Shoreic Acid Research Articles

Extracts and purified substances of Cabralea canjerana inhibit hatching and extracts of Schinus terebinthifolius kill juveniles of meloidogyne incognita

Nematicidal substances have been identified from plants and are potentially useful for the management of plant-parasitic nematodes. Cabralea canjerana, (Meliaceae) and Schinus terebinthifolius (Anacardiaceae) produce bioactive compounds during their secondary metabolism and little is known about the effect of such substances on plant-parasitic nematodes. In the present study, we assessed the effect of aqueous and ethanolic extracts of C. canjerana and S. terebinthifolius at 1% (m:v) and purified substances from C. canjerana (gedunin, ocotillone, cabraleadiol, a mixture of ocotillone + cabraleadiol and a mixture of shoreic acid + eichlerianic acid) on hatching and mortality of Meloidogyne incognita juveniles. Aqueous extracts of C. canjerana fruits and seeds reduced hatching by 70.3 to 95.7%. Aqueous extracts of S. terebinthifolius fruits killed 42.8 to 77.1% of juveniles. The purified substances of C. canjerana inhibited the hatching of M. incognita from 57 to 90% and did not increase the mortality of juveniles. Therefore, C. canjerana extracts and its purified substances reduce M. incognita hatching and aqueous extracts of S. terebinthifolius kill J2 of this nematode.

New cytotoxic protolimonoids from the stem bark of Aglaia argentea (Meliaceae)

Two new protolimonoid compounds, namely, argentinin A (1) and B (2) along with five known triterpenoid compounds, dammar-24-en-3α-ol (3), 3-epi-cabraleahydroxy lactone (4), (E)-25-hydroperoxydammar-23-en-3β,20-diol (5), mixture of eichlerianic acid and shoreic acid (6a and 6b), and dammar-24-en-3α,20-diol (7), were isolated from the stem bark of Aglaia argentea. The structure of new compounds were elucidated by spectroscopic methods including one and two-dimensional NMR as well as high-resolution mass spectrometric analysis. All of the compounds were tested for their cytotoxic effects against P-388 murine leukemia cells in vitro. Among those isolated compounds, argentinin A (1) showed the strongest activity with an IC50 value of 1.27μg/mL (3.05μM).

Chemical Constituents of Cleome rupicola Growing in Saudi Arabia

Phytochemical investigations of extracts from the aerial parts of Cleome rupicola resulted in the isolation of two new and three known secondary metabolites corresponding to three secodammarane triterpenes: cleomdiolic acid (1), shoreic acid (3), foveolins B (4), and two flavonol glycosides: isorhamnetin-3,7-O-α-L-dirhamnoside-3′′-O-acetyl (2) and isorhamnetin-3-β-D-glucoside-7-α-L-rhamnoside (5). The structures of these compounds were characterized and identified by spectral 1D and 2D NMR and MS analyses in addition to comparison with spectral data of related known compounds. Compounds 1 and 2 are new. This is the first phytochemical investigation of the extract of the aerial part of Cleome rupicola. Bioactivity assay on HeLa cells showed the cytotoxicity of the new compounds (1) (IC50 = 64.7 μg/mL) and (2) (IC50 = 112.6 μg/mL).

Cytotoxicity and Synergistic Effect of the Constituents from Roots of Aglaia odorata (Meliaceae)

Twelve compounds were isolated from the roots of Aglaia odorata. Their structures were established on the basis of NMR and MS data as rocaglaol (1), rocaglamide (2), eichlerialactone (3), sapelins A (4), isofouquierone (5), eichlerianic acid (6), shoreic acid (7), agladupol E (8), 3-epimeliantriol (9), cleomiscosins B (10), 2β,3β-dihydroxy-5α-pregnane-16-one (11) and β-d-glucopyranos-1-yl N-methylpyrrole-2-carboxylate (12). Among them, compounds 1 and 2 showed significant cytotoxicity against human cancer cell (HL-60, SMMC-7721, A-549, MCF-7 and SW480) with IC50 values of 0.007–0.095 μM, while compounds 3–5 and 10 and 11 showed moderate to no cytotoxicity (IC50 0.43 to values >40 μM). Compound 6 showed only weak cytotoxicity (IC50 6.87 to >40 μM) and its epmier 7 was completely inactivite (IC50>40 μM) in the assay. However, potent synergistic effect was observed when the molar ratio of 6 to 7 is between 4:1 and 1:1.

Chemical constituents from stems of Dysoxylum laxiracemosum

Twelve compounds were separated from stems of Dysoxylum laxiracemosum and their structures were identified by spectrum analysis as shoreic acid (1), cabraleahydroxylactone (2), cabralealactone (3), cinchonain (5), catechin (6), scopoletin (7), vanillic acid (8), p-hydroxybenzoic acid (9), docosanol (10), beta-sitosterol (11), daucosterol (12). Of them, compounds 1-6,8-12 were separated from this plant for the first time, and compounds 4-6 were reported from this plant genus for the first time.

Preparative Isolation of Antimycobacterial Shoreic Acid from Cabralea canjerana by High Speed Countercurrent Chromatography

High speed countercurrent chromatography (HSCCC) was used to isolate the dammarane type triterpene shoreic acid from the dichloromethane extract of leaves of Cabralea canjerana, which showed activity against Mycobacterium tuberculosis. A preparative scale-up of the process was also developed.

21,28-Epoxy-18β,21β-Dihydroxbaccharan-3-one and Other Terpenoids from the Liverwort Lepidozia Chordulifera T. Taylor

A new triterpenoid, 21,28-epoxy-18β,21β-dihydroxybaccharan-3-one (1), with a spiro-hemiketal side-chain, has been isolated from the liverwort Lepidozia chordulifera. The plant also yielded (6S*, 7S*)-3-norhimachal-1-en-3-one (3), an epimer of a known norhimachalane, the rare 3β-hydroxy-22,23,24,25,26,27-hexanordammaran-20-one and the triterpenoids shoreic acid, taraxerol, betulinic acid, betulonic acid and ursolic acid. Their structures have been assigned on the basis of their spectroscopic properties.

Silvaglins and related 2,3-secodammarane derivatives – unusual types of triterpenes from Aglaia silvestris

Lipophilic crude extracts of leaves, stem and root bark of six different provenances of Aglaia silvestris were compared to determine species-specific chemical trends as well as infraspecific variability. 3,4-Secodammarane triterpenes formed the basic chemical equipment accompanied by the 2,3-seco derivative aglasilvinic acid, probably representing the precursor of the silvaglin A and isosilvaglin A characterised by a five membered ring A. In addition, the pregnane steroid pregnacetal was isolated and identified together with the known sesquiterpenes α-muurolene and viridiflorol, and the bisamide pyramidatin. Depending on the collection site all major triterpenes showed two different stereochemical trends either towards 20 R or 20 S configuration, giving rise to isolation and identification of the two isomers methylisofoveolate B (20 S,24 R) and methylfoveolate B (20 R,24 S) as well as the known derivatives shoreic acid (20 S,24 R), isoeichlerianic acid (20 R,24 S), and methylisoeichleriate (20 R,24 S). The structures were elucidated by 2D-NMR experiments and silvaglin A additionally by X-ray diffraction. The structural diversity and distribution of triterpenoids within the genus Aglaia is highlighted with respect to chemotaxonomic implications.

Isoeichlerianic acid from Aglaia silvestris and revision of the stereochemistry of foveolin B

A new series of 20,24-epoxy (tetrahydrofuryl) type dammarane triterpenoids were established. So far two series were described, based on the stereochemistries of the tetrahydrofurane ring linked to the D ring of the triterpenoid skeleton. Eichlerianic acid was characterised by the absolute configuration (20 S,24 S) and shoreic acid by (20 S,24 R). Foveolins A and B were correlated with these compounds and published also as (20 S,24 S) and (20 S,24 R), respectively. 13C NMR analysis of a further stereoisomer of the acids isolated from Aglaia silvestris allowed the conclusion that the new isoeichlerianic acid, its methyl ester and the known foveolin B belonged to the new stereochemical series (20 R,24 S).

Dammarane triterpenes from Cabralea canjerana (Vell.) Mart. (Meliaceae): Their chemosystematic significance

The stem of Cabralea canjerana (Vell.) Mart. yielded three new dammarane triterpenes 20 S,24 S-epoxy-7β,25-dihydroxy-3,4-secodammar-4(28)-en-3-oic acid, 20 S,24 S-epoxy-7β,15α,25-trihydroxy-3,4-secodammar-4(28)-en-3-oic acid and 20 S,24 R-epoxy-7β,22ξ,25-trihydroxy-3,4-secodammar-4(28)-en-3-oic acid, which were identified on the basis of spectroscopic methods. The known dammarane triterpenes ocotillone, eichlerianic acid, shoreic acid and the sterols sitosterol, campesterol, stigmasterol, sitostenone and stigmast-5-en-3-one were also isolated and identified. The branches yielded the above three known dammaranes and eichlerialactone. The dammaranes in C. canjerana display strong similarities with Trichilieae tribe, which contains several dammaranes. The data reported herein thus provide firm support for placing Cabralea within the subfamily Melioideae, Trichilieae tribe.

Cytotoxic constituents of the twigs and leaves of Aglaia rubiginosa.

Activity-guided fractionation of a CHCl(3)-soluble extract of the twigs of Aglaia rubiginosa, using human oral epidermoid carcinoma (KB) cells as a monitor, led to the isolation of a new naturally occurring cyclopenta[b]benzofuran, 1-O-acetylrocaglaol (1), along with seven known compounds, methyl rocaglate (2), rocagloic acid (3), 1-O-acetylmethyl rocaglate (4), desyclamide, eryodictiol, 5-hydroxy-3,7,4'-trimethoxyflavone, and naringenin. A CHCl(3) extract of the leaves of A. rubiginosa yielded the new compound (3S,4R,22R)-cholest-7,24-diene-3,4,22-triol (5), as well as 11 known compounds, including 2 and 4 and cabraleone, dammarelonic acid, (20S,23E)-20,25-dihydroxy-3,4-secodammara-4(28),23-dienoic acid, (20S,23E)-20,25-dihydroxy-3,4-secodammara-4(28),23-dienoic acid methyl ester, (3beta,4beta,22R)-ergosta-5,24(24')-diene-3,4,22-triol, ocotillone, shoreic acid, beta-sitosterol, and beta-sitosterol glycoside. The structures of 1 and 5 were elucidated by spectral and chemical methods. Isolates were evaluated with a human cancer cell panel, and compounds 1-4 were found to exhibit potent cytotoxic activity.

Ent-Pimarane derivatives from Dysoxylum hainanense

Four ent-pimarene diterpenoids, ent-18-acetoxy-8(14)-pimarene-15 S,16-diol, ent-18-acetoxy-16-hydroxy-8(14)-pimaren-15-one, ent-16,18-dihydroxy-8(14)-pimaren-15-one and ent-19-nor-4,16,18-trihydroxy-8(14)-pimaren-15-one, together with three known damarane triterpenoids, richenoic acid, eichlerianic acid and shoreic acid were isolated from the bark of Dysoxylum hainanense Merr. Their structures were elucidated on the basis of spectroscopic techniques. The absolute configurations of four diterpenoids were assigned as ent-pimarene type by chemical transformation and by co-occurrence in the plant as well as by negative optical rotations for four compounds.

Dammarane Triterpenoids from Amoora yunnanensis

Four dammarane triterpenoids, 20S,24-epoxy-24,25-dihydroxydammar-3-one, 20S,23 R,24R-23-chloro-20,24-epoxy-dammarane-3 alpha ,24,25-triol 3-acetate, 20S,23R,24S-23-chloro-20,24-epoxy-dammarane-3 alpha ,24,25-triol 3-acetate, and 20S,24-epoxy-24,25-dihydroxy-3,4-secodammar-4(28)-en-3-oic acid, in addition to eight known dammarane triterpenoids, 3-acetylcabraleadiol, cabraleadiol, cabralea-hydroxylactone, ocotillone, cabraleone, 24,25-dihydroxy-dammar-20-en-3-one, shoreic acid, and 20S,24-epoxy-25,26,27-trisnor-24-oxo-3,4-secodammar-4(28)-en-3-oic acid, were isolated from the bark of Amoora yunnanensis. Their structures were elucidated by a combination of 1D and 2D NMR spectral analysis and comparison with closely related compounds.

Di-and Triterpenoids from the Liverwort Blepharidophyllum densifolium

Abstract 22 ent-kaurane and ent-pimarane type diterpenoids, ten of which are new, ent- 19-acetoxykaur- 16-en-15-one, ent-19-oxo-kaur-16-en-15-one, ent-11α-acetoxy-20-oxo-kaur-16-en-15-one, enf-11α-acetoxy-15-oxo-kaur-16-en-20-acid,-11α-acetoxy-7β-hydroxy-kaur-16-en-15-one, ent-11α-acetoxy-19-hydroxy-kaur-16-en- 15-one, ent-19-acetoxy-11α-hydroxy-kaur-16-en-15- one, ent-11α-acetoxy-6β, 19-dihydroxy-kaur-16-en-15-one, ent-11α-acetoxy-19-hydroxykauran- 15-one and em -19-acetoxy-11α-hydroxy-kauran-15-one were isolated from the liverwort Blepharidophyllum densifolium. Furthermore three known triterpenoids cabraleadiol, cabraleadiolacetate and shoreic acid have been found. Their structures were established by NMR spectroscopy

Dammarane triterpenes and pregnane steroids from Aglaia lawii and A. tomentosa

Three known dammaranes, cabraleone, eichlerianic acid and shoreic acid, together with two new ones, aglinins A and B, were isolated from the bark of Aglaia lawii. A. tomentosa also contained dammarane triterpenes: the known, cabraleone, cabraleadiol 3-acetate, 3-epiocotillol, cabralealactone, cabralealactone 3-acetate and the new aglinins C and D. In addition, two new pregnane steroids, aglatomins A and B, were isolated from A. tomentosa along with the known cytotoxic cyclopentatetrahydrobenzofuran, rocaglaol. The structure of the new compounds was determined by spectral means, essentially 2D NMR experiments.

Foveolins A and B, dammarane triterpenes from Aglaia foveolata

Three known dammarane triterpenes, 3-epi-ocotillol, eichlerianic acid and shoreic acid, together with two new ones, foveolins A and B, have been isolated from the bark of Aglaia foveolata. Structural elucidation was achieved by 2D NMR experiments.

Complete1H and13C NMR Spectral Assignment of Cabraleadiol, a Dammarane Triterpene fromDysoxylum malabaricumBedd

Three dammarane triterpenoids, cabraleone (20S,24S-eopxy-25-hydroxydammaran-3-one), cabraleadiol (20S,24S-epoxydammarane-3α,25-diol) and shoreic acid (20S,24S-epoxy-25-hydroxy-3,4-secodammar-4(28)-en-3-oicacid), were isolated for the first time from the stem bark of Dysoxylummalabaricum Bedd. (Meliaceae). The complete 1H and 13C NMR spectral assignment of one of these compounds, namely cabraleadiol, and its 3-O-acetyl derivative were achieved by 2D NMR spectroscopy and NOE difference spectroscopy. The C-20 and C-24configurations in these compounds are discussed on the basis of the present NMR spectroscopic data.

Dammarane triterpenoids from Dysoxylum richii

Four new dammarane-type triterpenoids, named methyl richenoate, richenone, richenol and richenoic acid, together with four known triterpenoids, ocotillone, cabraleone, shoreic acid and eichlerianic acid, were isolated from the fruits of Dysoxylum richii. The proposed structures were established by chemical interconversions, spectral analysis and comparisons among closely related compounds.

Cabralea eichleriana dc. (meliaceae)—I structure and stereochemistry of wood extractives

From Cabralea eichleriana DC. (Meliaceae) nine compounds having a dammarane skeleton have been isolated and identified. They are cabraleone 2, ocotillone 3, cabraleadiol 4a, cabralealactone 5, cabraleahydroxylactone 6a, eichlerianic acid 7a, shoreic acid 8a, dammarenolic acid 9a and eichlerialactone 10a. The only limonoid present is fissinolide 1. Compounds 7a and 10a are hereby reported for the first time as occurring in Nature. Configurations of ocotillone and cabraleone are revised and have been assigned 20 S, 24 S and 20 S, 24 R respectively.

Constituants sesquiterpéniques et triterpéniques des résines du genre Shorea

The resins of thirty-five species from the genus Shorea Roxb. ex Gaertn. f. have been studied. The following polyterpenes have been characterized: the sesquiterpene hydrocarbons copaene, β-elemene, caryophyllene, α-gurjunene and cyperene; the sesquiterpene alcohols spathulenol and alcohols 'K' (under investigation); the triterpenes β-amyrin, ursolic aldehyde, dipterocarpol, dammarenediol 20-S, dammaradienone, hydroxyhopanone, shoreic acid and dammarenolic acid. In the genus Shorea, the sesquiterpene hydrocarbons show only little variation; the variable occurrence of the sesquiterpene alcohols and the triterpenes enables the sub-genus Anthoshorea to be distinguished from the sub-genera Shorea, Richetia and Rubroshorea. At the family level, the copaene, β-elemene and caryophyllene association is a feature peculiar to the genus; the occurrence of shoreic acid and oxygenated sesquiterpenes appears at the present time to be specific to the genus Shorea.