first detail assignment of their NMR data.     

Pleiocarpumlignan A,a new dineolignan from Piper pleiocarpum Chang ex Tseng

Abstract

The investigation of chemical constituents from the whole plants Piper pleiocarpum Chang ex Tseng resulted in the isolation of one new dineolignan, pleiocarpumlignan A (1), along with one known benzoate derivative, trans-2,3-diacetoxy-1-[(benzoy1oxy)methyl]-cyclohexa-4,6-diene (2), and two known neolignans (3–4) as (±)-trans-dehydrodiisoeugenol (3), (7R,8R,3′S)-△^8′-3′,6′-dihydro-3′-methoxy-3,4-methylenedioxy-6′-oxo-8,3′,7,O,4′-lignan (4). Their structures were elucidated through extensive spectroscopic analyses including 1D, 2D NMR, HR-ESI-MS, and by comparison with the literature. All compounds (1–4) were firstly isolated from Piper pleiocarpum Chang ex Tseng. The ¹³C NMR spectra of 2 were completely assigned for the first time. Cytotoxic activities of these isolated compounds against five human cancer cell lines (including A-549, SMMC-7721, HL-60, MCF-7, and SW-480) were evaluated.     

A New Lycopodine-type Alkaloid from Lycopodium japonicum

A new lycopodine-type alkaloid, 12β-hydroxy-acetylfawcettiine N-oxide (1), together with seven known analogues, acetyllycoposerramine M (2), lycopodine (3), lycoclavine (4), diphaladine A (5), lycoposerramine K (6), 11β-hydroxy-12-epilycodoline (7) and fawcettiine (8), were isolated from Lycopodium japonicum. Their structures were established by mass spectrometry and 1D and 2D NMR techniques. The isolated alkaloids were assayed for their inhibition activities against acetylcholinesterase, but no inhibitory activities for the compounds were detected.     

Isolation of a new lycodine alkaloid from Lycopodium japonicum

A new lycodine alkaloid, N-methylhydroxypropyllycodine (1), was isolated from the club moss Lycopodium japonicum Thunb, together with five known compounds, N-methyllycodine (2), huperzinine (3), β-obscurine (4), α-obscurine (5) and des-N-methyl-α-obscurine (6). Their structures were elucidated by spectroscopic analyses, including 2D NMR techniques.     

New C20-gibberellin diterpene from the leaves of Schefflera sessiliflora De P. V.

From the leaves of Schefflera sessiliflora De P. V., one new C₂₀-gibberellin diterpene 2β,12β-dihydroxygibberellin (12β-hydroxy-GA₁₁₀ or 2β-hydroxy-GA₁₁₂) (1), together with three known compounds, trans-tiliroside (2), kaempferol 3-O-β-d-glucuronopyranoside (3), 5-p-trans-coumaroylquinic acid (4), was isolated for the first time from the genus Schefflera by various chromatography methods. Their structures were elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and comparison with previous reported data. The α-glucosidase inhibitory activity of all compounds was measured. The isolates (2, 3) showed better α-glucosidase inhibitory activity (IC₅₀ = 134.60, 147.10 μM, respectively) than the standard drug acarbose (IC₅₀ = 214.50 μM).     

A new furanosteroid from Talaromyces sp. lgt-4, a fungal endophyte isolated from Tripterygium wilfordii

Wortmannolol (1), a new furanosteroid, along with five known compounds, wortmannolone (2), ergosterol (3), p-hydroxyphenyl ethanol (4), trans-6-dodecene (5), (2Z, 4E) -5-(8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo [3.2.1] octan-8-yl) -3-methylpenta-2,4-dienoic acid (6) were isolated from a fungal endophyte Talaromyces sp. lgt-4. Their structures were elucidated by IR, MS, 1D and 2D NMR spectra. Compound 1 show weak monoamine oxidase inhibitory activity.     

Two new flavonol glycosides from Dimocarpus longan leaves

From the extracts of Dimocarpus longan Lour leaves, 2 unusual flavonol glycosides, quercetin 3-O-(3″-O-2?-methyl-2?-hydroxylethyl)-β-d-xyloside (1) and quercetin 3-O-(3″-O-2?-methyl-2?-hydroxylethyl)-α-l-rhamnopyranoside (2), as well as 10 known compounds including 2 flavonol glycosides, afzelin (3) and kaempferol-3-O-α-l-rhamnopyranoside (4), 2 flavans, ( ? )-epicatechin (5) and proanthocyanidin A-2 (6), 3 triterpenoids, friedelin (7), epifriedelanol (8) and β-amyrin (9), a peptide, N-benzoylphenylalanyl-N-benzoylphenylalaninate (10), and 2 sterols, β-sitosterol (11) and daucosterol (12) were isolated and identified by using combination of mass spectrometry and various 1D and 2D NMR techniques. This is the first report of flavonoid glycosides possessing a 2-methyl-2-hydroxylethoxyl group in sugar moiety from D. longan.     

A new butanolide from the leaves of <Emphasis Type="Italic">Cinnamomum reticulatum</Emphasis>

A new butanolide, isoreticulide ((4R,3E)-4-hydroxy-5-methylene-3-octadecylidenedihydrofuran-2-one) (1), along with nine compounds including one sesquiterpenoid, (3-methoxy-5H-9,11dioxabenzo[3,4]cyclohepta[1,2-f])inden-7-yl)-methanol (2); six benzenoids, p-hydroxybenzoic acid (3), p-hydroxybenzaldehyde (4), protocatechuic acid (5), ferulic acid (6), trans-methyl p-coumarate (7), and p-dihydrocoumaric acid (8), and two amides, N-trans-feruloyltyramine (9) and dihydroferuloyltyramine (10), were isolated from the leaves of Cinnamomum reticulatum Hayata (Lauraceae). These compounds were characterized and identified by physical and spectral evidence.     

New chalcanonol glycoside from the seeds of saw palmetto: antiproliferative and antioxidant effects

A new chalcanonol glycoside dimer, bis-O-[(I-4′) → (II-6′)]-α-hydroxyphloretin-2′-O-β-glucoside (1), in addition to six known compounds, namely ( ? )-epicatechin (2) and ( ? )-epiafzelechin (3), 4-hydroxybenzoic acid (4), protocatechuic acid (5), methylgallate (6), β-sitosterol (7) and β-sitosterol-3-O-glucoside (8), was isolated from the seeds of saw palmetto. The structures of the isolated compounds were established from the analysis of their MS and 1D and 2D NMR spectroscopic data. The antiproliferative activities of the isolated compounds towards PC3, the human prostate cancer cells were investigated. Amongst the isolated compounds, the new compound and the sterolic derivatives showed antiproliferative effects. Screening of the antioxidant effects of the isolated compounds by 2,2′-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid radical assay revealed that the isolated phenolics were active free radical scavengers.     

A new flavonol derivative from <Emphasis Type="Italic">Fagopyrum dibotrys</Emphasis>

A new flavonol derivative 3, 8-dihydroxy-10-methoxy-5-H-isochromeno[4, 3-b]chromen-7-one (1) together with four known compounds, glutinone (2), luteolin (3), acacetin 7-O-α-L-rhamnopyranosyl- (1→6)-β-D-glucopyranoside (4), and rutin (5) were isolated from the dried roots of Fagopyrum dibotrys. Their structures were determined by UV, IR, MS, ¹H, and ¹³C NMR spectroscopic analysis, including 2D NMR. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 567–568, November–December, 2008.     

Inhibition effect of phenyl compounds from the Oryza sativa roots on melanin production in murine B16-F10 melanoma cells

Five phenyl compounds, vanillin (1), methyl trans-ferulate (2), trans-p-coumaric acid methyl ester (3), N-benzoyltryptamine (4), and N-(trans-cinnamoyl)tryptamine (5), were isolated from the roots of Oryza sativa L. and identified on the basis of spectroscopic data. Compounds 3 and 5 showed strong inhibition effect on melanin production in murine B16-F10 melanoma cells and tyrosinase activity. Also, the quantitative analysis of the compounds was carried out using LC/MS/MS experiment. Compounds 3 and 5 could be used as skin-whitening agents.     

A new arbutin derivative from the leaves of Vaccinium dunalianum wight

A new arbutin derivative, namely dunalianosides J (1), along with six known compounds, arbutin (2), robustaside A (3), 6′-O-caffeoylarbutin (4), dunalianoside D (5), kaempferol 3-O-β-D-glucopyranoside (6) and kaempferol 3-O-β-D-sambubioside (7) were isolated from the leaves of Vaccinium dunalianum Wight (Ericaceae). The structure of 1 was elucidated by extensive 1D and 2D NMR, HR-MS and CD spectroscopic analyses. In which, kaempferol 3-O-β-D-sambubioside (7) was isolated from the genus Vaccinium for the first time.     

Synthesis and Anticancer Activity of Novel Nonfused Bicyclic Thiazolidinone Derivatives

A series of new 2-{4-oxo-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidin-5-yl}-N-arylacetamides ( 4a–e ), 5-(2-oxo-2-aryl-ethyl)-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidine-4-ones ( 5a–d ), 2-(4-oxo-2-[(2-oxothiazolidin-4-ylidene)-hydrazono]-thiazolidin-5-yl)-N-arylacetamides ( 7a–e ), and 5-(2-oxo-2-aryl-ethyl)-2-[(2-oxothiazolidin-4-ylidene)-hydrazono]-thiazolidine-4-ones ( 8a–d ) have been synthesized starting from 2-thioxothiazolidin-4-one and 4-thioxothiazolidin-2-one through a multistep reaction sequence. 2-Thioxothiazolidin-4-one was alkylated via the intermediate formation of the triethylammonium salt 1 by ethyl chloroacetate. Compound 2 and 4-thioxothiazolidin-2-one reacted with thiosemicarbazides to give the 1-(4-thiazolidinone-2-ylidene)-4-R-thiosemicarbazones ( 3a,b ) and 1-(2-thiazolidinone-4-ylidene)thiosemicarbazones ( 6a,b ), respectively. Following [2+3]-cyclization of thiazolidinone-substituted thiosemicarbazones ( 3a,b and 6a,b) with N-arylmaleimides and aroylacrylic acids as equivalents of dielectrophilic synthon [C₂]^{2 +}, novel non-fused bicyclic thiazolidinones ( 4a–e, 5a–d, 7a–e, 8a–d ) were synthesized. The structures of the new compounds ( 4a–e, 5a–d, 7a–e, 8a–d ) were established on the basis of their elemental analysis and ¹H NMR and mass spectral data. Eight of the synthesized compounds were tested, and three of them displayed different levels of antitumor activity. The most efficient antitumor agent—2-{4-oxo-3-furylmethyl-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidin-5-yl}-N-4-chlorophenylacetamide ( 4d ) was found to be active against leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancer cell lines with mean lgGI₅₀ and lgTGI values of –5.35 and –4.78, respectively.     

A new alkaloid from Portulaca oleracea L. and its antiacetylcholinesterase activity

A new alkaloid, (10E, 12E)-9-ureidooctadeca-10, 12-dienoic acid, named oleraurea (1) and 10 known compounds, p-hydroxybenzaldehyde (2), p-hydroxybenzoic acid (3), p-hydroxyacetophenone (4), benzamide (5), (E)-p-coumaramide (6), (E)-ferulamide (7), soyalkaloid A (8), β-carboline-3-carboxylic acid (9), 2, 3, 4, 9-tetrahydro-1H-pyrido [3, 4-b] indole-3-carboxylic acid (10), (1S, 3S)-1-methyl-1, 2, 3, 4-tetrahydro-β-carboline-3-carboxylic acid (11) were obtained from Portulaca oleracea L., in which, compounds 4, 5, 8–11 were isolated from the plant for the first time. The structure of the compound 1 was identified using spectroscopic methods including 1D and 2D NMR, HR-ESI-TOF-MS. The compounds 1, 5–11 presented anticholinesterase activities, but the P. oleracea extract (POE) presented very low anticholinesterase activity.