Alkaloids of Haplophyllum acutifolium

Accelerated dereplication of crude extracts using HPLC–PDA–MS–SPE–NMR: Quinolinone alkaloids of Haplophyllum acutifolium

“…The constituent eluted as peak 4 (compound 4) was assigned the molecular formula C 16 H 19 NO (HRESIFTMS), and the 1 H NMR spectrum showed signals corresponding to a 4-quinolinone moiety and a hept-4-en-1-yl moiety. The 1 H NMR data were in agreement with those reported for acutine, previously isolated from H. acutifolium (Razzakova et al, 1975). Acutine was initially formulated as 2-(hept-4-enyl)quinolin-4(1H)-one (Gulyamova et al, 1974) without any information about the configuration of the double bond, but the coupling patterns observed for H-4 0 and H-5 0 in the present investigation (H-4 0 : d 5.38, dtt, J 4 0 -5 0 = 10.8 Hz, J 3 0 -4 0 = 7.1 Hz, J 4 0 -6 0 = 1.4 Hz; H-5 0 : d 5.44, dtt, J 4 0 -5 0 = 10.8 Hz, J 5 0 -6 0 = 7.1 Hz, J 3 0 -5 0 = 1.2 Hz) proved that compound 4, and thus acutine, is 2-[(4Z)hept-4-en-1-yl]quinolin-4(1H)-one.…”

“…However, the authors were only able to identify the compound as either 2-(nona-3,6-dien-1-yl)quinolin-4(1H)one or 2-(nona-2,6-dien-1-yl)quinolin-4(1H)-one, and without any information about configuration of the double bonds. Later, Razzakova et al (1986) isolated a constituent named 2-nonadie- Fig. 3.…”

“…Around 30 of these species are represented in Iran, 14 of which are endemic to the country. Haplophyllum is known as a rich source of quinoline alkaloids, and several phytochemical investigations of different species have been reported in recent years (Michael, 2008), including investigations of H. acutifolium collected in Turkmenistan (Razzakova et al, 1975(Razzakova et al, , 1986, and references cited therein). Extracts of various Haplophyllum species are used in traditional medicine as analgesics, antispasmodics, diuretics, and sedatives, as well as topical agents against skin diseases (Nazrullaev et al, 2001).…”

Alkaloids and Coumarins from Ruta graveolens

“…Compounds 1±10 and 17 have already been isolated from R. graveolens [3,4,8,9]. Of the series of 4-quinolones 10±17 containing long alkyl chains in position 2, 2-heptyl-4(1H)-quinolone (13), 2-octyl-4(1H)-quinolone (14), and 2-decyl-4(1H)-quinolone (16) were isolated from plants for the ®rst time, hitherto known only from synthesis [5,10,11]. The alkaloid 1-methyl-2-decyl-4(1H)-quinolone (11) proved to be a new compound.…”

Inter-Species Variability of Haplamine Metabolism and Identification of its Phase I Metabolites from Liver Microsomes

“…Haplamine was isolated from the aerial parts of Haplophyllum acutifolium G. Don fil. during flower bud formation [2] and from the above-ground parts of H. perforatum Kar. et Kir.…”