Recent developments in the enzymatic modifications of steroid scaffolds
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(18), С. 3559 - 3583
Опубликована: Янв. 1, 2024
This
review
highlights
the
recent
advancements
in
enzymatic
modifications
of
steroid
scaffolds,
emphasizing
hydroxylation,
ketoreduction,
dehydrogenation,
cascade
reactions,
and
other
modifications.
Язык: Английский
Biocatalytic Steroidal 9α‐Hydroxylation and Fragmentation Enable the Concise Chemoenzymatic Synthesis of 9,10‐Secosteroids
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(16)
Опубликована: Фев. 20, 2024
Abstract
9,10‐Secosteroids
are
an
important
group
of
marine
steroids
with
diverse
biological
activities.
Herein,
we
report
a
chemoenzymatic
strategy
for
the
concise,
modular,
and
scalable
synthesis
ten
naturally
occurring
9,10‐secosteroids
from
readily
available
in
three
to
eight
steps.
The
key
feature
lies
utilizing
Rieske
oxygenase‐like
3‐ketosteroid
9α‐hydroxylase
(KSH)
as
biocatalyst
achieve
efficient
C9−C10
bond
cleavage
A‐ring
aromatization
tetracyclic
through
9α‐hydroxylation
fragmentation.
With
synthesized
9,10‐secosteroides,
structure–activity
relationship
was
evaluated
based
on
bioassays
terms
previously
unexplored
anti‐infective
activity.
This
study
provides
experimental
evidence
support
hypothesis
that
biosynthetic
pathway
which
formed
nature
shares
similar
fragmentation
cascade.
In
addition
development
biomimetic
approach
9,10‐secosteroid
synthesis,
this
highlights
great
potential
strategies
chemical
synthesis.
Язык: Английский
Rare Chlorinated C19 Steroids Hocarnoids A and B from Hoya carnosa: Isolation, Semisynthesis, and Anti-inflammation
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 20, 2025
Steroids
have
consistently
drawn
scientific
attention
due
to
their
diverse
structures
and
exceptional
pharmacological
activities.
However,
halogenated
natural
steroids
remain
relatively
rare,
especially
for
those
derived
from
plants.
In
this
study,
two
chlorinated
C19
hocarnoids
A
(1)
B
(2)
were
identified
the
folk
medicinal
plant
Hoya
carnosa,
representing
first
examples
of
C-16
steroids.
Semisynthesis
compounds
1
2
was
completed
in
4
5
linear
steps
with
28.2%
25.3%
overall
yields
through
a
modified
approach,
corroborating
further
structures.
total
collection
11
steroids,
including
intermediates
obtained
during
synthesis,
evaluated
anti-inflammatory
activity
against
lipopolysaccharide
(LPS)-induced
inflammation-related
RAW
264.7
macrophages.
Among
them,
product
hocarnoid
displayed
strongest
an
IC50
value
3.62
±
0.08
μM,
which
also
attenuated
mRNA
levels
proinflammatory
cytokines
IL-1β,
IL-6,
IL-10,
TNF-α.
Язык: Английский
Naturally Occurring Nor-Steroids and Their Design and Pharmaceutical Application
Опубликована: Апрель 16, 2024
The
main
focus
of
this
review
is
to
introduce
readers
the
fascinating
class
lipid
molecules
known
as
norsteroids,
exploring
their
distribution
across
various
biotopes
and
biological
activities.
provides
an
in-depth
analysis
modified
steroids,
including
A,
B,
C,
D-norsteroids,
each
characterized
by
distinct
structural
alterations.
These
modifications,
which
range
from
removal
specific
methyl
groups
changes
in
steroid
core,
result
unique
molecular
architectures
that
significantly
impact
activity
therapeutic
potential.
discussion
on
D-norsteroids
sheds
light
configurations
how
these
modifications
influence
pharmacological
properties.
also
presents
examples
natural
sources
produce
a
diverse
array
steroids
with
structures,
aforementioned
D-nor
variants.
compounds,
sourced
marine
organisms
like
sponges,
soft
corals
starfish,
well
terrestrial
entities
such
plants,
fungi,
bacteria.
exploration
encompasses
biosynthesis,
ecological
significance,
potential
medical
applications,
highlighting
crucial
area
interest
pharmacology
product
chemistry.
emphasizes
importance
researching
for
drug
development,
particularly
addressing
diseases
where
conventional
medications
are
inadequate
or
conditions
lacking
sufficient
options.
Examples
norsteroid
synthesis
provided
illustrate
practical
applications
research.
Язык: Английский
Naturally Occurring Norsteroids and Their Design and Pharmaceutical Application
Biomedicines,
Год журнала:
2024,
Номер
12(5), С. 1021 - 1021
Опубликована: Май 6, 2024
The
main
focus
of
this
review
is
to
introduce
readers
the
fascinating
class
lipid
molecules
known
as
norsteroids,
exploring
their
distribution
across
various
biotopes
and
biological
activities.
provides
an
in-depth
analysis
modified
steroids,
including
A,
B,
C,
D-norsteroids,
each
characterized
by
distinct
structural
alterations.
These
modifications,
which
range
from
removal
specific
methyl
groups
changes
in
steroid
core,
result
unique
molecular
architectures
that
significantly
impact
activity
therapeutic
potential.
discussion
on
D-norsteroids
sheds
light
configurations
how
these
modifications
influence
pharmacological
properties.
also
presents
examples
natural
sources
produce
a
diverse
array
steroids
with
structures,
aforementioned
D-nor
variants.
compounds
are
sourced
marine
organisms
like
sponges,
soft
corals,
starfish,
well
terrestrial
entities
such
plants,
fungi,
bacteria.
exploration
encompasses
biosynthesis,
ecological
significance,
potential
medical
applications,
highlighting
crucial
area
interest
pharmacology
product
chemistry.
emphasizes
importance
researching
for
drug
development,
particularly
addressing
diseases
where
conventional
medications
inadequate
or
conditions
lacking
sufficient
options.
Examples
norsteroid
synthesis
provided
illustrate
practical
applications
research.
Язык: Английский
Biocatalytic Steroidal 9α‐Hydroxylation and Fragmentation Enable the Concise Chemoenzymatic Synthesis of 9,10‐Secosteroids
Angewandte Chemie,
Год журнала:
2024,
Номер
136(16)
Опубликована: Фев. 20, 2024
Abstract
9,10‐Secosteroids
are
an
important
group
of
marine
steroids
with
diverse
biological
activities.
Herein,
we
report
a
chemoenzymatic
strategy
for
the
concise,
modular,
and
scalable
synthesis
ten
naturally
occurring
9,10‐secosteroids
from
readily
available
in
three
to
eight
steps.
The
key
feature
lies
utilizing
Rieske
oxygenase‐like
3‐ketosteroid
9α‐hydroxylase
(KSH)
as
biocatalyst
achieve
efficient
C9−C10
bond
cleavage
A‐ring
aromatization
tetracyclic
through
9α‐hydroxylation
fragmentation.
With
synthesized
9,10‐secosteroides,
structure–activity
relationship
was
evaluated
based
on
bioassays
terms
previously
unexplored
anti‐infective
activity.
This
study
provides
experimental
evidence
support
hypothesis
that
biosynthetic
pathway
which
formed
nature
shares
similar
fragmentation
cascade.
In
addition
development
biomimetic
approach
9,10‐secosteroid
synthesis,
this
highlights
great
potential
strategies
chemical
synthesis.
Язык: Английский
Cofactor-dependence alteration of 7β-hydroxysteroid dehydrogenase: Enhancing one-pot synthesis efficiency of chenodeoxycholic acid to ursodeoxycholic acid through cofactor self-recycling
International Journal of Biological Macromolecules,
Год журнала:
2024,
Номер
280, С. 136328 - 136328
Опубликована: Окт. 6, 2024
Язык: Английский