José M. Miguel del Corral

Sesquiterpenoids and phenolics of pulicaria paludosa

Abstract Thirteen sesquiterpenoids of the skeletal types caryophyllane, cadinane, oplopane, eudesmane, allo-aromadendrane and 4-epi-guaiane, were isolated from Pulicaria paludosa. Their structures were established mainly by NMR techniques and chemical transformations. Four of them are new natural products. Three flavonoids and some simple phenolic derivatives were also isolated.

The distribution of lignanoids in the order coniferae

Lignan distribution in the Coniferae order, which includes six families, has been reviewed from 1967 to 1994. The occurrence of lignanoids in five of the six families of this order has been reported and the predominant lignan type is different for each one.

Lignans from Juniperus sabina

Abstract Four new natural products, β-peltatin-B methyl ether, podorhizol acetate, 2′-methoxyepipicropodophyllotoxin and 2′-methoxypicropodophyllotoxin, were isolated from the lignan fraction of a n -hexane extract from the leaves of Juniperus sabina , along with picropodophyllotoxone, epipodophyllotoxin, (+)-dihydrosesamin, podorhizol, anhydropodorhizol, epipicropodophyllotoxin and 2′-methoxypodophyllotoxin.

Lignans from Juniperus thurifera

Abstract The isolation and identification of two new natural lignans, (-)epi-podorhizol and deoxypicropodophyllotoxin, and 12 known lignans from a hexane extract of Juniperus thurifera is described.

Acetylated lignans from Juniperus sabina

Abstract Two new natural products, the acetates of epipodophyllotoxin and epipicropodophyllotoxin, were isolated from the lignan fraction of a n -hexane extract of the leaves of Juniperus sabina , along with deoxypodophyllotoxin, deoxipicropodophyllotoxin, (−)-deoxypodorhizon, β-peltatin A methyl ether and picropodophyllotoxin.

Cytotoxic cyclolignans related to podophyllotoxin

The cyclolignan family of natural products includes compounds with important antineoplastic and antiviral properties such as podophyllotoxin and two of their semisynthetic derivatives, etoposide and teniposide. The latter are included in a wide variety of cancer chemotherapy protocols. Due to these biological activities, cyclolignans have been the objective of numerous studies focused to prepare better and safer anticancer drugs. Several cyclolignans related to podophyllotoxin have been prepared and evaluated for their cytotoxic activities on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28); some of them have antiviral and immunosuppressive activities.

Terpenoids from Juniperus sabina

Abstract Twenty-two diterpenoids with labdane, pimarane and abietane skeletons and two sesquiterpenoids were isolated or identified from the hexane extract of berries of Juniperus sabina .

Synthesis and antineoplastic activity of cyclolignan aldehydes.

Several aldehydes related to methyl 9-deoxy-9-oxo-alpha-apopicropodophyllate, a selective antitumour agent against the HT-29 colon carcinoma, have been prepared and evaluated for their cytotoxic activities on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28). All of them lacked the lactone ring but maintained their cytotoxicity at, or under, the microM level.

Synthesis and cytotoxicity of podophyllotoxin analogues modified in the A ring

Several podophyllotoxin derivatives lacking the methylenedioxy group or with different functionalization of the A-ring of the cyclolignan skeleton have been prepared and evaluated for their cytotoxic activities on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28). Most of them maintained their cytotoxicity at the microM level.

3,4-dihydroisocoumarins from Ononis natrix

Abstract Further studies on the composition of Ononis natrix have led to the isolation and identification of five new 3-alkyl-3,4-dihydroisocoumarins and one derivative of orsellinic acid.