(+)-12alpha-Hydroxysophocarpine, a new quinolizidine alkaloid and related anti-HBV alkaloids from Sophora flavescens.

  title={(+)-12alpha-Hydroxysophocarpine, a new quinolizidine alkaloid and related anti-HBV alkaloids from Sophora flavescens.},
  author={Pei-lan Ding and Zhi-Xin Liao and Hai Huang and Pei Zhou and Dao-feng Chen},
  journal={Bioorganic \& medicinal chemistry letters},
  volume={16 5},
(+)-12alpha-Hydroxysophocarpine (8), a new quinolizidine alkaloid was isolated from the roots of Sophora flavescens, together with 10 known quinolizidine alkaloids, (+)-oxymatrine (1), (+)-matrine (2), (+)-9alpha-hydroxymatrine (3), (+)-allomatrine (4), (+)-oxysophocarpine (5), (-)-sophocarpine (6), (-)-9alpha-hydroxysophocarpine (7), (+)-lehmannine (9), (-)-13,14-dehydrosophoridine (10), and (-)-anagyrine (11). Their structures were elucidated by spectroscopic methods, and the stereochemistry… Expand
Antiviral Matrine-Type Alkaloids from the Rhizomes of Sophora tonkinensis.
Alkaloids 2, 6, 11, and 13 exhibited antiviral activity against the Coxsackie virus B3 (CVB3), and alkaloids 7, 8, and 17 inhibited influenza virus A/Hanfang/359/95 (H3N2) replication with IC50 values of 63.46 μM. Expand
Matrine-Type Alkaloids from the Roots of Sophora flavescens and Their Antiviral Activities against the Hepatitis B Virus.
Eight new matrine-type alkaloids, flavesines G-J (1-4), alopecurine B (5), 7,11-dehydro-oxymatrine (6), 10-oxy-5,6-dehydromatrine (7), and 10-oxysophoridine (8), along with nine known analoguesExpand
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
Two new alkaloids, hypserpanines A and B, together with eleven known compounds, were isolated from Hypserpa nitida Miers and chemically elucidated through spectral analyses and evaluated for their anti-HBV activities in vitro using the HBV transfected Hep G2.2.15 cell line. Expand
Quinolizidine alkaloids from Sophora alopecuroides with anti-inflammatory and anti-tumor properties.
Forty-three quinolizidine alkaloids, including twelve new matrine-type ones, sophalodes A-L, were isolated from the seeds of Sophora alopecuroides, and additional research showed that compound 16 exhibited marginal cytotoxicity against HeLa cell lines, with an IC50 value of 24.27 μM. Expand
Quinolizidine alkaloids from the roots of Sophora flavescens.
Seventeen quinolizidine alkaloids, including a new matrine-type one, sophcence A (1), were isolated from the roots of Sophora flavescens Alt. The structure of compound 1 was elucidated by means of 1DExpand
Four new quinolizidine alkaloids from the flowers of Sophora viciifolia
Four new quinolizidine alkaloids were isolated from the flowers of Sophora viciifolia, and none of them were active towards these assays for their anti-inflammatory and anti-influenza virus activities. Expand
Water-soluble matrine-type alkaloids with potential anti-neuroinflammatory activities from the seeds of Sophora alopecuroides.
  • Ding Luo, Qiang Lin, +10 authors Yu-bo Zhang
  • Medicine
  • Bioorganic chemistry
  • 2021
Mechanical study revealed that compound 39 suppressed the phosphorylation of IκBα and p65 subunit to regulate the NF-κB signaling pathway, which can suppress those two mediator secretions in a dose-dependent manner. Expand
Inhibitory activities of prenylated flavonoids from Sophora flavescens against aldose reductase and generation of advanced glycation endproducts
S. flavescens and its prenylated flavonoids inhibit the processes that underlie diabetic complications and related diseases and may therefore have therapeutic benefit. Expand
Phytochemical information and biological activities of quinolizidine alkaloids in Sophora: A comprehensive review.
The diversity of chemical compounds based on the alkaloid scaffold to make a biological compound library needs to be extended, which may reduce toxicity and find new bioactivities of quinolizidine alkaloids. Expand
Dimeric Matrine-Type Alkaloids from the Roots of Sophora flavescens and Their Anti-Hepatitis B Virus Activities.
Six unusual matrine-type alkaloid dimers, flavesines A-F (1-6, respectively), together with three proposed biosynthetic intermediates (7-9) were isolated from the roots of Sophora flavescens and represented an unprecedented dimerization pattern constructed by matrine and (-)-cytisine. Expand


(-)-14β-Acetoxymatrine and (+)-14α-Acetoxymatrine, Two New Matrine-Type Lupin Alkaloids from the Leaves of Sophora tonkinensis
Two new lupin alkaloids, which are the first ester derivatives of matrine-type lupin alkaloids, (-)-14β-acetoxymatrine and (+)-14α-acetoxymatrine, were isolated from the leaves of Sophora tonkinensisExpand
Lupin alkaloids from seeds of Sophora viciifolia
Abstract Three new lupin alkaloids, (−)-14β-hydroxysophoridine, (−)-12β-hydroxysophocarpine and (−)-9α-hydroxysophocarpine, were isolated from the seeds of Sophora viciifolia together with 10 knownExpand
(-)-14β-Hydroxymatrine, a New Lupine Alkaloid from the Roots of Sophora tonkinensis
A new lupine alkaloid, (-)-14β-hydroxymatrine (1) was isolaed from the dry roots of Sophora tonkinensis together with 11 known lupine alkaloids. The absolute structure (5S, 6S, 7R, 11R, 14S) of theExpand
(+)-9α-Hydroxymatrine from Sophora macrocarpa
Abstract A new quinolizidine alkaloid, (+)-9α-hydroxymatrine, was isolated from the leaves of Sophora macrocarpa . Its structure was determined by a combination of spectroscopic methods, among whichExpand
Assignment of the 1H and 13C NMR spectra of the quinolizidine alkaloid anagyrine and determination of its conformation
The 1H NMR spectrum of the quinolizidine alkaloid ( − )‐ anagyrine has been studied at 200 and 600 MHz. A full assignment of the 1H signals has been achieved by application of a variety of NMRExpand
Studies on lupin alkaloids. VIII. A new stereoisomer of sophocarpine.
A new stereoisomer (I) of (-)-sophocarpine (II) was isolated from epigeal part of Sophora flavescens. The relative configuration and stereochemistry were determined by X-ray diffraction studies withExpand
Antiviral Chinese medicinal herbs against respiratory syncytial virus.
Forty-four medicinal herbs were tested for antiviral activities against respiratory syncytial virus (RSV) by means of the cytopathologic effect (CPE) assay, and anagyrine, oxymatrine, sophoranol, wogonin, and oroxylin A were identified as the potent anti-RSV components. Expand
Effect of oxymatrine on murine fulminant hepatitis and hepatocyte apoptosis.
Oxymatrine protects mice from fulminant hepatitis induced by GalN/LPS and may block hepatocyte apoptosis and subsequent necrosis through downregulating the production of serum tumor necrosis factor alpha and the expression of Fas and Fas ligand in liver tissue. Expand
[The pharmacological studies on matrine and oxymatrine].
  • M. Yamazaki
  • Chemistry, Medicine
  • Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
  • 2000
The results suggest that the protective effect of oxymatrine on stress ulcer is possibly due to a decrease of acid secretion and inhibition of gastric motility, and may play an important role in the protection of the restraint and water immersion stress Ulcer formetion. Expand
Effect of matrine on lipopolysaccharides/D-galactosamine-induced hepatitis and tumor necrosis factor release from macrophages in vitro.
Mat protected the D-GalN-treated mice from the development of fatal hepatitis induced by LPS, and inhibited the LPS-induced TNF release from mouse PMO. Expand