Cytotoxic pterosins from Pteris multifida roots against HCT116 human colon cancer cells

Two new pterosin glycosides, (2S,3S)-pterosin C 3-O-β-d-(4′-(E)-caffeoyl)-glucopyranoside (1) and (2S,3S)-pterosin C 3-O-β-d-(6′-(E)-p-coumaroyl)-glucopyranoside (2), were isolated from Pteris multifida (Pteridaceae) roots along with ten known pterosin compounds (3–12). The chemical structures of the isolated compounds were elucidated by extensive analysis of the 1D, 2D NMR, HRESIMS, and CD spectroscopic data. The cytotoxicities of 1–12 against HCT116 human colorectal cancer cell line were evaluated. Among the isolates, compound 1 showed moderate antiproliferative activity in HCT116 cells with an IC₅₀ value of 8.0 ± 1.7 μM. Additionally, 1 induced the upregulation of the caspase-9 and procaspase-9 levels in Western blots and increased the annexin V/propidium iodide (PI)-positive cell population in flow cytometry.     

Chemical constituents of Pteris wallichiana J.Agardh (Pteridaceae)

Chemical investigation on the whole plants of Pteris wallichiana J. Agardh led to the isolation and identification of a new pterosin glycoside, ptemuloside A (1), along with other seventeen known compounds (2–18) (Fig. 1). The structure of compound 1 was elucidated by means of spectroscopic techniques, including HRESIMS, and 1D and 2D NMR experiments. Compounds 2, 3, and 5–17 are first time reported from the title plant. The pterosins in P. wallichiana could serve as its chemotaxonomic markers.     

Two new pterosin sesquiterpenes from Pteris multifida Poir

Two new pterosin sesquiterpenes named as 2R,3R-13-hydroxy-pterosin L 3-O-β-d-glucopyranoside (1) and 2R,3S-acetylpterosin C (2), along with a known one, 2S,3S-acetylpterosin C (3), were isolated from the whole plant of Pteris multifida and the 1D and 2D NMR data of 3 were reported for the first time in this paper. Their structures were elucidated on the basis of mass and spectral evidence. Compounds 1–3 showed cytotoxicity against HL 60 cells (human leukemia) with the IC₅₀ values of 14.6, 48.3 and 35.7 μM, respectively.     

Guaianolides and homoditerpenes from Lasiolaena morii

The investigation of Lasiolaena morii afforded in addition to known compounds four new guaianolides, three diterpenes derived from geranyl nerol in     

New germacranolides and other constituents from Trichogoniopsis morii

Trichogoniopsis morii afforded, in addition to known compounds, a new toxol derivative, two diterpenes, a labdane and an ent-kaurane derivative, an eudesmanolide and five germacranolides, a furanoheliangolide and four 1-oxo-germacranolides. The structures were elucidated by spectroscopic methods and a few chemical transformations. The chemotaxonomy of the genus Trichogoniopsis is discussed briefly.     

Five new species of Solanum section Geminata (Solanaceae) from South America

Five new species of South AmericanSolanum are described:S. morii from French Guiana,S. superbum andS. tumescens from Bolivia,S. platycypellon from southern Bolivia and northern Argentina andS. gertii from southeastern Brazil. An illustration and distribution map for each species is provided and relationships to close relatives are discussed.     

New species in begonia section gireoudia (Begoniaceae) from central America

Begonia buseyi, B. croatii, B. dressleri andB. morii from Panama andB. louis-williamsii from Guatemala are described as new, illustrated and 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 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.     

A new acorane sesquiterpenes of Lysionotus pauciflorus maxim. Form Guizhou province,China

A new acorane sesquiterpene (1), together with fourteen known compounds were isolated from the whole plant of Lysionotus pauciflorus Maxim. The chemical structures of the compounds were identified by physio-chemical properties and 1D-NMR, 2D-NMR, ESI-MS, IR and ECD spectra. Among them, six compounds (1, 4, 6, 7, 13, 15) were first found in the genus Lysionotus. The chemotaxonomic significance of the isolated compounds in the genus Lysionotus and family Gesneriaceae were discussed.     

New sesquiterpenes from the endophyte Microdiplodia sp. TT-12 and their antimicrobial activity

Four new compounds, phomadecalin F (1), 8α-monoacetoxyphomadecalin D (2), 3-epi-phomadecalin D (3), and 13-hydroxylmacrophorin A (4), were isolated from the endophyte, Microdiplodia sp. TT-12 together with two known compounds, phomadecalins C (5) and D (6). The structures of the compounds were elucidated by NMR spectroscopic and mass spectrometric analyses in combination with chemical means. The antibacterial activities of the isolated compounds were evaluated. Compound 4 was weakly active against Raffaelea quercivora.     

Antibacterial constituents from Leucosceptrum canum

Four new long-chain compounds, leucoperoxyterpene (1), leucoester (2), leucoic acid (3), and leucoenoic acid (4) has been isolated from aerial parts of the medicinal plant Leucosceptrum canum together with fifteen known compounds. Compound 1 was found to be a member of the rare class of peroxy open chain natural products. The structures of all compounds were assigned by means of modern spectroscopic techniques. All compounds were tested for their antibacterial activities against Bacillus subtilis, Escherichia coli, Micrococcus luteus, Pseudomonas agarici, Streptococcus minor, and Streptococcus ferus, in which, compounds 1, and 10–15 exhibited potent to moderate activities.     

Caged xanthones displaying protein tyrosine phosphatase 1B (PTP1B) inhibition from Cratoxylum cochinchinense

Four new caged xanthones (1–4) and two known compounds (5, 6) were isolated from the roots of Cratoxylum cochinchinense, a polyphenol rich plant, collected in China. The structures of the isolated compounds (1–6) were characterized by obtaining their detailed spectroscopic data. In particular, compounds 1 and 6 were fully identified by X-ray crystallographic data. The isolated compounds (1–6) were evaluated against protein tyrosine phosphatase 1B (PTP1B), which plays an important role in diabetes, obesity, and cancer. Among these compounds, 3, 4, and 6 displayed significant inhibition with IC₅₀ values of 76.3, 43.2, and 6.6 µM, respectively. A detailed kinetic study was conducted by determining K_m, V_max, and the ratio of K_ik and K_iv, which revealed that all the compounds behaved as competitive inhibitors.     

New hexalactone derivatives and a pair of new oxaspiro-carbon epimeric glycosides from the fruits of Illicium lanceolatum

Five new compounds (1–5), including three hexalactone derivatives (1–3) and a pair of new oxaspiro-carbon epimeric glycosides (4 and 5), and six known compounds (6–11) were obtained from the fruits of Illicium lanceolatum. The structures of the new compounds were elucidated using extensive spectroscopic data. The absolute configurations of compounds 1–3 were determined by an analysis of their CD spectra. It was determined that compounds 4 and 5, which are epimeric at C-5, possess the same 1-oxaspiro[4,5]decane-7α,8α,9β-triol moiety. Plausible biogenetic pathways for 4 and 5 derived from the key precursor shikimic acid were proposed. Compounds 1–11 were all assayed on monosodium glutamate-induced human neuroblastoma SH-SY5Y cell damage. The results demonstrated that compounds 4, 5, and 8–10 possess potential neuroprotective effects. The anti-inflammatory, antiviral, and cytotoxic activities of 1–11 were also evaluated.     

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.     

Naphthoquinone and flavonoid constituents from the carnivorous plant Nepenthes mirabilis and their anti-osteoporotic and antioxidant activities

The methanolic extract of Nepenthes mirabilis (Nepenthaceae) showed significant in vitro antioxidant (peroxyl radical-scavenging and reducing effects) and anti-osteoporotic (pre-osteoclastic RAW 264.7 cells) activities. Phytochemical investigation of chloroform and ethyl acetate partitions of N. mirabilis branches and leaves allowed to isolate 13 compounds (1–13), including two new naphthoquinones, nepenthones F (1) and G (2), together with 11 known compounds. The structures of the isolated compounds were established mainly by extensive analysis of the 1D and 2D NMR, as well as HRMS data. The isolated compounds also were further evaluated for in vitro antioxidant and anti-osteoclast activities. Among them, compounds 10 and 11 showed potent antioxidant effects. While compounds 4 and 12 showed significant inhibition on receptor activation for nuclear factor κB ligand (RANκL)-induced osteoclast formation in murine bone-marrow macrophages.     

Further chemical constituents from Sinningia canescens and S. leucotricha (Gesneriaceae)

Four new compounds were isolated from the tubers of Sinningia canescens and S. leucotricha: one naphthoquinone, 7-methoxy-8-hydroxy-α-dunnione (1); two arylbenzofurans, sinningial A (2) and B (3); and one sesquiterpene, 11-epi-subergorgiol (4). Seventeen additional known compounds were isolated and identified. The structures of all compounds were determined by spectroscopic and MS analysis.     

Chemical constituents of sponge Pseudoceratina sp. and their chemotaxonomic significance

The chemical investigation of Pseudoceratina sp. led to the isolation of six compounds including tyrosine brominated isoxazoline alkaloids (1 and 2), polyketide (3), and 5α,8α-epidioxysterols (4–6). The structures of these compounds were identified by comparison of NMR and MS spectroscopic data with those previously reported. Compounds 3–6 were isolated for the first time from sponges of the genus Pseudoceratina. The chemotaxonomic significance of these compounds was discussed.