scholarly journals Medelamine C, A New ω-Hydroxy Alkylamine Derivative from Endophytic Streptomyces sp. YIM 66142

2014 ◽  
Vol 9 (1) ◽  
pp. 1934578X1400900
Author(s):  
Ju-Cheng Zhang ◽  
Ya-Bin Yang ◽  
Hao Zhou ◽  
Tian-Feng Peng ◽  
Fang-Fang Yang ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Biosynthetic Pathway ◽  
2D Nmr ◽  
Sw480 Cell ◽  
Hydroxyl Group ◽  
Genus Streptomyces ◽  
Streptomyces Sp ◽  
Endophytic Streptomyces ◽  
Common Fatty Acid ◽  
Mcf 7

A new alkylamine derivative and a common fatty acid were isolated from Streptomyces sp. YIM 66142. On the basis of spectral data, including HRMS, NMR and 2D NMR, their structures were determined as medelamine C (1) and isomyristic acid (2). The ω-hydroxyl group in structure 1 is rare in a natural alkylamine. The possible biosynthetic pathway in the genus Streptomyces from isomyristic acid (2) to medelamines is proposed. Compound 1 showed no obvious cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, SW480 cell lines. The ω-hydroxyl and the acetyl at NH in compound 1 decreased its cytotoxicity in comparison with that of medelamine.

scholarly journals Antimicrobial Metabolites from Endophytic Streptomyces sp. YIM61470

2014 ◽  
Vol 9 (9) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Xueqiong Yang ◽  
Yun Liu ◽  
Shuquan Li ◽  
Fangfang Yang ◽  
Lixing Zhao ◽  
...  
Keyword(s):  
Spectral Analysis ◽  
Microbial Activity ◽  
Natural Source ◽  
Genus Streptomyces ◽  
Streptomyces Sp ◽  
Endophytic Streptomyces ◽  
Antimicrobial Metabolites ◽  
First Time

Six compounds were isolated from Streptomyces sp. YIM61470, and their structures elucidated by spectral analysis as ( R)-1- O-(phenylacetyl)glycerol (1), 4′,5-dihydroxy-6-(3,3–dimethylallyl)-7-methoxyflavanone (2), (32 R,33 R,34 S)-32,33,34,35-bacteriohopanetetrol (3), MKN-003C (4), cyclo (L-Pro-L-Gly) (5), and cyclo(L-Pro-L-Tyr) (6). Compound 1, an chiral monoacylglycerol, was isolated from a natural source for the first time. Compound 2 was first found in microorganisms, and compound 3, a bacteriohopanoid, was found first in the genus Streptomyces. Compounds 1-6 showed weak anti-microbial activity.

scholarly journals Novel 1,3-Benzodioxole From Marine-Derived Actinomycete in East Vietnam Sea

2020 ◽  
Vol 15 (5) ◽  
pp. 1934578X2092004
Author(s):  
Dao Phi Thi ◽  
Huong Doan Thi Mai ◽  
Duc Danh Cao ◽  
Quyen Vu Thi ◽  
Mai Anh Nguyen ◽  
...  
Keyword(s):  
2D Nmr ◽  
Culture Broth ◽  
Genus Streptomyces ◽  
Nmr Data ◽  
Actinomycete Strain ◽  
Spectral Data Analysis ◽  
And Staphylococcus Aureus ◽  
16Srrna Gene ◽  
Mcf 7 ◽  
C Nmr

Analysis of an antimicrobial extract from the culture broth of the marine-derived actinomycete Streptomyces sp. G261 led to the isolation of a new 1,3-benzodioxole derivative (1), together with 10 known compounds 2-11. The actinomycete strain G261 was isolated from sediment, collected at Cu Lao Cham, Quang Nam in Vietnam. The taxonomic identification of the strain G261 was achieved by analysis of 16SrRNA gene sequences. On the basis of morphological and phylogenetic evidence, the actinomycete strain G261 was assigned to the genus Streptomyces. The structures of the isolated compounds were established by their spectral data analysis, including mass spectrometry, 1-dimensional nuclear magnetic resonance (1D-NMR), and 2D-NMR. The structure of 1 was confirmed by comparison of the calculated with experimental 13C NMR data. Compound 1 exhibited antimicrobial activity against Enterococcus faecalis and Staphylococcus aureus with minimum inhibitory concentration values of 128 and 256 µg/mL, respectively. Whereas, compound 1 had a weak inhibition when tested against 4 cancer cell lines, KB, LU-1, HepG-2, and MCF-7.

scholarly journals Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173

Biomolecules ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 1187
Author(s):  
Xinqian Shen ◽  
Xiaozheng Wang ◽  
Tingting Huang ◽  
Zixin Deng ◽  
Shuangjun Lin
Keyword(s):  
Antibacterial Activity ◽  
Biosynthetic Pathway ◽  
Biological Activities ◽  
Structural Diversity ◽  
2D Nmr ◽  
Chemical Diversity ◽  
Spectroscopic Techniques ◽  
Amino Group ◽  
Streptomyces Sp ◽  
Resolution Mass

Naphthoquinone-based meroterpenoids are hybrid polyketide-terpenoid natural products with chemical diversity and a broad range of biological activities. Here, we report the isolation of a group of naphthoquinone-containing compounds from Streptomyces sp. B9173, and their structures were elucidated by using a combination of spectroscopic techniques, including 1D, 2D NMR, and high-resolution mass (HRMS) analysis. Seven flaviogeranin congeners or intermediates, three of which were new, have been derived from common naphthoquinone backbone and subsequent oxidation, methylation, prenylation, and amino group incorporation. Both flaviogeranin B1 (1) and B (2) contain an amino group which was incorporated into the C8 of 1,3,6,8-terhydroxynaphthalene (THN). Flaviogeranin D (3) contains an intact C-geranylgeranyl residue attached to the C2 of THN, while the O-geranylgeranyl group of 2 links with the hydroxyl on the C2 site of THN. Four compounds were selected and tested for antibacterial activity and cytotoxicity, with 3 and flaviogeranin C2 (5) displaying potent activity against selected bacteria and cancer cell lines. In light of the structure features of isolated compounds and the biosynthetic genes, a biosynthetic pathway of naphthoquinone-based flaviogeranins has been proposed. These isolated compounds not only extend the structural diversity but also represent new insights into the biosynthesis of naphthoquinone-based meroterpenoids.

scholarly journals Alkaloids from an Endophytic Streptomyces sp. YIM66017

2013 ◽  
Vol 8 (10) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Hao Zhou ◽  
Yabin Yang ◽  
Jucheng Zhang ◽  
Tianfeng Peng ◽  
Lixing Zhao ◽  
...  
Keyword(s):  
Culture Filtrate ◽  
Spectroscopic Analysis ◽  
Crystallographic Analysis ◽  
Natural Source ◽  
Streptomyces Sp ◽  
X Ray ◽  
Alpinia Oxyphylla ◽  
Endophytic Streptomyces ◽  
First Time ◽  
Mcf 7

Three alkaloids, flavensomycinoic acid (1), a linear polyketide, alpiniamide (2), and cyclo (L-Trp-L-Ala) (3), were isolated from the culture filtrate of endophytic Streptomyces sp. YIM66017 from Alpinia oxyphylla. Their structures were elucidated by spectroscopic analysis and the structure of 1 was confirmed by X-ray crystallographic analysis. Compound 1 was isolated from a natural source for the first time, and compound 2 is a new compound. Compound 1 showed cytotoxicity to MCF-7 with an IC 50 value of 17.0 μM.

scholarly journals Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco

Metabolites ◽  
2019 ◽  
Vol 9 (10) ◽  
pp. 223 ◽  
Author(s):  
Abeer H. Elmaidomy ◽  
Rabab Mohammed ◽  
Hossam M. Hassan ◽  
Asmaa I. Owis ◽  
Mostafa E. Rateb ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
2D Nmr ◽  
Hydroxyl Group ◽  
Hydrogen Bond Donor ◽  
Hydrogen Bond Acceptor ◽  
Metabolomic Profiling ◽  
Phytochemical Investigation ◽  
Phenyl Rings ◽  
Ic50 Values ◽  
Mcf 7

Metabolomic profiling of different Premna odorata Blanco (Lamiaceae) organs, bark, wood, young stems, flowers, and fruits dereplicated 20, 20, 10, 20, and 20 compounds, respectively, using LC–HRESIMS. The identified metabolites (1–34) belonged to different chemical classes, including iridoids, flavones, phenyl ethanoids, and lignans. A phytochemical investigation of P. odorata bark afforded one new tetrahydrofurofuran lignan, 4β-hydroxyasarinin 35, along with fourteen known compounds. The structure of the new compound was confirmed using extensive 1D and 2D NMR, and HRESIMS analyses. A cytotoxic investigation of compounds 35–38 against the HL-60, HT-29, and MCF-7 cancer cell lines, using the MTT assay showed that compound 35 had cytotoxic effects against HL-60 and MCF-7 with IC50 values of 2.7 and 4.2 µg/mL, respectively. A pharmacophore map of compounds 35 showed two hydrogen bond acceptor (HBA) aligning the phenoxy oxygen atoms of benzodioxole moieties, two aromatic ring features vectored on the two phenyl rings, one hydrogen bond donor (HBD) feature aligning the central hydroxyl group and thirteen exclusion spheres which limit the boundaries of sterically inaccessible regions of the target’s active site.

scholarly journals A New Cyclopeptide from Endophytic Streptomyces sp. YIM 64018

2013 ◽  
Vol 8 (12) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Xueqiong Yang ◽  
Yabin Yang ◽  
Tianfeng Peng ◽  
Fangfang Yang ◽  
Hao Zhou ◽  
...  
Keyword(s):  
Amino Acid ◽  
2D Nmr ◽  
Planar Structure ◽  
Broth Culture ◽  
Spectroscopic Techniques ◽  
Amino Acid Residues ◽  
Streptomyces Sp ◽  
The Absolute ◽  
Endophytic Streptomyces

One new cyclopeptide, cyclo(L-Phe-L-Ala-L-Phe-Gly), named as vinaceuline (1) and three known cyclodipeptides, cyclo (Phe-Gly), cyclo (Phe-4-hydroxyl-Pro) and cyclo (Phe-Ile) were isolated from broth culture of endophytic Streptomyces YIM 64018 associated with Paraboea sinensis. The planar structure of the new compound was assigned on the basis of 1D and 2D NMR spectroscopic techniques, while the absolute configurations of the amino acid residues were determined by application of the advanced Marfey method. Cyclotetrapeptides are rarely found as Streptomycete metabolites.

Modification of fatty acid profile and biosynthetic pathway in symbiotic corals under eutrophication

2021 ◽  
Vol 771 ◽  
pp. 145336
Author(s):  
Taihun Kim ◽  
Jetty C.Y. Lee ◽  
Do-Hyung Kang ◽  
Nicolas N. Duprey ◽  
Kin Sum Leung ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Fatty Acid Profile ◽  
Biosynthetic Pathway

scholarly journals Bufadienolides from the Skin Secretions of the Neotropical Toad Rhinella alata (Anura: Bufonidae): Antiprotozoal Activity against Trypanosoma cruzi

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4217
Author(s):  
Candelario Rodriguez ◽  
Roberto Ibáñez ◽  
Luis Mojica ◽  
Michelle Ng ◽  
Carmenza Spadafora ◽  
...  
Keyword(s):  
Vero Cells ◽  
Chemical Diversity ◽  
Hydroxyl Group ◽  
Antitrypanosomal Activity ◽  
The Family ◽  
Toad Venom ◽  
Skin Secretions ◽  
Pharmacological Potential ◽  
First Time ◽  
Mcf 7

Toads in the family Bufonidae contain bufadienolides in their venom, which are characterized by their chemical diversity and high pharmacological potential. American trypanosomiasis is a neglected disease that affects an estimated 8 million people in tropical and subtropical countries. In this research, we investigated the chemical composition and antitrypanosomal activity of toad venom from Rhinella alata collected in Panama. Structural determination using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy led to the identification of 10 bufadienolides. Compounds identified include the following: 16β-hydroxy-desacetyl-bufotalin-3-adipoyl-arginine ester (1), bufotalin (2), 16β-hydroxy-desacetyl-bufotalin-3-pimeloyl-arginine ester (3), bufotalin-3-pimeloyl-arginine ester (4), 16β-hydroxy-desacetyl-bufotalin-3-suberoyl-arginine ester (5), bufotalin-3-suberoyl-arginine ester (6), cinobufagin-3-adipoyl-arginine ester (7), cinobufagin-3-pimeloyl-arginine ester (8), cinobufagin-3-suberoyl-arginine ester (9), and cinobufagin (10). Among these, three new natural products, 1, 3, and 5, are described, and compounds 1–10 are reported for the first time in R. alata. The antitrypanosomal activity assessed in this study revealed that the presence of an arginyl-diacid attached to C-3, and a hydroxyl group at C-14 in the structure of bufadienolides that is important for their biological activity. Bufadienolides showed cytotoxic activity against epithelial kidney Vero cells; however, bufagins (2 and 10) displayed low mammalian cytotoxicity. Compounds 2 and 10 showed activity against the cancer cell lines MCF-7, NCI-H460, and SF-268.

scholarly journals Targeted Isolation of Xenicane Diterpenoids from Taiwanese Soft Coral Asterospicularia laurae

Marine Drugs ◽  
2021 ◽  
Vol 19 (3) ◽  
pp. 123
Author(s):  
Yu-Chi Lin ◽  
Yi-Jen Chen ◽  
Shu-Rong Chen ◽  
Wan-Ju Lien ◽  
Hsueh-Wei Chang ◽  
...  
Keyword(s):  
Cytotoxic Effect ◽  
Soft Coral ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Ionization Mass ◽  
Spectroscopic Analyses ◽  
Potential Source ◽  
First Case ◽  
The Family ◽  
Mcf 7

Application of LC-MS/MS-based molecular networking indicated the ethanol extract of octocoral Asterospicularia laurae is a potential source for the discovery of new xenicane derivatives. A natural product investigation of this soft coral resulted in the isolation of four new xenicane diterpenoids, asterolaurins O‒R (1‒4), together with six known compounds, xeniolide-A (5), isoxeniolide-A (6), xeniolide-B (7), 7,8-epoxyxeniolide-B (8), 7,8-oxido-isoxeniolide-A (9), and 9-hydroxyxeniolide-F (10). The structures of isolated compounds were characterized by employing spectroscopic analyses, including 2D-NMR (COSY, HMQC, HMBC, and NOESY) and high-resolution electrospray ionization mass spectrometry (HRESIMS). Asterolaurin O is the first case of brominated tricarbocyclic type floridicin in the family Xeniidae. Concerning bioactivity, the cytotoxic activity of those isolates was evaluated. As a result, compounds 1 and 2 demonstrated a selective cytotoxic effect against the MCF-7 cell line at IC50 of 14.7 and 25.1 μM, respectively.

scholarly journals Chemical Constituents of the Marine Sponge Aaptos aaptos (Schmidt, 1864) and Their Cytotoxic Activity

2021 ◽  
Vol 16 (2) ◽  
pp. 1934578X2199334
Author(s):  
Do Thi Trang ◽  
Bui Huu Tai ◽  
Dan Thuy Hang ◽  
Pham Hai Yen ◽  
Phan Thi Thanh Huong ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Spectral Data ◽  
Absolute Configuration ◽  
Marine Sponge ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Extensive Analysis ◽  
First Time ◽  
Tddft Method ◽  
Mcf 7

Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configuration of 1 was determined from the experimental ECD spectrum and comparison of this with the theoretical ECD calculations using the TDDFT method. Compounds 1 and 2 were isolated from nature for the first time. Compound 3 induced cytotoxic activity against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values of 41.27 ± 2.63, 40.70 ± 2.65, 34.31 ± 3.43, and 36.63 ± 1.40 µM, respectively.

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