Triterpenoids From Kadsura coccinea With Their Anti-inflammatory and Inhibited Proliferation of Rheumatoid Arthritis-Fibroblastoid Synovial Cells Activities

One new 3,4-seco-17,13-friedo-lanostane triterpenoid heilaohuacid A (1), one new 3,4-seco-17,14-friedo-lanostane triterpenoid heilaohuacid B (2), five new 3,4-seco-lanostane triterpenoids heilaohuacids C-D (3–4) and heilaohumethylesters A-C (7–9), one new 3,4-seco-cycloartane triterpenoid heilaohuacid E (5), and one new intact-lanostane triterpenoid heilaohuacid F (6), together with twenty-two known analogues (10–31), were isolated from heilaohu. Their structures were determined using HR-ESI-MS data, 1D and 2D NMR spectra, 13C NMR calculations, and electronic circular dichroism (ECD) calculations. Heilaohuacids A and B (1 and 2) contain a 3,4-seco ring A and unprecedented migration of Me-18 from C-13 to C-17 or C-14 to C-18. This type of lanostane triterpenoid derivatives was rarely reported so far. More importantly, all compounds against inflammatory cytokines IL-6 and TNF-α levels on LPS-induced RAW 264.7 macrophages were evaluated, and compounds 4 and 31 significantly inhibited the release level of IL-6 with IC50 values of 8.15 and 9.86 μM, respectively. Meanwhile, compounds 17, 18, and 31 significantly inhibited proliferation of rheumatoid arthritis-fibroblastoid synovial (RA-FLS) cells in vitro with IC50 values of 7.52, 8.85, and 7.97 μM, respectively.

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Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.14.280 ◽

2018 ◽

Vol 14 ◽

pp. 3011-3017

Author(s):

Akın Sağırlı ◽

Yaşar Dürüst

Keyword(s):

Nmr Spectra ◽

2D Nmr ◽

Synthetic Route ◽

X Ray ◽

H Nmr ◽

2D Nmr Spectra ◽

Tof Ms ◽

C Nmr

The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted-1,2,4-oxadiazol-5-ylpropanes. To the best of our knowledge, the current synthetic route leading to decyanated products will be the first in terms of a decyanation process which allows the transformation of trisubstituted acetonitriles into alkanes by the incorporation of KCN with the association of in situ-formed HCN and most likely through the extrusion of cyanogen which could not be detected or isolated. In addition, the plausible mechanisms were proposed for both transformations. The structures of the title compounds were identified by means of IR, 1H NMR, 13C NMR, 2D NMR spectra, TOF–MS and X-ray measurements.

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A New Bioactive Steroidal Saponin from Leaves of Furcraea gigantea

Zeitschrift für Naturforschung B ◽

10.1515/znb-2006-0916 ◽

2006 ◽

Vol 61 (9) ◽

pp. 1153-1157 ◽

Cited By ~ 2

Author(s):

Bernadete P. da Silva ◽

José P. Parente

Keyword(s):

Nmr Spectra ◽

Capillary Permeability ◽

Structural Identification ◽

2D Nmr ◽

In Vitro Assays ◽

Steroidal Saponin ◽

Spectroscopic Techniques ◽

C Nmr

Abstract A new bidesmosidic furostanol saponin was isolated from leaves of Furcraea gigantea Vent. Its structure was established as 3-[(O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β -D-glucopyranosyl-( 1→3)-O-[O-β -D-glucopyranosyl-(1→3)-β -D-glucopyranosyl-(1→2)-O-β -D-glucopyranosyl- (1→4)-β -D-galactopyranosyl)oxy]-(3β ,5α,15α,22α,25R)-26-(β -D-glucopyranosyloxy)-15,22-dihydroxy- furost-12-one. Its structural identification was performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (DEPT, COSY, HETCOR and COLOC) and chemical conversions. The steroidal saponin showed no haemolytic effects in the in vitro assays and demonstrated inhibition of the capillary permeability activity.

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NMR-spektroskopische Untersuchung des Problems der Valenzisomerie zwischen 1,2-Dithiin und (Z)-But-2-en-1,4-dithion / NMR Spectroscopic Investigation Concerning the Problem of Valence Isomerism between 1,2-Dithiine and (Z)-But-2-ene-1,4-dithione

Zeitschrift für Naturforschung B ◽

10.1515/znb-1988-0519 ◽

1988 ◽

Vol 43 (5) ◽

pp. 605-610 ◽

Cited By ~ 14

Author(s):

Reiner Radeglia ◽

Helmut Poleschner ◽

Werner Schroth

Keyword(s):

Nmr Spectra ◽

Chemical Shifts ◽

2D Nmr ◽

Ring Structure ◽

Coupling Constants ◽

Nmr Parameters ◽

Spectrum Simulation ◽

2D Nmr Spectra ◽

Transoid Conformation ◽

C Nmr

3,6-Diaryl-1,2-dithiines and their precursors, (Z,Z)-1,4-bis(organylthio)-buta-1,3-dienes, are investigated by 1H and 13C NMR spectroscopy. The chemical shifts and coupling constants, which are relevant to the investigated problem, are determined and assigned, respectively, by different techniques (shift increments, spectrum simulation, heteronuclear 2D J-resolved and heteronuclear shift correlated 2D NMR spectra, anomalous off-resonance splittings and selective decoupling experiments). The NMR parameters are discussed in relation to the molecular structure. The 13C shift values prove the ring structure of 1,2-dithiines and exclude existence of the valence isomer (Z)-but-2-ene-1,4-dithione (absence of thiocarbonyl resonances). The vicinal 1H,1H coupling constants of the C4 unit of the investigated compounds verify (1) the (Z,Z) configuration of the organylthio groups in 1,4 position of butadiene, (2) the s-transoid conformation of acyclic butadienes and (3) the forced s-cis structure in the cyclic 1,2-dithiines.

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1H and13C NMR spectroscopic studies of half-esters from monohydrolysis of dialkyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylates

Spectroscopy An International Journal ◽

10.1155/2004/451925 ◽

2004 ◽

Vol 18 (3) ◽

pp. 469-483

Author(s):

Yoshikazu Hiraga ◽

Satomi Niwayama

Keyword(s):

Nmr Spectra ◽

Chemical Shifts ◽

2D Nmr ◽

Spectroscopic Studies ◽

Carboxyl Group ◽

1H And13c Nmr ◽

Nmr Chemical Shifts ◽

2D Nmr Spectra ◽

Spectral Assignment ◽

C Nmr

The structures of the half-esters from the monohydrolysis of (exo,exo)-, (endo,endo)-, and (endo,exo)-dialkyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylates were determined by1H and13C NMR as well as 2D NMR spectra, and the complete spectral assignment has been made. After conversion of one of the carboalkoxy groups to a carboxyl group, different tendencies were observed for the differences in1H and13C NMR chemical shifts between half-esters and the corresponding diesters.

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Steroids with potential anti-inflammatory activity from the roots of Datura metel L.

Canadian Journal of Chemistry ◽

10.1139/cjc-2019-0282 ◽

2020 ◽

Vol 98 (2) ◽

pp. 74-78 ◽

Cited By ~ 1

Author(s):

Yan Liu ◽

Wei Guan ◽

Chun-li Yang ◽

Yu-meng Luo ◽

Yuan Liu ◽

...

Keyword(s):

Nitric Oxide ◽

Nmr Spectra ◽

2D Nmr ◽

Raw 264.7 ◽

Nitric Oxide Production ◽

Raw 264.7 Macrophages ◽

Datura Metel ◽

2D Nmr Spectra ◽

Anti Inflammatory ◽

Different Levels

One new C21-steroid, pregnane A (1), and two new anolides daturafolisides X and Y (2 and 3), together with six known with anolides (4–9), were isolated from the roots of Datura metel L. The structures of these compounds were established by 1D and 2D NMR spectra and mass spectroscopy by comparing our results with the literature values. Compounds 1–9 were evaluated for inhibition against nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages. It was found that the isolated compounds showed the different levels of anti-inflammatory activities with IC50 values ranging from 24.2 to 43.4 μmol/L.

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The 1H and 13C NMR Chemical Shift Assignments for Thirteen Bufadienolides Isolated from the Traditional Chinese Drug Ch'an Su

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20011841 ◽

2001 ◽

Vol 66 (12) ◽

pp. 1841-1848 ◽

Cited By ~ 12

Author(s):

Yoshiaki Kamano ◽

Toshihiko Nogawa ◽

Ayano Yamashita ◽

George R. Pettit

Keyword(s):

Chemical Shift ◽

13C Nmr ◽

Nmr Spectra ◽

2D Nmr ◽

Chinese Drug ◽

Chemical Shift Assignments ◽

1H And 13C Nmr ◽

Nmr Chemical Shift Assignments ◽

2D Nmr Spectra ◽

C Nmr

The 1H and 13C NMR spectra of thirteen natural bufadienolides, which were isolated from the Chinese drug Ch'an Su, were assigned using a combination of 2D NMR spectra that included 1H-1H COSY, NOESY, HMQC, and HMBC techniques.

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A New Meroterpene, A New Benzofuran Derivative and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Acremonium persicinum KUFA 1007 and Their Anticholinesterase Activities

Marine Drugs ◽

10.3390/md17060379 ◽

2019 ◽

Vol 17 (6) ◽

pp. 379 ◽

Cited By ~ 4

Author(s):

Ana J. S. Alves ◽

José A. Pereira ◽

Tida Dethoup ◽

Sara Cravo ◽

Sharad Mistry ◽

...

Keyword(s):

Marine Sponge ◽

Nmr Spectra ◽

2D Nmr ◽

Electronic Circular Dichroism ◽

Benzofuran Derivative ◽

Extensive Analysis ◽

Stereogenic Centers ◽

2D Nmr Spectra ◽

Inhibitory Activities

Previously unreported meroterpene, acremine S (1), and benzopyran derivative, acremine T (2), were isolated, together with lumichrome (3), ergosterol (4) and ergosterol 5,8-endoperoxide, from cultures of the marine sponge-associated fungus Acremonium persicinum KUF1007. The structure of the previously unreported compounds was established based on an extensive analysis of 1D and 2D NMR spectra as well as HRMS data. The absolute configurations of the stereogenic centers of 1 were established, unambiguously, based on NOESY correlations and comparison of calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 1–3 were tested for their in vitro acetylcholinesterase and butyrylcholinesterase inhibitory activities.

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Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an Aquilaria Plant

Molecules ◽

10.3390/molecules27010198 ◽

2021 ◽

Vol 27 (1) ◽

pp. 198

Author(s):

Jing-Zhe Yuan ◽

Yi-Ling Yang ◽

Wei Li ◽

Li Yang ◽

Hao-Fu Dai ◽

...

Keyword(s):

Absolute Configuration ◽

Ethyl Ether ◽

Nmr Spectra ◽

2D Nmr ◽

Raw264.7 Cells ◽

No Production ◽

Ether Extract ◽

Ic50 Value ◽

2D Nmr Spectra

Nine new sesquiterpenoids (1–9) were isolated from ethyl ether extract of agarwood originated from Aquilaria sp., including three novel sesquiterpenoids (1–3) derived from zizaane, together with six zizaane-type sesquiterpenoids (4–9). All structures were unambiguously elucidated based on 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of sesquiterpenoids was determined by comparison of the experimental and computed ECD spectra. In vitro anti-inflammatory assessment showed that compound 9 exhibited inhibition of NO production in LPS-stimulated RAW264.7 cells with an IC50 value of 62.22 ± 1.27 μM.

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Halo-phenolic metabolites and their in vitro antioxidant and cytotoxic activities from the Red Sea alga Avrainvillea amadelpha

Zeitschrift für Naturforschung C ◽

10.1515/znc-2020-0221 ◽

2021 ◽

Vol 76 (5-6) ◽

pp. 213-218

Author(s):

Usama W. Hawas ◽

Lamia T. Abou El-Kassem ◽

Radwan Al-farawati ◽

Fekri M. Shaher

Keyword(s):

2D Nmr ◽

Cytotoxic Activities ◽

Dpph Radical ◽

Srb Assay ◽

Phenolic Metabolites ◽

2D Nmr Spectra ◽

New Compounds ◽

Benzaldehyde Derivatives ◽

Mcf 7

Abstract From the green alga Avrainvillea amadelpha, two new naturally halo-benzaldehyde derivatives were isolated by various chromatographic methods along with 10 known metabolites of bromophenols, sulfonoglycolipid, and steroids. Based on the 1D and 2D NMR spectra as well as on MS data, the structures of the new compounds were identified as 5-bromo-2-(3-bromo-4-hydroxybenzyl)-3,4-dihydroxybenzaldehyde named avrainvilleal (1), and 3-iodo-4-hydroxy-benzaldehyde (2). Using SRB assay, both compounds showed mild and weak cytotoxic activity against HeLa and MCF-7 cancer cell lines, compared to the good activity of their extract (IC50 values 3.1 and 4.3 μg/mL, respectively). However, avrainvilleal (1) displayed an effective scavenged DPPH radical activity with IC50 value 3.5 μM, compared to the antioxidant quercetin with IC50 value 1.5 μM.

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E-Homolupane Derivatives Substituted in Position 17 and 22a. 1H NMR, 13C NMR and IR Spectra

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19950619 ◽

1995 ◽

Vol 60 (4) ◽

pp. 619-635 ◽

Cited By ~ 1

Author(s):

Václav Křeček ◽

Stanislav Hilgard ◽

Miloš Buděšínský ◽

Alois Vystrčil

Keyword(s):

Nmr Spectra ◽

2D Nmr ◽

Coupling Constants ◽

Side Chain ◽

Oxidation Reactions ◽

H Nmr ◽

Complete Assignment ◽

Nmr Techniques ◽

Intramolecular Association ◽

C Nmr

A series of derivatives with various oxygen functionalities in positions 17,22a or 19,20 was prepared from diene I and olefin XVI by addition and oxidation reactions. The structure of the obtained compounds was confirmed by 1H NMR, 13C NMR and IR spectroscopy. The kind of intramolecular association of the 17α-hydroxy group was studied in connection with modification of the side chain and substitution in position 22a. Complete assignment of the hydrogen signals and most of the coupling constants was accomplished using a combination of 1D and 2D NMR techniques. The 1H and 13C NMR spectra are discussed.

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