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 of the medicinal plant Indigofera spicata Forsk (Fabaceae) and their chemophenetic significance

The chemical investigation of the whole plant of Indigofera spicata Forsk (Fabaceae), a medicinal plant from Cameroon, resulted in the isolation of a new benzofuran, named spibenzofuran (1a), together with ten known secondary metabolites including one benzofuran (2), one flavonoid (3), one saponin (6), two triterpenes (4 and 5), two steroids (8 and 11), one phthalate (7) and two fatty acids (9 and 10). All these compounds have been isolated for the first time from this plant. The structures of the isolated compounds were established by spectroscopic analysis including HR-ESI-MS, 1D and 2D NMR and by comparison of our data with the reported data. The isolated compounds might be considered as the chemophenetic markers of this species, and antibacterial and urease inhibitory activities of some isolated compounds were assessed.     

Natural products from the medicinal plant Duguetia staudtii (Annonaceae)

The phytochemical investigation of the ethyl acetate soluble fraction of Duguetia staudtii stem bark led to the isolation of eight compounds consisting into a new bisnorlignan named pachypolignan (1), a known bisnorlignan (2), four flavonoids (3–6), one alkaloid (7), and one triterpenoid (8). The structures of all the compounds were established with help of spectral data including IR, UV, MS, 1D- and 2D-NMR spectroscopic data, as well as by comparison with previously-reported data in literature. The anti-inflammatory and urease inhibitory activities of the isolated compounds were assessed. Furthermore, the chemotaxonomic significance of these compounds was discussed.     

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.     

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 Dictamnus dasycarpus Turcz.

Fifteen compounds (1–15) were isolated from Dictamnus dasycarpus Turcz. The structures of all compounds were elucidated on the basis of spectroscopic data. Their structures were identified as dictamnine (1), skimmianine (2), haplopine (3), γ-fagarine (4), dasycarine (5), glycolone (6), 8,9-dimethoxygeibalansine (7), 7,8-dimethoxymyrtopsine (8), 8-methoxyflindersine (9), 3-formylindole (10), kihadanin A (11), fraxinellone (12), β-sitosterol (13), radicol (14), and magnolol (15). Among them, compounds 10 and 15 were isolated for the first time in the genus Dictamnus and this is the first report of the presence of compound 14 in the Dictamni dasycarpus Turcz.     

Neoflavonoids as potential osteogenic agents from Dalbergia sissoo heartwood

The present study was undertaken to investigate and rationalize the in vitro antiosteoporotic activity of neoflavonoids, isolated from Dalbergia sissoo heartwood. Neoflavonoids were isolated using extensive column chromatography and identified as dalsissooal (1) a new compound and cearoin (2), dalbergin (3), 4-methoxy dalbergion (4), dalbergiphenol (5), dalbergichromene (6), methyl dalbergin (7) and latinone (8) as known compounds by comparison their spectroscopic data with those reported in the literature. Among the screened compounds, compounds 1, 3, 5–8 significantly increased proliferation as assessed by alkaline phosphatase activity and mineralization in calvarial osteoblast cells.     

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.     

Chemical constituents from Cistanche sinensis (Orobanchaceae)

Phytochemical investigation of 70% aqueous EtOH extract of Cistanche sinensis led to the isolation of fifteen compounds (1–15), including nine phenylethanoid glycosides (PhGs, 1–9), five iridoid glycosides (10–14), and one lignan glycoside (15). Their structures were determined on the basis of 1D- and 2D-NMR experiments and by comparison with physical data of known compounds. Among the isolated compounds, 1 was identified as a new compound, three compounds (9, 14, and 15) were firstly reported from the genus Cistanche, and seven compounds (2–6, 11, and 12) were isolated from C. sinensis for the first time. PhGs with a 6′-O-rhamnosyl moiety such as cistansinenside B (1), poliumoside (7), and 2′-O-acetylpoliumoside (9) could serve as chemotaxonomic markers to differentiate C. sinensis from other species of Cistanche.     

Inhibitory constituents of the heartwood of Dalbergia odorifera on nitric oxide production in RAW 264.7 macrophages

Two new isoflavanones (1 and 13), along with 25 known compounds (2–12, 14–27), were isolated from the EtOAc-soluble fraction of the heartwood of Dalbergia odorifera by following their potential to inhibit the LPS-induced nitric oxide production in RAW 264.7 cells. The structures of the isolated compounds were established by spectroscopic data such as ¹D, ²D NMR and MS spectrometry. Among the isolated compounds, (2S)-pinocembrin (26), showed the most potent inhibitory effect with IC₅₀ value of 18.1 μM.     

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.     

A pair of new sesquiterpene isomers containing spiro heterocyclic skeleton from plant-derived fungus Botryosphaeria dothidea

A pair of new sesquiterpene isomers containing a spiro heterocyclic skeleton, dothimes A (1) and B (2), together with six known compounds, quindoline (3), (S)-3-(3-indolyl)lactic acid methyl ester (4), dankasterone B (5), dibutyl phthalate (6), (1S,3R,4R,7S)-3,4-dihydroxy-α-bisabolol (7), and p-hydroxybenzaldehyde (8), were isolated from the plant-derived fungus Botryosphaeria dothidea. The structures of all isolated compounds were determined based on extensive spectroscopic analyses, including 1D/2D nuclear magnetic resonance (NMR), and high resolution electrospray ionization mass spectrometry (HRESIMS) data, as well as by comparison with literature reports. Compounds 1 and 2 exhibited inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production with IC₅₀ values of 63.66 and 58.29 μM, respectively.     

Diterpenoids from the root bark of Jatropha curcas and their cytotoxic activities

Three new diterpenoids, named epi-jatrophol (1), jatrophaldehyde (2) and epi-jatrophaldehyde (3), along with nine known ones (4–12), were isolated from the root bark of Jatropha curcas. The new compounds were identified by spectroscopic data, and their relative configurations were confirmed by X-ray crystallography or chemical methods. The cytotoxic activities of the isolated compounds were evaluated against HEPG2 and LOVO tumor cell lines. Compounds 8, 9 and 10 were found to be cytotoxic toward HEPG2 cells for the first time.     

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.     

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 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.     

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.     

Chemical constituents from leaves of Cinnamomum subavenium

A new eudesmane sesquiterpene glycoside, 1α,6β-dihydroxy-5,10-bis-epi-eudesm-15-carboxaldehyde-6-O-β-d-Glucopyranoside (1), together with eleven known compounds (2–12) were isolated from the leaves of Cinnamomum subavenium Miq. Their structures were elucidated by a combination of spectroscopic data analysis and comparison with literature data. All compounds were isolated from C. subavenium for the first time. The chemotaxonomic significance of the isolated compounds was summarized.     

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.     

Phytochemical investigation on the fruits of Camptotheca acuminata and their chemotaxonomic significance

A phytochemical investigation on the fruits of Camptotheca acuminata led to the isolation of 13 compounds, including five coumarins (1–5), two alkaloids (6 and 7), two triterpenoids (8 and 9), three lactones (10–12) and a sesquiterpene (13). The structures of these compounds were elucidated by extensive spectroscopic methods and comparion with literature data. All compounds were isolated from the Nyssaceae family for the first time. Additionally, it should be noted that this is the first report of coumarins in the C. acuminata. The chemotaxonomic significance of the isolated compounds was summarised.