SEARCH · PubMed Health

Results for “Isodon”

Explore indexed PubMed citations for clinical trials, systematic reviews and public health research. Read source abstracts and follow each citation to its original PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 37 records · Page 2Linked to original sources

PubMed2006

Bisrubescensins A-C: three new dimeric ent-kauranoids isolated from isodon rubescens.

[reaction: see text] A phytochemical study of the secondary metabolites produced by the species of Isodon rubescens has led to the isolation of three new dimeric ent-kauranoids and two known ones. The most important of these compounds are bisrubescensin A (1), which contains an unprecedented C(23) ent-kaurane unit, and bisrubescensin C (3), which is the precursor of bisrubescensin B (2) from the viewpoint of biosynthesis. Their structures were determined on the basis of extensive spectroscopic analysis and chemical evidence.

Antineoplastic Agents, Phytogenic↗

PubMed2006

Maoecrystal Z, a cytotoxic diterpene from Isodon eriocalyx with a unique skeleton.

[structure: see text] A novel diterpene with an unprecedented tetracyclic 6,7:8,15-di-seco-7,20-olide-6,8-cyclo-ent-kaurane skeleton, named maoecrystal Z (1), has been isolated from the leaves of a Chinese medicinal herb, Isodon eriocalyx (Labiatae). Its structure was determined by comprehensive NMR and MS spectroscopic analysis coupled with single-crystal X-ray crystallographic diffraction. Compound 1 exhibited comparable inhibitory effect against human K562 leukemia, MCF7 breast, and A2780 ovarian tumor cells with IC(50) = 2.90, 1.63, and 1.45 microg/mL and with camptothecin and paclitaxel as the positive controls.

Antineoplastic Agents, Phytogenic↗

PubMed2006

Diterpenoids from Isodon species and their biological activities.

Isodon species (Labiatae) are widely distributed plants, many of which are used in folk medicine. Over the past twenty years, they have received considerable phytochemical and biological attention. Thestructures of their many diterpenoids constituents, especially those with an ent-kaurane skeleton, have been elucidated. The significant phytochemical and pharmacological diterpenoids form the subject of this review. There are 290 references.

Diterpenes↗

PubMed2002

Cytotoxic ent-kaurane diterpenoids from Isodon sculponeata.

Four new ent-kaurane diterpenoids, sculponeatins F-I (1-4), together with six known compounds, sculponeatin E (5), epi-nodosin (6), epi-nodosinol (7), enmein (8), and macrocalyxoformins A and B (9 and 10), were isolated from the leaves of Isodon sculponeata. Also obtained were ursolic acid, 2alpha,3beta-dihydroxy-urs-12-en-28-oic acid, 2alpha,3beta,19alpha-trihydroxy-urs-12-en-28-oic acid, beta-sitosterol, daucosterol, quercetin, pedalitin, rosmarinic acid, caffeic acid and ethyl caffeic acid. Their structures were determined by spectral methods (1D-, 2D-NMR and MS). Some diterpenoids were tested for their cytotoxicity to inhibit three kinds of human tumor cells K562, A549 and T24. Compounds 3, 4, 6, 8, and 10 showed significant inhibitory effect toward K562 with IC(50) values ranging from 3.2 microg/ml to 8.2 microg/ml, while 3 and 6 exhibited potent antitumor activity against T24, but none exhibited cytotoxicity toward the cells of A549.

Antineoplastic Agents, Phytogenic↗

PubMed2002

ent-Kaurane diterpenoids from the leaves of Isodon xerophilus.

From the ethanolic extract of the leaves of Isodon xerophilus, three new ent-kaurane diterpenoids named xerophilusins L-N (1 - 3), together with three known ones designated as rabdoternin A (4), longikaurin F (5) and ponicidin (6), were isolated and structurally elucidated. Compound 6 demonstrated most potent cytotoxic activity against K562 and T24 human tumor cell lines with IC(50) = 0.09 and 0.32 microg/ml, respectively.

Antineoplastic Agents, Phytogenic↗

PubMed2003

Cytotoxic diterpenoids from Isodon enanderianus.

Five new ent-kaurane diterpenoids, enanderianins K-O (1-5), and one new ent-abietane diterpenoid, enanderianin P (6), together with five known ent-kaurane diterpenoids, rabdocoetsin A (7), rabdocoetsin B (8), rabdocoetsin D (9), megathyrin A (10), megathyrin B (11) were isolated from the aerial parts of Isodon enanderianus. Their structures were determined by spectral means. Some diterpenoids were tested for their cytotoxicity against the human tumor K562 cells. Compounds 1, 2, 6, 8, 9 showed significant inhibitory activities against K562 cells with IC50 values ranging from 0.13 to 0.87 microg/mL.

Antineoplastic Agents, Phytogenic↗

PubMed2004

Cytotoxic ent-kaurane diterpenoids from Isodon rubescens var. rubescens.

Five new ent-kauranoids, xindongnins C - G ( 1 - 5), together with five known ones, xindongnins A and B ( 6 and 7), melissoidesin G ( 8), dawoensin A ( 9), and glabcensin V ( 10), were isolated from the leaves of Isodon rubescens var. rubescens, and structurally elucidated. Compounds 1, 4, and 6 - 10 showed inhibitory effects against human tumor K562 cells with IC (50) values ranging from 0.3 to 7.3 microg/mL. The structure of 6 was revised on the basis of its 2D-NMR spectral data.

Antineoplastic Agents, Phytogenic↗

PubMed2004

A novel cytotoxic oxetane ent-kauranoid from Isodon japonicus.

A novel ll,20: 1,20-diepoxy-ent-kaurane diterpenoid, maoyecrystal 1 (1), was isolated from Isodan japonicus, and its structure was elucidated by spectroscopic methods and comparison with another new ent-kauranoid, rubescensin W (2) from Isodon rubescens var. taihangensis. The structure of 2 was determined by single crystal X-ray diffraction analysis. A bioassay of their cytotoxity against K562 cells showed that the oxetane group of 1 might be a bioactive moiety.

Antineoplastic Agents, Phytogenic↗

PubMed2006

Antiproliferative ent-Kauranoids from Isodon parvifolius.

Nine new 7alpha,20-epoxy- ENT-kaurane diterpenoids, parvifolines O - W (1 - 9), together with five known analogues, lasiocarpanin (10), rosthorin A (11), longikaurin E (12), adenolin D (13) and longikaurin B (14), were isolated from the leaves of Isodon parvifolius. Their structures were determined by means of spectroscopic analysis. Selected diterpenoids (1 - 10) were tested for their antiproliferative activity against A549, HT-29 and K562 cells. Compounds 3, 7, 8 and 10 showed moderate inhibitory activity against all three cell lines.

Antineoplastic Agents, Phytogenic↗

PubMed2004

Cytotoxic ent-kauranoids from Isodon leucophyllus.

Two new compounds, baiyecrystals D and E (1, 2), together with eight known analogues, xerophilusin B (4), macrocalin B (5), oridonin (6), rosthorin A (7), lasiocarpanin (8), rabdoternin A (9) and phyllostachysin A (10) and B (11), were isolated from the aerial parts of Isodon leucophyllus. The structures of 1 and 2 and 4-11 were elucidated on the basis of spectroscopic methods, especially the 2D NMR spectral analysis. Compounds 2, 6-8 and 10 were evaluated for their antineoplastic activities in vitro. Among them, lasiocarpanin (8) showed significant inhibitory activities against K562 and Bcap37 cells, with the IC50 values of 0.13 and 1.26 microg mL(-1), respectively, which were lower than those of the positive control.

Antineoplastic Agents, Phytogenic↗

PubMed2005

Ent-kauranoids from Isodon rubescens var. taihangensis.

Two new compounds, rubescensins Q and R (1 and 2), and a new acetonide derivative (3) of lasiodonin, together with thirteen known analogues, oridonin (4), ponicidin (5), wikstroemioidin B (6), lasiodonin (7), lasiokaurin (8), enmenol (9), 1-O-beta-D-glucopyranosyl-enmenol (10), trichokaurin (11), the acetonide of maoyecrystal F (12), rabdoternins A-D (13-16), have been isolated from Isodon rubescens var. taihangensis. The structures of the new compounds were elucidated on the basis of spectroscopic methods, especially the 2D NMR spectral analysis. Compound 3 exhibited cytotoxicity against K562, Bcap37, CA, CNE, BIU87, BGC823, and HeLa cell lines.

Antineoplastic Agents, Phytogenic↗

PubMed2005

Three new compounds from Isodon melissoides.

Reinvestigation of the aerial parts of Isodon melissoides has afforded two new ent-diterpenoids, melissoidesins V (1) and W (2), together with five known ones, glabcensin W (3), melissoidesin C (4), melissoidesin A (5), melissoidesin B (6) and melissoidesin D (7), one new ionone derivative 3alpha,4alpha-isopropyliden-beta-ionol (8), as well as three analogues, 3-hydroxy-4-oxo-beta-ionol (9), megastigma-7-en-3,5,6,9-tetraol (10) and blumenol A (11), and three phenolic compounds salicylic acid (12), syringic acid (13) and cirsiliol (14). The new structures were elucidated on the basis of spectroscopic techniques, especially the 2D-NMR spectral analysis.

Chromatography, Gel↗

PubMed2006

Two new rearranged abietane diterpenoids from tropical Isodon coetsa.

Two new rearranged abietane diterpenoids, sincoetsin A (1) and sincoetsin B (2), were isolated from the aerial part of Isodon coetsa (Buth-Ham ex D.Don) Hara collected in Singapore, and their structures were determined by spectroscopic methods, especially 2D NMR techniques.

Abietanes↗

PubMed2004

Isodon japonicus inhibits mast cell-mediated immediate-type allergic reactions.

The effect of aqueous extract of Isodon japonicus Hara (Labiatae) (IJAE) on mast cell-mediated immediate-type allergic reactions was investigated. IJAE inhibited systemic allergic reaction induced by compound 48/80. When IJAE was pretreated at the same concentrations with systemic allergic reaction test, the plasma histamine levels were reduced in a dose-dependent manner. IJAE also inhibited local allergic reaction activated by anti-dinitrophenyl (DNP) IgE antibody. IJAE dose-dependently inhibited the histamine release from rat peritoneal mast cells (RPMC) activated by compound 48/80 or anti-DNP IgE. IJAE inhibited the secretion of tumor necrosis factor-alpha (TNF-alpha) and interleukin (IL)-6 in phorbol 12-myristate 13-acetate (PMA) plus calcium ionophore A23187-stimulated human mast cell line (HMC-1) cells. In addition, the expression of TNF-alpha mRNA in HMC-1 cells was inhibited by IJAE. These results indicate that IJAE may be beneficial in the regulation of immediate-type allergic reaction.

Animals↗

PubMed2006

A novel synthetic analogue of a constituent of Isodon excisus inhibits transcription of CYP1A1, -1A2 and -1B1 by preventing activation of the aryl hydrocarbon receptor.

We investigated the effect of a novel synthetic analogue of a constituent from the Chinese medicinal herb Isodon excisus, 3-(3-methoxy-phenyl)-N-(3, 4, 5-trimethoxy-phenyl)-acrylamide (compound 343), on the carcinogen activation pathway mediated by the aryl hydrocarbon receptor (AhR) in human hepatoma HepG2 cells. We found that compound 343 inhibited the upregulation of cytochrome P-450 (CYP) enzyme activity in cells treated with the AhR ligands and potent carcinogens, dimethylbenz[a]anthracene (DMBA) or 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD). Compound 343 also inhibited the DMBA- or TCDD-induced increase in CYP1A1, -1A2 and -1B1 mRNA levels. Carcinogen-induced transcription of CYP genes was also suppressed by compound 343, as measured by a reporter gene controlled by the xenobiotic-responsive element (XRE). This was confirmed by measuring the amount of carcinogen-induced CYP1A1 heterogeneous nuclear RNA. Compound 343 blocked the DMBA- or TCDD-induced activation of the AhR DNA-binding capacity for the XRE, as measured by a chromatin immunoprecipitation assay. Compound 343 also inhibited CYP enzyme activity in microsomes isolated from DMBA- or TCDD-treated cells, as well as the activity of recombinant CYP1A1, -1A2 and -1B1, indicating that compound 343 directly inhibits CYP enzymes. These results indicate that compound 343 is both a potent inhibitor of carcinogen-induced CYP enzyme expression, as well as a direct inhibitor of CYP enzymes.

9,10-Dimethyl-1,2-benzanthracene↗

PubMed2005

Novel mechanism of inhibition of nuclear factor-kappa B DNA-binding activity by diterpenoids isolated from Isodon rubescens.

The development of specific inhibitors that can block nuclear factor-kappaB (NF-kappaB) activation is an approach for the treatment of cancer, autoimmune, and inflammatory diseases. Several diterpenoids, oridonin, ponicidin, xindongnin A, and xindongnin B were isolated from the herb Isodon rubescens. These compounds were found to be potent inhibitors of NF-kappaB transcription activity and the expression of its downstream targets, cyclooxygenase-2 and inducible nitric-oxide synthase. The mechanisms of action of the diterpenoids against NF-kappaB are similar, but significant differences were also identified. All of the diterpenoids directly interfere with the DNA-binding activity of NF-kappaB to its response DNA sequence. Oridonin and ponicidin have an additional impact on the translocation of NF-kappaB from the cytoplasm to nuclei without affecting IkappaB-alpha phosphorylation and degradation. The effect of these compounds on the interaction of NF-kappaB with consensus DNA sequences is unique. Different inhibitory effects were observed when NF-kappaB bound to various DNA sequences. Both p65/p65 and p50/p50 homodimers, as well as p65/p50 heterodimer association with their responsive DNA, were inhibited. Kinetic studies on NF-kappaB-DNA interaction indicate that the diterpenoids decrease the B(max app) but have no effect on K(d app). This suggests that this class of compounds interacts with both p65 and p50 subunits at a site other than the DNA binding site and subsequently modulates the binding affinity of the transcription factor toward DNA with different NF-kappaB binding sequences. The diterpenoid structure could therefore serve as a scaffold for the development of more potent and selective NF-kappaB inhibitors that target regulated gene transcription.

Animals↗

PubMed2004

Isodon japonicus decreases immediate-type allergic reaction and tumor necrosis factor-alpha production.

BACKGROUND: The immediate-type allergic reaction is involved in many allergic diseases such as asthma, allergic rhinitis and sinusitis. The discovery of drugs for the treatment of immediate-type allergic disease is a very important subject in human health. Isodon japonicus Hara (Labiatae) (IJAE) has been used for centuries as a traditional medicine in Korea and is known to have an anti-inflammatory effect. However, its specific mechanism of action is still unknown. In this report, we investigated the effect of IJAE on the immediate-type allergic reaction and studied its possible mechanisms of action, focusing on the mast cell-mediated allergic reaction. METHODS: IJAE extracts were anally administered to mice for high and fast absorption. Compound 48/80-induced mortality and compound 48/80- or immunoglobulin E (IgE)-induced histamine release were measured to evaluate the antiallergic effects of IJAE. The effect of IJAE on the model of local allergic reaction in vivo, passive cutaneous anaphylaxis (PCA), was investigated. The production of tumor necrosis factor-alpha (TNF-alpha) was measured by Western blotting. RESULTS: IJAE inhibited compound 48/80-induced systemic reactions and plasma histamine release in mice. IJAE decreased the PCA reaction activated by anti-dinitrophenyl (DNP) IgE antibody. IJAE dose-dependently reduced histamine release from rat peritoneal mast cells activated by compound 48/80 or anti-DNP IgE. Furthermore, IJAE decreased the production of TNF-alpha in phorbol 12-myristate 13-acetate plus calcium ionophore A23187-stimulated human mast cells. CONCLUSION: Our findings provide evidence that IJAE inhibits mast cell-derived immediate-type allergic reactions, and also demonstrate the involvement of TNF-alpha in these effects. We propose the clinical use of IJAE in mast cell-mediated immediate-type allergic diseases.

Administration, Rectal↗

PubMed2003

Four new diterpenoids from Isodon melissoides.

Three new 11beta,16beta-epoxy-ent-kauranoids melissoidesins I-K (1-3) and one new ent-abietanoid melissoidesin L (4) were obtained from the aerial parts of Isodon melissoides (BENTHAM) H. HARA, their structures were established on the basis of the spectral methods, especially two dimensional (2D) NMR spectroscopy.

Diterpenes↗