Data on characteristics of simplicia, phytoconstituents, and antioxidant activity of Moringa oleifera leaves ethanol extract.

The article reports data on the chemical and pharmacological characteristics of Moringa oleifera simplicia and ethanol extract consisting of water content, acid-insoluble ash content, microbial contamination, heavy metal contamination, phytochemical analysis, TLC analysis, chemical profiling using LC-MS/MS, and the antioxidant activity. The M. oleifera leaves simplicia meet quality standards, except for ash content that exceeds the specified standards. Qualitative phytochemistry indicates that the ethanol extract of M. oleifera leaves contains flavonoids, tannins, and steroids. In total of 39 phytoconstituents were tentatively identified; the top 10 active compounds with the highest relative abundance percentage (%) are 4-undecylbenzenesulfonic acid (4,83), apigetrin (3,34), quercetin-3ß-D-glucoside (3,28), D-(-)-quinic acid (1,69), corchorifatty acid F (1,52), 4-hydroxybenzaldehyde (1,47), isopropylmalic acid (1,17), 13(S)-HOTrE (1,08), astragalin (0,99), and D-(+)-phenyllactic acid (0,70). The ethanol extract of M. oleifera leaves contained a total phenolic content 7728,02 mg/kg, total flavonoids as quercetin content 1,19%, and antioxidant activity IC50 1422,45 mg/kg.

Stereochemical determination of NMR chemical shifts in marine terpenoids, antheliol and sangiangol B, using DFT calculations.

Stereochemical determination of the flexible trinor-guaiane sesquiterpenoid, antheliol (1a) and the flexible diterpenoid, sangiangol B (2a), isolated from a marine soft coral, Anthelia sp., was supported by quantum chemical calculations of NMR chemical shifts at DFT levels. The relative configuration of antheliol is now revealed, as 1S*, 4S*, 7S*, 10R* as in 1b, whereas sangiangol B (2c) has complete stereochemistry as 1S*, 7R*, 8R*, 10R*, 11R*, 12S*.

Oxy-Polybrominated Diphenyl Ethers from the Indonesian Marine Sponge, Lamellodysidea herbacea: X-ray, SAR, and Computational Studies.

Polybrominated diphenyl ether (PBDE) compounds, derived from marine organisms, originate from symbiosis between marine sponges and cyanobacteria or bacteria. PBDEs have broad biological spectra; therefore, we analyzed structure and activity relationships of PBDEs to determine their potential as anticancer or antibacterial lead structures, through reactions and computational studies. Six known PBDEs (1-6) were isolated from the sponge, Lamellodysdiea herbacea; 13C NMR data for compound 6 are reported for the first time and their assignments are confirmed by their theoretical 13C NMR chemical shifts (RMSE < 4.0 ppm). Methylation and acetylation of 1 (2, 3, 4, 5-tetrabromo-6-(3', 5'-dibromo-2'-hydroxyphenoxy) phenol) at the phenol functional group gave seven molecules (7-13), of which 10, 12, and 13 were new. New crystal structures for 8 and 9 are also reported. Debromination carried out on 1 produced nine compounds (1, 2, 14, 16-18, 20, 23, and 26) of which 18 was new. Debromination product 16 showed a significant IC50 8.65 ± 1.11; 8.11 ± 1.43 µM against human embryonic kidney (HEK293T) cells. Compounds 1 and 16 exhibited antibacterial activity against Gram-positive Staphylococcus aureus and Gram-negative Klebsiella pneumoniae with MID 0.078 µg/disk. The number of four bromine atoms and two phenol functional groups are important for antibacterial activity (S. aureus and K. pneumoniae) and cytotoxicity (HEK293T). The result was supported by analysis of frontier molecular orbitals (FMOs). We also propose possible products of acetylation and debromination using analysis of FMOs and electrostatic charges and we confirm the experimental result.

Sangiangols A and B, Two New Dolabellanes from an Indonesian Marine Soft Coral, Anthelia sp.

A new, rare trinor-dolabellane diterpenoid, sangiangol A (1), and one new dolabellane diterpenoid, sangiangol B (2), together with known cembranes and dolabellanes (3-8), were isolated from the ethyl acetate layer of an extract of an Indonesian marine soft coral, Anthelia sp. Compounds 1-8 exhibited moderate cytotoxicity against an NBT-T2 cell line (0.5-10 µg/mL). The structures of the new compounds were determined by analyzing their spectra and a molecular modelling study. A possible biosynthetic pathway for sangiangols A (1) and B (2) is presented. Cytotoxicity requires two epoxide rings or a chlorine atom, as in 4 (stolonidiol) and 5 (clavinflol B).

Marine Natural Products from Indonesian Waters.

Natural products are primal and have been a driver in the evolution of organic chemistry and ultimately in science. The chemical structures obtained from marine organisms are diverse, reflecting biodiversity of genes, species and ecosystems. Biodiversity is an extraordinary feature of life and provides benefits to humanity while promoting the importance of environment conservation. This review covers the literature on marine natural products (MNPs) discovered in Indonesian waters published from January 1970 to December 2017, and includes 732 original MNPs, 4 structures isolated for the first time but known to be synthetic entities, 34 structural revisions, 9 artifacts, and 4 proposed MNPs. Indonesian MNPs were found in 270 papers from 94 species, 106 genera, 64 families, 32 orders, 14 classes, 10 phyla, and 5 kingdoms. The emphasis is placed on the structures of organic molecules (original and revised), relevant biological activities, structure elucidation, chemical ecology aspects, biosynthesis, and bioorganic studies. Through the synthesis of past and future data, huge and partly undescribed biodiversity of marine tropical invertebrates and their importance for crucial societal benefits should greatly be appreciated.

A New Trinor-guaiane Sesquiterpene from an Indonesian Soft Coral Anthelia sp.

A new trinor-guaiane sesquiterpene has been isolated from an Indonesian soft coral Anthelia sp. The planar structure, possessing an octahydroazulene skeleton, and relative stereochemistry were established by analyzing 1D and 2D NMR data, including NOE experiments. Its absolute stereochemistry was elucidated to be 1S, 4S, 7R, and 10R by comparing observed and calculated optical rotation values. The new compound showed weak cytotoxicity against NBT-T2 cells.

Sea foam as a source of fungal inoculum for the isolation of biologically active natural products.

Due to a rate increase in the resistance of microbial pathogens to currently used antibiotics, there is a need in society for the discovery of novel antimicrobials. Historically, fungi are a proven source for antimicrobial compounds. The main goals of this study were to investigate the fungal diversity associated with sea foam collected around the coast of Prince Edward Island and the utility of this resource for the production of antimicrobial natural products. Obtained isolates were identified using ITS and nLSU rDNA sequences, fermented on four media, extracted and fractions enriched in secondary metabolites were screened for antimicrobial activity. The majority of the isolates obtained were ascomycetes, consisting of four recognized marine taxa along with other ubiquitous genera and many 'unknown' isolates that could not be identified to the species level using rDNA gene sequences. Secondary metabolite isolation efforts lead to the purification of the metabolites epolones A and B, pycnidione and coniothyrione from a strain of Neosetophoma samarorum; brefeldin A, leptosin J and the metabolite TMC-264 from an unknown fungus (probably representative of an Edenia sp.); and 1-hydroxy-6-methyl-8-hydroxymethylxanthone, chrysophanol and chrysophanol bianthrone from a Phaeospheria spartinae isolate. The biological activity of each of these metabolites was assessed against a panel of microbial pathogens as well as several cell lines.

Four new polyoxygenated gorgosterols from the gorgonian Isis hippuris.

Four new polyoxygenated steroids (1-4) together with four known ones (5-8) have been isolated from the gorgonian Isis hippuris. The structures of the new compounds have been elucidated by spectroscopic analysis and chemical conversion. All of the new steroids showed moderate cytotoxicity against cultured NBT-T2 cells.

Symbiopolyol, a VCAM-1 inhibitor from a symbiotic dinoflagellate of the jellyfish Mastigias papua.

A super-carbon-chain compound, symbiopolyol (1a), was isolated from a symbiotic dinoflagellate of the jellyfish Mastigias papua. Although a direct comparison between symbiopolyol (1a) and lingshuiol B has not been completed, symbiopolyol (1a) is suggested to be the enantiomer of lingshuiol B. The structure of 1a, including its partial relative configuration, was elucidated on the basis of interpretation of spectroscopic data and chemical transformations. This compound exhibited significant inhibitory activity against the expression of VCAM-1 in human umbilical vein endothelial cells (HUVEC).

A new antimicrobial fatty acid from the calcareous sponge Paragrantia cf. waguensis.

A new acetylenic fatty acid, 1, has been isolated from the title sponge. The structure of the molecule was elucidated to contain an enyne and a thiophene by spectroscopic methods. Compound 1 showed a weak cytotoxic effect against NBT-T2 rat bladder epithelial cells (IC(50) > 20 microg/ml), and antimicrobial activity with minimal-inhibitory concentrations (MIC) of 64 and 128 microg/ml against Staphylococcus aureus and Escherichia coli, respectively.

Deoxymanoalides from the nudibranch Chromodoris willani.

Two sesterterpenes, deoxymanoalide (1) and deoxysecomanoalide (2), were isolated from the nudibranch Chromodoris willani collected in Okinawa and their structures determined on the basis of spectroscopic data and chemical conversions. The mollusk feeds on a sponge containing manoalide (3) and secomanoalide (4) and is likely to biotransform them into 1 and 2. Both 1 and 2 showed moderate antimicrobial activity against Escherichia coli and Bacillus subtilis and inhibited snake venom phospholipase A2 at 0.2 to 0.5 microM.

A new polyunsaturated brominated fatty acid from a Haliclona sponge.

A new polyunsaturated brominated fatty acid possessing acetylenic bonds 1 was isolated from the Indonesian sponge Haliclona sp. The structure of compound 1 was elucidated by analyzing its spectral data. It showed moderate cytotoxicity against cultured cells.

Polybrominated diphenyl ethers from the Indonesian sponge Lamellodysidea herbacea.

Four new (1-4) and 10 known polybrominated diphenyl ethers (5-14) have been isolated from the title sponge. The structures of the new entities were elucidated by interpretation of spectroscopic data and chemical transformations. These metabolites showed potent antimicrobial activity against Bacillus subtilis and moderate/weak cytotoxicity against NBT-T2 rat bladder epithelial cells. The major constituent 14 was treated under debromination conditions to give eight derivatives, which were subjected to a structure-activity relationship study. The results indicated that the presence of two phenolic hydroxyl groups and bromines at C-2 and/or C-5, as in 2, is important for the exhibition of antibacterial activity.