4 research outputs found
Bioactive Asarone-Derived Phenylpropanoids from the Rhizome of <i>Acorus tatarinowii</i> Schott
Eight new (<b>1a</b>/<b>1b</b>, <b>2a</b>, <b>3a</b>, <b>4a</b>/<b>4b</b>, and <b>5a</b>/<b>5b</b>) and seven known (<b>2b</b>, <b>3b</b>, and <b>6</b>–<b>10</b>) asarone-derived phenylpropanoids,
a known asarone-derived lignan (<b>12</b>), and four known lignan
analogues (<b>11</b> and <b>13</b>–<b>15</b>) were isolated from the rhizome of <i>Acorus tatarinowii</i> Schott. The structures were elucidated via comprehensive spectroscopic
analyses, modified Mosher’s method, and quantum chemical calculations.
Compounds <b>1</b>–<b>8</b> were present as enantiomers,
and <b>1</b>–<b>5</b> were successfully resolved
via chiral-phase HPLC. Compounds <b>1a</b>/<b>1b</b> were
the first cases of asarone-derived phenylpropanoids with an isopropyl
C-3 side-chain tethered to a benzene core from nature. Hypoglycemic,
antioxidant, and AChE inhibitory activities of <b>1</b>–<b>15</b> were assessed by the α-glucosidase inhibitory, ORAC,
DPPH radical scavenging, and AChE inhibitory assays, respectively.
All compounds except <b>3a</b> showed α-glucosidase inhibitory
activity. Compound <b>3b</b> has the highest α-glucosidase
inhibitory effect with an IC<sub>50</sub> of 80.6 μM (positive
drug acarbose IC<sub>50</sub> of 442.4 μM). In the antioxidant
assays, compounds <b>13</b>–<b>15</b> exhibited
ORAC and DPPH radical scavenging activities. The results of the AChE
inhibitory assay indicated that all compounds exhibited weak AChE
inhibitory activities
Lycibarbarspermidines A–O, New Dicaffeoylspermidine Derivatives from Wolfberry, with Activities against Alzheimer’s Disease and Oxidation
Fifteen new dicaffeoylspermidine
derivatives, lycibarbarspermidines
A–O (<b>1</b>–<b>15</b>), were isolated
from the fruit of Lycium barbarum (wolfberry).
The structures were unambiguously determined by spectroscopic analyses
and chemical methods. Dicaffeoylspermidine derivatives, a rare kind
of plant secondary metabolites, are primarily distributed in the family
of Solanaceae. Only six compounds were structurally identified, and
all of them are acyclic aglycones. Compounds <b>1</b>–<b>15</b> are the first glycosidic products of dicaffeoylspermidine
derivatives, and compounds <b>14</b>–<b>15</b> are
the first cyclization products of dicaffeoylspermidine derivatives.
Moreover, dicaffeoylspermidine derivatives were first isolated and
identified from wolfberry. The short-term memory assay on a transgenic
fly Alzheimer’s disease (AD) model showed that <b>1</b>–<b>15</b> exhibited different levels of anti-AD activity.
The oxygen radical absorbance capacity assay revealed that <b>1</b>–<b>15</b> all displayed antioxidant capacity. Both
anti-AD and antioxidant functions are related to the effects of wolfberry.
Therefore, dicaffeoylspermidine derivatives are considered beneficial
constituents responsible for the antiaging, neuroprotective, anti-AD,
and antioxidant effects of wolfberry
Houttuynoid M, an Anti-HSV Active Houttuynoid from <i>Houttuynia cordata</i> Featuring a Bis-houttuynin Chain Tethered to a Flavonoid Core
Houttuynoid M (<b>1</b>), a
new houttuynoid, and the related
known compound houttuynoid A (<b>2</b>) were isolated from <i>Houttuynia cordata</i>. Their structures were defined using
NMR data analysis, HR-MS<sup><i>n</i></sup> experiment,
and chemical derivatization. Houttuynoid M is the first example of
a houttuynoid with a bis-houttuynin chain tethered to a flavonoid
core. A putative biosynthetic pathway of houttuynoid M (<b>1</b>) is proposed. The anti-herpes simplex virus (anti-HSV) activities
of <b>1</b> and <b>2</b> (IC<sub>50</sub> values of 17.72
and 12.42 μM, respectively) were evaluated using a plaque formation
assay with acyclovir as the positive control
A microbial model of mammalian metabolism: biotransformation of 4,5-dimethoxyl-canthin-6-one using <i>Cunninghamella blakesleeana</i> CGMCC 3.970
<p>1. A filamentous fungus, <i>Cunninghamella blakesleeana</i> CGMCC 3.970, was applied as a microbial system to mimic mammalian metabolism of 4,5-dimethoxyl-canthin-6-one (<b>1</b>). Compound <b>1</b> belongs to canthin-6-one type alkaloids, which is a major bioactive constituent of a traditional Chinese medicine (the stems of <i>Picrasma quassioides</i>).</p> <p>2. After 72 h of incubation in potato dextrose broth, <b>1</b> was metabolized to seven metabolites as follows: 4-methoxyl-5-hydroxyl-canthin-6-one (<b>M1</b>), 4-hydroxyl-5-methoxyl-canthin-6-one (<b>M2</b>), canthin-6-one (<b>M3</b>), canthin-6-one <i>N</i>-oxide (<b>M4</b>), 10-hydroxyl-4,5-dimethoxyl-canthin-6-one (<b>M5</b>), 1-methoxycarbonl-<i>β</i>-carboline (<b>M6</b>), and 4-methoxyl-5-<i>O</i>-<i>β</i>-D-glucopyranosyl-canthin-6-one (<b>M7</b>).</p> <p>3. The structures of metabolites were determined using spectroscopic analyses, chemical methods, and comparison of NMR data with those of known compounds. Among them, <b>M7</b> was a new compound.</p> <p>4. The metabolic pathways of <b>1</b> were proposed, and the metabolic processes involved phase I (<i>O</i>-demethylation, dehydroxylation, demethoxylation, <i>N</i>-oxidation, hydroxylation, and oxidative ring cleavage) and phase II (glycosylation) reactions.</p> <p>5. This was the first research on microbial transformation of canthin-6-one alkaloid, which could be a useful microbial model for producing the mammalian phase I and phase II metabolites of canthin-6-one alkaloids.</p> <p>6. <b>1</b>, <b>M1</b>−<b>M5</b>, and <b>M7</b> are canthin-6-one alkaloids, whereas <b>M6</b> belongs to <i>β</i>-carboline type alkaloids. The strain of <i>Cunninghamella blakesleeana</i> can supply an approach to transform canthin-6-one type alkaloids into <i>β</i>-carboline type alkaloids.</p