Reduced perylenequinone derivatives from an endophytic Alternaria sp. isolated from Pinus ponderosa

The consecutive solvent extraction of endophytic Alternaria sp. (DC401) isolated from Pinus ponderosa followed by chromatographic techniques led to the isolation of five perylenequinone compounds and one dihydronaphthaquinone derivative, which include three new perylenequinones (1–3). The compounds were identified as 6-methoxy-3,6a,7,10-tetrahydroxy-4,9-dioxo-4,5,6,6a,6b,7,8,9-octahydroperylene (1), 3,6a,9,10-tetrahydroxy-7,8-epoxy-4-oxo-4,5,6,6a,6b,7,8,9-octahydroperylene (2), 6-methoxy-3,6a,9,10-tetrahydroxy-7,8-epoxy-4-oxo-4,5,6,6a,6b,7,8,9-octahydroperylene (3), 3,6a,7,10-tetrahydroxy-4,9-dioxo-4,5,6,6a,6b,7,8,9-octahydroperylene (altertoxin I) (4), 3,6a,7,10-tetrahydroxy-4,9-dioxo-4,6a,6b,7,8,9-hexahydroperylene (dehydroaltertoxin I) (5), and 7-chloroscytalone (6). Structure of compounds 1–6 was determined on the basis of detailed spectroscopic analysis, as well as by comparison with literature reports. The antileismanial, antimicrobial, antimalarial and in vitro cytotoxic activities of compounds 1–6 were evaluated.     

Antibacterial and antioxidant activities of compounds isolated from the leaves of Symphonia globulifera (Clusiaceae) and their chemophenetic significance

The phytochemical study was done on the methanol extract from of the leaves of Symphonia globulifera. This plant has been used in traditional medicine to treat of different ailments such as malaria, diseases of the skin, diabetes, cough, intestinal worms, pre-hepatic jaundice and fever. Chromatographic fractionation and purification of this extract led to the isolation and characterization of twelve compounds (1–12) including pristriol (1), robustaflavone (2), polycarpol (3), 7''-O-methylrobustaflavone (4), amentoflavone (5), stigmasterol glucoside (6), epicatechin (7), apigenin (8), luteolin (9), 1,5-dihydroxyxanthone (10), β-sitosterol 3-β-D-glucopyranoside (11) and a mixture of stigmasterol and β-sitosterol (12). The structures of compounds 1–12 were elucidated on the basis of 1D and 2D NMR, mass spectrometric and the spectroscopic data as well as comparison with the literature. All these compounds were isolated for the first time from Symphonia genus. The NMR spectra and structure elucidation of compound 1 were reported for the first in the literature. The antibacterial and antioxidant activities of three of these compounds were evaluated. The chemophenetic significance of these compounds is also discussed.     

A new meroterpenoid from endophytic fungus Talaromyces amestolkiae CS-O-1

Talaromyces amestolkiae CS-O-1, isolated from Tripterygium Wilfordii Hook. f., was identified based on its ITS and 18S rDNA gene sequencing. A new meroterpenoid, chrodrimanin T (1), along with six known compounds, nicotinamide (2), penipyridone D (3), penipyridone A (4), 3-benzylidene-8,8a-dihydroxy-2-methyl-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione (5), butyl-isobutyl-phthalate (6), and aspergillumarin A (7), were isolated from Talaromyces amestolkiae CS-O-1. The structures and relative configurations of these compounds were established by the analysis of HRMS, 1D and 2D-NMR spectroscopy and the comparison with data in the literature. The compounds 2–6 were first isolated from Talaromyces genus. Herein, the chemotaxonomic significance of these compounds is described.     

Phytochemical and chemotaxonomic studies on Libanotis laoshanensis W. Zhou et Q. X. Liu

Sixteen compounds, including one polyacetylene (1), twelve coumarins (2–7, 9–14), one sterol (8), as well as two sugar derivatives (15, 16), were obtained from Libanotis laoshanensis by modern phytochemical isolation methods such as column chromatography and preparative TLC. Their structures were identified by spectroscopic methods and in comparison with the published data in the references. All the compounds were reported from L.laoshanensis for the first time. The chemotaxonomic significance of these compounds was also discussed, which demonstrated the relationships between L. laoshanensis and some other species of Apiaceae.     

Chemical constituents from the aerial parts of Impatiens hypophylla Makino var. hypophylla

Seven flavonoids such as luteolin (1), luteolin 7-O-β-glucopyranoside (2), luteolin 3'-O-β-glucopyranoside (3), chryseriol (4), apigenin (5), apigenin 7-O-β-glucopyranoside (6) and astragalin (7) and one coumarin, scopoletin (8) were isolated from the aerial parts of Impatiens hypophylla Makino var. hypophylla (Family: Balsaminaceae). Structures of these compounds were elucidated on the basis of spectroscopic methods. All these compounds were isolated for the first time from I. hypophylla var. hypophylla.     

Chemical constituents from aerial parts of Thymelaea lythroides

Chemical investigation of the EtOAc extract of the medicinal plant Thymelaea lythroides yielded eight secondary metabolites, including bassiatin (1), daphenone (2), daphnelone (3), daphnoretin (4), δ-sesamin (5), wikstromol (6), trans-tiliroside (7), and rutarensin (8). The structures of the isolated compounds were determined on the basis of 1D and 2D NMR spectroscopy as well as mass spectrometry. Compounds 1–8 were reported from T. lythroides for the first time and the chemotaxonomic significance of these compounds is summarized.     

Chemotaxonomic value of flavonoids in Chromolaena congesta (Asteraceae)

The phytochemical investigation on the aerial parts of Chromolaena congesta led to the isolation of nine flavonoids, known in the literature as genkwanin (1) kumatakenin (2) acacetin (3), kaempferol 3-methyl ether (4), apigenin (5), apigenin 5,7-dimethyl ether (6), apigenin 5-methyl ether (7), luteolin (8) and kaempferol (9). The chemical structures were established on the basis of spectral evidence. All the compounds were isolated from this species for the first time. The results from the present study provide further information about the flavonoids as taxonomic marker of the genus Chromolaena, and the chemotaxonomic significance of these compounds were also summarized.     

Phytochemical constituents from the stem barks of Goniothalamus tapis Miq

Phytochemical investigation on the stem bark of Goniothalamus tapis Miq. led to the isolation of seven known styryl-lactones, 3-acetyl-isoaltholactone (1), goniothalamin (2), isoaltholactone (3), cheliensisin A (4), 7-epi-goniofufurone (5), goniopypyrone (6), garvensintriol (7), and two steroids, stigmasterol (8) and β-sitosterol (9). The structures of all the compounds were elucidated based on the analysis of spectroscopic data and comparison with reported literature. The chemotaxonomic significance of all these compounds were summarized. Among all the styryl-lactones, compound 1 was isolated naturally from plant for the first time while compounds 4, 5 and 7 have not been previously reported in Goniothalamus tapis Miq. Compound 2 was the first styryl-lactone isolated from many species of Goniothalamus including other families such as Cucurbitaceae, Lauraceae, Stemonaceae and Apocynaceae). Compounds 3 and 6 were found in ten species of Goniothalamus where the latter were also found in other genus (Polyalthia Blume).     

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.     

Phenolic compounds from the leaves and stem bark of Pseudospondias microcarpa (A. Rich.) Engl. (Anacardiaceae)

Phytochemical study of the leaves and the stem bark of Pseudospondias microcarpa (A. Rich.) Engl. afforded eight phenolic compounds: scopoletin (1), ferulic acid (2), isovitexin (3), rhoifolin (4), quercetin 3-O-α-L-rhamnopyranoside (5), justicialoside A (6), granduloside A (7) and pithecellobiumol B (8). The structures of the isolated compounds were elucidated by spectroscopic means including 1D and 2D NMR and MS, and by comparison with previously reported data. This is the first report on the isolation of these compounds from the genus Pseudospondias. The chemotaxonomic significance of the isolated compounds within the family Anacardiaceae is discussed.     

Chemical constituents from the roots of Peucedanum praeruptorum Dunn and their chemotaxonomic significance

Chemical investigation on the roots of Peucedanum praeruptorum Dunn afforded 15 compounds, including five linear furocoumarins (1–5), six angular pyranocoumarins (6–11), two simple coumarins (12 and 13), a benzaldehyde derivative (14), and a phenylpropanoid glycoside (15). The structures of these compounds were established via spectroscopic analysis and comparison of their NMR data with the literature. Compound 1 was a new linear furocoumarin glycoside, while compounds 10–12, 14 and 15 were isolated from P. praeruptorum for the first time. The chemotaxonomic significance of these isolated compounds was summarized herein.     

Pentacyclic triterpenoids and other constituents isolated from the leaves of Gambeya lacourtiana and their antibacterial activity

The phytochemical study was done on the leaves of Gambeya lacourtiana. This plant has been used in traditional medicine to treat of different ailments such as uterine heamorrhage, metritis and other vaginal infections. Chromatographic fractionation and purification on the leaves crude extract afforded lupeol acetate (1), lupenone (2), lupeol (3), taraxerol (4) stigmasterol (5), erythrodiol (6), chamaedrydiol (7), methyl pheophorbide-a (8), corosolic acid (9), tormentic acid (10), epicatechin (11) and 22-dihydrospinasterol 3-O-β-D-glucopyranoside (12). The structures of compounds 1–12 were elucidated on the basis of 1D and 2D NMR, mass spectrometric and the spectroscopic data as well as comparison with the literature. Compounds 4, 7–10 and 12 were isolated for the first time from Gambeya genus. Crude extract, fractions and compounds 6–12 were evaluated for their antibacterial activity. Methyl pheophorbide-a (8) demonstrated moderate activity against Salmonella typhi CPC with MIC values of 62.5 μg/mL. The chemophenetic significance of these compounds is also discussed.     

A new bicyclic sesquiterpenoid from Merremia yunnanensis

A new sesquiterpenoid, 1α,4β,8β,9β-eudesmane-tetrol-1-O-β-D-glucopyranoside (1), together with nine known compounds (2–10), were isolated from Merremia yunnanensis. The structures of these compounds were elucidated by spectroscopic methods and compared to data in the literature. All these compounds (1–10) were firstly isolated from this plant, and compounds 3, 5, 7, and 10 were reported from the Merremia genus for the first time. The significance of the chemotaxonomy for these compounds is described herein.     

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.     

Vernoguinamide: A new ceramide and other compounds from the root of Vernonia guineensis Benth. and their chemophenetic significance

The chemical investigation of the roots of Vernonia guineensis Benth. (Asteraceae) resulted in the isolation of a new ceramide, named vernoguinamide (1), together with fifteen known compounds, including three anthraquinones, physion (2), erythroglaucin (3) and emodin (4), three triterpenoids, hop-17(21)-en-3β-yl acetate (5), lupeol (6) and betulinic acid (7), six steroids, vernoguinoside A (8), vernoguinoside (9), β-sitosterol 3-O-β-D-glucoside (10), stigmasterol 3-O-β-D-glucoside (11), stigmasterol (12) and β-sitosterol (13) and three fatty acid derivatives, tetracosanoic acid (14), tricosanic acid (15) and arachidic acid glycerol ester (16). The structure of the new compound as well as those of the known compounds were established by spectrometric analysis including HRESI-MS, 1D and 2D-NMR and by comparison with the previously reported data. Among these compounds, the anthraquinones 2–4 and the triterpene 5 were isolated for the first time from Vernonia genus and compounds 6, 7 and 14–16 were extracted for the first time from the species. The isolated compounds were tested for their antibacterial activity and 3, 8 and 9 were the most active compounds against the tested bacteria. Furthermore, the chemophenetic relationships of the isolated compounds and their significance were also discussed.     

α-Pyrone derivatives from the endolichenic fungus Nectria sp.

Five new α-pyrone derivatives, necpyrones A–E (1–5), together with seven known compounds (6–12), were isolated from the extract of an endolichenic fungus Nectria sp. Chemical structures of these compounds were elucidated by spectroscopic analyses (HRESIMS and NMR). The absolute configurations of C-6 in the pyrone ring as well as the chiral carbons at the aliphatic side chain resulted from hydroxyl substitute were finally determined on the basis of measurement of ECD and Kusumi–Mosher method.     

Phytochemical and chemotaxonomic study on Saussurea medusa Maxim. (Compositae)

A phytochemical investigation of Saussurea medusa Maxim. led to the isolation of eleven compounds, including neoechinulin A (1), 8-hydroxypinoresinol (2), caruilignan D (3), 7(S)-hydroxyarctigenin (4), pinoresinol (5), arctigenin (6), arctii (7), epipinoresinol (8), loliolide (9), apigenin (10), and luteolin (11). Their structures were elucidated by spectroscopic methods and comparison with previously reported spectral data. Among them, compounds 1 and 2 were firstly obtained from this species, compounds 3 and 4 were isolated from the genus Saussurea for the first time. Furthermore, the chemotaxonomic significance of these compounds was discussed in details.     

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.     

Chemical constituents from Pteris ensiformis Burm. (Pteridaceae)

Phytochemical study of Pteris ensiformis Burm. resulted in the isolation of eleven compounds, including three sesquiterpenoids (1–3), one alkaloid (5), one amino acid (6), one flavonoid (7), four phenolic acids (4, 8, 9 and 10), and one coumarin (11). Structures of these compounds were deduced from the ESI-MS and NMR data. This is the first report on the isolation of compounds 1, 2, 7 and 11 from P. ensiformis, compounds 6 and 9 from the genus Pteris, and compound 5 from the family Pteridaceae. In addition, a detailed discussion of the chemotaxonomic significance of these compounds was presented.     

Chemical constituents from Psychotria yunnanensis and its chemotaxonomic study

Phytochemical investigation on the aerial parts of Psychotria yunnanensis led to the isolation of four norisoprenoids (1–4), one monoterpenoid (5), and eleven phenolic compounds (6–16). To our knowledge, all compounds were isolated from this plant for the first time. Compounds 2–16 were reported for the first time from the genus Psychotria. The chemotaxonomic significances of these compounds were summarized.