scholarly journals Anti-Mycoplasma Activity of Bacilotetrins C–E, Cyclic Lipodepsipeptides from the Marine-Derived Bacillus subtilis and Structure Revision of Bacilotetrins A and B

Marine Drugs ◽  
2021 ◽  
Vol 19 (10) ◽  
pp. 528
Author(s):  
Hwa-Sun Lee ◽  
Hee Jae Shin
Keyword(s):  
Amino Acids ◽  
Bacillus Subtilis ◽  
Fatty Acid ◽  
Detailed Analysis ◽  
Hydroxy Fatty Acid ◽  
2D Nmr ◽  
Positive Control ◽  
Etoac Extract ◽  
Inhibitory Activities ◽  
Mic Value

Mycoplasma hyorhinis most commonly causes polyserositis and arthritis in swine and is a common contaminant during the cell culture in the laboratory. In our continuing research for diverse bioactive compounds from Bacillus subtilis 109GGC020, we discovered uncommon cyclic lipotetrapeptides showing inhibitory activities against M. hyorhinis with similar structures to previously reported bacilotetrins A and B. Bacilotetrins C–E (1–3), new cyclic lipodepsipeptides, were isolated from the EtOAc extract obtained from the fermentation of marine-derived Bacillus subtilis isolated from a marine sponge sample collected from the Gageo reef, Republic of Korea. The structures of 1–3, consisting of three leucine residues, one glutamic acid, and a β-hydroxy fatty acid, were elucidated by detailed analysis of 1D, 2D NMR, and HR-ESIMS data. The absolute configurations of the amino acids and β-hydroxy fatty acid were established by advanced Marfey’s method and Mosher’s method, respectively. The localization of L- and D-amino acids within the compounds was determined by retention time comparison of each purchased dipeptide standard to the partial hydrolysate products using LC-MS. Compounds 1–3 exhibited anti-mycoplasma activity, with an MIC value of 31 μg/mL, twofold stronger than that of the positive control, BioMycoX®. Detailed analysis and comparison of the spectroscopic data between bacilotetrins A (4) and B (5) and 1–3 led us to revise the structures of 4 and 5.

scholarly journals Monoterpene Indole Alkaloids from the Twigs of Kopsia arborea

2014 ◽  
Vol 9 (10) ◽  
pp. 1934578X1400901
Author(s):  
Sarot Cheenpracha ◽  
Achara Raksat ◽  
Thunwadee Ritthiwigrom ◽  
Surat Laphookhieo
Keyword(s):  
Antibacterial Activity ◽  
Nmr Spectroscopy ◽  
Indole Alkaloids ◽  
2D Nmr ◽  
Positive Control ◽  
Ache Inhibition ◽  
2D Nmr Spectroscopy ◽  
E Coli ◽  
Inhibitory Activities ◽  
Mic Value

The phytochemistry of Kopsia arborea Blume has received considerable attention, which has resulted in the isolation of a number of new unusual indole alkaloids with intriguing structures. In this study, a new eburnane-type alkaloid, phutdonginin (1), together with eight known alkaloids: 19-OH-(-)-eburnamonine (2), melodinine E (3), kopsinine (4), kopsilongine (5), kopsamine (6), (-)-methylenedioxy-11,12-kopsinaline (7), decarbomethoxykopsiline (8), and vincadifformine (9), were isolated from the twigs of K. arborea. Their structures were characterized extensively by 1D and 2D NMR spectroscopy and HR-ESI-MS. All compounds were submitted to TLC screening for acetylcholinesterase inhibitory activities. Only kopsamine and decarbomethoxykopsiline showed AChE inhibition with MIR values of 12.5 and 6.25 μg, respectively, compared with galanthamine (positive control, 0.004 μg). In addition, compounds 1 and 2 inhibited moderate antibacterial activity against E. coli TISTR 780 with the MIC value of 32 μg/mL.

scholarly journals Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3927
Author(s):  
Jing-Shuai Wu ◽  
Xiao-Hui Shi ◽  
Ya-Hui Zhang ◽  
Chang-Lun Shao ◽  
Xiu-Mei Fu ◽  
...  
Keyword(s):  
Aspergillus Terreus ◽  
Epigenetic Modification ◽  
2D Nmr ◽  
Etoac Extract ◽  
One Dimensional ◽  
X Ray ◽  
Deacetylase Inhibitor ◽  
Ic50 Values ◽  
First Time ◽  
Mic Value

Chemical epigenetic modification on a marine-derived fungus Aspergillus terreus RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-1, which further separated chirally as a pair of new enantiomers, (+)- and (−)-asperfuranone (1), together with two new benzyl pyrones, asperpyranones A (2) and B (3). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-1, (+)-1, (−)-1, and 2 displayed the antifungal activities against Candida albicans with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC50 values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound 2 exhibited antibacterial activity against Pseudomonas aeruginosa with the MIC value of 32 μg/mL.

scholarly journals New Trisulfated Steroids from the Vietnamese Marine Sponge Halichondria vansoesti and Their PSA Expression and Glucose Uptake Inhibitory Activities

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 445 ◽  
Author(s):  
Kseniya M. Tabakmakher ◽  
Tatyana N. Makarieva ◽  
Vladimir A. Denisenko ◽  
Roman S. Popov ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Prostate Cancer ◽  
Glucose Uptake ◽  
Detailed Analysis ◽  
Cancer Cells ◽  
Marine Sponge ◽  
2D Nmr ◽  
Chemical Transformations ◽  
Human Prostate Cancer ◽  
Prostate Cancer Cells ◽  
Inhibitory Activities

Seven new unusual polysulfated steroids—topsentiasterol sulfate G (1), topsentiasterol sulfate I (2), topsentiasterol sulfate H (3), bromotopsentiasterol sulfate D (4), dichlorotopsentiasterol sulfate D (8), bromochlorotopsentiasterol sulfate D (9), and 4β-hydroxyhalistanol sulfate C (10), as well as three previously described—topsentiasterol sulfate D (7), chlorotopsentiasterol sulfate D (5) and iodotopsentiasterol sulfate D (6) have been isolated from the marine sponge Halichondria vansoesti. Structures of these compounds were determined by detailed analysis of 1D- and 2D-NMR and HRESIMS data, as well as chemical transformations. The effects of the compounds on human prostate cancer cells PC-3 and 22Rv1 were investigated.

scholarly journals Charantoside L, A New Cucurbitane-Type Glycoside from Momordica charantia L. with α-Glucosidase Inhibitory Activities

2022 ◽  
Vol 17 (1) ◽  
pp. 1934578X2110689
Author(s):  
Duong Thi Hai Yen ◽  
Pham Hai Yen ◽  
Nguyen Quang Hop ◽  
Nguyen Anh Hung ◽  
Ha Thi Thu Tran ◽  
...  
Keyword(s):  
Ethanol Extract ◽  
2D Nmr ◽  
Positive Control ◽  
Momordica Charantia ◽  
Spectroscopic Methods ◽  
Inhibitory Effects ◽  
Chemical Structures ◽  
Glucosidase Activity ◽  
Inhibitory Activities ◽  
Reported Data

A new cucurbitane-type glycoside (1) and two known compounds (2-3) were isolated from the ethanol extract of the fruits of Momordica charantia L. Their chemical structures were determined as (19 S,23 E)-5 β­,19-epoxy-19-methoxycucurbita-6,23-diene-3 β,25-diol 3 -O-β-D-allopyranoside (1), goyaglycoside d (2), and (19 S,23 E)-5 β,19-epoxy-19-methoxycucurbita-6,23-diene-3 β,25-diol (3) on the basis of the extensive spectroscopic methods, including 1D, 2D NMR, HRESIMS, and in comparison with the reported data. Compounds 1 to 3 were evaluated for α-glucosidase inhibitory effects. Compounds 1 and 2 showed anti α-glucosidase activity with IC50 values of 134.12 ± 11.20 and 163.17 ± 13.71 µM, respectively, compared with the positive control, acarbose, IC50 160.99 ± 14.30 μM. Compounds 2 and 3 were first isolated from plant M. charantia growing in Vietnam.

scholarly journals SECONDARY METABOLITES FROM MICROMONOSPORA SP. (G044)

2017 ◽  
Vol 55 (3) ◽  
pp. 251
Author(s):  
Cao Duc Tuan ◽  
Doan Thi Mai Huong ◽  
Truong Bich Ngan ◽  
Vu Thi Quyen ◽  
Le Thi Hong Minh ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Secondary Metabolites ◽  
Phenylacetic Acid ◽  
Screening Program ◽  
2D Nmr ◽  
Etoac Extract ◽  
Nmr Data ◽  
Clinically Significant ◽  
Mic Value

In the course of our screening program, the EtOAc extract of a Micromonospora sp. (strain G044) from sponge Tethya aurantium of the sea of Côtô - Thanh Lân exhibited antimicrobial activity against Enterococcus faecalis, Bacillus cereus and Candida albicans. In this paper, we reported the isolation and structural elucidation of six secondary metabolites Cyclo-(Pro-Trp) (1), Cyclo-(Pro-Met) (2), Cyclo-(Pro-Val) (4), N-acetyltryptamine (3), uridine (5), and 2-phenylacetic acid (6) from the cultures broth of Micromonospora sp. (strain G044). The structures of 1 – 6 were determined by analyses of MS and 2D NMR data. All compounds were evaluated for their antimicrobial activity against a panel of clinically significant microorganisms. Compound 1 inhibited Escherichia coli with a MIC value of 128 µg/ml.

scholarly journals Evaluation of the Antibacterial, Antioxidant and α-Glucosidase Inhibitory Activities of Withanolides from Physalis gracilis

2018 ◽  
Vol 5 (01) ◽  
pp. e1-e4
Author(s):  
Gerardo Padierna ◽  
Ana Pérez-Castorena ◽  
Mahinda Martínez ◽  
Antonio Nieto-Camacho ◽  
Jesús Morales-Jiménez ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Bacillus Subtilis ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
Chemical Investigation ◽  
Gram Negative Bacteria ◽  
Gram Negative ◽  
Inhibitory Activities

AbstractA chemical investigation of the leaves, flowers, and stems of Physalis gracilis led to the isolation of three withanolides identified as withanolide D (1), 24,25-dihydrowithanolide D (2), and withaphysacarpin (3). The structures of these compounds were determined by analyses of their spectroscopic data, including 1D and 2D NMR. The antibacterial, antioxidant, and α-glucosidase inhibitory activities of compounds 1 and 3 and derivatives 4 and 5 were evaluated. None of the compounds showed antioxidant or glucosidase inhibitory activity. Also, they were inactive against gram-negative bacteria. However, compound 3 was found active against Bacillus subtilis (MIC=65.5 µM) and compound 5 against Staphylococcus aureus (MIC=27.9 µM).

scholarly journals New Alkaloids From a Hawaiian Fungal Strain Aspergillus felis FM324

2021 ◽  
Vol 9 ◽  
Author(s):  
Cong Wang ◽  
Ariel M. Sarotti ◽  
KH Ahammad Uz Zaman ◽  
Xiaohua Wu ◽  
Shugeng Cao
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Bacillus Subtilis ◽  
Fungal Strain ◽  
Inhibitory Activities ◽  
Physicochemical Data ◽  
New Compounds ◽  
First Time ◽  
Weak Antibacterial Activity ◽  
Mic Value

Two new alkaloids tryptoquivaline Y (1) and pseurotin I (2), together with eight known compounds (3–10), were purified from a fungal strain Aspergillus felis FM324, which was isolated from a Hawaiian beach soil sample. The absolute configuration and physicochemical data of tryptoquivaline Z (3) were reported for the first time here in this paper. Compound 1 is an uncommon tryptoquivaline analog containing a 3-O-isobutanoyl group. The structures of the new compounds 1–2 and known compound 3 were elucidated through HRESIMS, NMR spectroscopy and ECD analysis. All the compounds were evaluated for their antiproliferative, antibacterial and NF-κB inhibitory activities. Compound 4 showed weak antibacterial activity against Staphylococcus aureus, methicillin resistant Staphylococcus aureus and Bacillus subtilis with the same MIC value of 59.2 µM. Compounds 3 and 2 inhibited NF-κB with IC50 values of 26.7 and 30.9 μM, respectively.

scholarly journals Effect of Starter Culture on the Fatty Acid and Amino Acid Profile of Fermented Parkia biglobosa Seeds

2020 ◽  
Vol 9 ◽  
pp. 15-22
Author(s):  
Ayowole Victor Atere ◽  
Victor O. Oyetayo ◽  
Felix A. Akinyosoye
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Bacillus Subtilis ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Fatty Acid Profile ◽  
Bacterial Load ◽  
Starter Culture ◽  
Amino Acid Profile ◽  
Parkia Biglobosa

Iru , a condiment used for seasoning soup is often obtained from the fermentation of Parkiabiglobosa seeds. The present study therefore investigates the effect of different starter culture on the amino and fatty acid profile of Parkiabiglobosa seed fermented to produce iru. Starter culture of Lactobacillus plantarum, Bacillus subtilis and Leuconostoc sp were used to ferment Parkiabiglobosa seeds. The bacterial load increased from 0.00 log10cfu/g in boiled raw sample to 8.67 log10cfu/g in naturally fermented sample. Fermentation significantly (P<0.05) increased the quantity of the amino acids in fermented samples. Aspartic acid (25.85 g/100g) and linoleic acid (42.99 %) were the highest amino and fatty acids respectively in the fermented samples. The result from this study reveals that fermentation significantly increase the amino and fatty acid profile of Parkiabiglobosa fermented to produce iru, a Nigerian condiment.

scholarly journals Scalarane Sesterterpenoids with Antibacterial and Anti-Proliferative Activities from the Mushroom Neonothopanus nambi

Molecules ◽  
2021 ◽  
Vol 26 (24) ◽  
pp. 7667
Author(s):  
Awat Wisetsai ◽  
Ratsami Lekphrom ◽  
Sureeporn Bua-art ◽  
Thanapat Suebrasri ◽  
Sophon Boonlue ◽  
...  
Keyword(s):  
Bacillus Subtilis ◽  
Cell Line ◽  
Spectroscopic Data ◽  
Optical Rotation ◽  
Vero Cells ◽  
2D Nmr ◽  
Bacterial Strains ◽  
Ic50 Values ◽  
Hct 116 ◽  
Mic Value

Seven undescribed scalarane sesterterpenoids, nambiscalaranes B–H (1–7), together with two known compounds, nambiscalarane (8) and aurisin A (9) were isolated from the cultured mycelium of the luminescent mushroom Neonothopanus nambi. Their structures were elucidated by thorough analysis of their 1D and 2D NMR spectroscopic data. The absolute configurations of 1–8 were determined by electronic circular dichroism (ECD) calculations and optical rotation measurements. The isolated sesterterpenoids were evaluated against A549, HT29, HeLa, and HCT-116 cancer cell lines, and against five bacterial strains. Compounds 3, 5, and 7 showed strong cytotoxicity against HCT-116 cell line, with IC50 values ranging from 13.41 to 16.53 µM, and showed no cytotoxicity towards Vero cells. Moreover, compound 8 inhibited the growth of Bacillus subtilis with a MIC value of 8 µg/mL, which was equivalent to the MIC value of the standard kanamycin.

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