Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A New 1,3-Benzodioxole Compound from Hypecoum erectum and Its Antioxidant Activity.

ABSTRACT: The purpose of this study was to identify the chemical components in aerial parts of Hypecoum erectum. A new 1,3-benzodioxole derivative, identified as Hypecoumic acid (1), was isolated, together with the three known compounds: protopine (2), coptisine (3), and cryptopine (4). Their structures were identified based on extensive spectroscopic experiments, including nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectra (HR-ESI-MS), as well as comparison with those reported in the literature. Meanwhile, the in vitro antioxidative activity of all compounds was determined using a DPPH-scavenging assay, and compound 1 (IC₅₀ = 86.3 ± 0.2 μM) was shown to have moderate antioxidative activity.

SUBMITTER: Xu N

PROVIDER: S-EPMC9570887 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A New 1,3-Benzodioxole Compound from Hypecoum erectum and Its Antioxidant Activity.

Xu Ning N Bao Wenli W Xin Jiletu J Xiao Hua H Yu Jiaqi J Xu Liang L

Molecules (Basel, Switzerland) 20221007 19

The purpose of this study was to identify the chemical components in aerial parts of Hypecoum erectum. A new 1,3-benzodioxole derivative, identified as Hypecoumic acid (1), was isolated, together with the three known compounds: protopine (2), coptisine (3), and cryptopine (4). Their structures were identified based on extensive spectroscopic experiments, including nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectra (HR-ESI- ...[more]

PMID: 36235194

Similar Datasets

Synthesis and initial screening of lactate dehydrogenase inhibitor activity of 1,3-benzodioxole derivatives.

Project description:Cancer is one of the main causes of mortality in the world. Many cancer cells produce ATP through high-level lactic acid fermentation catalyzed by lactate dehydrogenase (LDH), which converts pyruvic acid to lactic acid. LDH plays a dominant role in the Warburg effect, wherein aerobic glycolysis is favored over oxidative phosphorylation. Due to the high lactic acid production level in cancer cells, LDH-targeting could be a potential cancer treatment strategy. A few approaches, such as drug treatment, reportedly inhibited LDH activity. In this study, we describe new 1,3-benzodioxole derivatives that might be potential small molecule candidates for LDHA inhibition. The synthesis was carried out by trans-esterification between aryl ester and alcohol groups from piperonyl alcohol. Compounds 2 and 10 exhibited a selective LDHA IC50 value of 13.63 µM and 47.2 µM, respectively. Whereas only compound 10 showed significant cytotoxicity in several lines of cancer cells, especially in human pancreatic cancer PANC-1 cells. These synthesized compounds possess 2 aromatic rings and -CF3 moiety, which expectedly contributes to LDHA inhibition. The presented products have the potential to become a promising LDHA inhibitor drug candidate.

| S-EPMC7669867 | biostudies-literature

5-(1H-Inden-2-yl)-1,3-benzodioxole.

Project description:In the title compound, C(16)H(12)O(2), the non-H atoms are coplanar with a mean r.m.s. deviation of 0.0260 (2) Å. The deviations of the bond angles from normal values at the indenyl junction C atom and the indenyl bridgehead C atom nearest the junction are imposed by the five-membered ring geometry. Due to conjugation, the single bond linking the two ring systems [1.455 (3) Å] is significantly shorter than the formal single bonds in the five-membered carbocyclic ring [1.500 (3) and 1.489 (3) Å].

| S-EPMC2960328 | biostudies-literature

6-Hy-droxy-2H-1,3-benzodioxole-5-carbaldehyde.

Project description:The title compound, C(8)H(6)O(4), crystallizes with two independent mol-ecules in the asymmetric unit. The benzodioxole ring system is almost planar in each mol-ecule, with maximum deviations of 0.008 (1) and 0.007 (1) Å. The mol-ecular structure is characterized by strong electrostatic intra-molecular O⋯O contacts [2.649 (3) Å] and intra-molecular O-H⋯O hydrogen-bonding inter-actions. Inter-molecular O⋯O inter-actions [3.001 (2) Å] are observed in the crystal structure.

| S-EPMC3201492 | biostudies-literature

Crystal structure of 5-(1,3-di-thian-2-yl)-2H-1,3-benzodioxole.

Project description:In the title compound, C11H12O2S2, two independent but virtually superimposable mol-ecules, A and B, comprise the asymmetric unit. In each mol-ecule, the 1,3-di-thiane ring has a chair conformation with the 1,4-disposed C atoms being above and below the plane through the remaining four atoms. The substituted benzene ring occupies an equatorial position in each case and forms dihedral angles of 85.62 (9) (mol-ecule A) and 85.69 (8)° (mol-ecule B) with the least-squares plane through the 1,3-di-thiane ring. The difference between the mol-ecules rests in the conformation of the five-membered 1,3-dioxole ring which is an envelope in mol-ecule A (the methyl-ene C atom is the flap) and almost planar in mol-ecule B (r.m.s. deviation = 0.046 Å). In the crystal, mol-ecules of A self-associate into supra-molecular zigzag chains (generated by glide symmetry along the c axis) via methyl-ene C-H⋯π inter-actions. Mol-ecules of B form similar chains. The chains pack with no specific directional inter-molecular inter-actions between them.

| S-EPMC4350690 | biostudies-literature

(S)-(-)-5,5'-Bis(diphenyl-phosphino)-4,4'-bi-1,3-benzodioxole.

Project description:In the chiral title compound, C(38)H(28)O(4)P(2), the intra-molecular P⋯P separation is 3.671 (2) Å and the dihedral angle between the two benzene rings in the biphenyl unit is 77.9 (2)°.

| S-EPMC2977819 | biostudies-literature

1,3-Benzodioxole Derivatives Improve the Anti-Tumor Efficiency of Arsenicals.

Project description:Arsenicals have been widely used in the treatment of cancers such as leukemia and other tumors. However, their side effects limit their clinical application. Stiripentol, a second-line adjunctive treatment for epilepsy with a good safety profile, inhibits microsomal cytochrome-P450-family enzymes to extend the retention time of co-administration. Inspired by the metabolism of stiripentol, the 1,3-benzodioxole responsible for the inhibition and its metabolic derivatives were conjugated with arsenical precursors. The fabricated arsenicals were eliminated much slower in mice and maintained an efficient concentration in the blood for a longer time than that of the arsenical precursors. They also performed better in anti-proliferation by inhibiting the thioredoxin system to induce oxidative stress, and concomitantly to initiate apoptosis in vitro and in vivo. The fabricated arsenicals reversed the hemogram of tumor-bearing mice to normal and eliminated the tumor without causing damage to any organs, exhibiting a good design strategy and pre-clinical application for leukemia and other tumors.

| S-EPMC9266561 | biostudies-literature

Hypecotumines A-D, new isoquinoline alkaloids with potential PCSK9 inhibition activity from Hypecoum erectum L.

Project description:Four new isoquinoline alkaloids, hypecotumines A-D (1-4), were isolated and identified from the whole herbs of Hypecoum erectum L. Their structures were determined by a combination of HRESIMS, NMR, and X-ray diffraction analysis methods. Compounds 1-4 were characterized by a terminal double bond at C-9 and their plausible biosynthetic pathway was hypothesized. Since PCSK9 plays a key role in the development of cardiovascular disease (CVD), exploration of PCSK inhibitors from natural products are beneficial for drug discovery of CVD treatment. SPR and Western blot assays showed compound 4 had PCSK9 inhibition activity with KD value of 59.9 µM and thus elevated the LDLR level. Further molecular docking studies demonstrated that 4 and PCSK9 could form stable interactions via key hydrogen bonds.

| S-EPMC11480295 | biostudies-literature

Methyl 6-bromo-7-meth-oxy-1,3-benzodioxole-5-carboxyl-ate.

Project description:The non-H atoms of the title compound, C(10)H(9)BrO(5), are essentially coplanar, with the exception of the ester group [the O=C-O-C torsion angle is -143.4 (3)°].

| S-EPMC2962051 | biostudies-literature

6-Meth-oxy-meth-oxy-7-trifluoro-methyl-1,3-benzodioxole-5-carbaldehyde.

Project description:The title compound, C(11)H(9)F(3)O(5), crystallizes with three mol-ecules in the asymmetric unit. One -CF(3) group is disordered by rotation, with the F atoms split over two sets of sites with occupancies which converged to 0.888 (6) and 0.112 (6). Weak π-π inter-actions are observed between adjacent benzene rings [the shortest centroid-centroid distance is 3.8858 (4) Å], resulting in the formation of a supra-molecular chain along [100].

| S-EPMC3393257 | biostudies-literature

N'-(2-Hydr-oxy-3-methoxy-benzyl-idene)-1,3-benzodioxole-5-carbohydrazide monohydrate.

Project description:Single crystals of the title compound, C(16)H(14)N(2)O(5)·H(2)O, were obtained from a condensation reaction of 1,3-benzodioxole-5-carbohydrazide and 3-methoxy-salicylaldehyde in a 95% ethanol solution. The asymmetric unit consists of a Schiff base mol-ecule, which assumes an E configuration with respect to the C=N bond, and a water mol-ecule of crystallization. The dihedral angle between the two substituted benzene rings is 12.7 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, forming layers parallel to the bc plane.

| S-EPMC2967948 | biostudies-literature