A new pyrrole alkaloid from the roots of Cissampelos pareira

Abstract

Phytochemical investigation of the roots of Cissampelos pareira Linn. led to the isolation of one new pyrrole alkaloid, cissampeline (1), together with ten known alkaloids, (-)-curine (2), (-)-cyclanoline (3), (+)-tetrandrine (4), (+)-obaberine ( 5), (+)-obamegine ( 6), (-)-oblongine ( 7), (+)-homoaromoline ( 8), (-)-nor-N ‫׳‬ -chondrocurine (9), trans-N-feruloyltyramine (10) and (+)-coclaurine (11). Their structures were elucidated by extensive NMR and MS spectroscopic analyses. Interestingly, compound 1 represents the first example of pyrrole alkaloid found in the genus Cissampelos. Moreover, compounds 5-11 were isolated for the first time from this genus. Among them, compound 6 showed the highest antiacetylcholinesterase activity with an IC 50 value of 3.26 µM, whereas compound 8 displayed the most potent cytotoxicity against human colon cancer (HT29) cells with an IC 50 value of 7.89 µM.

Phytochemical Constituents and Biological Activities of Plants from the GenusCissampelos

“…Among them, hayatinine ( 20 ), isochondrondendrine ( 25 ), pelosine ( 28 ) and warifteine exhibited affinities to the inhibiting enzymes MAPK p38 alpha, PKC beta, PKC theta and PKC zeta. In contrast, the cissampeloflavone ( 81 ) had no potential inhibitory activity against PKC zeta or had no affinity for the PKC alpha [20] . In a paw edema model, milonine ( 60 ) extracted from C. sympodialis inhibited histamine release of activated mast cells [71] .…”

“…Previous chemical investigations have showed that alkaloids were the major secondary metabolites of the genus Cissampelos. Up to now, a total number of80 alkaloids have been isolated and identified from C. pareira [20] toberberinic alkaloids (62-65), five tropoloisoquinolinic alkaloids (66)(67)(68)(69)(70), two azafluorantene alkaloids (71 -72), two stephaoxocane alkaloids (73)(74), three pro-aporphic alkaloids (75 -77) one monoterpenoid indole alkaloid (78), one phenylethylamine alkaloid (79) and one pyrrolidine alkaloid (80).…”

“…A large number of studies have been conducted on the pharmacological properties of the genus Cissampe-Table 3. 13 C-NMR data of the main biologically active compounds 27, [35] 35 [38] and 37 [20] Position 27 [b] ) 35 [a] ) 37 [a] ) [a] ) Recorded in CDCl 3 . [b] ) Recorded inC 5 D 5 N.…”

“…Wariftein (8) and methylwariftein (9) extracted from C. sympodialis had the effect of tracheal relaxation. [7] Hayatinine (20) and cycleanine (14) isolated from C. pareira showed significant cytotoxic activity. [8] Modern pharmacological studies show that the plants in Cissampelos genus have bronchodilator, antiinflammatory, cytotoxic, antimicrobial, anti-oxidant and antifertility activities, et al For instance, C. pareira Linn.…”

Introduction to Kris, a traditional weapon of Indonesia: Preserved-lingering issues of facts

“…In this respect, the more deadly poisons were, the better they would be for the weapons to kill or Preserved-lingering issues of facts. EduLite: Journal of English Education,Literature,and Culture,6 (2), 397-410. http://dx.doi.org/10.30659/e.6.2.397-410 injure hunts or enemies (Rukachaisirikul et al, 2021;van Huis, 2021;Zvejniece et al, 2021). Therefore, in fighting between tribes for example each of them was extremely careful not to be scratched by even the slightest injury as it might lead to the death due to the danger of the poison.…”