Two new polyhydroxylated triterpenoids from Salvia urmiensis and their cytotoxic activity

Two new polyhydroxylated triterpenoids were isolated from the acetone extract of the aerial parts of Salvia urmiensis Bunge. Their structures were elucidated by 1D and 2D NMR and HR-ESI-MS analyses as olean-12-ene-1β,3β,11α,22α-tetraol (1) and urs-12-ene-1β,3β,11β,22α-tetraol (2). The effect of these compounds on cell viability of MCF-7 cells was investigated by the MTT assay. Compounds 1 and 2 showed weak cytotoxicity with IC₅₀ values of 110.23 ± 0.12 and 88.35 ± 0.09 μM, respectively.     

Complete 1H and 13C NMR assignments of three new polyhydroxylated sterols from the South China Sea gorgonian Subergorgia suberosa

Three new polyhydroxylated sterols, 3beta,6alpha,11,20beta,24-pentahydroxy- 9,11-seco-5alpha-24-ethylcholest-7,28-diene-9-one (1), 3-(1',2'-ethandiol)-24- methylcholest-8(9),22E-diene-3beta,5alpha,6alpha,7alpha,11alpha-pentaol (2), 24-methylcholest-7,22 E-diene-3beta,5alpha,6beta,25-tetraol (3) together with five known sterols, were isolated from the EtOH/CH2Cl2 extract of the South China Sea gorgonian Subergorgia suberosa. The complete assignments of the 1H and 13C NMR chemical shifts for these new compounds were achieved by means of 1D and 2D NMR techniques, including HSQC, HMBC, 1H--1H COSY, and NOESY spectra.     

Three new naphthoquinone derivatives from Diospyros maritima Blume

Three new naphthoquinone derivatives, 6-(1-ethoxyethyl)plumbagin (16), ethylidene-3,3'-biplumbagin (17), and ethylidene-3,6'-biplumbagin (18), were isolated, in addition to six known naphthoquinones, isozeylanone (10), 3,3'-biplumbagin (11), chitranone (12), methylene-3,3'-biplumbagin (13), 2,3-epoxyplumbagin (14), and 3,8'-biplumbagin (15), from the fruits of Diospyros maritima Blume (Ebenaceae). The structures of the new compounds were established by spectroscopic methods. The eight naphthoquinones 11-18 were examined for ichthyotoxic activity and germination inhibitory activity. The quinones 11, 12, and 14-16 showed strong ichthyotoxic activity and the quinone 14 mild germination inhibitory activity.     

Six new compounds from the heartwood of Diospyros maritima

Six new compounds, diospyrolide (1), diospyrolidone (2), diethyl (2R)-malate (3), 3-(E)-coumaroylbetulin-28-yl ethyl nonanedioate (4), 3-(E)-coumaroylbetulin-28-yl ethyl succinate (5), and 3-(E)-coumaroylbetulin-28-yl ethyl (2R)-2-hydroxysuccinate (6), have been isolated from the heartwood of Diospyros maritima. Compounds 1 and 2 are novel trinorlupanes, and 4, 5 and 6 are lupane derivatives. Their structures were determined using spectral and chemical methods.     

Bufadienolides and a new lignan from the bulbs of Urginea maritima

Thirty three compounds were obtained from the bulbs of Urginea maritima (Liliaceae). The compounds were identified by means of fast atom bombardment mass spectrometry (FAB-MS), nuclear magnetic resonance (1H-NMR), (13C-NMR), nuclear overhauser effects (NOE) and two dimensional (2D) NMR. Ten of them were new natural compounds. Nine were bufadienolides and only one was lignan in these compounds.     

Creation of quaternary stereocentres: synthesis of new polyhydroxylated indolizidines

(6R,7S,8aR)- and (6S,7R,8aR)-8a-tert-butyldimethylsilyloxymethyl-6,7-dihydroxy-indolizidin-3-ones 14 and 15 were synthesized from bicyclic silyloxypyrrole 2 by the selective formation of a quaternary stereogenic centre and a ring-closing metathesis as the main steps. They were converted into new polyhydroxyindolizidines 20 and 21 with high diastereoselectivity.     

Synthesis of polyhydroxylated aza-bicyclic compounds from sugar allyltins

Highly functionalized polyhydroxylated dienoaldehyde, readily obtained from allyltin and d-glucose, served as a convenient precursor for a variety of configurationally different aza-bicyclic polyols. Such derivatives were deprotected and the activity of these free compounds against glycosidases was also tested.     

A new method for fluorination of sterols

Diethylaminosulfurtrifluoride (DAST) is a good fluorinating reagent for sterols. The fluorinating reactions proceed through SN₂ mechanism, while reactions through free carbonium ion are responsible for rearrangements and eliminations.     

Synthesis of polyhydroxylated carbo-bicyclic compounds from sugar allyltins

A highly functionalized polyhydroxylated dienoaldehyde, readily obtained from a d-glucose allyltin, served as a convenient precursor for a variety of configurationally different carbo-bicyclic polyols available in a free (deprotected) form. The activity of the free polyols against glycosidases was also tested.     

Tupisteroide A–C,three new polyhydroxylated steroidal constituents from the roots of Tupistra chinensis

Three new steroidal compounds with polyhydroxy groups, tupisteroide A–C (1–3), were obtained from the roots of Tupistra chinensis, together with one known compound (4) that was isolated from this plant for the first time. The structures of tupisteroide A–C were determined on the basis of one‐ and two‐dimensional NMR spectroscopy, including ¹H–¹H Correlation Spectroscopy, Heteronuclear Multiple Bond Correlation, and Heteronuclear Single Quantum Coherence experiments. The isolated compounds were evaluated for their cytotoxic activities against A549, HepG2, and CaSki cancer cell lines in vitro. Among them, compounds 1, 2, and 4 did not show significant inhibitory activity, but compound 3 showed cytotoxicity against A549 cancer cell lines with IC₅₀ values of 25.0 μM. Copyright © 2012 John Wiley & Sons, Ltd.     

Two new triterpenoids from Gypsophila oldhamiana

Two new triterpenoids (1–2) were isolated and elucidated from the roots of Gypsophila oldhamiana, together with four known triterpenoids (3–6). Their structures were identified to be 3β-hydroxyolean-13(18)-ene-23, 28-dioic acid (1), 3β, 12α-dihydroxy-23-carboxyolean-28, 13β-olide (2), 3β, 16α-dihydroxy-23-oxoolean-13(18)-en-28-oic acid (3), gypsogenin (4), quillaic acid (5) and gypsogenic acid (6) by spectral methods. All compounds were tested for their cytotoxicities against human tumour cell lines (lung cancer H460 and gastric cancer SGC-7901) and for their antiangiogenic effects using a zebra fish model. All compounds showed interesting antiangiogenic activities and the significant cytotoxicities against H460.     

Two new alkaloids from Capparis himalayensis

Two new alkaloids, Capparin A (1) and B (2), along with seven known compounds 6-methoxyindoline-2,3-dione (3), wogonin (4), oroxylin A (5), kaempferol (6), apigenin (7), quercetin (8) and luteolin (9), were isolated from the whole plant of Capparis himalayensis. Their structures have been established on the basis of spectral methods and the structure of 1 was confirmed by X-ray crystallographic analysis.     

Two new diarylheptanoids from Alnus nitida

Two new diarylheptanoids, trivially named nitidone A and nitidone B, have been isolated from Alnus nitida. The structure elucidation of the compounds was based primarily on 2D-NMR spectroscopic techniques and by comparison with literature data.     

Two new sesquiterpenes from Sarcandra glabra

Phytochemical study of the ethanol extract of Sarcandra glabra resulted in the isolation of two new sesquiterpenes, glabranols A (1) and B (2). Their structures were elucidated as 8alpha,9alpha,15-trihydroxylinden-4,7(11)-dien-12,8beta-olide (1) and 1beta,4alpha,7beta,11-tetrahydroxyeudesmane (2), by spectroscopic methods including 1D- and 2D-NMR and FTICR-MS.     

Two new isoflavonoids from Bowdichia virgilioides

Two new isoflavonoids 7,8,4'-trimethoxyisoflavone and 7,8,4'-trimethoxyisoflavanone and calycosin (7,3'-hydroxy-4'-methoxyisoflavone) were isolated from the wood of the leguminous tree Bowdichia virgilioides by usual chromatographic procedures. Besides these compounds the pterocarpane (-)-maackianin, isoliquiritigenin (4,2',4'-trihydroxychalcone), and the hydrobenzylfurane derivative bowdenol were also obtained. The structures of these new compounds were determinated by MS and 1D and 2D NMR spectral analysis.     

Two new C-glycosylflavones from Mimosa pudica

Two new C-glycosylflavones were isolated from the whole plant of Mimosa pudica,and their structures were determined as 6,7,3′,4′-tetrahydroxyl-8-C-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranosyl flavone(1),5,7,3′,4′-tetrahydroxy-8-C[β-D- apiose-(1→4)]-β-D-glycopyranosyl flavone (2).Their structures elucidated by chemical and spectroscopic analysis including IR,MS,1D and 2D NMR spectra.     

Two new alkaloids from Miliusa cuneata

Two new isoquinoline alkaloids, 2,10-dimethoxy-3,11-dihydroxy-5,6-dihydroprotoberberine (1) and 1,9-dihydroxy-2,11 -dimethoxy-4,5-dihydro-7-oxoaporphine (2), together with thirteen known alkaloids, were isolated from the ethanolic extracts of the stem and leaves of Miliusa cuneata (Graib). Their structures were elucidated predominantly by spectral evidence.     

Two new norsesquiterpenes from Ligularia lapathifolia

Two new norsesquiterpenes were isolated from the extracts of the roots and rhizomes of Ligularia lapathifolia (Franch.) Hand.-Mazz. Their structures were identified as 2-acetyl-3a-methyl-5-(2-methyl-but-2-enoyloxy)-3a,4,5,6,7,7a-hexahydro-H-indene-4-carboxylic acid (1) and 2-acetyl-8a-methyl-2-(2-methyl-but-2-enoyloxy)-6-oxo-1,2,3,4,4a,5,6,8a-octahydro-naphthalene-1-carboxylic acid (2), respectively, on the basis of spectral data and for 1 by single-crystal X-ray analysis.     

Two new polyporusterones from Polyorus umbellatus

Two new polyporusterones named as porusterone I and polyprosterone II were isolated from polyourus umbellatus. Their structures have been established on the basis of spectroscopic analysis.     

Two new quinones from Iris bungei

Two new benzoquinone derivatives, bungeiquinone (1) and dihydrobungeiquinone (2), and two known derivatives, 3-hydroxyirisquinone (3) and 3-hydroxydihydroirisquinone (4), were isolated from the roots of Iris bungei. The structures of the new compounds were established on the basis of spectroscopic methods.