9 research outputs found
Cyclic Heptapeptides, Cordyheptapeptides C–E, from the Marine-Derived Fungus <i>Acremonium persicinum</i> SCSIO 115 and Their Cytotoxic Activities
Three new cycloheptapeptides, cordyheptapeptides C–E
(<b>1</b>–<b>3</b>), were isolated from the fermentation
extract of the marine-derived fungus <i>Acremonium persicinum</i> SCSIO 115. Their planar structures were elucidated on the basis
of extensive MS, as well as 1D and 2D (COSY, HMQC, and HMBC) NMR spectroscopic
data analyses. The absolute configurations of the amino acid residues
were determined by single-crystal X-ray diffraction, Marfey’s
method, and chiral-phase HPLC analysis. Compounds <b>1</b> and <b>3</b> displayed cytotoxicity against SF-268, MCF-7, and NCI-H460
tumor cell lines with IC<sub>50</sub> values ranging from 2.5 to 12.1
μM
Cytotoxic pyrone derivatives from the deep-sea-derived fungus <i>Cladosporium halotolerans</i> FS702
Two new compounds (R)-6-((8S)-hydroxypropyl)-2-methyl-5,6-dihydro-4H-pyran-4-one (1) and (R)-6-((8R)-hydroxypropyl)-2-methyl-5,6-dihydro-4H-pyran-4-one (2), together with four known compounds were isolated from the marine-derived fungus Cladosporium halotolerans FS702. The structures of these compounds were determined on the basis of extensive spectroscopic analysis including 1D/2D NMR, IR, UV, HRESIMS, ECD calculations as well as the modified Mosher’s method. Cytotoxic assay results showed that compound 2 had significant cytotoxic activity against SF-268, MCF-7, HepG-2, and A549 cells lines with IC50 values of 0.16, 0.47, 0.33 and 0.23 µM, respectively.</p
Halogenated Anthraquinones from the Marine-Derived Fungus <i>Aspergillus</i> sp. SCSIO F063
Metabolomic investigations focusing on the marine-derived
fungus <i>Aspergillus</i> sp. SCSIO F063 have unveiled seven
new chlorinated anthraquinones (<b>1</b>–<b>7</b>) related to averantin, together with five known analogues (<b>11</b>–<b>15</b>) when the fungus was fermented using
sea salt-containing potato dextrose broth. Through the addition of
sodium bromide to the broth, two new brominated anthraquinones (<b>8</b>, <b>9</b>) and one new nonhalogenated anthraquinone
(<b>10</b>) were obtained from the fungal mycelia. Their structures
were elucidated by extensive spectroscopic analyses including MS and
1D and 2D NMR data. One metabolite, 6-<i>O</i>-methyl-7-chloroaveratin
(<b>2</b>), displayed inhibition activity against three human
tumor cell lines, SF-268, MCF-7, and NCI-H460, with IC<sub>50</sub> values of 7.11, 6.64, and 7.42 μM, respectively
Cytotoxic and Antibacterial Marfuraquinocins from the Deep South China Sea-Derived Streptomyces niveus SCSIO 3406
Four new sesquiterpenoid naphthoquinones,
marfuraquinocins A–D
(<b>1</b>–<b>4</b>), and two new geranylated phenazines,
phenaziterpenes A (<b>5</b>) and B (<b>6</b>), were isolated
from the fermentation broth of Streptomyces niveus SCSIO 3406, which originated from a South China Sea sediment sample
obtained from a depth of 3536 m. The structures of <b>1</b>–<b>6</b> were elucidated on the basis of extensive MS and one-dimensional
and two-dimensional NMR spectroscopic analyses. In a panel of cytotoxicity
and antibacterial assays, <b>1</b> and <b>3</b> were found
to inhibit a NCI-H460 cancer cell line with IC<sub>50</sub> values
of 3.7 and 4.4 μM, respectively. Compounds <b>1</b>, <b>3</b>, and <b>4</b> exhibited antibacterial activities against Staphylococcus aureus ATCC 29213 with equivalent
MIC values of 8.0 μg/mL; compounds <b>3</b> and <b>4</b> each showed antibacterial activity against methicillin-resistant Staphylococcus epidermidis (MRSE) shhs-E1 with MIC
values of 8.0 μg/mL
Cytotoxic pimarane-type diterpenes from the marine sediment-derived fungus <i>Eutypella</i> sp. FS46
<p>Two new pimarane-type diterpenes, scopararanes H-I (<b>1</b>–<b>2</b>), along with five known ones (<b>3</b>–<b>7</b>) were isolated from the culture broth of a marine sediment-derived fungus <i>Eutypella</i> sp. FS46, which was obtained from the South China Sea. Their structures were established by extensive spectroscopic analysis. All of them were evaluated for their cytotoxic activities against MCF-7, NCI-H460 and SF-268 tumour cell lines. Scopararane I (<b>2</b>) showed moderate inhibitory activities.</p
Heronamides D–F, Polyketide Macrolactams from the Deep-Sea-Derived <i>Streptomyces</i> sp. SCSIO 03032
Three new macrolactams, heronamides
D–F (<b>1</b>–<b>3</b>), were isolated from
the deep-sea-derived <i>Streptomyces</i> sp. SCSIO 03032
upon changing cultivation conditions. The planar
structures of heronamides D–F (<b>1</b>–<b>3</b>) were elucidated by extensive MS and NMR spectroscopic analyses
and comparisons with the closely related heronamides A–C. The
relative configurations of <b>1</b>–<b>3</b> were
deduced by detailed analysis of <sup>3</sup><i>J</i><sub>HH</sub> values and NOESY data. The absolute configurations of <b>1</b> and <b>2</b> were determined by chemical modifications
and application of the modified Mosher’s method. None of the
compounds exhibited obvious antimicrobial or cytotoxic activities
Fluostatins I–K from the South China Sea-Derived <i>Micromonospora rosaria</i> SCSIO N160
The strain SCSIO N160 was isolated from a South China
Sea sediment
sample and was characterized as a <i>Micromonospora rosaria</i> species on the basis of its 16S rRNA gene sequence. Three new fluostatins,
I–K (<b>1</b>–<b>3</b>), were isolated from
the culture of <i>M. rosaria</i> SCSIO N160, together with
six known compounds, fluostatins C–F (<b>4</b>–<b>7</b>), rabelomycin (<b>8</b>), and phenanthroviridone (<b>9</b>). The structure of fluostatin D (<b>5</b>) was confirmed
by an X-ray crystallographic study. The absolute configuration of <b>1</b> and <b>3</b> was assigned by electronic circular dichroism
calculations. Compounds <b>8</b> and <b>9</b> exhibited
good antimicrobial activities against <i>Staphylococcus aureus</i> ATCC 29213 with MIC values of 1.0 and 0.25 μg/mL, respectively.
Compound <b>9</b> also exhibited significant in vitro cytotoxic
activities toward SF-268 (IC<sub>50</sub> 0.09 μM) and MCF-7
(IC<sub>50</sub> 0.17 μM)
Indimicins A–E, Bisindole Alkaloids from the Deep-Sea-Derived <i>Streptomyces</i> sp. SCSIO 03032
Five new bisindole alkaloids, indimicins
A–E (<b>1</b>–<b>5</b>), bearing a unique
1′,3′-dimethyl-2′-hydroindole moiety, were isolated
from the marine-derived <i>Streptomyces</i> sp. SCSIO 03032,
along with two new compounds, lynamicins F and G (<b>6</b> and <b>7</b>). Their planar structures were elucidated by detailed interpretation
of their MS and NMR spectroscopic data, and the absolute configurations
were determined by X-ray crystallographic analysis (for <b>1</b>), comparison of CD spectra (for <b>2</b>–<b>4</b>), and quantum chemical calculations (for <b>5</b>). Indimicin
B (<b>2</b>) exhibited moderate cytotoxic activity toward the
MCF-7 cell line
Variecolortins A–C, Three Pairs of Spirocyclic Diketopiperazine Enantiomers from the Marine-Derived Fungus <i>Eurotium</i> sp. SCSIO F452
Three pairs of spirocyclic
diketopiperazine enantiomers, variecolortins
A–C (<b>1</b>–<b>3</b>), were isolated from
marine-derived fungus <i>Eurotium</i> sp. SCSIO F452. Compound <b>1</b> possesses an unprecedented highly functionalized <i>seco</i>-anthronopyranoid carbon skeleton featuring a 2-oxa-7-azabicyclo[3.2.1]Âoctane
core. Compounds <b>2</b> and <b>3</b> represent rare examples
of a 6/6/6/6 tetracyclic cyclohexene–anthrone carbon scaffold.
Their structures were determined by spectroscopic analyses, X-ray
diffraction, and ECD calculations. Their enantiomers exhibited different
antioxidative and cytotoxic activities, and their modes of action
were investigated