Diterpenes and kawalactone from the rhizomes of Amomum uliginosum J.Koenig

Seven compounds, including three labdane diterpenes (1, 4, 6), one bisnorlabdane diterpene (2), one steroid (3), one sesquiterpene (5) and one kawalactone (7) were isolated from the rhizomes of Amomum uliginosum J.Koenig. Compounds 1–4, 6 and 7 were firstly isolated from the genus Amomum. This work represented the first phytochemical study on this plant. The chemotaxonomic significance of these compounds was summarized.     

Chemical constituents from the fruits of Solanum incanum L

Phytochemical investigation of the fruits of Solanum incanum L. resulted in the isolation of nine compounds, including three steroidal glycoalkaloids (1-3), two neolignans (4–5), two simple phenolics (6–7), one monoterpene glycoside (8), and one coumarin glucoside (9). The structure elucidation of isolated compounds was determined based on NMR and mass spectral data. Compounds 4 and 9 were isolated for the first time from the genus Solanum and their chemotaxonomic significance was discussed.     

Chemical constituents from Artemisia argyi and their chemotaxonomic significance

Twelve compounds, including one monoterpene (1), two sesquiterpene lactones (2–3), six flavonoids (4–9), one phenolic glycoside (10), one chromone (11) and one phenolic acid (12), were isolated and identified from the leaves of Artemisia argyi. Compounds 1–2, 4 and 6–7 have not been recorded before in this plant. Compounds 3, 9 and 11 were isolated from the genus Artemisia for the first time. This paper is the first report on the presence of compound 10 in species of Asteraceae. In addition, the chemotaxonomic significance of these compounds was summarized.     

Phenolic compounds and triterpenes from the roots of Vaccinium dunalianum Wight and their chemotaxonomic significance

Eight phenolic compounds, including two catechins (1 and 2), two proanthocyanidins (3 and 4), three lignans (5–7), and one phenol (8), were isolated from roots of Vaccinium dunalianum Wight (Ericaceae), together with two triterpenes (9 and 10). All of them were isolated from the title plant for the first time. Their chemical structures were established based on the extensive MS and NMR spectroscopic analysis. Compounds 6–10 acquired initially from the genus Vaccinium, showed some significances in chemotaxonomy.     

Three new arylbenzofurans from Lavandula angustifolia and their bioactivities

Three new arylbenzofurans, 2-(7-methoxy-2-(4-methoxyphenyl)-3-methylbenzofuran-5-yl)ethanol (1), 4-(5-(2-hydroxyethyl)-7-methoxy-3-methylbenzofuran-2-yl)phenol (2), and 2-(6-methoxy-2-(4- methoxyphenyl)-3-methylbenzofuran-5-yl)ethanol (3), together with three known ones (4–6) were isolated from the whole plant of Lavandula angustifolia. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1–3 and 5 were tested for their anti-tobacoo mosaic virus (TMV) activities, and Compounds 1–6 were tested for their cytotoxicity activities. In our assay, Compounds 1–3 showed high anti-TMV activity with inhibition rate of 38.2, 35.2, and 34.0%, which superior to positive control Ningnanmycin. Compounds 1–6 also showed weak inhibitory activities against some tested human tumor cell lines with IC50 values in the range of 2.2–8.2 μM.     

Isoflavones from the leaves of Nicotiana tabacum and their anti-tobacco mosaic virus activities

Three new isoflavones, 4′,8-dihydroxy-6,7-dimethoxyisoflavone (1), 4′,6-dihydroxy-8-methoxycarbonyl-7-methoxyisoflavone (2), 4′,7-dimethoxy-8-hydroxymethyl-6-hydroxyisoflavone (3), together with three known flavones (4–6), were isolated from the leaves of Nicotiana tabacum. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D NMR techniques. Compounds 1–3 were evaluated for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compounds 1–3 (at the concentration of 20 μM) exhibited anti-TMV activities with inhibition rates of 25.2, 22.6, and 27.4%, respectively.     

Chemical constituents from the buds of Lonicera macranthoides in Sichuan,China

The phytochemical investigation of the dried buds of L. macranthoides Hand. -Mazz. Symb. Sin. collected in Sichuan, China resulted in the isolation of three aliphatic glycosides (1–3), a caffeoyl glucoside (4), a secoiridoid glycoside (5), and two caffeoylquinic acid analogs (6 and 7). Among them, compound 1 was novel and identified as n-butyl-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside based on the detailed spectroscopic analyses and chemical studies. Compounds 1–4 were isolated for the first time from Caprifoliaceae family; compounds 5–7 were isolated for the first time from L. macranthoides. The chemotaxonomic significance of these compounds was summarized.     

Chemical constituents from Melodinus cochinchinensis (Lour.) Merr. and their chemotaxonomic significance

A phytochemical investigation on the twigs and leaves of Melodinus cochinchinensis (Lour.) Merr. resulted in the isolation and identification of 22 compounds, including seven sesamin-type lignans (1–7), three pentacyclic triterpenes (8–10), one anthraquinone (11), one flavanone (12), two phenolic compounds (13 and 14), five aspidosperma-type indole alkaloids (15–19), and three eburnan-type indole alkaloids (20–22). The structures of these compounds were elucidated by means of spectroscopic analysis, including HREIMS together with 1D and 2D NMR experiments, and comparison with reported data. Among them, compounds 1/4, 2/5, and 3/6 are three pairs epimers at C-7''. Compounds 1–6, 8 and 11 were firstly isolated from the family Apocynaceae, whereas 17 was isolated from Melodinus species for the first time. Compound 8 was only found in Juglans hopeiensis, while 11 was only found in roots of Rubia cordifolia. Compounds 1–6, 8, 11 and 15–22 could be considered as chemotaxonomic markers for M. cochinchinensis. Furthermore, the chemotaxonomic significance and distribution of these isolates in Melodinus genus are discussed in detail.     

Separation and identification of chemical constituents of Morchella conica isolated from Guizhou Province China

Morchella conica, isolated from Southwest China, was identified based on its microstructure and ITS rDNA sequence. Nine chemical constituents (1–9) were separated from M. conica through fermentation, and their structures were identified according to spectroscopic data and chemical evidence as follows: two unsaturated fatty acid and ester (1–2), three sterols (3–5), one aromatic carboxylic acid (6) and derivatives (7), one base (8), and chlorinated aromatic esters (9). Subsequently, the chemotaxonomic significance of Compounds 2, 7, and 9, which are the first to be reported in Morchella spp., was summarized.     

Phenol derivatives from the cold-seep fungus Aspergillus sydowii 10–31

Two bisabolane-type sesquiterpenoid phenols inclusive of the known (7 S)-flavilane A (1) and the new (7 S)− 4-iodo-flavilane A (2), along with a new tetraphenyl ether, bisviolaceol II (3), were isolated from the cold-seep fungus Aspergillus sydowii 10–31. Their structures were identified through spectroscopic methods, such as MS, IR, and NMR, and the absolute configurations of 1 and 2 were ascertained by comparison of ECD curves. Compounds 1 and 2 represent rarely encountered sulfur-bearing sesquiterpenes in nature, and the iodination in 2 makes it unique in particular. Additionally, 3 is the first tetraphenyl ether derivative from the fungal species A. sydowii. Compounds 1-3 inhibited the growth of several Vibrio bacteria and harmful microalgae.     

Chemical constituents from the leaves of Cinnamomum parthenoxylon (Jack) Meisn. (Lauraceae)

Phytochemical investigation of the ethanolic extract from the leaves of Cinnamomum parthenoxylon (Jack) Meisn. led to the isolation of (3R, 4R, 3′R, 4′R)-6,6′-dimethoxy-3, 4, 3′, 4′-tetrahydro-2H, 2′H-[3, 3′]bichromenyl-4, 4′-diol (1), 4-hydroxybenzaldehyde (2), 1,2,4-trihydroxybenzene (3), kaempferol-3-O-α-l-rhamnoside (4), herbacetin (5), quercetin-3-O-α-l-rhamnoside (6), daucosterol (7), and β-sitosterol (8). The structures were established by extensive analysis of their MS and NMR spectroscopic data and comparison with literature data. In the present research, all of the isolated compounds 1–8 are reported for the first time in the species C. parthenoxylon. Compounds 1–6 were firstly isolated from genus Cinnamomum. Compounds 1, 3, 5 and 6 have not been reported from any species in Lauraceae family. The chemotaxonomic significance of the isolated compounds is discussed.     

Diterpenoids from the South China Sea soft coral Sarcophyton solidum

Chemical investigation of the South China Sea soft coral Sarcophyton solidum has led to the isolation of one new (1) and seven known (2–8) diterpenoids, including three sarsolenanes (1–3), two capnosanes (4 and 5), and three cembranes (6–8). Sarsolilide B (4) was firstly confirmed by single-crystal X-ray diffraction. Compounds 1, 3, 4, and 6–8 were isolated from S. solidum for the first time, and 1, 2, and 4–7 were considered as the chemotaxonomic markers for the species S. solidum.     

Phenolic compounds and ecdysteroids of Diplazium esculentum (Retz.) Sw. (Athyriaceae) from Japan and their chemotaxonomic significance

Four phenolic compounds, (2R)-3-(4′-hydroxyphenyl) lactic acid, trans-cinnamic acid (2), protocatechuic acid (3) and rutin (4), and three ecdysteroids, amarasterone A1 (5), makisterone C (6) and ponastrone A (7) were isolated and identified from the young fronds of Diplazium esculentum (Retz.) Sw. (Athyriaceae). The structures of these compounds were elucidated on the basis of NMR spectral data and comparison with literature values. Compounds 1, 2 and 5–7 were isolated for the first time from title plant. Their structure elucidation and chemotaxonomic significance are explained in detail.     

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.     

Chemical constituents from Euphorbia stracheyi Boiss

The chemical investigation of whole plants Euphorbia stracheyi Boiss. led to the isolation of 14 compounds, including eight diterpenes (1–8), one monoterpene (9), three coumarins (10–12), and two phenols (13–14). Their structures were elucidated by extensive spectroscopic analyses and by comparison with the literature. Compounds 1–6, and 8–12 were firstly isolated from E. stracheyi, while compounds 6, and 9 were isolated from Euphorbia genus for the first time. The chemotaxonomic significance of these isolated compounds is discussed.     

Cytotoxic abietane-type diterpenoids from twigs and leaves of Croton laevigatus

Seven new abietane-type diterpenoids, crotolaevigatones A–G (1–7), one new aromatic compound, hexyl Z-ferulate (8), along with three known diterpenoids (9–11) and one known aromatic ester, hexyl E-ferulate (12), were obtained from the twigs and leaves of Croton laevigatus. The structures of all isolated compounds were established on the basis of extensive NMR and MS spectroscopic analyses. Compounds 2 and 7 exhibited weak anti-proliferative activity against the A549 and MDA-MB-231 cancer cells, while compound 10 selectively showed significant inhibitory activity against the A549 cancer cells.     

Chemical constituents from Bupleurum chinese and their chemotaxonomic significance

A phytochemical investigation of the roots of Bupleurum chinese DC. led to the isolation of eighteen compounds, including three chromones (1–3), seven flavonoids (4–10), one dihydrochalcone (11), two phenylpropanoid glycosides (12–13), one lignan (14), three sterols (15–17) and one stilbenoid (18). Their structures were elucidated on the basis of NMR spectroscopic analysis and comparison with literature data. Compounds 6–7, 11–14 and 18 were firstly reported from the genus Bupleurum and the family Apiaceae. Moreover, the chemotaxonomic value of the isolates was also discussed.     

Phytochemical investigation of Eremostachys moluccelloides Bunge (Lamiaceae)

Phytochemical investigation of the aerial parts of Eremostachys moluccelloides Bunge led to the identification of a new diterpene, 2β,14-dihydroxy −11-formyl- 12-carboxy-13-des-isopropyl-13-hydroxymethyl-abieta-8,11,13- triene- 16(17)- lactone (1), along with the known compounds 12, 18-dicarboxy-14-hydroxy-13-des -isopropyl-13-hydroxymethyl- abieta-8,11,13-triene-16(17)-lactone (2), 5-hydroxy-3′,4′,7-trimethoxyflavone (3), 5-hydroxy-4’,7-dimethoxyflavone (4), luteolin-7-O-β-glucoside (5), verbascoside (6), luteolin 7-O-(6″-O-β-D-apiofuranosyl) -β-D-glucopyranoside (7), chlorogenic acid (8), echinacoside (9), apigenin-7-O-β-D-glucoside (10), p-coumaric acid (11), vanillic acid (12), apigenin-7-O-(6″-E-p-coumaroyl)-β-D-glucopyranoside (13), apigenin-7-O-(3″,6″-E-p-dicoumaroyl)-β-glucoside (14), lamalbide (15), 6β-hydroxy-7-epi-loganin (16), phloyoside II (17) The structures were elucidated on the basis of 1D and 2D NMR spectroscopy, UV, MS and by comparison with compounds previously reported in the literature. Compounds 1–4, 8, 9, 11, 12, 14 have not been reported previously from any species within the genus Eremostachys. Compounds 1–14, 17 were obtained from this species for the first time. The chemotaxonomic significance of the isolated compounds is discussed.     

Stachybotrysams A–E,prenylated isoindolinone derivatives with anti-HIV activity from the fungus Stachybotrys chartarum

Four new farnesylated isoindolinone derivatives, named stachybotrysams A–D (2–5), and one new farnesyl-cyclized analogue, named stachybotrysam E (6), as well as one known congener (1), were isolated from the filamentous fungus Stachybotrys chartarum CGMCC 3.5365. The structures of these compounds were elucidated on the basis of spectroscopic data analysis and by comparison with reported data. Compounds 2–4 exhibited significant HIV-inhibitory activity with IC₅₀ values of 9.3, 1.0, and 9.6 μM, respectively.     

A dihydrochalcone and several homoisoflavonoids from Polygonatum odoratum are activators of adenosine monophosphate-activated protein kinase

Adenosine monophosphate (AMP)-activated protein kinase (AMPK) is a major cellular energy sensor and master regulator of metabolic homeostasis; thus, AMPK plays a central role in studies on diabetes and related metabolic diseases. From the rhizomes of Polygonatum odoratum (Mill.) Druce, six homoisoflavonoids (1–6) and one dihydrochalcone (7) were isolated, and the structures of polygonatones A–D (4–7) were elucidated by various spectroscopic analyses. Compounds 1–7 were evaluated for their effect on AMPK activation. The amount of active phosphorylated AMPK and acetyl-CoA carboxylase in rat liver epithelial IAR-20 cells increased when the cells were incubated with the aforementioned compounds. Specifically, (3R)-5,7-dihydroxyl-6-methyl-8-methoxyl-3-(4′-hydroxylbenzyl)-chroman-4-one (1), (3R)-5,7-dihydroxyl-6,8-dimethyl-3-(4′-hydroxylbenzyl)-chroman-4-one (2), (3R)-5,7-dihydroxyl-6-methyl-3-(4′-hydroxylbenzyl)-chroman-4-one (3), and polygonatone D (7) exhibited significant activation effects.