Withanolide Compounds from the Flower of Datura metel L.

Three new withanolide compounds named baimantuoluoline A ( 1 ), B ( 2 ), and C ( 3 ) and the two known withanolides withafastuosin E ( 4 ) and withametelin C ( 5 ) were isolated from the fraction exhibiting activity for psoriasis in the flower of Datura metel L. The three new structures were determined as (5α,6α,7α,12β,15β,22R)‐6,7‐epoxy‐5,12,15‐trihydroxy‐1‐oxowitha‐2,24‐dienolide ( 1 ), (5α,6β,15β,22R)‐ 5,6,15,21‐tetrahydroxy‐1‐oxowith‐24‐enolide ( 2 ), and (5α,6β,12β,22R)‐5,6,12,21‐tetrahydroxy‐27‐methoxy‐1‐oxowitha‐2,24‐dienolide ( 3 ) on the basis of extensive spectroscopic data (HR‐ESI‐MS, ¹H‐ and ¹³C‐NMR, ¹H,¹H‐COSY, HSQC, HMBC, and NOESY) (withanolide=22‐hydroxyergostan‐26‐oic acid δ‐lactone).     

Baimantuoluolines D – F,Three New Withanolides from the Flower of Datura metel L.

Three new withanolide compounds, named baimantuoluolines D–F, along with three known withanolides and a lignan were isolated from the flower of Datura metel L., the parts effective against psoriasis. The structures of the new compounds were elucidated as (5α,6β,12β,20R,22R,24R,25S)‐21,24‐epoxy‐5,6,12‐trihydroxy‐27‐methoxy‐1‐oxowith‐2‐enolide ( 1 ), (5α,6β,12β,20R,22R,24R,25S)‐21,24‐epoxy‐5,6,12,27‐tetrahydroxy‐1‐oxowith‐2‐enolide ( 2 ), and (5α,6β,12β,22R)‐5,6,12,21‐tetrahydroxy‐1‐oxowith‐24‐enolide( 3 ) on the basis of physicochemical evidence.     

Eremosides A – C,New Iridoid Glucosides from Eremostachys loasifolia

Eremosides A–C ( 1 – 3 ), three new iridoid glucosides, were isolated from the AcOEt‐soluble fraction of the EtOH extract of the whole plant of Eremostachys loasifolia, along with buddlejoside B ( 4 ), 10‐O‐benzoylcatalpol ( 5 ), and pakiside A ( 6 ) reported for the first time from this species. The structures of these compounds were elucidated by spectroscopic data including 2D‐NMR, FAB‐MS, ESI‐MS, as well as by acid and basic hydrolyses.     

Debilosides A–C: Three New Megastigmane Glucosides from Equisetum debile

Debilosides A–C ( 1 – 3 ), three new megastigmane glucosides, were isolated from the whole plant of Equisetum debile, together with the four known constituents blumenol A, corchoinoside C, sammangaoside A, and (3S,5R,6R,7E,9S)‐9‐[(β‐D ‐glucopyranosyl)oxy]megastigm‐7‐ene‐3,5,6‐triol ( 4 ). Their structures were elucidated on the basis of in‐depth spectroscopic analyses including 2D‐NMR techniques.     

Three New Monoterpene Glucosides from Lamium amplexicaule

Three new monoterpene glucosides, lamiuamplexosides A–C ( 1 – 3 ), along with thirteen known glucosides, were isolated from the whole plant of Lamium amplexicaule L. The structures of 1 – 3 were elucidated on the basis of spectroscopic, chemical, and physicochemical evidence.     

Caragisides A – C,New Isoflavone Glucosides from Caragana conferta with Inhibition of Platelet Aggregation

Caragisides A–C ( 1 – 3 , resp.), three new isoflavone glucosides, were isolated from the BuOH sub‐fraction of the EtOH extract of the whole plant of Caragana conferta, along with ononoside ( 4 ), reported for the first time from this species. The structures of the new compounds were elucidated by spectroscopic techniques including MS and 2D‐NMR spectroscopy. Compounds 1 – 3 showed significant inhibition of platelet aggregation.     

Three New Dimeric Orcinol Glucosides from Curculigo orchioides

Three new phenolic glucosides named orcinosides A, B, and C ( 1, 2 , and 3 , resp.) were isolated in low yields (4.0×10⁻⁶, 11.5×10⁻⁶, 4.5×10⁻⁶%, resp.) from the rhizomes of Curculigo orchioides. Their structures were elucidated by comprehensive spectroscopic analyses including FAB‐MS, HR‐ESI‐MS, IR, and 1D‐ and 2D‐NMR (HSQC, HMBC) data. Compounds 1 – 3 contained two orcinol‐glucoside moieties linked through a CH₂ group.     

Chemical composition and cytotoxicity of the essential oil from different parts of Datura metel L.

The essential oil from different parts of Datura metel L. were extracted using hydrodistillation and GC–MS was used to analyse the essential oil. The main components of flowers were ketone (23.61%) and ethyl palmitate (15.84%). The main components of leaves were ketone (18.84%) and phytol (18.71%). Ketone (39.45%) and phytol (31.32%) were the major components of petioles. Palmitic acid (30.60%) and ethyl linoleate (21.56%) were the major components of seeds. The major ingredient of roots was palmitic acid (52.61%). The main ingredients of the stems were palmitic acid (38.38%) and ethyl linoleate (17.38%). All the different parts of essential oil were screened for cytotoxicity. The roots and stems showed the inhibitory effects against HepG-2 with IC₅₀ levels of 613.88 and 341.12 mg/L. The leaves and roots showed the inhibitory effects against HeLa with IC₅₀ levels of 267.76 and 348.35 mg/L. All the six parts have inhibitory effects against SGC-7901 cell lines.     

Xylocosides A – G,Phenolic Glucosides from the Stems of Xylosma controversum

Seven new phenolic glucosides, xylocosides A–G ( 1 – 7 ), together with 18 known compounds were isolated from the stems of Xylosma controversum Clos . In compounds 3 – 6 , the glucose residue is esterified at C(6) by 2‐hydroxycyclopentanecarboxylic acid. These new structures were established by spectroscopic‐data interpretation and chemical methods.     

Three New Pteridines,Hirudinoidines A – C,from Hirudo nipponica Whitman

Three new pteridines, hirudinoidines A – C ( 1 – 3 , resp.), with novel structural features were isolated from Hirudo nipponica Whitman , and their structures were elucidated on the basis of extensive spectroscopic analyses and by comparison of their spectral data with those of related metabolites. The configuration of 1 was unequivocally confirmed by single‐crystal X‐ray diffraction (Fig. 2).     

Three New Polyyne (=Polyacetylene) Glucosides from the Edible Roots of Codonopsis cordifolioidea

Three new linear C₁₄ polyyne (=polyacetylene) glucosides, cordifolioidynes A–C ( 1 – 3 ), together with two known polyynes, lobetyol ( 4 ) and lobetyolin ( 5 ), and five known phenylpropanoids, i.e., sinapinaldehyde ( 6 ), coniferaldehyde ( 7 ), coniferoside ( 8 ), sachaliside ( 9 ), and isoconiferin ( 10 ), were isolated from the roots of Codonopsis cordifolioidea. The structures of 1 – 3 were established from spectral evidences and by characterization of their hydrolysis products. Acid hydrolysis of 1 afforded the aglycone 1a , while hydrolysis of 2 and 3 gave the cyclization products 2a and 3a , respectively. Compounds 4 – 10 were isolated from this plant for the first time. The antibacterial activity of compounds 1 – 5 were assessed against eight microbial strains by the agar dilution method, none of them exhibited antibacterial effects at concentrations up to 100 μg/ml.     

Splendidins A – C,Three New Clerodane Diterpenoids from Salvia splendens

Three new clerodane diterpenoids, splendidins A–C ( 1 – 3 , resp.), were isolated from Salvia splendens, together with six known ones. Their structures were elucidated by extensive spectroscopic analysis. Splendidin C ( 3 ) was the first diterpenoid glucoside reported from this plant. These compounds were evaluated for their cytotoxic activity; however, none of them were cytotoxic.     

New Pentacyclic Cucurbitane Glucosides from the Fruits of Citrullus colocynthis Schrad.

Colocynthins A–C ( 1 – 3 , resp.), new pentacyclic cucurbitane type triterpene glucosides, have been isolated from the AcOEt‐soluble fraction of the fruits of Citrullus colocynthis, along with three known compounds, β‐sitosterol 3‐O‐β‐D ‐glucopyranoside, elaterinide, and bryoamaride. Their structures were determined on the basis of ¹H‐ and ¹³C‐NMR spectra, DEPT, and COSY, NOESY, HMQC, and HMBC experiments.     

Spleen and thymus metabolomics strategy to explore the immunoregulatory mechanism of total withanolides from the leaves of Datura metel L. on imiquimod-induced psoriatic skin dermatitis in mice

Our previous work demonstrated that total withanolides of Datura metel L. leaves (TWD) exhibited excellent therapeutic effects on psoriasis. However, current knowledge of its mechanisms is incomplete. In this study, integrated spleen and thymus untargeted metabolomics were used to analyze the changes in endogenous metabolites underlying the immunosuppressive activity of TWD on psoriasis animal models induced by imiquimod. The results suggested that TWD treatment markedly attenuated imiquimod-induced psoriasis and showed significant immunosuppressive activity as evidenced by decreased elevation index of spleen and thymus. Meanwhile, TWD significantly reversed the elevation of immunoregulatory factors, including IL-10, IL-17, IL-22 and IL-23. Multivariate trajectory analysis revealed that TWD treatment could restore the psoriasis-disturbed spleen and thymus metabolite profiles towards the normal metabolic status. A total of 25 and 27 metabolites associated with the immunomodulatory effects for which levels changed markedly upon treatment have been identified in spleen and thymus, respectively. These differential metabolites were mainly involved in amino acid metabolism, nucleotide metabolism, fatty acid metabolism and lipid metabolism. Our investigation provided a holistic view of TWD for intervention in psoriasis through immunoregulation and provided further scientific information in vivo about a clinical value of TWD for psoriasis.     

Three New Sesquiterpenoids from Chrysanthemum indicum L.

Phytochemical investigation of the flowers of Chrysanthemum indicum L. led to the isolation of three new sesquiterpenoids, indicumolide A ( 1 ), indicumolide B ( 2 ), and indicumolide C ( 3 ). Their structures were elucidated by various spectroscopic methods.     

Dimorphamides A – C,New Polyphenolic Amides from Atriplex dimorphostagia

Dimorphamides A–C ( 1 – 3 , resp.), three new polyphenolic amides, have been isolated from the BuOH‐soluble fraction of the whole plant of Atriplex dimorphostagia, along with two known compounds, thymidine and N‐[(E)‐feruloyl]tyramine. Their structures have been determined on the basis of spectral studies.     

Evollionines A–C,Three New Alkaloids Isolated from the Fruits of Evodia rutaecarpa

A phytochemical study of the CHCl₃ extract of the dried unripe fruits of Evodia rutaecarpa (Juss. ) Benth. (Rutaceae) resulted in the isolation of three new alkaloids, evollionines A–C ( 1 – 3 , resp.), together with two known compounds, evodianinine and wuzhuyumide I. The structures of the new compounds were elucidated on the basis of detailed spectroscopic evidence and confirmed in the case of compound 1 by single‐crystal X‐ray analysis.     

Three New C19‐Diterpenoid Alkaloids from Aconitum transsectum

Three new C₁₉‐diterpenoid alkaloids, named aconitramines A ( 1 ), B ( 2 ), and C ( 3 ), were isolated from Aconitum transsectum. By UV, IR, 1D‐ and 2D‐NMR, and MS analyses, their structures were elucidated as 18‐methoxyvilmoraconitine, 18‐demethoxydolichotine A, and 18‐demethoxydolichotine B. Compound 1 is the second known C₁₉‐diterpenoid alkaloid with a three‐membered ring formed by C(8), C(9), and C(10).     

Tuberculariols A – C,New Sesquiterpenes from the Mutant Strain M‐741 of Tubercularia sp. TF5

Three new sesquiterpenes, tuberculariols A–C ( 1 – 3 , resp.), were isolated from the mutant strain M‐741 of Tubercularia sp. TF5, an endophytic fungus of Taxus mairei. Their structures were elucidated by spectroscopic analyses including 1D‐ and 2D‐NMR experiments, and HR‐Q‐TOF‐MS. Antitumor and antibacterial properties of these compounds were evaluated.     

Three New Alkaloids,Paxiphyllines C – E,from Daphniphyllum paxianum

Nine Daphniphyllum alkaloids, including three new ones, paxiphyllines C–E ( 1 – 3 , resp.), were isolated from the twigs and the leaves of Daphniphyllum paxianum. Paxiphylline C ( 1 ) represents the first example of Daphniphyllum alkaloids with a carbonyldioxy group. Their structures were elucidated on the basis of spectroscopic data.