Chemical constituents from starfish Culcita novaeguineae

Seven polyhydroxylated steroidal glycosides (1–7) and two polyhydroxylated sterols (8, 9) were isolated and identified from the 75% ethanol extract of starfish Culcita novaeguineae which was collected in Xisha Islands of South China Sea. The structures of the isolated compounds were elucidated on the basis of spectroscopic data, physical and chemical evidence, MS spectrum and assisted by comparison with the reported data. To the best of our knowledge, this is the first time to report compounds 1–6, 8 and 9 from genus Culcita. Moreover, compounds 1, 4–6, 8 and 9 were isolated from family Oreasteridae for the first time. And the chemotaxonomic significance of the isolated compounds was discussed.     

Chemical constituents from Valeriana officinalis L. var. Iatifolia Miq. and their chemotaxonomic significance

Twenty-one compounds, including four monoterpenoids (1–4) (two new natural products, 1 and 2), four sesquiterpenes (5–8), two iridoids (9 and 10), four steroids (11–14), five phenolic compounds (15–19), and two alkaloids (20 and 21), were isolated from the roots of Valeriana officinalis L. var. Iatifolia Miq. Their chemical structures were established by spectroscopic methods and further confirmed by comparison with published data in the literature. Among them, eight compounds (1, 2, 6–8, 13, 18, and 21) are being reported from the family Valerianaceae for the first time, and compounds 9–12 were obtained from V. officinalis for the first time. The chemotaxonomic significance of the isolated compounds is discussed.     

Xanthone derivatives from Aspergillus sydowii,an endophytic fungus from the liverwort Scapania ciliata S. Lac and their immunosuppressive activities

Three new xanthone derivatives, including two first reported containing sulfur as natural products: sydoxanthone A (1) and sydoxanthone B (2), and 13-O-acetylsydowinin B (3) were isolated from an endophytic fungus Aspergillus sydowii, occurring in the livewort Scapania ciliata S. Lac, together with seven known biosynthetically related compounds (4–10). Their structures were established primarily by NMR, UV and MS data. In vitro suppression test on the Con A- and LPS-induced proliferations of mouse splenic lymphocytes showed that compounds 7 and 8 displayed moderate immunosuppressive activities.     

α-pyrone derivatives from endophytic fungus Diaporthe sp. RJ-41

A new α-pyrone derivative 1 and six known α-pyrone derivatives 2–7, along with known compounds 8–10 were isolated from the fermentation products of the endophytic fungus Diaporthe sp. RJ-41. Among them, nine compounds (1–9) were reported for the first time from the genus Diaporthe. This work expanded the knowledge of the chemical diversity of the genus Diaporthe, and the chemotaxonomic significance of the isolates was also discussed.     

Chemical constituents isolated from Valeriana officinalis L

Phytochemical investigations on the leaves of Valeriana officinalis L. led to the isolation of 18 compounds, including eight lignans (1–8), three sesquiterpenoids (9–11), five iridoids (12–16), and two aldehydes (17–18) The structure elucidation of isolated compounds was achieved on the basis of NMR and mass spectral data. Among them, three compounds (9–16, 18) are reported from V. officinalis for the first time and one compound (5) was isolated from the genus Valeriana for the first time. In addition, six compounds (2, 4, 6–8, 17) are isolated for the first time from Valerianaceae family. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Melampolides from Argentinean Acanthospermum australe

The investigation of the ethanol extract of Acanthospermum australe, collected in the province of Misiones, Argentina, yielded eight melampolides (1–8) of the acanthospermal type. Two of them, 8β-hydroxy-9α-(2-methylbutyryloxy)-14-oxo-acanthospermolide (3) and 9α-hydroxy-8β-(2-methylbutyryloxy)-14-oxo-acanthospermolide (7) are new compounds. Two other compounds (4 and 8) have been previously reported, and the NMR data of 4 are corrected. Compounds 1, 2, 5 and 6 have not been previously reported, but are probably artifacts formed during extraction. Compounds 3, 6 and 7 showed slight antibiotic activity against Gram-positive bacteria.     

Chemical constituents from Gentianella turkestanorum (Gentianaceae)

Phytochemical investigation of Gentianella turkestanorum (Gentianaceae) afforded nineteen compounds, including six xanthones (1–6), two triterpenoids (7–8), eight flavones (9–16) and three iridoids (17–19). Here, we firstly reported that 1-hydroxy-3,5-dimethoxyxanthone (4), 1, 8-dihydroxy-3-methoxyxanthone (5), apigenin (9), quercetin (10), luteolin-7-O-glucoside (12) and three other compounds (1, 8-dihydroxy-3-methoxyxanthone (5), apigenin-7-O-gluco (1″ → 3‴) glucoside (15) and luteolin-7-O-gluco (1″ → 3‴) glucoside (16)) could be isolated from G. turkestanorum. The occurrence of chemical data and the sequence data might be employed as common constituents of the genera Gentianella, Lomatogonium and Swertia.     

Phytochemical and network-based chemotaxonomic study of Lonicera japonica Thunb

Phytochemical research on the flower buds of Lonicera japonica Thunb. led to the isolation of 15 compounds, including nine terpenoids (1–9), three phenylpropanoid glycosides (10–12), two alkyl glycosides (13–14) and an alkaloid (15). The structures of these compounds were determined by NMR spectroscopy and comparison with data from previous literatures. Among them, eleven compounds (2–5, 8, 10 and 11–15) were reported from the genus Lonicera for the first time and compounds 3, 4, 5, 10 and 11–15 were firstly reported from the family Caprifoliaceae. Network analysis was carried out to explore the chemotaxonomic significance of these compounds for L. japonica in this study.     

Sesquiterpenoids from Saussurea laniceps and their chemotaxonomic significance

Twenty-five sesquiterpenoids including seventeen guaiane-type sesquiterpenoids and glucose glycosides (1–17), six eudesmane-type sesquiterpenoids (18–23), and two germacrane-type sesquiterpenoids (24 and 25) were isolated from the aerial parts of Saussurea laniceps Hand.-Mazz. Their structures were elucidated by spectroscopic methods and comparison with previously reported spectral data. Among them, compounds (6 and 8) are new, and seven compounds (2, 9, 12, 18–19, 22–23) are reported for the first time from the genus Saussurea. This paper deals with the isolation, structural elucidation and chemotaxonomic significance of these sesquiterpenoids from S. laniceps.     

Chemical constituents from Syringa reticulata (Bl.) Hara

A previously undescribed secoiridoid aglycone, syrinretin (1), together with a reported secoiridoid aglycone (2), three phenylethanoids (3, 4 and 6), phenolic acid (5) and two coumarins (7 and 8) were isolated from the stem bark of Syringa reticulata (Bl.) Hara (Oleaceae). The structures were elucidated from 1D and 2D NMR spectroscopic data by comparison with reported literature values. Compound 1 and compounds 2, 4–6 and 8 were identified in the genus Syringa for the first time. The chemotaxonomic significance of these compounds is 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 from the pericarps of Zanthoxylum bungeanum and their chemotaxonomic significance

The phytochemical study of the pericarps of Zanthoxylum bungeanum Maxim under the guidance of bioactivity led to the isolation of 18 compounds, including a new isobutylhydroxyamide (1) and 17 known compounds, i.e. six alkylamides (2–7), five coumarins (8–12), one benzene derivative (13), three flavonoids (14–16), and two sterols (17–18). Their structures were elucidated based on extensive spectroscopic methods (HRESIMS, 1D and 2D NMR experiments) and by comparison with literature data. New compound (1) and known compound (2) are cis-trans isomeric isobutylhydroxyamides. Among them, compounds 9, 10, and 12 were isolated for the first time from Z. bungeanum, compound 11 was firstly recovered from the genus Zanthoxylum, and compound 14 was reported for the first time from the Rutaceae family. The chemotaxonomic significance of isolated compounds from Z. bungeanum is discussed.     

Chemical constituents from Orobanche cernua Loefling

Phytochemical study of Orobanche cernua Loefling afforded 17 compounds, including eleven phenylpropanoid glycosides (1–11), two flavonoids (12, 13), one lignan (14), and three phenolic acids (15–17) were isolated from the fresh whole plant of O. cernua. Their structures were identified by spectroscopic analyses and by comparison of their spectral data with those reported in the literature. This is the first report of isolation of compounds (6, 8, 9, 11, 14–16) from O. cernua and compounds (14, 15) from the family Orobanchaceae, respectively. Compound 14 was obtained from natural source for the first time, the chemotaxonomic significance of these compounds was summarized.     

Chemical constituents with prenyl substitution from the stem and root of Daphne giraldii Nitsche. (Thymelaeaceae)

Phytochemical characterization of the stem and root bark of Daphne giraldii Nitsche. led to the isolation of eight flavones (1–8), six flavans (9–14) and six coumarins (15–20). The structures of these compounds were examined with spectroscopic methods, and also by comparing to previously reported spectroscopic data. Among them, ten compounds (1–3, 9 and 15–20) are reported for the first time for this species, and all compounds with prenyl substitutions have not been identified in other species of genus Daphne, or even in the family Thymelaeaceae. We also describe the chemotaxonomic significance of these compounds.     

Chemical constituents from Schefflera leucantha R.Vig. (Araliaceae)

Processive phytochemistry and pharmacological investigation of Schefflera leucantha R.Vig. (Araliaceae) led to the isolation of fifteen known compounds: a nucleobase (1), six small aromatic molecules (2–7), three phenylpropanoids (8–10), four lignans (11–14) and a fatty acid derivative (15). Spectroscopic methods were used to establish the structure and configuration of isolates, followed by their unambiguous confirmation with literature data. We report for the first time (to the best of our knowledge), the isolation of β-amino-3-methoxy-4-hydroxybenzene-ethanol (4) from a natural source. Furthermore, compounds 1, 5, 9–15 are being reported from Araliaceae family for the first time, whereas compounds 2, 3, 6–8 from the genus Schefflera for the first time. The biological screening results show that compounds 9 and 10 induce a moderate inhibitory effect on aldose reductase, while compounds 3, 5, and 8 display significantly high neuroprotective activities.     

Cytotoxic terpenoids from Nardophyllum bryoides

The investigation of the ethanol extract of fresh aerial parts of the Patagonian shrub Nardophyllum bryoides collected in the province of Chubut, Argentina, yielded eleven terpenoids. These include: three seco-ent-halimane diterpenoids (1–3), two ent-halimanes (4–5) and six pentacyclic oleanane and ursane triterpenoids (6–11). Four of these compounds (2, 6, 8 and 11) are hitherto unknown, while two others (1 and 4) have been previously reported but only as synthetic products. Several of these compounds showed moderate cytotoxicity against a human pancreatic adenocarcinoma cell line while compounds 4 and 5 were active at micromolar concentrations. The main component, seco-chiliolidic acid (1), could be isolated from this extract in large amounts, turning N. bryoides into a sustainable source of this bioactive compound.     

Phytochemical and chemotaxonomic study on Dictamnus angustifolius G. Don ex Sweet (Rutaceae)

A phytochemical investigation of Dictamnus angustifolius led to the isolation of 14 compounds, including six furoquinoline alkaloids (1–6), two sesquiterpenoids (7, 8) and six flavonoids (9–14). The structures of these compounds were identified by spectroscopic methods and a comparison of their data with those reported in the literature. This is the first report of three furoquinoline alkaloids 1–3 and six flavonoids 9–14 from the genus Dictamnus and the first isolation of compounds 4–8 from D. angustifolius. The chemotaxonomic significance of furoquinoline alkaloids and sesquiterpenoids has also been summarized.     

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.     

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.     

Investigation of chemical compounds from Chlamydomonas sp. KSF108 (Chlamydomonadaceae)

Nine compounds (1–9) including one norisoprenoid (1), one polyol-glycoside (2), three sterols (3–5), three phenols (6, 8, and 9), and one fatty acid (7) were isolated from Chlamydomonas sp. KSF108. Their chemical structures were established using NMR spectroscopic techniques and compared with published data. None of the compounds have been previously reported from the genus Chlamydomonas and they may therefore serve as chemotaxonomic markers for Chlamydomonas sp. KSF108 within the genus.