scholarly journals Cytotoxicity and Antibacterial Potential of Halogenated Chamigrenes from Malaysian Red Alga, Laurencia majuscula

2019 ◽  
Vol 6 (02) ◽  
pp. e36-e40
Author(s):  
Takashi Kamada ◽  
Chin-Soon Phan ◽  
Tatsufumi Okino ◽  
Charles Santhanaraju Vairappan
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Red Alga ◽  
Antibiotic Resistant ◽  
North Borneo ◽  
Bioactive Secondary Metabolites ◽  
Laurencia Majuscula ◽  
Mcf 7 ◽  
Antibacterial Potential ◽  
New Metabolites

AbstractRed algae of the genus Laurencia have been known to produce a wide array of bioactive secondary metabolites. Here, we report the isolation of two new halogenated chamigrenes, lauremantanones A (1) and B (2), along with seven known compounds, dendroidiol (3), (+)-elatol (4), cartilagineol (5), obtusol (6), (+)-laurencenone B (7), 2-chloro-3-hydroxy-α-chamigren-9-one (8), and puertitol A (9), from a population of Laurencia majuscula (Harvey) Lucas from Mantanani Island (North Borneo). The structures of the two new metabolites were determined based on spectroscopic data (IR, 1D and 2D NMR, and MS). Compounds isolated from this alga exhibited potent cytotoxic (HeLa, MCF-7, P-388) and antibacterial (against antibiotic-resistant clinical bacteria) activities. The major metabolite of this population has significant importance in the geographical distribution of this species globally.

New Bioactive Secondary Metabolites from Bornean Red Alga, Laurencia similis (Ceramiales)

2013 ◽  
Vol 8 (3) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Takashi Kamada ◽  
Charles Santhanaraju Vairappan
Keyword(s):  
Antibacterial Activity ◽  
Secondary Metabolites ◽  
Secondary Metabolite ◽  
Red Alga ◽  
Algal Population ◽  
Cytotoxic Effects ◽  
Antibiotic Resistant ◽  
Good Antibacterial Activity ◽  
Bioactive Secondary Metabolites ◽  
Red Algal

A Bornean red algal population of Laurencia simlis Nam et Saito was analyzed for its secondary metabolite composition. Seven compounds were identified: ent -1(10)-aristolen-9β-ol (1), (+)-aristolone (2), axinysone B (3), 9-aristolen-1α-ol (4), 2,3,5,6-tetrabromoindole (5), 1-methyl-2,3,5,6-tetrabromoindole (6), and 1-methyl-2,3,5-tribromoindole (7). Compound 1 was identified as a new optical isomer of 1(10)-aristolen-9β-ol. Compounds 1, 4 and 5 exhibited good antibacterial activity against antibiotic resistant clinical bacteria and cytotoxic effects against selected cancer cell lines.

scholarly journals (22E,24S)-24-Propylcholest-5en-3α-acetate: A New Steroid from the Stembark Aglaia angustifolia (Miq.) (Meliaceae)

Molbank ◽  
10.3390/m1112 ◽  
2020 ◽  
Vol 2020 (1) ◽  
pp. M1112
Author(s):  
Ricson P. Hutagaol ◽  
Desi Harneti ◽  
Ace T. Hidayat ◽  
Nurlelasari Nurlelasari ◽  
Rani Maharani ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Spectroscopic Data ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Spectroscopy Analysis ◽  
Weak Activity ◽  
High Resolution Mass Spectroscopy ◽  
Mass Spectroscopy Analysis ◽  
Resolution Mass ◽  
Mcf 7

A new propylcholesterol-type steroid, namely (22E,24S)-24-propylcholest-5en-3α-acetate (1), has been isolated from the stembark of Aglaia angustifolia (Miq.). The structure of 1 was determined on the basis of spectroscopic data including 1D- and 2D-NMR as well as high resolution mass spectroscopy analysis. Compound 1 showed weak activity against the MCF-7 breast cancer cell line.

Pseurotin A1 and A2, two new 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-diones from the holothurian-derived fungus Aspergillus fumigatus WFZ-25

2011 ◽  
Vol 89 (1) ◽  
pp. 72-76 ◽  
Author(s):  
Fa-Zuo Wang ◽  
De-Hai Li ◽  
Tian-Jiao Zhu ◽  
Min Zhang ◽  
Qian-Qun Gu
Keyword(s):  
Circular Dichroism ◽  
Aspergillus Fumigatus ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
Esi Ms ◽  
Extensive Analysis ◽  
Circular Dichroïsm ◽  
New Metabolites

Two new metabolites containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione core, pseurotin A1 (1) and A2 (2), as well as pseurotin A (3), were isolated from the holothurian-derived fungus Aspergillus fumigatus WFZ-25. These compounds were determined using extensive analysis of their spectroscopic data, including 1D and 2D NMR, HR-ESI-MS, and circular dichroism (CD) experiments.

scholarly journals 3-Hydroxy-8,14-secogammacera-7,14-dien-21-one: A New Onoceranoid Triterpenes from Lansium domesticum Corr. cv kokossan

Molbank ◽  
10.3390/m1157 ◽  
2020 ◽  
Vol 2020 (4) ◽  
pp. M1157
Author(s):  
Zulfikar ◽  
Nurul Putri ◽  
Sofa Fajriah ◽  
Muhammad Yusuf ◽  
Rani Maharani ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Breast Cancer Cell Lines ◽  
Spectroscopy Analysis ◽  
Weak Activity ◽  
Lansium Domesticum ◽  
High Resolution Mass Spectroscopy ◽  
Mass Spectroscopy Analysis ◽  
Resolution Mass ◽  
Mcf 7

A new onoceranoid triterpenes, namely 3-hydroxy-8,14-secogammacera-7,14-dien-21-one (1), has been isolated from the fruit peels of Lansium domesticum Corr. cv kokossan. The structure of 1 was determined on the basis of spectroscopic data including infrared, 1D and 2D-NMR, as well as high resolution mass spectroscopy analysis. Compound 1 showed a weak activity against MCF-7 breast cancer cell lines.

scholarly journals Flavonoids from Twigs of Millettia pubinervis

2014 ◽  
Vol 9 (12) ◽  
pp. 1934578X1400901
Author(s):  
Zhi Na ◽  
Qi-Shi Song ◽  
Hua-Bin Hu
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Spectroscopic Data ◽  
Human Cancer ◽  
Data Interpretation ◽  
2D Nmr ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Phytochemical Investigation ◽  
Mcf 7

A new flavone, 3-methoxy-5-hydroxy-[2”,3”:7,8] furanoflavone, pubinerone (1), was isolated from the twigs of Millettia pubinervis Kurz, together with ten known flavonoids, karanjin (2), kanjone (3), 3,6-dimethoxy-[2”,3”:7,8] furanoflavone (4), pongaglabrone (5), pongapin (6), pongaflavone (7), 3,6-dimethoxy-6”,6”-dimethylchromene-[2”,3”:7,8] flavone (8), pongachromene (9), 3,6-dimethoxy-3′,4′-methylenedioxy-6”,6”-dimethylchromene-[2”,3”:7,8] flavone (10) and demethoxykanugin (11). This is the first phytochemical investigation of this plant. The structure of compound 1 was elucidated on the basis of spectroscopic data interpretation, including 1D and 2D NMR and HREIMS analysis. The cytotoxicity of 1 against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7 and SW480, was evaluated, but it was inactive (IC50>40μM).

Seven New Metabolites from the Marine Red Alga Laurencia majuscula

1993 ◽  
Vol 56 (3) ◽  
pp. 394-401 ◽  
Author(s):  
Anthony D. Wright ◽  
Gabriele M. König ◽  
Rocky de Nys ◽  
Otto Sticher
Keyword(s):  
Red Alga ◽  
Laurencia Majuscula ◽  
New Metabolites

scholarly journals Secondary Metabolites from Indonesian Kigelia africana (Bignoniaceae)

2019 ◽  
Vol 2 (2) ◽  
pp. 114 ◽  
Author(s):  
Purwantiningsih Sugita ◽  
Dina Anggraini ◽  
Gustini Syahbirin ◽  
Dyah Utami Cahayaning Rahayu ◽  
Auliya Ilmiawati
Keyword(s):  
Secondary Metabolites ◽  
Anticancer Activity ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
Resistant Mouse ◽  
Mouse Leukemia ◽  
Mtt Method ◽  
Diphenyl Tetrazolium Bromide ◽  
Methyl Ferulate ◽  
Mcf 7

From the fruit of Kigelia africana three fractions of secondary metabolites were isolated. Fraction 1 (CD-1) was characterized by using UV-Vis, FTIR, 1D and 2D NMR and MS, meanwhile fraction 2 (CD-2) and 3 (B-1) were characterized by LCMS and compared with literature. All these fractions were screened for anticancer activity by using (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) method to calculate IC50 toward Michigan Cancer Foundation-7 MCF-7 breast cancer and menogaril-resistant mouse leukemia P388 cells. Based on spectroscopic data, CD-1 fraction was identified as methyl ferulate (1). On the other hand, the B-1 and CD-2 fraction did not pure, yet. Based on LCMS data that analyzed by chemspider and masslink software, CD-2 fraction was estimated as compound mixture with dominant compounds like viscumside (2), specioside (3), caffeic acid glucoside (4), ferulic acid (5), meanwhile B-1 fraction was estimated as compound mixture with dominant warfarin alcohol (6), p-Coumaroyl glucose (7) and β - Sitosterol (8) compounds. Nevertheless, all isolated fractions did not show anticancer activity towards both the cancer cells since it had different constituent compared with previous results.

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 Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum

Marine Drugs ◽  
2020 ◽  
Vol 19 (1) ◽  
pp. 9
Author(s):  
Ya-Ping Liu ◽  
Sheng-Tao Fang ◽  
Zhen-Zhen Shi ◽  
Bin-Gui Wang ◽  
Xiao-Nian Li ◽  
...  
Keyword(s):  
Deep Sea ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
Penicillium Oxalicum ◽  
Marine Phytoplankton ◽  
Cold Seep ◽  
Phytoplankton Species ◽  
X Ray ◽  
X Ray Crystallography ◽  
Quinazoline Derivatives

Three new phenylhydrazones, penoxahydrazones A–C (compounds 1–3), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occurring phenylhydrazone tautomers. Compounds 4 and 5 are enantiomers that feature quinazoline and cinnamic acid units. Some isolates exhibited inhibition of several marine phytoplankton species and marine-derived bacteria.

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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