Three new diterpenes and two new sesquiterpenoids from the endophytic fungus Trichoderma koningiopsis A729

Three new diterpenes koninginols A-C (1–3) and two new sesquiterpenoids 11-hydroxy-15-drimeneoic acid (4), koninginol D (5), together with twelve known compounds (6–17) were isolated from the endophytic fungus Trichoderma koningiopsis A729 derived from Morinda officinalis. Their structures were fully assigned with the aid of extensive spectroscopic analysis and reported data from the previous literatures. Koninginols A and B were disclosed as intriguing diterpene alkaloids, whereas the koninginol C was disclosed as one of the two examples of harziandione diterpene. All the isolates were evaluated for their antitumor activity, and compounds 1–2, 4–6, 11–13, 16–17 were evaluated for their antibacterial activity, wherein the new compounds 1 and 2 exhibited significant antibacterial activity against Bacillus subtilis with MIC values of 10 and 2 μg/mL, respectively.     

Three new compounds from Artemisia anomala and their antitumor activities

Three new compounds were isolated from Artemisia anomala, and their structures were determined using HR-ESI-MS, IR, UV, and NMR. The antitumor activities of the three compounds were evaluated in the human lung cancer cell line A549 and the human colorectal cancer cell line HCT116. The results showed that compound 2 significantly inhibited cell viability and proliferation and promoted apoptosis of HCT116 and A549 cells, suggesting that compound 2 may be used for colon and lung cancer treatments in clinical practice.     

Two new phenolic compounds from the white flower of Impatiens balsamina

During the course of our continuing search for biologically active compounds from Korean medicinal sources, we investigated the white flower of Impatiens balsamina. From the MeOH extract, two new phenolic compounds (1–2) containing a nitrile group and eleven known phenolic compounds (3–13) were isolated. The chemical structures of new compounds (1–2) were determined through NMR, HRMS, and CD data. We tested the isolated compounds (1–13) for their cytotoxic activities by determining their inhibitory effects on human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15) in vitro using the sulforhodamine B (SRB) assay. We also investigated their neuroprotective activity by determining their effects on nerve growth factor (NGF) secretion in C6 cells, and anti-neuroinflammatory activity by measuring nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated BV-2 cells.     

Two new alkaloid metabolites produced by endophytic fungus Stagonosporopsis oculihominis isolated from Dendrobium huoshanense

Two new alkaloids (1–2), together with six known compounds (3–8), were isolated from cultures of the endophytic fungus Stagonosporopsis oculihominis. Their structures were elucidated through extensive spectroscopic methods including 2D NMR and HRMS analyses. The absolute configurations of 1 was determined by the comparison of experimental and theoretical electronic circular dichroism spectra. The new compounds were investigated for their cytotoxicity against five human cancer cell lines.     

Two new cembranic diterpenoids from the flowers of Nicotiana tabacum L.

Two new cembranoids, together with fifteen known ones, were isolated from the flowers of Nicotiana tabacum L. The structures of the new compounds were established as (1βH,2E,4αOH,6αOH,7E,10αH,11αH,12βOH)-10,11-epoxy-2,7-cembradiene-4,6,12-triol (1) and (1βH,2E,4αOH,6αOH,7E,10βH,11βH,12αOH)-10,11-epoxy-2,7-cembradiene-4,6, 12-triol (2) by using spectroscopic analysis, including HRESIMS, IR, one- and two-dimensional NMR. A plausible biogenetic relationship of the isolated cembranoids was proposed. The antitumor activities of selected compounds against a panel of three human cancer HepG2, A549 and HCT-116 cell lines were evaluated by the MTT assay. Compound 5 exhibited moderate activity against Hep-G2 cell lines with an IC₅₀ value of 14.38 μM.     

Two new triterpene saponins from the roots of Ilex pubescens

Two new triterpene saponins, namely, ilexpublesnin S (1) and T (2), and six known saponins were isolated from the roots of Ilex pubescens. The structures of the new compounds were elucidated through extensive spectroscopic methods (IR, HR-ESI-MS, 1D and 2D NMR). Sugar residues obtained after acid hydrolysis were identified through TLC and HPLC. Compound 1 contains a 24-aldehyde group, which is rare for triterpene saponins from Ilex.     

Four new sesquiterpenes from the rhizomes of Curcuma wenyujin

Four new sesquiterpenes, namely wenyujinols I – L (1 – 4), along with eleven known ones were isolated from the rhizomes of Curcuma wenyujin. The structures of new compounds were elucidated using spectroscopic and spectrometric data analyses. All isolated compounds were evaluated for their inhibitory effects on melanin production and tyrosinase activity in B16F10 cells. Compound 1 exhibited significant inhibition against melanin production.     

Two new sesquiterpene coumarins from the seeds of Ferula sinkiangensis

Two new sesquiterpene coumarins, namely, sinkiangenorin F (1) and 8-O-acetyl sinkiangenorin F (2) were isolated from the seeds of Ferula sinkiangensis. The structures of the new compounds, including the relative stereochemistry and the absolute configuration were elucidated through extensive spectroscopic methods. The two compounds were tested against the K562, HeLa, and AGS human cancer cell lines and showed cytotoxic activities with 50% inhibitory concentration values between 27.1 and 62.7 μM.     

Five new phenolic glycosides from Hedyotis scandens

Five new phenolic glycosides, hedyotosides A–E (1–5), including a new cyanogenic glycoside (1), along with 10 known compounds (6–15) were isolated from the whole plants of Hedyotis scandens. The structures of compounds 1–5 were established by extensive spectroscopic analyses and acid hydrolysis. All the isolated compounds were evaluated for their in vitro antiviral activity against respiratory syncytial virus (RSV) with cytopathic effect (CPE) reduction assay. Compounds 6 and 15 showed anti-RSV effects with IC₅₀ values of 20 and 25 μg/mL, respectively.     

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.     

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.     

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.     

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.     

Two new quinic acid derivatives from the fruits of Chaenomeles speciosa

Two new quinic acid derivatives (1, 2), together containing eighteen (3–20) known compounds, were isolated from the fruits of Chaenomeles speciosa. Spectroscopic methods and previous data retrieved from the literature were used to determine the chemical structures of the compounds. Among the compounds, quinic acid derivatives (3, 4, 6, 7), phenolic acid compounds (8, 10, 11) and catechin derivatives (18, 19, 20) were isolated for the first time from the family Chaenomeles. The chemotaxonomic significance of the compounds was also discussed.     

A new secoiridoid and a new xanthone glycoside from the whole plants of Lomatogonium rotatum

A new secoiridoid (1) and a new xanthone glycoside (2), together with fourteen known compounds (3−16) were isolated from the dried whole plants of Lomatogonium rotatum (L.) Fries ex Nym. The chemical structures were elucidated based on extensive spectroscopic experiments, including 1D and 2D NMR as well as HR-ESI-MS, and comparison with those reported in the literature. All the compounds were evaluated for anti-complementary activity against the alternative pathways. Compounds 12 and 16 exhibited anti-complementary activity.     

Three new cucurbitane triterpenoids from Hemsleya penxianensis and their cytotoxic activities

Two new cucurbitane glycosides, hemslepenside A (1) and 16,25-O-diacetyl-cucurbitacin F-2-O-β-d-glucopyranoside (3), one new cucurbitacin, 16-O-acetyl-cucurbitacin F (2), along with three known cucurbitane compounds, were isolated from the roots of Hemsleya penxianensis. The structures of 1–6 were established on the basis of extensive spectroscopic and chemical methods. The isolated compounds were evaluated for their cytotoxic activities against different three human cancer cell lines, with IC₅₀ values in the low microgram range.     

A new phenylpropanoid ester from the roots of Anthriscus sylvestris and its chemotaxonomic significance

A new phenylpropanoid ester, anthriscusin I (1), along with six known compounds (2–7) were isolated from the Anthriscus sylvestris (L.) Hoffm roots. The new compound structure was elucidated via spectroscopic analyses, while the known compounds were identified via comparison literature. The chemotaxonomic significance of these compounds was discussed.     

Two new flavonoids from Derris laxiflora Benth

Two new compounds, derriscoumaronochromone (1) and cis-3,4′-dihydroxy- 5,7-dimethoxyflavan (2), as well as trans-4'-O-methylcatechin (3) were isolated from Derris laxiflora, The structures of these compounds were determined by analysis of their spectroscopic data.     

Two new compounds from the aerial parts of Elsholtzia densa

Two new compounds, named edensa acid (1), and edensaoside A (2), as well as twenty-nine known compounds (3–31) were isolated from the aerial parts of Elsholtzia densa Benth. The chemical structures of the new compounds were determined by spectrometric data interpretation using NMR, HRESIMS, IR and UV spectroscopy. In addition, all compounds were evaluated for their anti-influenza virus activities against A/WSN/33(H1N1). Among these, compounds 18 and 19 exhibited moderate anti-influenza virus activities with IC₅₀ values of 18.79 μM and 59.87 μM respectively.     

A new phenolic acid from Zanthoxylum nitidum var. tomentosum (Rutaceae) and its chemotaxonomic significance

A new compound, nitomentosin (1), along with sixteen known compounds (2–17), were isolated from Zanthoxylum nitidum var. tomentosum (Rutaceae). The structure of compound 1 including absolute configurations was determined by detailed spectroscopic information (HRESIMS and NMR) and from the electronic circular dichroism (ECD) spectra. From the present investigation, compound 3 is a new natural compound although it has been reported previously as a synthetic substance, and compound 15 is found for the first time in a plant. All these compounds except 2, 5–10 and 12 were isolated from Z. nitidum for the first time. Furthermore, the chemotaxonomic significance of the isolated compounds is discussed.