Browse
Submit Data
Databases
API
Help

Dataset Information

16 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Four new diterpenoids from Isodon eriocalyx var. laxiflora

ABSTRACT: Four new diterpenoids, laxiflorins S-V (1–4), bearing four different types, and one known compound, laxiflorin O (5), were isolated from Isodon eriocalyx var. laxiflora. Compound 1 was the first example of ent-kauranoids bearing a unique C24 carbon framework and compound 4 was the first example of 3,4-seco-ent-abietane diterpenoids from the Isodon genus. Their structures were determined by spectroscopic methods (UV, IR, MS, NMR).

Electronic Supplementary Material

Supplementary material is available for this article at 10.1007/s13659-013-0057-0 and is accessible for authorized users.

SUBMITTER: Wang W

PROVIDER: S-EPMC4131582 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Isorosthornins A-C, new ent-kaurane diterpenoids from Isodon rosthornii

Project description:Three new ent-kauranoids, isorosthornins A-C (1–3), and a new natural product, dihydroponicidin (4), together with five known ones were isolated from the aerial parts of Isodon rosthornii. The structures were determined by means of extensive spectroscopic analysis. All diterpenoids isolated were evaluated for their cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines, and compounds 5 and 7 showed significant inhibitory effects on all cell lines. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-011-0031-7 and is accessible for authorized users.

| S-EPMC4131646 | biostudies-literature

Rubesanolides A and B: diterpenoids from Isodon rubescens.

Project description:From the medicinal plant Isodon rubescens, we isolated two novel diterpenes, rubesanolides A (1) and B (2). The compounds contain a unique β-lactone subgroup. This is the first discovery for a natural diterpene having rings A, B, and C in chair, boat, and twist-chair conformations, respectively. The structures were elucidated by analysis of spectroscopic data, and the absolute configuration of 1 was determined by X-ray diffraction.

| S-EPMC3057937 | biostudies-literature

Four New ent-Kaurane Diterpene Glycosides from Isodon henryi.

Project description:To obtain diterpene glycosides from an aqueous extract of the aerial parts of Isodon henryi and further investigate their cytotoxicities, in this study, a total of seven compounds were isolated, including six ent-kaurane diterpene glycosides (1-6) and one diterpene aglycon (7). Among the seven ent-kaurane diterpenes obtained, four were novel compounds, including ent-7,20-epoxy- kaur-16-en-1α,6β,7β,15β-tetrahydroxyl-11-O-β-d-glucopyranoside (1), ent-7,20-epoxy-kaur-16-en- 6β,7β,14β,15β-tetrahydroxyl-1-O-β-d-glucopyranoside (2), ent-7,20-epoxy-kaur-16-en-6β,7β,15β- trihydroxyl-1-O-β-d-glucopyranoside (3), and ent-7,20-epoxy-kaur-16-en-7β,11β,14α,15β-tetrahydr- oxyl-6-O-β-d-glucopyranoside (4), and three were isolated from this plant for the first time (5-7). Their structures were elucidated by utilizing spectroscopic methods and electronic circular dichroism analyses. Furthermore, the cytotoxicities of all seven compounds were investigated in four human cancer cell lines, including A2780, BGC-823, HCT-116, and HepG2. The IC50 values of these diterpenes ranged from 0.18 to 2.44 mM in the tested cell lines. In addition, the structure-cytotoxicity relationship of diterpene glycosides was also evaluated to study the effect of glycosylation on the cytotoxicity of diterpene compounds.

| S-EPMC6695894 | biostudies-literature

An ent-kaurane diterpenoid from Isodon japonica var. glaucocalyx.

Project description:The title compound, 14?-acet-oxy-7?-hydr-oxy-ent-kaur-16-ene-3,15-dione or glaucocalyxin B, C(22)H(30)O(5), a natural ent-kaurane diterpenoid, is composed of four rings with the expected cis and trans ring junctions. In the crystal structure, there are two mol-ecules in the asymmetric unit related by a noncrystallographic twofold screw axis, and ring A is disordered [ratio occupancies 0.829?(19):0.171?(19)], such that both chair and boat conformations are present, but with the boat conformation as the major component. In the crystal, mol-ecules are linked by inter-molecular O-H?O hydrogen bonds.

| S-EPMC2977125 | biostudies-other

Four new briarane diterpenoids from Taiwanese gorgonian Junceella fragilis.

Project description:Four new 8-hydroxybriarane diterpenoids, frajunolides P-S (1-4), together with umbraculolide A, juncenolide C, junceellonoid A and juncin R, were isolated from the acetone extract of the gorgonian Junceella fragilis, collected from the southeast coast of Taiwan. Compound 1 contains an unusual pivaloyloxy group at C-2, while 3 is a rare compound having a chlorine atom on the olefinic carbon (C-6). The structures of the isolated compounds were established by extensive spectroscopic analysis, including 1D- and 2D-NMR, as well as HRMS data. Compound 1 was further confirmed by X-ray crystallographic analysis. In the anti-inflammatory test, compounds 1 and 2 exhibited moderate inhibition on superoxide anion generation and elastase release by human neutrophils in response to formylmethionylleucyl-phenylalanine/dihydrocytochalasin B (fMLP/CB).

| S-EPMC3721220 | biostudies-literature

Aspidoptoids A-D: Four New Diterpenoids from Aspidopterys obcordata Vine.

Project description:Four new diterpenoids, named aspidoptoids A-D (1-4), together with two known analogues (5-6) were isolated from Aspidopterys obcordata vine. Aspidoptoids A-B (1-2) are the first examples of phenylethylene-bearing 20-nor-diterpenoids of which aspidoptoid B (2) possesses a rare 3,10-oxybridge. Their structures and absolute configuration were determined by extensive spectroscopic analyses (IR, HRESIMS, 1D and 2D NMR) and electronic circular dichroism (ECD) calculation. In addition, all the isolates were evaluated for their cytotoxic activities and inhibitory effects on the nitric oxide (NO) production.

| S-EPMC7036900 | biostudies-literature

Diterpenoids from <i>Isodon rubescens</i> and their nitric oxide production inhibitory activity.

Project description:Six new ent-kaurane diterpenoids, isodonrubescins A-F (1-6), together with twenty-five known ent-kaurane diterpenoids (7-31), a known ent-atisane diterpenoid (32), and two known ent-abietane diterpenoids (33-34), were isolated from Isodon rubescens. Their structures were established by means of extensive MS and NMR data analysis. Among the all isolates, compound 7 was found in a natural product for the first time, and ent-atisane diterpenoid was discovered from I. rubescens in Hubei Province, P. R. China for the first time. Furthermore, all the isolated compounds were tested for their NO production inhibitory activity in LPS stimulated RAW264.7 cells. Compounds 7-9, 12, 13, 16, and 17 displayed NO production inhibitory activities with IC50 values ranging from 1.36 to 18.25 μM, respectively.

| S-EPMC9076279 | biostudies-literature

Frajunolides L-O, four new 8-Hydroxybriarane diterpenoids from the Gorgonian Junceella fragilis.

Project description:Four new 8-hydroxybriarane diterpenoids, frajunolides L-O (1-4), were isolated from the Taiwanese gorgonian Junceella fragilis. The structures of compounds 1-4 were elucidated based on spectroscopic analysis, especially 2D NMR ((1)H-(1)H COSY, HSQC, HMBC and NOESY) and HRMS. Compounds 1 and 4 showed weak anti-inflammatory activity as tested by superoxide anion generation and elastase release by human neutrophil in response to fMLP/CB. Compound 3 showed selective inhibition on elastase release in vitro.

| S-EPMC3225929 | biostudies-literature

Functional diversified kaurene synthase like genes in Isodon rubescens shed light on chemical diversity evolution of diterpenoids in Lamiaceae

Project description:The Lamiaceae family contains numerous diterpenoids, offering a valuable model system for the study of diterpenoid chemical diversity. In this study we report that the ent-kaurene diterpenoids in I. rubescens have the largest diTPS gene family identified in Lamiaceae. Three genes are predicted to be involved in ent-kaurene diterpenoid synthesis while another two KSL genes are functional enzymes utilizing ent-CPP as a substrate. We also showed the presence of a normal-CPP mediated biosynthesis pathway in I. rubescens and that three KSL genes possessing different domain architectures are involved in this pathway. This study provides new information regarding the understanding of diterpenoid chemical diversity and this compounds’ evolution in the Lamiaceae family.

2017-09-08 | GSE96954 | GEO

Four new lignans from the leaves and stems of Schisandra propinqua var. sinensis

Project description:Four new tetrahydrofuran lignans, schpropinrins A-D (1–4), together with five known ones, were isolated from the leaves and stems of Schisandra propinqua var. sinensis. Their structures, including absolute configurations, were characterized by means of spectroscopic analysis and ECD calculation. Compounds 1–4 featured a ketal or hemiketal substructure at C-7 and all of the isolates were tested for their anti-HIV integrase activity. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-013-0017-8 and is accessible for authorized users.

| S-EPMC4131657 | 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