Günay Sariyar

Biodiversity in the alkaloids of Turkish Papaver species

There are about 35 Papaver species growing in Turkey, which are grouped into eight sections, namely Argemonidium, Carinata, Glauca, Miltantha, Oxytona, Papaver, Pilosa, and Rhoeadium. As a result of our extensive work on the alkaloids of Turkish Papaver species the presence of several chemotypes has been shown. Among these chemotypes, medicinally important alkaloids such as noscapine (=narcotine), papaverine- and thebaine-containing samples have been found as new sources for the production of them. The infraspecific variation encountered within the Papaver species has been demonstrated mainly in two sections of the genus, Miltantha and Oxytona. The alkaloids of seven species (Papaver armeniacum, P. curviscapum, P. cylindricum, P. fugax, P. persicum, P. polychaetum, and P. triniifolium) of the section Miltantha have been studied, and the existence of chemical strains has been shown mainly in P. fugax, P. persicum, and P. triniifolium. Investigations on the species of the section Oxytona indicated that there is a relationship between the major alkaloid content and the chromosome numbers of the samples. Isolation of new secoberbine-type alkaloids as well as promorphinane- and morphinane-types has revealed the biosynthetic relationship between the alkaloids of Miltantha and Oxytona species. Chemical races are also known for species of Papaver within other sections of the genus. P. lateritium of Turkish origin from section Pilosa yielded some secoberbine and protoberberine types, whereas P. rhopalothece of the section Rhoeadium contained narcotine as a major alkaloid. Isolation of spirobenzylisoquinoline type from P. argemone (sect. Argemonidium) was the first report of the occurrence of this type in the Papaveraceae.

Macrantaline and macrantoridine, new alkaloids from a turkish sample of Papaver pseudo-orientale

Abstract The major alkaloids of the aerial parts of a Turkish sample of Papaver pseudo-orientale are salutaridine and a new alkaloid, macrantaline, UV, IR, PMR, MS and CD have been used to establish the structure of macrantaline as 1-(2′-hydroxymethylene-3′,4′-dimethoxybenzyl)-2-methyl-6,7-methylenedioxy-8-methoxy-1,2,3,4-tetrahydroisoquinoline. The corresponding 2′-methyl substituted analogue prepared from (−)-α-narcotine and also from macrantaline proved to have identical properties, including CD spectra, thus confirming the structure and establishing the absolute configuration of macrantaline. A new minor alkaloid, macrantoridine, yielded macrantaline on lithium aluminium hydride reduction and differs from the latter in that the 2′-substituent is a carboxyl instead of hydroxymethylene. UV, IR, PMR, MS and CD data are reported for macrantoridine.

Alkaloids of turkish papaver tauricola

Abstract The major alkaloids of Papaver tauricola collected in three different parts of Anatolia have proved to be of the rhoeadine type. The three collections possessed different major alkaloids and the existence of chemical strains containing rhoeadine-type alkaloids, is indicated. In addition to the rhoeadine-type alkaloids (rhoeagenine, rhoeadine, oreogenine, oreodine, glaucamine, glaudine and epiglaudine), tetrahydroprotoberberine-(sinactine, scoulerine) and isopavine- (amurensinine) type alkaloids have been isolated as minor products. These findings contrast with the previous literature in which 1-benzyltetrahydroisoquinoline- and proaporphine types were reported to be the major alkaloids.

Alkaloids from Papaver fugax of Turkish origin

Abstract Thebaine, narcotine, rhoeadine and armepavine were identified in the aerial parts of Papaver fugax of Turkish origin.

Antimicrobial Activity and Phytochemical Studies on Turkish Samples of Papaver macrostomum.

Abstract Three alkaloids, cheilantifoline, mecambrine, and laudanosine, and two flavonoids, luteoline and tricine, have been isolated from two samples of Papaver macrostomum. Boiss. & Huet ex Boiss. (Papaveraceae) of Turkish origin. Antimicrobial tests have been performed on the extracts obtained from these species. It has been found that diethyl ether and acetone extracts of two samples obtained from the aerial parts of the plant have antimicrobial activity against almost all bacteria tested. The existence of flavonoids and the antimicrobial activity of this species are reported for the first time.

The photolysis of proaporphines

Abstract The stereochemical fastors involved in the photolysis of (+)-pakistan-amine ( 1 ) to (+)-lumipakistanine ( 2 ), of (-)-orientalinone ( 3 ) to (+)-isoboldine ( 5 ) and (+)-isothebaine ( 7 ), and of (-)-roemerialinone ( 4 ) to (+)-N-methyllauro-tetanine ( 6 ) and (+)-1-O-methylisothebaine ( 8 ), are deecribed.

Antimicrobial activity of four annual Papaver species growing in Turkey.

The extracts obtained from aerial parts of four annual Papaver (Papaveraceae) species from sections Argemonidium (P. argemone L. subsp. davisii Kadereit) and Rhoeadium (P. clavatum Boiss. & Hausskn. ex Boiss., P. dubium L. subsp. lecoqii var. lecoqii (Lamotte) Syme Kadereit and P. rhoeas L.) have been investigated for antimicrobial activity using a microbroth dilution technique. The antimicrobial activity of these species is reported for the first time. The petroleum ether and diethyl ether extracts of P. dubium subsp. lecoqii showed antibacterial activity against Staphylococcus aureus (MIC: 9.76 and 19.52 μg/mL, respectively). The diethyl ether and chloroform extracts of P. argemone subsp. davisii and diethyl ether, chloroform and acetone extracts of P. rhoeas had activity against S. aureus with a MIC value of 39.06 μg/mL.

Two new benzylisoquinoline alkaloids from Papaver triniifolium

From the aerial parts of Papaver triniifolium Boiss. (Papaveraceae) collected from Erzincan (Eastern Anatolia), two new benzylisoquinoline alkaloids, miltanthoridine and miltanthoridinone were isolated. Their structures were established through the use of UV, EIMS, and NMR techniques.

A new Dehydroaporphine Alkaloid from Papaver Fugax

A new dehydroaporphine alkaloid (−)-6a,7-dehydrofloripavidine has been isolated from the aerial parts of Papaver fugax Poir. (Papaveraceae) collected from Erzurum (Eastern Anatolia). (−)-Floripavidine (aporphine) and (−)-mecambrine (proaporphine) were isolated as major alkaloids. Other bases present were (+)-salutaridine (promorphinane) and argentinine (phenanthrene). The presence of argentinine has been shown for the first time in the Papaveraceae.

Flavonoids of Artemisia araratica

Artemisia araratica Krasch. is one of the 22 species growing in J. Cullen. In Flora of Turkey and the East Aegean Islands, P.H. Davis (Ed.), Vol. 5, University Press, Edinburgh (1975). In this report we have isolated seven flavonoids from the aerial parts of A. araratica.