N. D. Abdullaev

Diterpenoids ofPulicaria salviifolia. II. Structure of salvicin

A new diterpenoid acid of the clerodane series, C20H32O4, [α]D20 −75.4° (c 0.26; methanol), which has been called salvicin, and the known flavonoid rutin have been isolated from a chloroform extract of the epigeal part ofPulicaria salviifolia. The structure of salvicin has been established on the basis of spectral characteristics and chemical transformations.

Artenolide — A new disesquiterpenoid fromArtemisia absinthium

A new sesquiterpene lactone, artenolide — C30H40O8, mp 163–174°C (ethanol) — has been isolated from the epigeal part ofArtemesia absinthium L. On the basis of an analysis of spectral characteristics (IR, mass, and1H and13C NMR spectra) of the lactone itself and of a transformation product, a diguaiane structure is suggested for artenolide.

Anabsin — A new diguaianolide fromArtemisia absinthium

The new diguaianolide anabsin, C30H40O7, mp 276°C (decomp.), [α]25 +110° (c 1.7; acetone) has been isolated fromArtemisia absinthium L. Anabsin acetate, dehydroanabsin, and dehydroanabsin acetate have been obtained. A comparative study of the1H and13C NMR spectra of anabsin, absinthin, and anabsinthin has been made. The structure of anabsin has been established and structures have been suggested for absinthin and anabsinthin. The most probable biogenesis of anabsin in plants has been put forward.

Diterpenoids ofPulicaria salviifolia. I. Structures of salvin and salvinin

Two new diterpenoids of the clerodane series — salvin and salvinin — have been isolated from the epigeal part ofPulicaria salviifolia Bgl. in Mem. A structure and a most probable stereochemistry are proposed.

Structure of the sesquiterpene lactone tanacin

Summary1. A new sesquiterpene lactone which has been called tanacin has been isolated from the leaves ofTanacetum pseudoachillea C. Winkl.2. On the basis of an interpretation of the PMR spectrum of (I) using the method of multifrequency resonance, the structure of 6-angeloyloxy-1,10-epoxygermacr-4,11(13)-dien-8,12-olide has been established for tanacin.3. The chemical conversion of tanacin into chrysanin has been performed, which confirms the structure found.

A new melampolide and other secondary metabolites from Artemisia baldshuanica

The composition of secondary metabolites in benzene and alcohol extracts of the epigeal part of Artemisia baldshuanica Krasch. et Zarp. (Asteraceae) collected during the vegetative phase was investigated. A new melampolide, the structure of which was established based on spectral data and an x-ray crystal structure analysis, and known compounds were isolated.

Structure of fegolide

A chloroform extract of the seeds ofFerula penninervis Rgl et Schmahl has yielded a new sesquiterpene lactone of the guaiane type — fegolide: C20H28O5, mp 165–166°C [α]D −150°C (c 0.17; chloroform).

Structure of hanphyllin

Summary1.A new germacranolide, which has been called hanphyllin, has been isolated from the epigeal part ofHandelia trichophylla (Schrenk.) Heimerl.2.On the basis of an analysis of the PMR spectra using the method of multifrequency resonance and a paramagnetic shift reagent — Eu(FOD)3 — the structure of hanphyllin has been established as 3-hydroxy-3α, 6β, 7α-H-germacr-1(10),4(5),11(13)-trien-6,12-olide.3.Passage from hanphyllin to the known dihydronovanin has been effected.

A new lactone, isoridentin, fromAchillea biebersteinii

Summary1. A new lactone, isoridentin, with the composition C15H20O4, has been isolated from the epigeal part ofAchillea biebersteinii.2. On the basis of chemical and spectral information it has been established that isoridentin has the structure of 1,3-dihydroxygermacra-4,10(14),11(13)-trien-6,12-olide.

Structure of ergolide

The epigeal part ofErigeron khorassanicus Boiss. has yielded a new sesquiterpene lactone of the pseudoguaiane type — ergolide C17H22O5, mp 179–180°C (ethanol) [α]D20+123° (c 4.88; ethanol). On the basis of chemical transformations and spectral characteristics, its structure and configuration have been established as 6-acetoxy-4-oxo-1,7αH,6,8,10βH-pseudoguai-11(13)-en-8,12-olide.