Abietane Diterpenes Research Articles

Structure Elucidation of a New Rearranged Abietane Diterpene from a Biologically Active Plant, Salvia eriophora

A new rearranged abietane diterpenoid, eriophoroxide (1), was obtained from the root extract of Salvia eriophora Boiss. and Kotschy ex Boiss. Its structure was elucidated by spectroscopic methods and semi-empirical/ ab-initio calculations. DNA damaging, cytotoxic and antioxidant activities of the plant extract were tested.

Synthesis of Phenol Abietane Diterpenes Based on the Oxidative Radical Cyclization Utilizing the Mn(OAc)3/Ac2O System

A new route to phenol abietane diterpenes from trans-communic acid is reported. The key step is the transformation of a β-ketoester into the corresponding O-acetylsalicilate, via a manganese(III)-based oxidative free-radical cyclization carried out in Ac2O. Utilizing this, the first synthesis of (-)-sugikurojin A has been achieved. The immunosuppressor 19-hydroxyferruginol has also been synthesized.

Regioselective routes towards 14-hydroxyabietane diterpenes. A formal synthesis of immunosuppressant (−)-triptolide from (+)-abietic acid

Two procedures to introduce an oxygenated function into the C-14 of abietane diterpenes with complete regioselectivity have been developed. Utilizing these, the synthesis of the antileishmanial quinone (−)-12-deoxyroyleanone ( 1) and a formal synthesis of antitumour and immunosuppressant (−)-triptonide ( 7) and (−)-triptolide ( 8) from (+)-abietic acid ( 13) have been carried out.

Oxidative C-Ring Opening of Abietane Diterpenes with Ammonium ­Cerium(IV) Nitrate

The oxidation reaction of 11,12-di-O-methylcarnosol with ammonium cerium(IV) nitrate (CAN) gave an abietane diterpene with the C-ring opened and a diester function. The structure of this diester was established by spectroscopic analysis and by chemical means. The reaction of 11,12-di-O-dimethylgaldosol with CAN gave a similar result, yielding a δ-lactone which structure was established as 7-hydroxy-11,12-seco-8,13-abietadien-12,7:20,6β-dilacton-11-oic acid methyl ester by spectroscopic analysis and chemical means. These results could be useful to accede to other natural ­products like rosmic acid.

C-methylated and C-prenylated isoflavonoids from root extract of Desmodium uncinatum

A pterocarpan, 1,9-dihydroxy-3-methoxy-2-methylpterocarpan (named uncinacarpan) and two isoflavanones, 5,7-dihydroxy-2′,3′,4′-trimethoxy-6-(3-methylbut-2-enyl)isoflavanone (named uncinanone D) and 5,4′-dihydroxy-7,2′-dimethoxy-6-methylisoflavanone (named uncinanone E), were isolated from the CH 2Cl 2 root extract of Desmodium uncinatum (Jacq.) DC and characterised by spectroscopic methods. In addition, a rare pterocarpan edudiol and two known abietane diterpenes, 7-oxo-15-hydroxydehydroabietic acid and 7-hydroxycallitrisic acid were identified. The fraction of the root extract that was analysed induced germination of Striga hermonthica seeds, but none of the isolated compounds showed this activity.

Two New Abietane Diterpenes from Cordia latifolia

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Isolation, chemical transformations, and antiproliferative activity against human cancer cell lines of abietane diterpenes from two Mexican Salvia species

Salvia, one of the largest plant genera of about 900 species, has been used in traditional medicinal systems for generations [1]. In the course of a study of the chemical composition of the flora used in Latin America popular medicine, we have performed the phytochemical studies of extracts from two Salvia species, S. pachyphylla Munz and S. clevelandii (A. Gray) E. Greene. Both are endemic from the North of Baja California (Mexico) and South of California (USA). Salvia pachyphylla is used by indigenous communities for its medicinal properties [2].

Antiplasmodial activity of abietane diterpenes isolated from five southern African Plectranthus species

Antiplasmodial activity of abietane diterpenes isolated from five southern African Plectranthus species

Antioxidant abietane diterpenoids from Salvia barrelieri

The root extract of endemic Algerian Salvia species Salvia barrelieri Ettling and its diterpenoids were investigated for potential antioxidant activity. From its acetone extract, a new natural abietane diterpenoid 7-oxoroyleanone-12-methyl ether ( 1) and six known diterpenoids 7 α-acetoxyroyleanone-12-methyl ether ( 2), royleanone ( 3), horminone ( 4), 7-acetylhorminone ( 5), cryptojaponol ( 6) and inuroyleanol ( 7) were isolated, and their structures were elucidated by spectroscopic means. Among the diterpenoids, the new diterpenoid 7-oxoroyleanone-12-methyl ether ( 1) showed highest superoxide anion scavenging activity while inuroyleanol ( 7) showed both the highest 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging activity and inhibition of lipid peroxidation in β-carotene–linoleic acid system. These findings indicate that S. barrelieri extract as well as isolated abietane diterpenes, particularly inuroyleanol are promising antioxidants which can be used as food additives.

Two new abietane diterpenes from Cordia latifolia

Two new abietane diterpenes cordioic acid and cordifolic acid were isolated from the methanolic extract of Cordia latifolia stem bark. The structures of these diterpenes were elucidated using spectroscopic techniques. To the best of our knowledge, this is the first instance of isolation of diterpenoids from this source. Furthermore, cordifolic acid is a rare 2,3- seco-abietane suggestive of its biogenesis from 3-keto-analogue.

Three Abietane Diterpenes and Two Diterpenes Incorporated Sesquiterpenes from the Bark of Cryptomeria japonica.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Salvidorol (I), a nor‐Abietane Diterpene with a Rare Carbon Skeleton and Two Abietane Diterpene Derivatives (II) from Salvia dorrii.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

New Abietane Diterpene Alkaloids Possessing an Oxazole Ring from Salvia trijuga

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cytotoxic Abietane Diterpenes from Hyptis martiusii Benth.

From roots of Hyptis martiusii Benth. two tanshinone diterpenes were isolated, the new 7beta-hydroxy-11,14-dioxoabieta-8,12-diene (1) in addition to the known 7alpha-acetoxy-12-hydroxy-11,14-dioxoabieta-8,12-diene (7alpha-acetoxyroyleanone) (2). Structures of 1 and 2 were established by spectroscopic means. The cytotoxic activity against five cancer cell lines was evaluated. Compounds 1 and 2 displayed considerable cytotoxic activity against several cancer cell lines with IC50 values in the range of 3.1 to 11.5 microg/ml and 0.9 to 7.6 microg/ml, respectively. The cytotoxic activity seemed to be related to inhibition of DNA synthesis, as revealed by the reduction of 5-bromo-2'-deoxyuridine incorporation and induction of apoptosis, as indicated by the acridine orange/ethidium bromide assay and morphological changes after 24 h of incubation in leukemic cells.

Salvidorol, a nor-abietane diterpene with a rare carbon skeleton and two abietane diterpene derivatives from Salvia dorrii

Salvidorol ( 1), a irregular nor-abietane-type diterpene, was isolated from the aerial parts of Salvia dorrii, in addition to two epimeric abietane diterpenes ( 2 and 3). This is the first report of a nor-diterpene with an irregular skeleton. The structures were established by high-field NMR techniques ( 1H– 1H COSY, DEPT, HMQC, HMBC, NOESY and HRMS) and in case of 2 was confirmed by X-ray analysis.

Three Abietane Diterpenes and Two Diterpenes Incorporated Sesquiterpenes from the Bark of Cryptomeria japonica

Three new abietane diterpenes, sugikurojins D (1), E (2), and F (3), and two new abietanes which incorporate cadinane, sugikurojins G (4) and H (5) were isolated from the bark of Cryptomeria japonica. These structures were elucidated primarily by extensive NMR experiments. The structure of sugikurojin D (1) was deduced to be 6alpha-acetoxy-7beta,11-dihydroxy-12-methoxy-8,11,13-abietatriene. Sugikurojin E (2) was deduced to be 6alpha-acetoxy-7beta,12-dihydroxy-8,11,13-abietatriene. Sugikurojin F (3) was 7alpha-methoxy-8,13-abietadien-11,12-dione. Sugikurojins G (4) and H (5) had a unique skeleton incorporating an alpha-cadinol or a 1alpha-hydroxy-T-cadinol in ferruginol, respectively. Also obtained in this investigation were the known diterpenes (6-14). An antibacterial activity of ten among these against Staphylococcus aureus and Escherichia coli was inactive at the (MIC: 125 microg/ml) level. Meanwhile, in the cytotoxic activity against HL-60, compounds 4, 8, and 11 showed moderate (IC50: 4, 35.4; 8, 28.0; 11, 52.4 microM) though weak (IC50: 4, 100; 8, 80.8; 11, 100 microM) activity against HCT-15.

New Abietane Diterpene Alkaloids Possessing an Oxazole Ring from Salvia trijuga

Two new diterpene alkaloids, isosalviamine-A (1) and B (2) and nine known tanshinones (3-11) were isolated from the MeOH extract of roots of S. trijuga. The structures of these new compounds were elucidated from 1 H and 13 C NMR spectra with the aid of COSY, NOESY, HMQC and HMBC experiments.

Abietane Diterpene Alkaloids from Salvia Yunnanensis

Nine new abietane diterpene alkaloids containing an oxazole ring, salviamines A-F (1-6) and isosalviamines C-E (7-9), together with 17 known abietane diterpenes, were isolated and characterized from the roots of Salvia yunnanensis. The structures of 1-9 were elucidated by interpretation of their spectroscopic data.

New Abietane and Secoabietane Diterpenes from the Roots of Taiwania cryptomerioides.

New Abietane and Secoabietane Diterpenes from the Roots of Taiwania cryptomerioides.

Quinone Derivatives by Chemical Transformations of 16-Hydroxycarnosol from Salvia Species

The known diterpenes 12,16-epoxycarnosol (2), isotanshinone II (6), and (+)-neocryptotanshinone (8) were obtained by partial synthesis from 16-hydroxycarnosol (1), a C-16 hydroxylated abietatriene diterpene isolated in relative abundance from the aerial part of Salvia mellifera GREENE. The physical and spectroscopic data of these semisynthetic diterpenes were identical to those given for the natural ones in the literature. These abietane diterpenes have very interesting biological activities and the semisynthetic approach described here represents an alternative to obtain them from other major diterpenes isolated from Salvia species. Additionally, seven new semisynthetic diterpene analogues, 11,14-dioxo-12,16-epoxy-8,12-abietadien-20,7beta-olide (3), 11,14-dioxo-12,16-epoxy-8,12,15(16)-abietatrien-20,7beta-olide (4), 15,16-didehydro-12,16-epoxycarnosol (5), 1-oxoisotanshinone II (7), 16-hydroxycolumbaridione (9), 12,16-diacetoxycolumbaridione (10), and 14-methoxy-12,16-epoxycarnosol (13), were obtained from 1. The structures of the new compounds were established based on their spectroscopic data.