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At least 19 recordsLinked to original sources

PubMed2005

Cytotoxic clerodane diterpenes from Glossocarya calcicola.

Three clerodane diterpenes were isolated and identified from leaf extract of Glossocarya calcicola. Compound has been characterised as (rel)-10betaH-trans-12xi-(2-methylbut-2(E)-enoyl)-1beta-(isobutanoyl)-6alpha,13xi-dihydroxyclerodan-4(20),8(18)-dien-7,15-dione-15,16-oxide, to which we have assigned the trivial name calcicolin-A. The other two compounds had the same skeletal structure and C-12 substituent but in compound, the C-1 esterifying group becomes 2-methylbut-2(E)-enoic acid and in it becomes 2-methylbutanoic acid. Although anti-insect activity was not observed for G. calcicola, cytotoxicity against insect and human carcinoma cell lines was detected.

Animals↗

PubMed2000

Cytotoxic clerodane diterpene esters from Laetia corymbulosa.

Three cytotoxic clerodane diterpene esters, corymbulosins A-C, were isolated from an organic extract of the fruit of Laetia corymbulosa (Flacourtiaceae) from Peru. The structures were determined by spectroscopic methods as clerodane diterpenes unsaturated at C-3, C-13(16) and C-14. Corymbulosin A was esterified at C-2 with a decadienoate moiety, while corymbulosins B and C were C-2 epimers esterified at C-6 with a decanoate moiety.

Antineoplastic Agents, Phytogenic↗

PubMed2006

Neo-clerodane diterpenes from the hallucinogenic sage Salvia divinorum.

Seven new neo-clerodane diterpenes, salvidivins A (2), B, (3), C (4), and D (5), salvinorins H (6) and I (7), and divinatorin [corrected] F (8), along with eight known neo-clerodane diterpenes, salvinorins A (1)-F, divinatorins A and B, and seven other constituents, were isolated from the hallucinogenic sage Salvia divinorum. The structures of 1-7 were elucidated on the basis of 2D NMR spectroscopic studies.

Diterpenes, Clerodane↗

PubMed2003

A new ent-clerodane diterpene from the aerial parts of Baccharis gaudichaudiana.

A new ent-clerodane diterpene, named bacchariol (1) was isolated from the aerial parts of Baccharis gaudichaudiana DC. (Compositae), together with known ent-clerodane diterpenes (2, 3), eight known flavonoids (4-11) and 3, 5-dicaffeoylquinic acid (12). Their structures were determined by spectroscopic analyses. Flavonoids (7, 8, 11) and 12 showed moderate scavenging activities toward 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radicals.

Baccharis↗

PubMed2001

New rearranged clerodane diterpenes from Tinospora baenzigeri.

Baenzigeroside B, a new rearranged clerodane diterpene glucoside, was isolated from the stems of Tinospora baenzigeri. The aglycone of baenzigeroside B, baenzigeride B (isolated as its acetate), was found together with baenzigeride A, baenzigerosides A and B in the leaves of the same plant. Baenzigeride B and baenzigeroside B are the first examples of a new class of rearranged clerodane diterpenes. The possible biogenesis of the compounds is discussed.

Acetylation↗

PubMed1999

Investigation of genotoxic activity of trans-dehydrocrotonin, a clerodane diterpene from Croton cajucara.

The genotoxic action of three doses of trans-dehydrocrotonin (t-DCTN), an active ingredient obtained from the bark extracts of an Amazon native plant, Croton cajucara, were examined in Swiss mouse bone marrow cells in vivo, submitted to acute intraperitoneal treatment, by micronucleus (MN) and chromosomal aberration (CA) tests. The statistical tests (Anova and Tukey) made to compare the results obtained in each of the three doses of t-DCTN with the negative-control group showed that the frequencies of MN and mitotic index were equal to the negative-control and that the frequencies of CA were lower than that observed in the negative-control. Therefore, based on our results it can be said that t-DCTN is not genotoxic nor cytotoxic to mouse bone marrow cells, submitted to acute intraperitoneal treatment in vivo. Teratogenesis Carcinog. Mutagen. 19:377-384, 1999.

Animals↗

PubMed1999

Anti-tumour activity of two 19-nor-clerodane diterpenes, trans-dehydrocrotonin and trans-crotonin, from Croton cajucara.

The effects of two nor-diterpenes, trans-dehydrocrotonin (DCTN) and trans-crotonin (CTN) from Croton cajucara (Euphorbiaceae), on the survival of mice bearing Sarcoma 180 and Ehrlich carcinoma ascitic tumours, on the proliferation of cultured Ehrlich cells and TNF alpha activity were determined. When the mice were treated with 80 and 120 mg/kg of DCTN or 38 mg/kg of 5-FU a significant anti-tumour activity was obtained (%T/C of 128-140). The cytotoxicity against Ehrlich carcinoma was 16 microM for DCTN and CTN whereas the flavonoid quercetin was cytotoxic at 44 microM in 48 h cell culture. No apoptosis was seen on in vitro electrophoresis of DNA extracted from the tumour cells treated with DCTN and CTN. A significant TNF alpha activity was detected in Ehrlich tumour-bearing mice treated with DCTN suggesting an enhanced immune function.

Animals↗

PubMed2001

Effect of trans-dehydrocrotonin, a 19-nor-clerodane diterpene from Croton cajucara on experimental hypertriglyceridaemia and hypercholesterolaemia induced by Triton WR 1339 (tyloxapol) in mice.

The effect of trans-dehydrocrotonin (t-DCTN) from Croton cajucara Benth. was investigated in mice on Triton WR 1339 (tyloxapol)-induced hypercholesterolaemia and hypertriglyceridaemia. Mice treated with single application of tyloxapol (400 mg/kg, i.p.) demonstrated significantly increased blood levels of total cholesterol and triglycerides at 24 h and 48 h after its injection, compared to normal controls. These increases were found to be markedly suppressed in animals treated orally with 25 and 50 mg/kg t-DCTN or 100 mg/kg gemfibrozil, an established antihypercholesterolaemic drug. These results suggest that t-DCTN may be a suitable candidate for combating pathologies associated with hyperlipaemia.

Animals↗

PubMed2001

Antigenotoxicity of trans-dehydrocrotonin, a clerodane diterpene from Croton cajucara.

The antigenotoxic action of three doses of trans-dehydrocrotonin (t-DCTN), the active ingredient obtained from the bark extract of Croton cajucara, a plant native to the Amazon, was determined in Swiss mice in vivo. Mice were submitted to acute intraperitoneal and gavage treatments, then their bone marrow cells were subsequently analyzed by micronucleus (MN) and chromosome aberration (CA) assays. Comparisons were performed between the three doses of t-DCTN and the negative-control group. Statistical analysis indicated that doses of 50 and 75 % of the LD(50), via intraperitoneal treatment or gavage injection, were antimutagenic with regard to cyclophosphamide. However, the dose of 25 % of the LD(50) was only antimutagenic when administered by gavage. Based on these observations, it can be suggested that gavage is the most effective method of administering t-DCTN. In addition, t-DCTN showed no cytotoxic effects in the bone marrow cells regardless of the route of exposure.

Animals↗

PubMed1996

Investigation of anti-inflammatory and antinociceptive activities of trans-dehydrocrotonin, a 19-nor-clerodane diterpene from Croton cajucara. Part 1.

The anti-inflammatory and antinociceptive effects of trans-dehydrocrotonin, isolated from the bark of Croton cajucara (Euphorbiaceae), were investigated using several animal models. The trans-dehydrocrotonin produced a significant inhibition of carrageenin-induced paw edema and cotton pellet granuloma in rats. It also inhibited the writhings in mice induced by acetic acid, but did not show a significant effect in the hot-plate test in mice. The LD50 of t-DCTN was 555.0 mg/kg (p.o.) for mice.

Analgesics↗

PubMed2003

A new clerodane diterpene with antifeedant activity from Teucrium tomentosum.

A new diterpene, viz. 3beta-acetoxy-4alpha,18:15,16-diepoxy-6beta,12-dihydroxyneocleroda-13(16),14-dien-19,20-olide, C(22)H(28)O(8), exhibiting antifeedant activity against Spodoptera litura was isolated from the aerial parts of Teucrium tomentosum and its structure is reported. One of the two fused rings has a distorted-chair conformation and the other has a chair conformation. The molecules in the crystal are stabilized via O--H...O and C--H...O hydrogen bonds.

Animals↗

PubMed1994

Cytotoxic clerodane diterpenes from Polyalthia barnesii.

Three cytotoxic clerodane diterpenes were purified from an ethyl acetate-soluble extract of the stem bark of Polyalthia barnesii, namely, 16 alpha-hydroxycleroda-3,13(14)Z-dien-15,16-olide, a known compound, and two novel compounds, 3 beta, 16 alpha-dihydroxycleroda-4(18),13(14)Z-dien-15,16-olide and 4 beta, 16 alpha-dihydroxyclerod-13(14)Z-en-15,16-olide. These compounds were found to exhibit broad cytotoxicity against a panel of human cancer cell lines.

Antineoplastic Agents, Phytogenic↗

PubMed2004

ent-Clerodane diterpenes and other constituents from the liverwort Adelanthus lindenbergianus (Lehm.) Mitt.

Eleven ent-clerodanes, 13-hydroxy-cis-ent-cleroda-3,14-diene, 15-hydroxy-cis-ent-cleroda-3,13(E)-diene, 1beta,12:15,16-diepoxy-cis-ent-cleroda-13(16),14-dien-18alpha,6alpha-olide, 8beta,12:15, 16-diepoxy-cis-ent-cleroda-13(16),14-dien-18alpha,6alpha-olide, 1beta,16:15,16-diepoxy-cis-ent-cleroda-12,14-dien-18alpha,6alpha-olide, 7beta,12:8beta,12-diepoxy-15-hydroxy-cis-ent-cleroda-13-en-16,15:18alpha,6alpha-diolide, 7beta,12:8beta,12-diepoxy-16-hydroxy-cis-ent-cleroda-13-en-15,16:18alpha,6alpha-diolide, 1alpha-acetoxy-8beta,12-epoxy-15-hydroxy-cis-ent-cleroda-13-en-16,15:18alpha,6alpha-diolide, 1beta,12-epoxy-16-hydroxy-cis-ent-cleroda-13-en-15,16:18alpha,6alpha-diolide, 8beta,12-epoxy-15-hydroxy-trans-cleroda-13-en-16,15:18alpha,6alpha-diolide, 8beta,12-epoxy-16-hydroxy-trans-cleroda-13-en-15,16:18alpha,6alpha-diolide along with the known clerodane diterpenes anastreptin and orcadensin have been isolated from the liverwort Adelanthus lindenbergianus (Lehm.) Mitt. Furthermore, three eudesmane sesquiterpenes together with the known (-)-1beta,10-epoxyaristolan, 3,4-seco-4(23),20(29)-lupadien-3,28-dicarboxylic acid dimethyl ester and two acetophenone derivatives were identified by spectroscopic methods, essentially MS and NMR experiments.

Chromatography, Gel↗

PubMed1997

Hypoglycemic effect of trans-dehydrocrotonin, a nor-clerodane diterpene from Croton cajucara.

trans-Dehydrocrotonin (t-DCTN), a 19-nor-clerodane diterpene isolated from the bark of Croton cajucara Benth. (Euphorbiaceae) demonstrated a significant hypoglycemic activity in alloxan-induced diabetic rats but not in normal rats, at oral doses of 25 and 50 mg/kg body weight. The drug also effectively lowered the blood sugar levels in glucose fed normal rats. The hypoglycemic effect of t-DCTN was almost comparable to that produced by glibenclamide (2 mg/kg), a clinically useful drug. The results indicate the antihyperglycemic potential of t-DCTN.

Animals↗

PubMed2001

The lipid-lowering effect of trans-dehydrocrotonin, a clerodane diterpene from Croton cajucara Benth. in mice fed on high-fat diet.

The clerodane diterpene trans-dehydrocrotonin extracted and isolated from the stem bark of Croton cajucara Benth. was investigated for its lipid-lowering effect in mice fed on a high-fat diet. Mice fed on a high-fat diet for a two-week period demonstrated significantly increased blood levels of total cholesterol and triglycerides, compared with normal controls. Oral treatment with trans-dehydrocrotonin at a dose of 25 or 50 mg kg(-1) daily markedly suppressed the high-fat-diet associated rise in total cholesterol and triglyceride levels. The hypocholesterolaemic effect of trans-dehydrocrotonin was more prominent at the dose of 50 mg kg(-1) with significant decreases in high-density lipoprotein, very-low-density lipoprotein and low-density lipoprotein cholesterol levels. The lower atherogenic index of the trans-dehydrocrotonin-treated groups suggests the hypolipidaemic potential of this plant-based drug. These results indicate that orally administered trans-dehydrocrotonin is effective in suppressing high-fat-diet-induced hyperlipidaemia in mice and suggest its likely beneficial use as anti-atherogenic agent.

Administration, Oral↗

PubMedDate not supplied

Ajugatansins, neo-clerodane diterpenes from Ajuga reptans.

New neo-clerodane diterpenes have been isolated from Ajuga reptans, and named ajugatansins, along with the previously reported ajugavensin A and ajugareptansone A. The structures of all the compounds were elucidated by spectroscopic means and comparison with closely related compounds reported in the literature. The new 6 alpha,19-diacetoxy-4 alpha,18-epoxy-1 beta-hydroxy-3 beta-(2-methyl-butanoyloxy)-neo-clerod-13-en-15,16-olide (ajugatansin A1) and 6 alpha,19-diacetoxy-4 alpha,18-epoxy-3 beta-hydroxy-12S-(2-methylbutanoyloxy)-neo-clerod-13-en-15,16-olide (ajugatansin B1) are structurally related to ajugarin I and (11S,13R,16S)-6 alpha, 19-diacetoxy-4 alpha,18:11,16:15,16-triepoxy-3 beta-(2-methylbutanoyloxy)-1 beta-[(E)-2-methyl-2-butenoyloxy]-neo-clerodan-2 beta-ol (ajugatansin D1) to dihydroclerodin.

Diterpenes↗

PubMed2002

Antitumor agents. Part 212. Bucidarasins A-C, three new cytotoxic clerodane diterpenes from Bucida buceras.

As part of a study on antitumor agents from rainforest plants, four new clerodane diterpenes, bucidarasins A--D (1-4), were isolated from Bucida buceras. Their structures were elucidated from detailed 2D NMR analyses. Compounds 1-3 showed potent cytotoxicity against human tumor cell lines with IC(50) values of 0.5-1.9 microM. The potency was retained in drug resistant lines.

Antineoplastic Agents, Phytogenic↗

PubMed1999

Antioestrogenic effect of trans-dehydrocrotonin, a nor-clerodane diterpene from Croton cajucara Benth. in rats.

This study examined trans-dehydrocrotonin (t-DCTN), a nor-clerodane diterpene isolated from the Brazilian medicinal plant Croton cajucara Benth., for a possible antioestrogenic activity using immature rats as a model system for bioassay of oestrogen, and for an antiimplantation effect in regularly cycling rats of proven fertility. In the antioestrogen test, t-DCTN (25 and 50 mg/kg) effectively prevented oestrogen-induced increases of uterine wet weights. In addition, the vaginal openings provoked by oestrogen were completely prevented by t-DCTN. However, blastocyst-implantation was only insignificantly affected in t-DCTN pretreated animals. These results suggest that t-DCTN may be an antioestrogen and warrants further studies with regard to its mechanism of action.

Animals↗