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.     

A new lactam alkaloid from Portulaca oleracea L. and its cytotoxity

A new lactam alkaloid named oleraciamide D (1), indentified as (5R)-4-(3-methoxy-4-hydroxyphenyl)-5-(4-hydroxyphenyl)-5,6-dihydropyridin-2(1H)-one, together with five known compounds, indole-3-aldehyde (2), portulacatone (3), N-trans-feruloyloctopamine (4), N-trans-feruloyl-3′-O-methyldopamine (5) and N-trans-feruloyltyramine (6) were isolated from Potulaca oleracea L. Among them, indole-3-aldehyde (2) was isolated from the medicine for the first time. The structure of the new alkaloid was elucidated via UHPLC-ESI-Q-TOF/MS, 1D NMR and 2D NMR. The five known compounds were established by comparing the ¹H-NMR and ¹³C NMR with the reported literature. Oleraciamide D (1) showed cytotoxicity against SH-SY5Y cells when concentration at 50 uM by CCK-8 method.     

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.     

Secondary metabolites from the endophytic fungus <Emphasis Type="Italic">Annulohypoxylon boveri</Emphasis> var. <Emphasis Type="Italic">microspora</Emphasis> BCRC 34012

A chemical study on the n-BuOH-soluble fraction of the 95% EtOH extract of long-grain rice (Oryza sativa) fermented with the endophytic fungus Annulohypoxylon boveri var. microspora (BCRC 34012) has resulted in the isolation of one new natural azaphilone derivative, designated as annulohypoxyboverin (1) together with 12 known compounds, (3R,6R,7E)-3-hydroxy-4,7-megstigma-dien-9-one (2), α-tocopheryl quinone (3), isofraxidin (4), coumarin (5), cinnamic acid (6), a mixture of palmitic acid (7) and stearic acid (8), N-cis-feruloyltyramine (9), luteolin (10), kaempferol (11), kaempferitrin (12), and 4,5,4′,5′-tetrahydroxy-1,1′-binaphthyl (13). Annulohypoxyboverin (1) contains a dihydrobenzofuran-2,4-dione backbone, 1-hydroxyhexyl side chain, and one γ-lactone ring. Their structures were elucidated by spectroscopic analyses including 1D and 2D NMR experiments, and by HR-ESI-MS. The relative configuration of 1 was confirmed by NOESY experiment. Other known compounds were identified by comparing their spectral data with those of literature data.     

Chemical constituents isolated from the fungus <Emphasis Type="Italic">Monascus</Emphasis> sp.

Further study of a 95% EtOH extract of red mold rice fermented with the yellow mutant of the fungus Monascus sp. led to the isolation of one new chroman derivative, namely monascuskaochroman (1), together with nine known compounds. The structure of the new compound was determined as 4-(1-hydroxy-1-methyl- ethyl)-chroman-4-carboxylic acid amide. The known compounds were identified as monascin (2), ankaflavin (3), (3R,6R,7E)-(+)-3-hydroxy-4,7-megstigmadien-9-one (4), vanillin (5), syringic acid (6), 3,4,5-trimethoxybenzoic acid (7), trans-methyl p-coumarate (8), ferulic acid (9), and methyl N-methyl anthranylate (10).This is the first report of a naturally occurring chroman skeleton isolated from Monascus species. Compounds 4–10 were isolated from this species for the first time. 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.     

The Constituents of Cananga odorata

Sixteen compounds, (+)-ushinsunine-β-N-oxide ( 1 ), cleistopholine ( 2 ), liriodenine ( 3 ), (-)-anonaine ( 4 ), (+)-nornuciferine ( 5 ), (+)-N-acetylnornuciferine ( 6 ), (-)-ushinsunine ( 7 ), (-)-norushinsunine ( 8 ), (-)-asimilobine ( 9 ), (+)-reticuline ( 10 ), N-trans-feruloyltyramine ( 11 ), β-sitosterol (12) and stigmasterol ( 13 ), lyscamine ( 14 ), (-)-anaxagoreine ( 15 ) and trans-cinnamic acid ( 16 ) were isolated from the methanolic extract of the Cananga odorata. Among them, 1 is a new stereoisomer of ushinsunine-β-N-oxide. The structures of these compounds were established by means of spectral experiments.     

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.     

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 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.     

A novel sesquiterpenoid from the leaves of <Emphasis Type="Italic">Cinnamomum subavenium</Emphasis>

A novel sesquiterpenoid, subamol ((3-methoxy-5H-9,10-dihydroxybenzo[3,4]cyclohepta[1,2-f])inden-7-yl)methanol)) (1), along with six compounds, including one ionone: (+)-abscisic acid (2); and five benzenoids: syringaldehyde (3), trans-coumaric acid (4), cis-coumaric acid (5), vanillic acid (6), and p-hydroxybenzoic acid (7), were isolated from the leaves of Cinnamomum subavenium Miq (Lauraceae). These compounds were identified and characterized by physical and spectral evidence.     

Xanthones isolated from Gentianella acuta and their protective effects against H2O2-induced myocardial cell injury

In the present study, two new xanthones, (5′S,8′S)-1,3,5,8-tetrahydroxyxanthone(7→2′)-1,3,5,8-tetrahydroxy-5′,6′,7′,8′-tetrahydroxanthone (1), 5-hydroxy-3,4,6-trimethoxyxanthone-1-O-β-D-glucopyranoside (2), and eight known xanthones (3–10) were isolated from the whole plants of Gentianella acuta. Their structures were identified by the spectroscopic analyses (HR-ESI-MS, and 1D and 2D NMR). Meanwhile, cell-protective effects against H₂O₂-induced H9c2 cardiomyocyte injury and cytotoxic activities of compounds 1–10 were also determined.     

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.     

New coumarin from the roots of Prangos pabularia

The new coumarin 1, yuganin A (7-methoxy-8-((1S,2S)-1,2,3-trihydroxy-3-methylbutyl)-2H-chromen-2-one) along with nine known coumarins, heraclenol 3′-O-β-D-glucopyranoside (2), oxypeucedanin hydrate 3′-O-β-D-glucopyranoside (3), heraclenol (4), oxypeucedanin hydrate (5), osthole (6), oxypeucedanin (7), heraclenin (8), isoimperatorin (9), imperatorin (10) and the disaccharide sucrose (11), have been isolated from the roots of Prangos pabularia, and the structures of these isolated compounds were elucidated by spectroscopic means, especially, UV, HR-ESIMS, and 1D and 2D NMR spectroscopy. Furthermore, the anti-melanogenic effect of yuganin A and its inhibitory effect on B16 cells were evaluated. Yuganin A may be useful in the treatment of hyperpigmentation and as a skin-whitening agent in the cosmetics industry.     

A bioactive cycloartane triterpene from Garcinia hombroniana

The dichloromethane bark extract of Garcinia hombroniana yielded one new cycloartane triterpene; (22Z,24E)-3β-hydroxycycloart-14,22,24-trien-26-oic acid (1) together with five known compounds: garcihombronane G (2), garcihombronane J (3), 3β acetoxy-9α-hydroxy-17,14-friedolanostan-14,24-dien-26-oic acid (4), (22Z, 24E)-3β, 9α-dihydroxy-17,14-friedolanostan-14,22,24-trien-26-oic acid (5) and 3β, 23α-dihydroxy-17,14-friedolanostan-8,14,24-trien-26-oic acid (6). Their structures were established by the spectral techniques of NMR and ESI-MS. These compounds together with some previously isolated compounds; garcihombronane B (7), garcihombronane D (8) 2,3’,4,5’-tetrahydroxy-6-methoxybenzophenone (9), volkensiflavone (10), 4’’-O-methyll-volkensiflavone (11), volkensiflavone-7-O-glucopyranoside (12), volkensiflavone-7-O-rhamnopyranoside (13), Morelloflavone (14), 3’’-O-methyl-morelloflavone (15) and morelloflavone-7-O-glucopyranoside (16) were evaluated for cholinesterase enzymes inhibitory activities using acetylcholinesterase and butyrylcholinesterase. In these activities, compounds 1–9 showed good dual inhibition on both the enzymes while compounds 10–16 did not reasonably contribute to both the cholinesterases inhibitory effects.     

Phenolic constituents from the stems of <Emphasis Type="Italic">Acanthopanax senticosus</Emphasis>

A new phenolic glycoside was isolated from the stems of Acanthopanax senticosus together with sixteen known compounds. The structure of the new compound was determined to be 2,6-dimethoxy-4-[(1E)-3,3-dimethoxy-1-propenyl]phenyl β-D-glucopyranoside (1) by means of physical, chemical, and spectroscopic methods. Of the known compounds, salvadoraside (7), (7R,8S)-dihydrodehydrodiconiferyl alcohol 4,9′-di-O-β-D-glucopyranoside (8), 3-(4-O-β-D-glucopyranosylferuloyl)quinic acid (15), rel-5-(1R,5S-dimethyl-3R,4R,8S-trihydroxy-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (16), and lycoperodine-l (17) were first reported from the title plant. The inhibitory activities of the isolated compounds against α-glucosidase from rat intestine were also reported.     

Chemical composition and antioxidant activity of aerial parts of Ferula longipes Coss. ex Bonnier and Maury

This is the first study on the phytochemistry and antioxidant activity of Ferula longipes Coss. ex Bonnier and Maury (Apiaceae). A new flavonoid quercetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-[2-O-caffeoyl]-glucopyranoside (1), along with 10 known compounds kaempferol-3-O-α-L-rhamnopyranoside (2), quercetin-3-O-α-L-rhamnopyranoside (3), kaempferol-3-O-ß-D-glucopyranoside-7-O-α-L-rhamnopyranoside (4), isorhamnetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-glucopyranoside (5), quercetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-glucopyranoside (6), isorhamnetin-3,7-di-O-β-D-glucopyranoside (7), apigenin (8), apigenin-7-O-ß-D-glucopyranoside (9), 3,5-dicaffeoylquinic acid (10), deltoin (11) were isolated from the aerial parts of Ferula longipes Coss. Structures elucidation was performed by comprehensive 1D and 2D NMR analyses, mass spectrometry and by comparison with literature data. The compounds 1, 3, 4, 6, 7 and 10 were evaluated for their antioxidant activity, compound 1 exhibited the best antiradical activity potential and showed IC₅₀ and A_0.5 values 5.70, 7.25, 5.00, and 2.63 μg/mL towards DPPH free radical-scavenging, ABTS, CUPRAC, and reducing power assays, respectively compared with BHA, BHT and ascorbic acid which were used as positive controls.     

Isolation,structural elucidation and cytotoxicity evaluation of a new pentahydroxy-pimarane diterpenoid along with other chemical constituents from Aerva lanata

Aervalanata possesses various useful medicinal and pharmaceutical activities. Phytochemical investigation of the plant has now led to the isolation of a new 2α,3α,15,16,19-pentahydroxy pimar-8(14)-ene diterpenoid (1) together with 12 other known compounds identified as β-sitosterol (2), β-sitosterol-3-O-β-D-glucoside (3), canthin-6-one (4), 10-hydroxycanthin-6-one (aervine, 5), 10-methoxycanthin-6-one (methylaervine, 6), β-carboline-1-propionic acid (7), 1-O-β-D-glucopyranosyl-(2S,3R,8E)-2-[(2′R)-2-hydroxylpalmitoylamino]-8-octadecene-1,3-diol (8), 1-O-(β-D-glucopyranosyl)-(2S,3S,4R,8Z)-2-[(2′R)-2′-hydroxytetracosanoylamino]-8(Z)-octadene-1,3,4-triol (9), (2S,3S,4R,10E)-2-[(2′R)-2′-hydroxytetracosanoylamino]-10-octadecene-1,3,4-triol (10), 6′-O-(4″-hydroxy-trans-cinnamoyl)-kaempferol-3-O-β-D-glucopyranoside (tribuloside, 11), 3-cinnamoyltribuloside (12) and sulfonoquinovosyldiacylglyceride (13). Among these, six compounds (8–13) are reported for the first time from this plant. Cytotoxicity evaluation of the compounds against five cancer cell lines (CHO, HepG2, HeLa, A-431 and MCF-7) shows promising IC₅₀ values for compounds 4, 6 and 12.     

A new sesquiterpene from Kalimeris integrifolia

A new sesquiterpene kalinturoside A (1), and 17 known compounds friedelan-3-ol (2), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (3), friedelin (4), syringaresinol (5), α-spinasterol (6), ciwujiatone (7), syringic acid (8), scopoletin (9), apocynin (10), 1-(3-hydroxy-4, 5-dimethoxyphenyl)ethan-1-one (11), apigenin (12), 5-hydroxymethylfurfural (13), stigmasterol-3-O-β-d-glucopy-ranoside (14), bidenoside C (15), citrusin (16), irioresinol A (17) and syringaresinol-4-O-β-d-glucopyranoside (18) were isolated from the herbs of Kalimeris integrifolia. The structures of these compounds were elucidated using spectroscopic techniques such as NMR and MS. All of the compounds were isolated from this genus for the first time.     

Identification of a new flavone glycoside from <Emphasis Type="Italic">Codonopsis nervosa</Emphasis>

A new flavone glycoside, luteolin 7-O-[(6″′-caffeoyl)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranoside (1), was isolated from Codonopsis nervosa, along with three other known compounds, luteolin 7-O-β-D-glucopyranoside (2), luteolin 7-O-gentiobioside (3), and tangshenoside VI (4). Their structures were determined on the basis of 1D and 2D NMR, IR, and HR-ESI-MS.     

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.