Cembrane diterpenoids from the soft coral Sarcophyton trocheliophorum Marenzeller as a new class of PTP1B inhibitors

A detailed investigation of the South China Sea soft coral Sarcophyton trocheliophorum Marenzeller yielded, along with six known terpenes (6?11), the new sarcophytonolides N?R (1?5), whose structures have been elucidated by detailed spectroscopic analysis. Sarcophytonolides N–R are mono- or bicyclic cembranoids characterized by the presence of three/four double bonds and oxidized methyl groups. Some of the isolated compounds showed significant inhibitory activity against human protein tyrosine phosphatase 1B (PTP1B) enzyme, a key target for the treatment of type-II diabetes and obesity, and some preliminary structure–activity relationships have been drawn. This is the first report on the anti-PTP1B activity of cembrane diterpenoids.     

Phytochemical and chemotaxonomic investigation from the roots of Anemone vitifolia Buch.-Ham. (Ranunculaceae)

Phytochemical investigation from the roots of Anemone vitifolia Buch.-Ham. led to the isolation of eight compounds, including one triterpenoid saponin, two sugars, one coumarin, one amide, one saturated alkane, one olefin and one fatty acid. The structures of these metabolites were elucidated by spectroscopic data and comparisons with the data available in the literature. Among them, compound 7 ((6Z,9Z,12Z)-6,9,12-Eicosatriene) was isolated for the first time as a natural product. Furthermore, compounds 2 (D-(+)-raffinose), 3 (mixture of β-D-fructopyranose and β-D-fructofuranose) and 5 (bonaroside) were obtained from the Ranunculaceae family for the first time. Compounds 4 (siderin) and 6 (n-hexadecane) were isolated from A. vitifolia for the first time. The chemotaxonomic significance of the isolated compounds was discussed.     

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.     

Flavonoids and polyacetylenes from the aerial parts of Bidens tripartita

Fourteen flavonoids (1–14) and two polyacetylenes (15 and 16) were isolated from the aerial parts of Bidens tripartita. Thirteen compounds (1–7, 9, 11, 12, and 14–16) were isolated from this species for the first time, of which a flavonoid (11) was obtained for the first time from the genus Bidens. The chemotaxonomic significance of these compounds was summarized.     

Chemical constituents from the roots of Euphorbia nematocypha Hand.-Mazz.

A new myrsinol-type diterpene (1), three myrsinol-type diterpenes (2–4), three ent-abietane-type diterpenes (5–7), one tigliane-type diterpene (8), two cycloartane-type triterpenes (9–10), and two tirucallane-type triterpenes (11–12) were isolated from the roots of Euphorbia nematocypha Hand.-Mazz. Their structures were identified by spectroscopic analyses and by comparison of their spectral data with those reported in the literature. Compound 12 was isolated and reported from plants for the first time. All compounds were isolated from E. nematocypha for the first time.     

Chemical constituents from Teucrium viscidum

A new guaiane sesquiterpenoid (1), two known guaiane sesquiterpenoids (2 and 3), and eleven known compounds (4–14), were isolated from Teucrium viscidum. Their structures were identified by spectroscopic analyses and by comparison of their spectral data with those reported in the literature. The absolute configuration of lipidiol (2) was determined by single-crystal X-ray diffraction analysis with Cu Kα radiation. Compounds 12 and 13 were isolated as natural products for the first time. All compounds were isolated from T. viscidum for the first time.     

The distribution of entomophilic nematodes (Heterorhabditidae and Steinernematidae) in North Carolina

Over 500 samples of soil from cropland, vineyards, orchards, pasture, and forest habitats throughout North Carolina were tested for the presence of steinernematid and heterorhabditid nematodes by baiting with Galleria mellonella larvae. Nematodes were isolated from 13 of 14 locations and from each habitat. Heterorhabditids (Heterohabditis heliothidis) were most commonly found (13 locations) with Steinernema (= Neoaplectana) glaseri, S. feltiae (= Neoaplectana carpocapsae), and an undescribed Steinernema species being found at one or two locations. The primary form of the bacterial symbiont of S. glaseri was isolated for the first time.     

Chemical constituents isolated from the roots and rhizomes of Smilacina japonica

Phytochemical investigation of the roots and rhizomes of Smilacina japonica A. Gray led to the isolation of 16 compounds, including six steroidal saponins (1-6), one amide (7), one fatty alcohol (8), one steroidal sapogenin (9), two flavones (10-11), one glycoside (12), one phenol (13), one aliphatic acid (14), and two sterols (15-16). All of these compounds were isolated for the first time from the roots and rhizomes of S. japonica while compounds 1-13 were identified for the first time from the genus Smilacina, of which compounds 9, 11, and 13 were isolated from the Liliaceae family for the first time. Furthermore, the isolation of compound 9 was reported for the first time in plants. Their structures were identified by spectroscopic methods and compared previously published data. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Chemical constituents from the fruiting bodies of Xylaria euglossa Fr. and its chemotaxonomic study

Three anthracenones (1–3), two lactams (4–5), three sterols (6–8), one ceramides (9), one long-strain fatty acid (10) were isolated from the fruiting bodies of Xylaria euglossa Fr. All the compounds were isolated from this fungus for the first time. Compound 1, 4 and 5 were isolated from the family Xylariaceae for the first time. Compound 1 and 4–5 were considered chemotaxonomically significant for the species Xylaria euglossa.     

Chemical constituents from Lomatogonium carinthiacum (Gentianaceae)

Lomatogonium carinthiacum (Wulfen) Rchb. (Gentianaceae) is an annual plant which used in the Mongolian system of medicine against liver and bile diseases. In the present study, three flavones (1–3), four xanthones (4–7), and two iridoids (8, 9) were isolated and identified. Among them, compounds 3–5, 7, 8 were firstly isolated from the species L. carinthiucum, compounds 3-5 were isolated from the genus Lomatogonium for the first time. The Chemotaxonomic significance of these compounds was discussed in the article.     

Sarcophytrols G – L,Novel Minor Metabolic Components from South China Sea Soft Coral Sarcophyton trocheliophorum Marenzeller

Minor metabolic components, six new cembranoids sarcophytrols G – L ( 1  –  6 ) along with two known related analogues 7 and 8 , were isolated from the South China Sea soft coral Sarcophyton trocheliophorum. Their structures were elucidated by extensive spectroscopic analyses (1D‐, 2D‐NMR, and ESI‐MS) as well as comparison with literature data. As part of our ongoing research project for discovering bioactive substances from Chinese marine invertebrates, compounds 1  –  8 were tested for their inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a key target for the treatment of Type‐II diabetes and obesity. However, none of them exhibited potent PTP1B inhibitory activities.     

Diterpenoid alkaloids and flavonoids from Delphinium albocoeruleum Maxim

Ten compounds (1–10) including two C₂₀-diterpenoid alkaloids, five C₁₉-diterpenoid alkaloids, one triterpenoid and two flavonoids were isolated from the whole plant material of Delphinium albocoeruleum Maxim for the first time. The chemotaxonomic significance of these compounds was summarized.     

Chemical constituents from the roots and rhizomes of Silene tatarinowii Regel

Chemical investigation of the root and rhizome of Silene tatarinowii Regel led to the isolation of nine ecdysteroids (1–9) and one sterol (10). All the compounds were determined on the basis of MS and NMR and by comparison with those in the literature. All these compounds were isolated from S. tatarinowii for the first time. Furthermore, compounds 7–10 were isolated from Silene genus for the first time, of which compounds 7 and 8 were isolated from Caryophyllaceae family members for the first time. This is the first study to report the chemical constituents of S. tatarinowii and the chemotaxonomic relationships between Silene and other genera of Caryophyllaceae.     

Antibacterial Compounds from Propolis of Tetragonula laeviceps and Tetrigona melanoleuca (Hymenoptera: Apidae) from Thailand

This study investigated the chemical composition and antimicrobial activity of propolis collected from two stingless bee species Tetragonula laeviceps and Tetrigona melanoleuca (Hymenoptera: Apidae). Six xanthones, one triterpene and one lignane were isolated from Tetragonula laeviceps propolis. Triterpenes were the main constituents in T. melanoleuca propolis. The ethanol extract and isolated compounds from T. laeviceps propolis showed a higher antibacterial activity than those of T. melanoleuca propolis as the constituent α-mangostin exhibited the strongest activity. Xanthones were found in propolis for the first time; Garcinia mangostana (Mangosteen) was the most probable plant source. In addition, this is the first report on the chemical composition and bioactivity of propolis from T. melanoleuca.     

Chemical constituents from Alnus mandshurica (Callier) Hand.-Mazz. and their chemotaxonomic significance

A new phenol compound, (9S)-9-hydroxy-9-[(2-hydroxyphenyl)methoxy]-nonanoic acid methyl ester (1) was isolated from the stem bark of Alnus mandshurica (Callier) Hand.-Mazz., along with eight known compounds (2–9). The structure of compound 1 was determined by spectral analyses, including HR-ESI-MS, 1D and 2D NMR (COSY, HMQC and HMBC) experiments. All the isolated compounds were reported for first time from A. mandshurica. Furthermore, compounds 3–9 were found in the family Betulaceae for the first time.     

Chemical constituents from the calyces of Physalis alkekengi var. franchetii

One new monoterpenoid glycoside (1), together with seven known compounds, including two alkaloids (2–3), three phenylpropanoids (4–6), and two nucleosides (7–8) were isolated from the calyces of Physalis alkekengi var. franchetii. Their structures were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. These eight compounds were isolated for the first time from the genus Physalis. The chemotaxonomic significance of these compounds was summarized.     

Halogenated anthraquinones from the rare southern Illinois lichen Lasallia papulosa

Abstract:Four anthraquinones were isolated from the foliose lichen, Lasallia papulosa (Ach.) Llano. Two of the anthraquinones are known compounds, previously isolated from Lasallia papulosa, while the other two were reported previously as secondary metabolites from laboratory-cultured Nephroma laevigatum, and are isolated here for the first time from lichens in their natural habitat. All compounds were characterized by UV spectrophotometry, mass spectrometry, ¹H NMR and ¹³C NMR. The products were identified as 7-chloroemodin, valsarin (7-chloro-5-hydroxyemodin), 5-chloro-1- O -methylemodin and 5-chloro-1- O -methyl-ω-hydroxyemodin.     

Chemical constituents from starfish Culcita novaeguineae

Seven polyhydroxylated steroidal glycosides (1–7) and two polyhydroxylated sterols (8, 9) were isolated and identified from the 75% ethanol extract of starfish Culcita novaeguineae which was collected in Xisha Islands of South China Sea. The structures of the isolated compounds were elucidated on the basis of spectroscopic data, physical and chemical evidence, MS spectrum and assisted by comparison with the reported data. To the best of our knowledge, this is the first time to report compounds 1–6, 8 and 9 from genus Culcita. Moreover, compounds 1, 4–6, 8 and 9 were isolated from family Oreasteridae for the first time. And the chemotaxonomic significance of the isolated compounds was discussed.     

Chemical constituents from the buds of Lonicera macranthoides in Sichuan,China

The phytochemical investigation of the dried buds of L. macranthoides Hand. -Mazz. Symb. Sin. collected in Sichuan, China resulted in the isolation of three aliphatic glycosides (1–3), a caffeoyl glucoside (4), a secoiridoid glycoside (5), and two caffeoylquinic acid analogs (6 and 7). Among them, compound 1 was novel and identified as n-butyl-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside based on the detailed spectroscopic analyses and chemical studies. Compounds 1–4 were isolated for the first time from Caprifoliaceae family; compounds 5–7 were isolated for the first time from L. macranthoides. The chemotaxonomic significance of these compounds was summarized.     

Chemical constituents isolated from Clematis akebioides (Maximowicz) Veitch

A phytochemical investigation of the aerial parts of Clematis akebioides (Maximowicz) Veitch led to the isolation of eighteen compounds, including two benzenoids (1, 2), one linear monoterpene glycoside (3), and fifteen triterpenoid saponins (4–18). The structural elucidation of these compounds was determined by using spectroscopic methods and comparison with the literature. All of these compounds were obtained from C. akebioides for the first time, and compounds 1, 2 and 18 were isolated from the Ranunculaceae family for the first time. Furthermore, the chemotaxonomic significance of these compounds was discussed.