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.     

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 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.     

Two new diterpenoids from the roots of Pygmacopremna herbacea

Two new diterpenoids, neobharangi-δ-lactone (1) and bharangi quinone (2) along with two known compounds neobharangin (3) and bharangin (4) were isolated from the ethyl acetate extract of root nodules of Pygmacopremna herbacea. The structures of the new compounds were established by 1D and 2D NMR spectroscopic data.     

Four new phenylpropanoid glycosides from Clausena dunniana var. robustaand their antiinflammatory activities

Four new phenylpropanoid glycosides, clausenaglycosides A–D (1–4), along with fourteen known compounds (5–18) were isolated from the leaves and twigs of Clausena dunniana var. robusta. The structures of the isolated compounds were determined by a combination of 1D and 2D NMR, MS, and CD spectroscopic data. The NF-κB inhibitory activity was evaluated in HeLa cells. Compound 17 displayed a moderate inhibition against NF-κB activation.     

Chemical constituents of the roots of Eupatorium chinense and their anti-inflammatory activities

In this study, three new compounds (1-3), together with fifteen known ones (4-18) were isolated from a petroleum ether extract of the roots of Eupatorium chinense. The structures of new compounds were elucidated by 1D, 2D nuclear magnetic resonance (NMR), circular dichroism spectrum (CD), mass spectrum (MS) along with other spectroscopy methods. In addition, twelve compounds were evaluated in vitro for their anti-inflammatory activities, while compounds 3 and 5 exhibited moderate activities with inhibition rates of 23.08 % and 25.19 %, respectively.     

Five new quassinoids and cytotoxic constituents from the roots of Eurycoma longifolia

Eurycoma longifolia has been widely used for various traditional medicinal purposes in South-East Asia. In this study, five new quassinoids, eurylactone E (1), eurylactone F (2), eurylactone G (3), eurycomalide D (4), and eurycomalide E (5), along with ten known quassinoids (6–15) were isolated from the roots of E. longifolia. Their structures were determined by extensive spectroscopic methods, including 1D and 2D NMR, and MS spectra data. Among the isolated compounds, 13β-methyl,21-dihydroeurycomanone (6) has been reported as a synthetic derivative. However, it was isolated from the natural product for the first time in this study. The cytotoxic activities of fifteen compounds were evaluated against human lung cancer cell line, A549 and human cervical cancer cell line, HeLa.     

Lactones from the pericarps of Litsea japonica and their anti-inflammatory activities

Five new lactones, litsenolide F₁ (1), lisealactone H₁ (10), lisealactone H₂ (11), akolactone D (13), and akolactone E (14), along with thirteen known compounds were isolated from the pericarps of Litsea japonica (Thunb.) Jussieu. Their chemical structures were elucidated by extensive spectroscopic analyses, including 1D and 2D NMR, HRMS, and chemical methods. The isolated compounds were evaluated for their inhibitory effects on NO production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Among them, 2-alkylidene-3-hydroxy-4-methylbutanolide derivatives (compounds 1–9) exhibited the most potent activity, with IC₅₀ values in the range of 2.9–12.8?μM. In additon, compounds 1, 3, 4, and 6 showed inhibition of iNOS and COX-2 expression in concentration-dependent manner. Compound 3 suppresses mRNA expression of iNOS, COX-2, IL-6, and TNF-α in LPS-stimulated RAW264.7 cells. Based on these evidence, the isolated lactones from L. japonica could be promissing candidates for the development of new anti-inflammatory agents.     

Two new secondary metabolites isolated from Avena sativa L. (Oat) seedlings and their effects on osteoblast differentiation

Seedlings of natural crops are valuable sources of pharmacologically active phytochemicals. In this study, we aimed to identify new active secondary metabolites in Avena sativa L. (oat) seedlings. Two new compounds, avenafuranol (1) and diosgenoside (2), along with eight known compounds (3–10) were isolated from the A. sativa L. seedlings. Their chemical structures were elucidated via 1D and 2D NMR spectroscopy, high-resolution ESIMS, IR spectroscopy, optical rotation analysis, and comparisons with the reported literature. The effect of each isolated compound on alkaline phosphatase (ALP) activity for osteoblast differentiation induced by bone morphogenetic protein-2 (BMP-2) was investigated using the C2C12 immortal mouse myoblast cell line. Compounds 1, 4, 6, 8, and 9 induced dose-dependent increases in ALP expression relative to ALP expression in cells treated with only BMP-2, and no cytotoxicity was observed. These results suggest that A. sativa L. seedlings are a natural source of compounds that may be useful for preventing bone disorders.     

Staphylopeptide A,a new cyclic tetrapeptide from culture broth of Staphylococcus sp.

Re-investigation of the culture broth of the marine bacterium Staphylococcus sp. (no. P-100826-4-6) afforded a new cyclic tetrapeptide namely staphylopeptide A (1), along with five known compounds, cyclo (l-prolyl-l-valine) (2), cyclo (l-prolyl-l-tyrosine), (3), cyclo (l-prolyl-l-alanine) (4), l-phenylalanine (5), and l-tryptophan (6). The structures of the isolated compounds were determined by extensive IR, 1D (¹H and ¹³C) and 2D (¹H-¹H COSY, HSQC, HMBC, and NOESY) NMR and HRFABMS spectral measurements. The antimicrobial activity of the isolated compounds (1–6) was evaluated.     

β-Resorcylic acid derivatives with α-glucosidase inhibitory activity from Lasiodiplodia sp. ZJ-HQ1, an endophytic fungus in the medicinal plant Acanthus ilicifolius

Three new β-resorcylic acid derivatives, compounds 1–3, along with six known analogues (4–9) were isolated from an endophytic fungus Lasiodiplodia sp. ZJ-HQ₁ derived from medicinal plant Acanthus ilicifolius. Their structures were elucidated by 1D and 2D NMR spectroscopic analysis, high resolution mass spectrometric (HREIMS) data, and X-ray crystallography. The absolute configurations of compounds 1 and 2 were determined by the modified Mosher’s method. Compounds 1–7 showed more potent inhibitory effects against α-glucosidase activity than the clinical α-glucosidase inhibitor acarbose.     

Cytotoxic sesquiterpenoids from Dysoxylum parasiticum (Osbeck) Kosterm. stem bark

Two undescribed sesquiterpenoid derivatives, 10β,11-dihydroxy-1β-hydroperoxide-4αH,5αH,7βH-guaiane (1) and 10β-hydroxy-4α,4β-dimethyl-5αH,7αH-eudesm-3-one (2) along with three known of guaiane, aromadendrane, and cadinane sesquiterpenoids (3-5) were isolated from the stem bark of Dysoxylum parasiticum (Osbeck) Kosterm. The chemical structure of the compounds were determined by detailed analysis of spectroscopic data, including MS, IR, 1D, and 2D NMR as well as through comparison with data of known analogues. The isolated compounds were also tested for cytotoxic properties against MCF-7 breast cancer line. Compound 4, was found to exhibit the strongest cytotoxic activity with an IC₅₀ value of 12.17 μM, while the other compounds showed moderate or no activity.     

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.     

Ecdysteroids from the flowers of Aerva javanica

Four new ecdysteroids (1–4), along with three known steroids, β-ecdysone (5), 5-β-2-deoxyintegristerone A (6) and 24-epi-makisterone A (7) (Fig. 1), were isolated from the methanolic extract of the flowers of Aerva javanica by using normal and reverse phase chromatography. The structures of the new compounds (1–4) were determined due to 1D (¹H and ¹³C), 2D NMR (HSQC, HMBC, COSY, NOESY) techniques and high resolution mass spectrometry (HREIMS). The known compounds (5–7) were characterized based on the 1D NMR spectroscopy and mass spectrometry and by comparison with the literature values. All isolates were evaluated for their inhibitory activities against enzymes acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and lipoxygenase (LOX).     

Oleanane glycosides from the roots of Alhagi maurorum

Three new oleanane-type triterpene glycosides (1–3), along with four known compounds (4–7) glycosides, were isolated from the roots of Alhagi maurorum. Their structures were elucidated by 1D and 2D-NMR experiments as well as ESI-MS analysis. The antiproliferative activity of the isolated compounds was evaluated against a small panel of cancer cell lines including human breast cancer (MCF-7), human lung adenocarcinoma (A549), human prostate cancer (PC-3) and human leukemia (U937) cell lines. None of the tested compounds, in a range of concentrations between 1 and 50 μM, caused a significant reduction of the cell number.     

Three new prenylated xanthones from Comastoma pedunculatum and their anti-tobacco mosaic virus activity

Comastomaxanthones A–C (1–3), three new xanthones with a rare 2-oxoprenyl substituent, along with three known ones (4–6) were isolated from the aerial parts of Comastoma pedunculatum. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. In addition, compounds 1–6 were tested for their anti-tobacco mosaic virus activity. The results showed that all isolated compounds exhibited weak anti-TMV activity with IC₅₀ values ranging from 122.7 to 242.9 μM.     

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.     

Evolvosides C–E,flavonol-4-O-triglycosides from Evolvulus alsinoides and their anti-stress activity

Phytochemical investigation of the n-butanol fraction of Evolvulus alsinoides (Linn.) led to the isolation of three new phenolic glycosides, evolvosides C, D and E (1–3) along with six known compounds (4–9). The structures of the compounds were elucidated on the basis of spectroscopic analysis, viz. 1D and 2D NMR experiments, chemical study, and comparison with literature data. Evolvoside C (1) was characterized as kaempferol 4′-O-β-d-glucopyranosyl-(1→2)-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside, whereas evolvosides D and E (2–3) were found to be mono and di-O-methyl derivatives of 1. The new compounds (1–3) represent rare triglycoside derivatives of flavonol at C-4′. The isolated compounds (1–6) were screened for acute stress-induced biochemical changes in male Sprague–Dawley rats at a dose of 40 mg/kg body weight. Compounds 1 and 2 displayed anti-stress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 3 and 6 were also found to be effective in normalizing most of these stress parameters, whereas compounds 4 and 5 were ineffective in normalizing most of these effects.     

Isolation and structural elucidation of two new labdane diterpenoids from the aerial part of Roylea cinerea

Two new labdane diterpenoids, cinereanoid A (1) and cinereanoid B (2), along with five known compounds, calyone (3), pilloin (4), 1-methylindole-3-carboxaldehyde (5), β-sitosterol (6) and stigmasterol (7) were isolated from the aerial parts of Roylea cinerea (Lamiaceae). The new structures were determined by using IR, MS, 1D, 2D NMR spectroscopy. The structure of both new compounds was further confirmed by single crystal X-ray crystallographic analysis. In this study we have also reported single crystal X-ray structure of compound 3 which unambiguously confirmed the relative stereochemistry of tertiary hydroxyl and methyl groups, as it was not established by earlier report. Compounds 4 and 5 were isolated for the first time from this plant. In view of very few reports about this species, this report has increased the phytochemical knowledge about R. cinerea.     

Isoprenylated flavonoids from the roots of Sophora tonkinensis

Two new isoprenylated flavanones, tonkinochromanes J (1) and K (2), and a new isoprenylated dihydrochalcone, tonkinochromane L (3), were isolated from the roots of Sophora tonkinensis along with four known compounds (4-7). Their structures were determined by means of spectroscopic analyses, including HRMS, IR, ¹H and ¹³C NMR and 2D experiments (COSY, HSQC, and HMBC), and comparison with known related compounds.