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

Molecules ◽  
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.

scholarly journals A New Megastigmane Glucoside and Other Constituents from Desmodium gangeticum

2020 ◽  
Vol 2020 ◽  
pp. 1-4
Author(s):  
Hau Viet Dang ◽  
Giang Hoang Do ◽  
Phuong Thi Ngo ◽  
Tien Dat Nguyen ◽  
Ha Minh Le
Keyword(s):  
Nmr Spectra ◽  
Aerial Part ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
Methyl Benzoate ◽  
Raw264.7 Cells ◽  
No Production ◽  
2D Nmr Spectra ◽  
Ic50 Values ◽  
Megastigmane Glucoside

A new megastigmane glycoside, gangeticoside (1), and three known compounds leonuriside A (2), methyl benzoate 2-O-β-D-glucopyranoside (3), and tortoside A (4) were isolated from the aerial part of Desmodium gangeticum. Their structures were determined by 1D and 2D NMR spectra. The isolated compounds were evaluated for their inhibitory effect on NO production in LPS-stimulated RAW264.7 cells. Among them, compounds 1, 2, and 3 exhibited strong effect with the IC50 values of 22.3, 15.6, 7.3 μM, respectively.

scholarly journals Antialactone: A New γ-Lactone from Antiaris Africana, and its Absolute Configuration Determined from TDDFT CD Calculations

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Vouffo Bertin ◽  
Hidayat Hussain ◽  
Simeon F. Kouam ◽  
Etienne Dongo ◽  
Gennaro Pescitelli ◽  
...  
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
Betulinic Acid ◽  
Spectroscopic Data ◽  
Nmr Spectra ◽  
2D Nmr ◽  
Stem Bark ◽  
Cd Spectra ◽  
2D Nmr Spectra ◽  
First Time

Four compounds were isolated from the stem bark of Antiaris africana. One of them, a γ-lactone named antialactone (1a), is reported for the first time as a natural product. The structures were determined by comprehensive analyses of their 1D and 2D NMR spectra and EI MS data. The absolute configuration of antialactone acetate (1b) was established by TDDFT CD calculations and comparison with measured CD spectra. The remaining three known compounds were identified, by comparing their spectroscopic data with those reported in the literature, as lichenxanthone, β-sitosterol, and betulinic acid.

A Neuroinflammation Inhibitor, Hypoxylon xanthone A, from Soil Fungus Hypoxylon sp.

2020 ◽  
Vol 17 (2) ◽  
pp. 116-120
Author(s):  
Ying Xiao ◽  
Bing Xu ◽  
You Kang ◽  
Yuedi Li ◽  
Yong Cui ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
Nmr Spectra ◽  
Soil Fungus ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
No Production ◽  
Dependent Manner ◽  
Solid Culture ◽  
2D Nmr Spectra ◽  
Dose Dependent

: Hypoxylon sp. was used to ferment at 25°C for 45 days. The solid culture of Hypoxylon sp. was extracted with 75% EtOH under ultrasonic for twice. And the dried combined extracts were then suspended in H2O and partitioned with ethyl acetate. EtOAc extracts were subjected to a silica gel column and eluted with petroleum ether - acetone to a.ord seven fractions. Sephadex LH-20 and RPHPLC were used subsequently to yield a novel xanthone metabolite (Hypoxylon xanthone A). Its structure was elucidated based on HR-ESI-MS, 1D-, 2D-NMR spectra, and the comparison of the experimental and calculated ECD spectra. The anti-neuroinflammatory assay of Hypoxylon xanthone A, as manifested by the inhibitory effect on LPS-induced NO production in BV-2 microglial cells, indicated almost the same inhibitory effect as minocycline in a dose-dependent manner within the concentration of 1-50 μM, suggesting that Hypoxylon xanthone A could be a new potential neuroinflammation inhibitor.

scholarly journals 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 ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 379 ◽  
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.

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

2021 ◽  
Vol 9 ◽  
Author(s):  
Yu-pei Yang ◽  
Yu-qing Jian ◽  
Yong-bei Liu ◽  
Muhammad Ismail ◽  
Qing-ling Xie ◽  
...  
Keyword(s):  
Rheumatoid Arthritis ◽  
Nmr Spectra ◽  
2D Nmr ◽  
Raw 264.7 Macrophages ◽  
Tnf Α ◽  
2D Nmr Spectra ◽  
Kadsura Coccinea ◽  
Lanostane Triterpenoid ◽  
C Nmr

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.

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

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.

scholarly journals New Truxinic and Truxillic Acid Sucrose Diesters From the Leaves of Trigonostemon honbaensis

2021 ◽  
Vol 16 (2) ◽  
pp. 1934578X2199914
Author(s):  
Ninh Khac Ban ◽  
Bui Huu Tai ◽  
Vu Kim Thu ◽  
Phan Van Kiem
Keyword(s):  
Nmr Spectra ◽  
Raw264.7 Cells ◽  
No Production ◽  
Inhibitory Effects ◽  
Esi Ms ◽  
Chemical Structures ◽  
Extensive Analysis ◽  
Truxillic Acid

A new δ-truxinic acid sucrose diester and a new ε-truxillic acid sucrose diester (named trigohonbanosides E and F) were isolated from the leaves of Trigonostemon honbaensis. Their chemical structures were determined by extensive analysis of their HR-ESI-MS and NMR spectra. At a concentration of 20 µM, trigohonbanosides E and F exhibited weak inhibitory effects on NO production in LPS-activated RAW264.7 cells with inhibitory percentages of 22.7% ± 1.1% and 18.5% ± 1.4%, respectively.

Differential Analysis of 2D NMR Spectra: New Natural Products from a Pilot-Scale Fungal Extract Library

2007 ◽  
Vol 46 (6) ◽  
pp. 901-904 ◽  
Author(s):  
Frank C. Schroeder ◽  
Donna M. Gibson ◽  
Alice C. L. Churchill ◽  
Punchapat Sojikul ◽  
Eric J. Wursthorn ◽  
...  
Keyword(s):  
Natural Products ◽  
Nmr Spectra ◽  
2D Nmr ◽  
Pilot Scale ◽  
Differential Analysis ◽  
Fungal Extract ◽  
2D Nmr Spectra

scholarly journals New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata

Marine Drugs ◽  
2019 ◽  
Vol 17 (3) ◽  
pp. 167 ◽  
Author(s):  
Pierre-Eric Campos ◽  
Emmanuel Pichon ◽  
Céline Moriou ◽  
Patricia Clerc ◽  
Rozenn Trépos ◽  
...  
Keyword(s):  
Plasmodium Falciparum ◽  
Minimum Inhibitory Concentration ◽  
Marine Sponge ◽  
Nmr Spectra ◽  
Inhibitory Concentration ◽  
Chemical Study ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
2D Nmr Spectra ◽  
Ic50 Values

Chemical study of the CH2Cl2-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6′-bis-(debromo)-gelliusine F (1), 6-bromo-8,1′-dihydro-isoplysin A (2) and 5,6-dibromo-8,1′-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the three known molecules from the same family, tryptamine (5), (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their antimicrobial and their antiplasmodial activities. Regarding antimicrobial activities, the best compounds are (2) and (3), with minimum inhibitory concentration (MIC) of 0.01 and 1 µg/mL, respectively, towards Vibrio natrigens, and (5), with MIC values of 1 µg/mL towards Vibrio carchariae. In addition the known 8-oxo-tryptamine (4) and the mixture of the (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7) showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 values of 8.8 and 8.0 µg/mL, respectively.

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