Isolation and crystal structure of grilactone, a new guaianolide from Ferula oopoda

New Guaiane Sesquiterpenes and Furanocoumarins fromNotopterygium incisum

“…In the high field region of the 1 H-NMR spectrum (CDCl 3 , 298 K), five methyl signals were observed: two secondary methyls for an isopropyl group ( δ = 1.07 and 0.93), one tertiary methyl ( δ = 1.13), one olefinic methyl ( δ = 1.75), and one acetyl methyl ( δ = 2.09). Based on these spectroscopic data and on the degrees of unsaturation, the backbone structure of 1 was elucidated to be a guaiane-type skeleton that was also found for the known compounds 5–12 [6], [7], [8], [9], [10], [11], [12]. …”

“…1), along with eight known guaiane sesquiterpenes ( 5–12 ) and fourteen known coumarins ( 13–26 ) as well as seven miscellaneous constituents ( 27–33 ). Comparing their MS and NMR data as well as the optical activity with the literature, the known compounds were identified as 4 β ,6 β -dihydroxy-1 α ,5 β ( H )-guai-9-ene ( 5 ) [6], teucladiol ( 6 ) [7], chrysothol ( 7 ) [8], teuclatriol ( 8 ) [7], hanamyol ( 9 ) [9], 1,5,11-trihydroxyguaiane ( 10 ) [10], grilactone ( 11 ) [11], 3,7(11),10(14)-guaiatrien-1 β ,5 β ( H )-12,6 β -olide ( 12 ) [12], notoptol ( 13 ) [4], isoimperatorin ( 14 ) [3], [13], notopterol ( 15 ) [2], [4], bergamottin ( 16 ) [14], anhydronotoptol ( 17 ) [4], bergapten ( 18 ) [3], [13], 6-methoxy-7-geranyloxycoumarin ( 19 ) [15], ostruthin ( 20 ) [16], scopoletin ( 21 ) [17], isofraxidin ( 22 ) [18], 7-isopentenyloxy-6-methoxycoumarin ( 23 ) [19], 5-geranyloxy-7-methoxycoumarin ( 24 ) [20], 5-isopentenyloxy-7-methoxycoumarin ( 25 ) [21], marmesin ( 26 ) [15], [22], phenethyl ferulate ( 27 ) [23], [24], pterostilbene ( 28 ) [25], pregnenolone ( 29 ) [26], falcarindiol ( 30 ) [2], falcarinol ( 31 ) [27], (2 E ,9 Z )-heptadecadiene-4,6-diyn-1-ol ( 32 ) [28] and 8-acetoxy-(1,9 Z )-heptadecadiene-4,6-diyn-3-ol ( 33 ) [29]. Among them, compounds 5–12 , 20–25 and 31–33 were reported from N. incisum for the first time.…”

Evaluation of Cytotoxic and Antioxidant Effect of Guaianolid Sesquiterpenes fromFerula hindukushensis

“…[22][23][24][25][26][27] With about 500 constituents, guaianolide sesquiterpenes are an essential subclass of sesquiterpene lactones, which are mainly found in the Apiaceae and Asteraceae families. [28] Guaianolides with 5 and 12 lactone rings are typical in Ferula spp.. [29][30][31][32] Many of these compounds are well known for their main pharmacological effects, including strong antitumor, antiproliferative, [15] antiprotozoal, [33] and anti-inflammatory activities. [34] Due to their suitable scaffold, guaianolide sesquiterpenes have been introduced as effective anticancer agents in recent studies.…”

“…Guaianolides with 5 and 12 lactone rings are typical in Ferula spp. [29–32] . Many of these compounds are well known for their main pharmacological effects, including strong antitumor, antiproliferative, [15] antiprotozoal, [33] and anti‐inflammatory activities [34] .…”