10 research outputs found
Bibenzyl-Based Meroterpenoid Enantiomers from the Chinese Liverwort <i>Radula sumatrana</i>
Six new pairs of bibenzyl-based meroterpenoid
enantiomers, (±)-rasumatranin
A–D (<b>1</b>–<b>4</b>) and (±)-radulanin
M and N (<b>5</b> and <b>6</b>), and six known compounds
were isolated from the adnascent Chinese liverwort, <i>Radula
sumatrana.</i> Their structures were elucidated based on spectroscopic
data and chiral phase HPLC-ECD analyses. The structures of <b>1</b> and <b>7</b> were also confirmed by single-crystal X-ray diffraction
analysis. Cytotoxicity tests of the isolated compounds showed that
6-hydroxy-3-methyl-8-phenylethylbenzoÂ[<i>b</i>]Âoxepin-5-one
(<b>8</b>) showed activity against the human cancer cell lines
MCF-7, PC-3, and SMMC-7721, with IC<sub>50</sub> values of 3.86, 6.60,
and 3.58 μM, respectively, and induced MCF-7 cell death through
a mitochondria-mediated apoptosis pathway
Highly Rigid Labdane-Type Diterpenoids from a Chinese Liverwort and Light-Driven Structure Diversification
Two unprecedented labdane-type diterpenoids
haplomintrins A (<b>1</b>) and B (<b>2</b>) with six rings
system were isolated
from a Chinese liverwort <i>Haplomitrium mnioides</i>. Light-driven
reaction of homologous haplomitrenonolides C (<b>6</b>), A (<b>4</b>), and D (<b>3</b>) afforded haplomintrins A–C
(<b>1</b>, <b>2</b>, and <b>7</b>), respectively,
while <b>4</b> was converted to more complex congeners haplomintrins
D–G (<b>8</b>–<b>11</b>) through intramolecular
cyclization. Formation of <b>1</b> and <b>2</b> from compounds <b>6</b> and <b>4</b>, respectively, helps us to postulate
that a photochemical reaction is involved in the biosynthetic pathway.
These structure features can be used as molecular markers of <i>H. mnioides</i>, and their allelopathic effects are also preliminarily
tested
Sacculatane Diterpenoids from the Liverwort Plagiochila nitens Collected in China
Seven new terpenoids, including six sacculatane diterpenoids
plagiochilarins
A–F (1–6), and one ent-2,3-seco-aromandrane sesquiterpenoid
plagiochilarin H (8) with a 6/7/3/5 tetracyclic scaffold,
alongside three known compounds, were obtained from the Chinese liverwort Plagiochila nitens Inoue. Plagiochilarin B (2) was unpredictably converted to the more stable artifact 7 under acid catalysis through cyclic ether formation. The
reaction mechanism was reasonably deduced and experimentally verified.
The structures of these terpenoids were determined by analysis of
MS and NMR spectroscopic data and single-crystal X-ray diffraction.
The inhibitory effect of all of the isolates was evaluated on the
growth of two C. albicans strains,
wild strain SC5314 and efflux pump-deficient strain DSY654. However,
only plagiochilarin H (8) showed a MIC value of 16 μg/mL
against C. albicans DSY654
Sacculatane Diterpenoids from the Liverwort Plagiochila nitens Collected in China
Seven new terpenoids, including six sacculatane diterpenoids
plagiochilarins
A–F (1–6), and one ent-2,3-seco-aromandrane sesquiterpenoid
plagiochilarin H (8) with a 6/7/3/5 tetracyclic scaffold,
alongside three known compounds, were obtained from the Chinese liverwort Plagiochila nitens Inoue. Plagiochilarin B (2) was unpredictably converted to the more stable artifact 7 under acid catalysis through cyclic ether formation. The
reaction mechanism was reasonably deduced and experimentally verified.
The structures of these terpenoids were determined by analysis of
MS and NMR spectroscopic data and single-crystal X-ray diffraction.
The inhibitory effect of all of the isolates was evaluated on the
growth of two C. albicans strains,
wild strain SC5314 and efflux pump-deficient strain DSY654. However,
only plagiochilarin H (8) showed a MIC value of 16 μg/mL
against C. albicans DSY654
Sacculatane Diterpenoids from the Liverwort Plagiochila nitens Collected in China
Seven new terpenoids, including six sacculatane diterpenoids
plagiochilarins
A–F (1–6), and one ent-2,3-seco-aromandrane sesquiterpenoid
plagiochilarin H (8) with a 6/7/3/5 tetracyclic scaffold,
alongside three known compounds, were obtained from the Chinese liverwort Plagiochila nitens Inoue. Plagiochilarin B (2) was unpredictably converted to the more stable artifact 7 under acid catalysis through cyclic ether formation. The
reaction mechanism was reasonably deduced and experimentally verified.
The structures of these terpenoids were determined by analysis of
MS and NMR spectroscopic data and single-crystal X-ray diffraction.
The inhibitory effect of all of the isolates was evaluated on the
growth of two C. albicans strains,
wild strain SC5314 and efflux pump-deficient strain DSY654. However,
only plagiochilarin H (8) showed a MIC value of 16 μg/mL
against C. albicans DSY654
Sacculatane Diterpenoids from the Liverwort Plagiochila nitens Collected in China
Seven new terpenoids, including six sacculatane diterpenoids
plagiochilarins
A–F (1–6), and one ent-2,3-seco-aromandrane sesquiterpenoid
plagiochilarin H (8) with a 6/7/3/5 tetracyclic scaffold,
alongside three known compounds, were obtained from the Chinese liverwort Plagiochila nitens Inoue. Plagiochilarin B (2) was unpredictably converted to the more stable artifact 7 under acid catalysis through cyclic ether formation. The
reaction mechanism was reasonably deduced and experimentally verified.
The structures of these terpenoids were determined by analysis of
MS and NMR spectroscopic data and single-crystal X-ray diffraction.
The inhibitory effect of all of the isolates was evaluated on the
growth of two C. albicans strains,
wild strain SC5314 and efflux pump-deficient strain DSY654. However,
only plagiochilarin H (8) showed a MIC value of 16 μg/mL
against C. albicans DSY654
Sacculatane Diterpenoids from the Liverwort Plagiochila nitens Collected in China
Seven new terpenoids, including six sacculatane diterpenoids
plagiochilarins
A–F (1–6), and one ent-2,3-seco-aromandrane sesquiterpenoid
plagiochilarin H (8) with a 6/7/3/5 tetracyclic scaffold,
alongside three known compounds, were obtained from the Chinese liverwort Plagiochila nitens Inoue. Plagiochilarin B (2) was unpredictably converted to the more stable artifact 7 under acid catalysis through cyclic ether formation. The
reaction mechanism was reasonably deduced and experimentally verified.
The structures of these terpenoids were determined by analysis of
MS and NMR spectroscopic data and single-crystal X-ray diffraction.
The inhibitory effect of all of the isolates was evaluated on the
growth of two C. albicans strains,
wild strain SC5314 and efflux pump-deficient strain DSY654. However,
only plagiochilarin H (8) showed a MIC value of 16 μg/mL
against C. albicans DSY654
Scapairrins A–Q, Labdane-Type Diterpenoids from the Chinese Liverwort <i>Scapania irrigua</i> and Their Cytotoxic Activity
Seventeen new labdane-type diterpenoids,
scapairrins A–Q (<b>1</b>–<b>17</b>), including
six pairs of diastereoisomers, and three known analogues (<b>18</b>–<b>20</b>) were isolated from the Chinese liverwort <i>Scapania irrigua</i>. The structures of <b>1</b>–<b>17</b> were determined based on a combination of the analysis
of their MS and NMR spectroscopic data, single-crystal X-ray diffraction,
and electronic circular dichroism calculations. Cytotoxicity testing
showed that compounds <b>7</b>–<b>10</b> exhibited
inhibitory activities against a small panel of human cancer cell lines
Marsupellins A–F, <i>ent</i>-Longipinane-Type Sesquiterpenoids from the Chinese Liverwort <i>Marsupella alpine</i> with Acetylcholinesterase Inhibitory Activity
Acetylcholinesterase (AChE) inhibitory
activity-guided fractionation
of the Chinese liverwort <i>Marsupella alpine</i> afforded
six new [marsupellins A–F (<b>1</b>–<b>6</b>)] and three known (<b>7</b>–<b>9</b>) <i>ent</i>-longipinane-type sesquiterpenoids. The structures were
determined from MS and NMR spectroscopic data, single-crystal X-ray
diffraction, and electronic circular dichroism calculations. Compounds <b>1</b>–<b>9</b> exhibited moderate to weak AChE inhibitory
activity
Hapmnioides A–C, Rearranged Labdane-Type Diterpenoids from the Chinese Liverwort <i>Haplomitrium mnioides</i>
Many
exceptional labdane-type diterpenoids have been exclusively
found in liverworts, which serve as taxonomic molecules or play important
ecological roles in interactions among organisms. Three unprecedented
labdane-type diterpenoids hapmnioides A (<b>1</b>), B (<b>2</b>), and C (<b>3</b>) formed through cascade rearrangement
from the Chinese liverwort <i>Haplomitrium mnioides</i> are
reported. Their structures were established by comprehensive spectroscopic
analysis coupled with single-crystal X-ray diffraction, and their
anti-inflammatory activities were also preliminarily tested