A new phenylpropanoid glycoside from the bark of Streblus ilicifolius (Vidal) Corner

A new compound, pheglycoside A (1), along with four known aromatic glycosides (2-5) and three known lignan glycosides (6–8) were isolated from Streblus ilicifolius (Vidal) Corner. The structure of compound 1 was determined by spectral analyses, including HRESIMS, 1D, and 2D NMR (COSY, HSQC, and HMBC) experiments. The absolute configuration of compound 1 was determined using the CD spectrum and experiment data. From the present investigation, all these compounds were isolated for the first time from S. ilicifolius. It is interesting that phenylpropanoid glycoside and aromatic glycosides are reported for the first time in the genus Streblus. The chemotaxonomic significance of these compounds was summarized.     

Chemical constituents from the pericarps of Zanthoxylum bungeanum and their chemotaxonomic significance

The phytochemical study of the pericarps of Zanthoxylum bungeanum Maxim under the guidance of bioactivity led to the isolation of 18 compounds, including a new isobutylhydroxyamide (1) and 17 known compounds, i.e. six alkylamides (2–7), five coumarins (8–12), one benzene derivative (13), three flavonoids (14–16), and two sterols (17–18). Their structures were elucidated based on extensive spectroscopic methods (HRESIMS, 1D and 2D NMR experiments) and by comparison with literature data. New compound (1) and known compound (2) are cis-trans isomeric isobutylhydroxyamides. Among them, compounds 9, 10, and 12 were isolated for the first time from Z. bungeanum, compound 11 was firstly recovered from the genus Zanthoxylum, and compound 14 was reported for the first time from the Rutaceae family. The chemotaxonomic significance of isolated compounds from Z. bungeanum is discussed.     

Chemical constituents from the root bark of Dictamnus dasycarpus Turcz. (Rutaceae) and their chemotaxonomic significance

This work described the isolation and characterization of seven compounds from Dictamnus dasycarpus Turcz., including one new ester, (2R)-4-(2,2-dimethyl-5-oxotetrahydrofuran-3-yl)-2-hydroxypent-3-anoic acid ethyl ester (1); and six known glycosides (2–7). The structure of compound 1 was elucidated on the basis of extensive spectral analyses, including IR, HR-ESIMS, 1D and 2D NMR (NOESY, HMBC and HSQC). All these compounds were described here for the first time from the genus Dictamnus. Moreover, the results provide further information about the diversity of compounds in the genus Dictamnus.     

New diplosporin and agistatine derivatives produced by the fungal endophyte Xylaria sp. isolated from Vitis labrusca

A Xylaria sp. was isolated as an endophyte from a surface-sterilized Concord grape leaf (Vitis labrusca). Dereplication and LC–MS analysis of the filtrate extracts identified two new structures, compound 1, 13-O-methyl-(5R) diplosporin, and 2 a new agistatine. Additionally, five known compounds 3–7 including an agistatine, coriloxin, (5R)-diplosporin, and two mellein derivatives were also isolated. This is the first report of these structurally-related metabolites isolated from the same fungus, suggesting they share a related biosynthesis. Metabolites were isolated using liquid chromatography-solid phase extraction (LC-SPE) and semi-preparative HPLC. Structures were elucidated on the basis of 1D and 2D NMR analysis, HRMS measurements and X-ray structural analysis for compound 1.     

A new C21 steroidal compound from the whole herb of Pachysandra terminalis Sieb. et Zucc

A new C21 steroidal compound (1), along with 12 known compounds (2–13) were isolated from the whole herb of Pachysandra terminalis Sieb. et Zucc. Their structures were determined by extensive analysis using various spectroscopic techniques. Notably, compound 6 was reported for the first time from P. terminalis, and compounds 3–5, 7 and 9 were isolated from the family Buxaceae for the first time.     

Chemical constituents isolated from Valeriana officinalis L

Phytochemical investigations on the leaves of Valeriana officinalis L. led to the isolation of 18 compounds, including eight lignans (1–8), three sesquiterpenoids (9–11), five iridoids (12–16), and two aldehydes (17–18) The structure elucidation of isolated compounds was achieved on the basis of NMR and mass spectral data. Among them, three compounds (9–16, 18) are reported from V. officinalis for the first time and one compound (5) was isolated from the genus Valeriana for the first time. In addition, six compounds (2, 4, 6–8, 17) are isolated for the first time from Valerianaceae family. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Secondary metabolites from Spiranthes sinensis (Orchidaceae)

One new flavonol glycoside (1) and nine known compounds (2–10) were obtained from the n-BuOH soluble fraction of the whole plants of Spiranthes sinensis. The structure of compound 1 was elucidated based on the combination of spectroscopic (¹H-NMR, ¹³C-NMR, HSQC, and HMBC as well as HR-ESI-MS) and chemical methods. The occurrences of eight compounds (2-9) in this genus were firstly reported while five of them (2–6) were obtained from Orchidaceae for the first time. Furthermore, the chemotaxonomic significance of these compounds was discussed.     

Diarylpentanoids from Diplomorpha canescens and Diplomorpha ganpi

Two new α-hydroxy ketone type diarylpentanoids, diplomorphanone A, 2(S)-hydroxy-1-(4-hydroxyphenyl)-5-phenyl-1-pentanone (1) and diplomorphanone B, 2(R)-hydroxy-1,5-diphenyl-1-pentanone (2) were isolated from aerial parts of Diplomorpha canescens (Meisn.) C.A. Meyer and roots of Diplomorpha ganpi (Sieb. et Zucc.) Nakai, respectively. Nine known compounds including diarylpentanoids (3–6), phenylpropanoid derivatives (7–9), (+)-afzelechin (10) and apiosylskimmin (11) were also isolated for the first time from D. ganpi. Structures of these compounds were elucidated on the basis of spectroscopic data.     

Antifungal cinnamic acid derivatives from Persian leek (Allium ampeloprasum Subsp. Persicum)

A cinnamic imidate, (1Z,2E)-methyl 3-(-p-hydroxy-m-methoxyphenyl)-N-(-p-hydroxyphenethyl) acrylimidate, named persicoimidate (1), has been isolated and characterized from bulbs and seeds of Persian leek, Allium ampeloprasum Subsp. Persicum. Two cinnamic acid derivatives, N-feruloyl tyramine (2) and N-caffeoyl tyramine (3) were isolated from bulbs and seeds. Compound 2 has been previously reported from garlic and leek, while compound 3 is described in Allium plants for the first time. The chemical structures of the isolated compounds have been elucidated unambiguously by spectroscopic methods, including 2D NMR and MS. The isolated compounds were evaluated for their antifungal activity against four fungal pathogens, the soil-borne pathogen Penicillium italicum, the air-borne pathogens Aspergillus niger and Botrytis cinerea, and the antagonistic fungi Trichoderma harzianum to evaluate the possible involvement of such compounds in resistance to pathogen attack.     

Minor phenolics from Angelica keiskei and their proliferative effects on Hep3B cells

A new coumarin, (?)-cis-(3′R,4′R)-4′-O-angeloylkhellactone-3′-O-β-d-glucopyranoside (1) and two new chalcones, 3′-[(2E)-5-carboxy-3-methyl-2-pentenyl]-4,2′,4′-trihydroxychalcone (4) and (±)-4,2′,4′-trihydroxy-3′-{2-hydroxy-2-[tetrahydro-2-methyl-5-(1-methylethenyl)-2-furanyl]ethyl}chalcone (5) were isolated from the aerial parts of Angelica keiskei (Umbelliferae), together with six known compounds: (R)-O-isobutyroyllomatin (2), 3′-O-methylvaginol (3), (?)-jejuchalcone F (6), isoliquiritigenin (7), davidigenin (8), and (±)-liquiritigenin (9). The structures of the new compounds were determined by interpretation of their spectroscopic data including 1D and 2D NMR data. All known compounds (2, 3, and 6–9) were isolated as constituents of A. keiskei for the first time. To identify novel hepatocyte proliferation inducer for liver regeneration, 1–9 were evaluated for their cell proliferative effects using a Hep3B human hepatoma cell line. All isolates exhibited cell proliferative effects compared to untreated control (DMSO). Cytoprotective effects against oxidative stress induced by glucose oxidase were also examined on Hep3B cells and mouse fibroblast NIH3T3 cells and all compounds showed significant dose-dependent protection against oxidative stress.     

A new flavone glycoside from the leaves of Agastache rugosa (Fisch. & C.A.Mey.) Kuntze

Agastache rugosa (Fisch. & C.A.Mey.) Kuntze has been widely used as a food spice and a remedy for colds in Korea, China and Japan. In this study, one new flavone glycoside (1) along with six flavonoids (2–7), nine phenyl glycosides (8–16) and three megastigmane glycosides (17–19) were isolated from the leaves of A. rugosa. By extensive spectroscopic methods including 1D and 2D NMR, and MS data, the structure of the new compound (1) was elucidated as acacetin 7-O-β-(6″-(E)-crotonylglucopyranoside). From present investigation, compound 1 and 7–19 were isolated for the first time from the genus Agastache and 1, 16, 18 and 19 in the Lamiaceae family.     

Phytochemistry and antiglycation activity of Aloe sinkatana Reynolds

A new anthraquinone along with 10 known compounds were isolated from the leaves of Aloe sinkatana Reynolds (Aloaceae), and their structures were elucidated as the new compound 2,8-dihydroxy-6-(hydroxymethyl)-1-methoxyanthracene-9,10-dione (1) and the known compounds Aloe-emodin (2), feralolide (3), 1-hydroxy-5-methoxy-3-methyl-9,10 dihydroanthracene 9,10-dione (4), β-sitosterol (5), β-sitosterol with glycosidic bond (6), microdontin (7), homoaloins A (8) and B (9) and aloins A (10) and B (11). Characterization of compounds 1–9 was based on spectral analyses and comparison with reported data, particularly the new compound 1 was identified by 1D- and 2D NMR, mass spectroscopic and X-ray crystallography analyses. Antiglycation activity of the extracts and isolated compounds were carried out using the hemoglobin-δ-gluconolactone and glucose–bovine serum albumin assays. The results obtained showed that MeOH and EtOAc extracts as well as compound 1 showed an inhibitory effect on early stage protein glycation. Compound 1 also showed significant inhibitory effects against glucose-induced advanced glycation end-products.     

Chemical constituents from the stem bark of Acer tegmentosum

A new phenolic glycoside, 4-hydroxyphenylethyl-1-O-β-D-[6′-O-(4-hydroxybenzoyl)]-glucopyranoside (1) was isolated from the stem bark of Acer tegmentosum, along with seven known phenolic compounds (2–8). The structure of compound 1 was determined by spectral analyses, including HR-ESI-MS, 1D and 2D NMR (COSY, HMQC and HMBC) experiments. Compounds 3 and 4 were found in the family Aceraceae for the first time.     

Chemical constituents from the fruits of Zanthoxylum bungeanum and their chemotaxonomic significance

The phytochemical study of the fruits of Zanthoxylum bungeanum Maxim led to the isolation of sixteen compounds, including a new compound zantharin (1) and fifteen other known compounds, which consist of ten coumarins (2–11), three alkaloids (12–14), and two phenols (15–16). Their structures were elucidated based on extensive spectroscopic methods (1D and 2D NMR, HRESIMS, UV, and IR experiments) and by comparison with literature data. In this work, all the compounds were isolated from Z. bungeanum for the first time, in which, compounds 5 and 13–16 were reported for the first time from the genus Zanthoxylum and the Rutaceae family, respectively. Moreover, the chemotaxonomic significance of isolated compounds is discussed.     

Chemical constituents from the roots of Zizyphus jujuba Mill. var. spinosa

One new flavonoid, named (R)-2-hydroxynaringenin (1), along with fifteen known compounds, including six flavonoids (2–7), six lignans (8–13), two phenolic glycosides (14–15) and one alkaloid (16) were isolated from the roots of Zizyphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chou. Their structures were established on the basis of spectroscopic evidence, including 1D and 2D NMR, circular dichroism (CD) curve analysis, and by comparison with literature data. Compounds 2, 3 and 8–16 were found in Z. jujuba Mill. var. spinosa for the first time, while compounds 8, 10 and 13–15 were new to the Rhamnaceae family. In addition, the chemotaxonomic significance of the isolates was discussed in this paper.     

Difuranonaphthoquinones from Plumbago zeylanica roots

The naphthoquinones, lapachol (1), plumbagin (2), 2-isopropenyl-9-methoxy-1,8-di-oxa-dicyclopenta[b,g]naphthalene-4,10-dione (3), 9-hydroxy-2-isopropenyl-1,8-dioxa-dicyclopenta[b,g]naphthalene-4,10-dione (4), 2-(1-hydroxy-1-methyl-ethyl)-9-methoxy-1,8-dioxa-dicyclopenta[b,g]naphthalene-4,10-dione (5) and 5,7-dihydroxy-8-methoxy-2-methyl-1,4-naphthoquinone (6) were isolated isolated from roots of Plumbago zeylanica. The new constituents (3–5) in addition to known compounds (1, 2 and 6) were characterized by spectral analysis (UV, IR, 1D & 2D NMR and MS).     

Indanone and mellein derivatives from the Garcinia-derived fungus Xylaria sp. PSU-G12

Two new compounds, one indanone (1) and one mellein (2), along with 3-hydroxy-4-methyl-1-indanone (3), griseofulvin (4), dechlorogriseofulvin (5), cytochalasin D (6) and three mellein derivatives (7–9) were isolated from the broth extract of the Garcinia-derived fungus Xylaria sp. PSU-G12. The structures were elucidated by spectroscopic analysis. This is the first report on the isolation of indanone derivatives from the genus Xylaria. The isolated compounds were evaluated for antioxidant activity in DPPH assay.     

Chemical constituents from Artemisia argyi and their chemotaxonomic significance

Twelve compounds, including one monoterpene (1), two sesquiterpene lactones (2–3), six flavonoids (4–9), one phenolic glycoside (10), one chromone (11) and one phenolic acid (12), were isolated and identified from the leaves of Artemisia argyi. Compounds 1–2, 4 and 6–7 have not been recorded before in this plant. Compounds 3, 9 and 11 were isolated from the genus Artemisia for the first time. This paper is the first report on the presence of compound 10 in species of Asteraceae. In addition, the chemotaxonomic significance of these compounds was summarized.     

Chemical constituents from the roots of Asarum sieboldii Miq. var. Seoulense Nakai

Fourteen compounds were isolated from the 95% ethanol reflux extract of Asarum sieboldii Miq. var. Seoulense Nakai, including five phenanthrene derivatives (1–5), three isobutyl amides (6–8), three phenylpropanoids (9–11) and three lignins (12–14). The structures of these compounds were identified by spectroscopic methods and by comparison with the reported spectroscopic data. Among them, compounds 6 and 11 were firstly reported from the family Aristolochiaceae, and compounds 3 and 4 were reported for the first time from the genus Asarum. Additionally, compounds 1, 2 and 8 were isolated from A. sieboldii Miq. var. Seoulense Nakai for the first time. These compounds have shown chemical relationships between A. sieboldii Miq. var. Seoulense Nakai and other species of Asarum as well as those found in the genus Aristolochia in the family Aristolochiaceae.     

Phytochemicals from the stem wood of Sorbus lanata (D. Don.) Schauer

Three new phenolic compounds, sorlanin (4-(3-(hydroxymethyl)-5-methoxy-7-phenyl-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)-2-methoxyphenol, 1), sorbanin (2-((3,5-dimethoxy-[1,1′-biphenyl]-4-yl)oxy)-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol, 2) and sorbalanin (4-(3-(hydroxymethyl)-5,6-dimethoxy-2,3-dihydrobenzo[b][1,4]dioxino[2,3-g]benzofuran-2-yl)-2-methoxyphenol, 3), together with eight known compounds, polystachyol (4), isolariciresinol (5), dihydrodehydrodiconiferyl alcohol (6), tuberculatin (7), ovafolinin E (8), aucuparin (9), 2′-methoxyaucuparin (10), and tetracosyl-3-(3,4-dihydroxyphenyl)acrylate (11), were isolated from Sorbus lanata. The structures of these phytoconstituents were elucidated through extensive spectroscopic techniques, including UV, IR, 1D and 2D NMR, ESI-MS and HRESI-MS experiments. All the compounds except 9 and 10 were isolated for the first time from the genus Sorbus. The isolated compounds were also tested in DPPH radical scavenging reaction where compounds 6, 7, 10 and 11 showed significant activities with IC₅₀ values of 9.2, 11.7, 23.0 and 33.7 μM, respectively.