Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Three New Indole Alkaloids from Tabernaemontana divaricata.

ABSTRACT: Three new monoterpene indole alkaloids, 3?-hydroxymethyl-ibogamine (1), 3?-acetatemethoxyl-ibogamine (2), 16?-hydroxyl-ibogamine (3) together with six known alkaloids were isolated from the branches and leaves of Tabernaemontana divaricata (Apocynaceae). The structures of these alkaloids were determined by spectroscopic analyses. All isolated compounds showed no significant cytotoxicity against SGC-7901 gastric cancer, HeLa, and A-549 lung cancer cell lines (IC50 > 20 µM).

SUBMITTER: Deng Y

PROVIDER: S-EPMC5971036 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Three New Indole Alkaloids from Tabernaemontana divaricata.

Deng Yan Y Bao Mei-Fen MF Shi Bao-Bao BB Wu Jing J Cai Xiang-Hai XH

Natural products and bioprospecting 20180512 3

Three new monoterpene indole alkaloids, 3α-hydroxymethyl-ibogamine (1), 3α-acetatemethoxyl-ibogamine (2), 16α-hydroxyl-ibogamine (3) together with six known alkaloids were isolated from the branches and leaves of Tabernaemontana divaricata (Apocynaceae). The structures of these alkaloids were determined by spectroscopic analyses. All isolated compounds showed no significant cytotoxicity against SGC-7901 gastric cancer, HeLa, and A-549 lung cancer cell lines (IC50 > 20 µM). ...[more]

PMID: 29754315

Similar Datasets

New Iboga-Type Indole Alkaloids from Tabernaemontana divaricata.

Project description:Two hitherto unknown iboga-type indole alkaloids, namely (3R)-7,19-di-epi-3-methoxytabernoxidine (1) and (3R,19R)-19-hydroxy-3-(2-oxopropyl)voacangine (2), together with eight known alkaloids (3-10), were isolated from the twigs and leaves of Tabernaemontana divaricata. Their structures were established on the basis of spectroscopic data interpretation, single crystal X-ray diffraction analysis and circular dichroism spectrum.

| S-EPMC6872691 | biostudies-literature

Three new indole alkaloids from Rauvolfia yunnanensis

Project description:One rare tetracyclic macroline-type indole alkaloid, named rauvoyunine A (1), and two new picraline-type alkaloids rauvoyunines B and C (2 and 3) were isolated from the aerial parts of Rauvolfia yunnanensis. Their structures were elucidated on the basis of extensive spectroscopic analysis. Compounds 2 and 3 were evaluated for their in vitro cytotoxicity against five human tumor cell lines. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-011-0023-7 and is accessible for authorized users.

| S-EPMC4131643 | biostudies-literature

Two new bisindole alkaloids from Tabernaemontana macrocarpa Jack.

Project description:Two new bisindole alkaloids, bisnaecarpamines A (1) and B (2), possessing a vobasine-sarpagine type skeleton were isolated from the bark of Tabernaemontana macrocarpa Jack. Their structures were elucidated by extensive spectroscopic methods and chemical correlation. The absolute configurations of compounds 1 and 2 were established using TDDFT-ECD calculation of the selected isomers. Bisnaecarpamine A exhibited potent antimalarial activity against Plasmodium falciparum 3D7 strain with IC50 value of 28.8 µM.

| S-EPMC8021936 | biostudies-literature

New Monoterpenoid Indole Alkaloids from Tabernaemontana crassa Inhibit β-Amyloid42 Production and Phospho-Tau (Thr217).

Project description:Eleven monoterpenoid indole alkaloids, including three new ones, tabercrassines A-C (1-3), were isolated from the seeds of Tabernaemontana crassa. Tabercrassine A (1) is an ibogan-ibogan-type bisindole alkaloid which is formed by the polymerization of two classic ibogan-type monomers through a C3 unit aliphatic chain. Their structures were established by extensive analysis of HRESIMS, NMR, and ECD spectra. Cellular assays showed that alkaloids 1-3 all reduce Aβ42 production and inhibit phospho-tau (Thr217), a new biomarker of Alzheimer's disease [AD] associated with BACE1-, NCSTN-, GSK3β-, and CDK5-mediated pathways, suggesting these alkaloids' potential against AD.

| S-EPMC9862887 | biostudies-literature

Virtual Screening of compounds from Tabernaemontana divaricata for potential anti-bacterial activity.

Project description:Virtual Screening and Molecular Docking analysis for Tabernaemontana divaricata derived 66 Law Molecular Weight Compounds (LMW) was conducted and to identified and predicted novel molecules as a inhibitor of Streptococcus pneumonia. The investigation has revealed several compounds with optimum binding towards Penicillin-binding proteins, Sialidases, Aspartate betasemialdehide dehydrogenase cell membrane protein of Streptococcus pneumonia. Docking results were computed in term of binding energy, ligand efficiency and number of hydrogen bonding. Apparicine (-5.14), 5-Hydroxyvoaphylline (-4.78), Voacangine (-4.7), 19-Hydroxycoronaridine (-4.44) and Coronaridine (-4.72) are identified as most suitable to bind with N-acetylglucosamine-1- phosphate uridyltransferase receptor. Ervaticine (-6.33), Ibogamine (-6.15), Methylvoaphylline (-5.74) and Coronaridine hydroxyindolenine (-5.32) has showed novel binding against the penicillin-binding proteins. Ervaticine (-6.42), 5-oxo-11-hydroxy voaphylline (-6.18), Conolobine B (-6.02) has found optimum binding against the active site of NanB sialidase of Streptococcus pneumonia. The compounds 3S-Cyanocoronaridine (-6.71), 19-Epivoacristine (-5.48) and Ervaticine(-5.45) interacting with aspartate beta-semialdehide and found suitable with least docking score.

| S-EPMC3974242 | biostudies-literature

Four new indole alkaloids from Plantago asiatica

Project description:Graphical abstract Four new indole alkaloids, plasiaticines A-D (1–4), together with two known ones, were isolated from the seeds of Plantago asiatica. The structures of the new compounds were elucidated on the basis of comprehensive analysis of spectroscopic data. All compounds were tested for their cytotoxic activity, and all compounds except 4 were tested for their acetylcholinesterase (AChE) inhibitory activities. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-012-0082-4 and is accessible for authorized users.

| S-EPMC4131610 | biostudies-literature

Three New Quinazoline-Containing Indole Alkaloids From the Marine-Derived Fungus Aspergillus sp. HNMF114.

Project description:By feeding tryptophan to the marine-derived fungus Aspergillus sp. HNMF114 from the bivalve mollusk Sanguinolaria chinensis, 3 new quinazoline-containing indole alkaloids, named aspertoryadins H-J (1-3), along with 16 known ones (4-19), were obtained. The structures of the new compounds were elucidated by the analysis of spectroscopic data combined with quantum chemical calculations of nuclear magnetic resonance (NMR) chemical shifts and electron capture detector (ECD) spectra. Structurally, compound 3 represents the first example of this type of compound, bearing an amide group at C-3. Compounds 10 and 16 showed potent α-glucosidase inhibitory activity with IC50 values of 7.18 and 5.29 μM, and compounds 13 and 14 showed a clear activation effect on the ryanodine receptor from Spodoptera frugiperda (sfRyR), which reduced the [Ca2+] ER by 37.1 and 36.2%, respectively.

| S-EPMC8206283 | biostudies-literature

Rauvotetraphyllines A-E, new indole alkaloids from Rauvolfia tetraphylla

Project description:Five new indole alkaloids rauvotetraphyllines A–E (1–5), together with eight known analogues, were isolated from the aerial parts of Rauvolfia tetraphylla. The structures were established by means of spectroscopic methods. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-012-0012-5 and is accessible for authorized users.

| S-EPMC4131588 | biostudies-literature

Taburnaemines A-I, Cytotoxic Vobasinyl-Iboga-Type Bisindole Alkaloids from Tabernaemontana corymbosa.

Project description:Nineteen vobasinyl-ibogan-type bisindole alkaloids, including nine new compounds, taburnaemines A-I (1-9), were isolated from the twigs and leaves of Tabernaemontana corymbosa. The structures and absolute configurations of the new alkaloids were determined by a combination of MS, NMR, and ECD analyses. Alkaloids 1-5 contain a rare 1,3-oxazinane moiety in the vobasinyl unit, while 6 has an uncommon 1,3-oxazolidine moiety in the iboga unit. The absolute configurations of alkaloid 1 and the known alkaloid tabernaecorymbosine A (10) were confirmed by single-crystal X-ray diffraction analysis. All of the bisindole alkaloids, except 2 and 16'-decarbomethoxytabernaecorymbosine A (14), showed antiproliferative activity (IC50 2.6-9.8 μM) against several human cancer cell lines, including A-549, MDA-MB-231, MCF-7, KB, and P-glycoprotein-overexpressing multidrug-resistant KB cells. The preliminary structure-activity relationship correlations are also discussed.

| S-EPMC7446768 | biostudies-literature

Discovery of Three New Monoterpenoid Indole Alkaloids from the Leaves of Gardneria multiflora and Their Vasorelaxant and AChE Inhibitory Activities.

Project description:Three novel monoterpenoid indole alkaloids gardflorine A (1), gardflorine B (2), and gardflorine C (3) were isolated from the leaves of Gardneria multiflora. Their structures, including absolute configurations, were established on the basis of spectroscopic methods (MS, UV, IR, 1D and 2D NMR) and circular dichroism experiments. All the compounds were evaluated for their vasorelaxant and acetylcholinesterase (AChE) inhibitory activities. Compound 1 exhibited potent vasorelaxant activity, with an EC50 value of 8.7 μM, and compounds 2 and 3 showed moderate acetylcholinesterase (AChE) inhibitory activities, with IC50 values of 26.8 and 29.2 μM, respectively.

| S-EPMC8659093 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data