Two new isoquinoline alkaloids from Cryptocarya wrayi and their biological activities

The Genus Cryptocarya: A Review on Phytochemistry and Pharmacological Activities

“…A total of 389 compounds are summarized in Table 1, in which similar chemical classes will be tabulated close to each other. Chemical isolates from Cryptocarya plants can be classified as alkaloids 1 – 110 , [2,14–53] α‐pyrones 111 – 194 , [7,9,11,54–80] monoterpene‐polyketide hybrids 195 – 206 , [8,9] arylalkyl/arylalkenyl derivatives 207 – 212 , [6,74,81] flavonoids 213 – 320 , [3–6,37,66,67,69,71,73,79,81–94] mono ‐phenols 321 – 341 , [47,84,89–91,94,95] lignans 342 – 350 , [94,96] terpenoids 351 – 359 , [11,75,89,94,95,97] aliphatic derivatives 360 – 366 , [32,90,94] sterols 367 – 371 , [73,85,89,94,95] stilbenes 372 – 374 , [85,86] co...…”

“…Taking alkaloidal pavines 1 – 24 into consideration, to date, they can be found in C. bracteolate , C. desiflora , C. laevigata , C. longifolia , C. wrayi , especially C. chinensis [2,14,16–18,24,31,36,38–40,43,47,50,52] . Together with five known metabolites (−)‐argemonine ( 1 ), (+)‐caryachine ( 3 ), (−)‐caryachine ( 4 ), (−)‐crychine ( 7 ), (+)‐eschscholtzidine ( 10 ), the extraction and separation of the 95 % ethanol extract of C. chinensis wood by acidization and chromatography resulted in the isolation of four new pavines (−)‐ N ‐demethylcrychine ( 9 ), (+)‐eschscholtzidine‐ N ‐oxide ( 11 ), (−)‐12‐hydroxycrychine ( 15 ), and (−)‐12‐hydroxyeschscholtzidine ( 16 ) [40] .…”

“…His research interests emphasize on natural products chemistry, and pharmacological drug development. [2,14,[16][17][18]24,31,36,[38][39][40]43,47,50,52] Together with five known metabolites (À )-argemonine (1), (+)-caryachine (3), (À )-caryachine (4), (À )-crychine ( 7), (+)-eschscholtzidine (10), the extraction and separation of the 95 % ethanol extract of C. chinensis wood by acidization and chromatography resulted in the isolation of four new pavines (À )-N-demethylcrychine ( 9), (+)-eschscholtzidine-N-oxide (11), (À )-12-hydroxycrychine (15), and (À )-12-hydroxyeschscholtzidine (16). [40] The other parts of this plant also contained seven new others (À )-caryachine-N-oxide (5), (À )-caryachine Nmethoperchlorate (6), (À )-crychine N-methoperchlorate (8), (À )-neocaryachine (23), (À )-neocaryachine Nmethoperchlorate (24), and (�)-isocaryachine-N-oxides (19 -20), along with six known ones (À )-bisnorargemonine (2), (À )-eschscholtzine (12), (�)-isocaryachines (17 -18), (À )-munitagine (21), and (À )-norargemonine (22) (Table 1).…”

“…A recent study conducted by Liu et al revealed that chromatographic procedure on the ethyl acetate fraction of the 95 % ethanol extract of C. wrayi twig can lead to the isolation two new isoquinoline alkaloids cryptowrayines A -B (86 -87). [2] Another new isquinoline, which is named 6,7-methylenedioxy-N-methylisoquinoline (89), was recorded in C. chinensis leaf, while the known compound papraline (90) originated from C. rugulosa bark. [39,46] From Table 1, an additional result in phytochemical investigations on this genus is the appearance of phenanthroindolizidines and phenanthroquinolizidines 91-104.…”

Complex Flavanones from Cryptocarya metcalfiana and Structural Revision of Oboflavanone A

“…The genus Cryptocarya , belonging to the family Lauraceae, contains 200–250 species mainly occurring in the tropical and subtropical regions of the world except for Central Africa . Previous phytochemical investigations on many species of Cryptocarya have reported a number of natural products including α-pyrones − and alkaloids, − along with two types of characteristic flavonoids, namely, cryptocaryanone-type flavonoids with a hydrogenated A-ring containing a C-5 acetic acid/lactone moiety − ,− and complex flavonoids composed of flavonoid and α-pyrone units. ,− , Many of these isolates have been revealed to exhibit diverse biological properties such as anti-inflammatory, antimalarial, antimicrobial, antitrypanosomal, antituberculosis, cholinesterase inhibitory, and, particularly, cytotoxic ,,,− activities.…”