Carbazole alkaloids from the fruits of Clausena anisum-olens with potential PTP1B and α-glucosidase inhibitory activities

Clausanisumine, a Prenylated Bicarbazole Alkaloid from the Fruits of Clausena anisum-olens and Its Potential Anti-HIV Activity

“…Its UV spectrum exhibited the UV absorption peaks at 236, 288, as well as 328 nm, which were the characteristic absorption bands of the carbazole alkaloids. 12,19 In its 1 H NMR spectrum, the existence of two sharp amino hydrogen signals which resonate at δ H 8.30 (1H, s, N−H) and 7.91 (1H, s, N′−H) revealed the presence of two amino groups. The presence of two groups of mutual coupling downfield protons, δ H 7.95 (1H, d, J = 8.0 Hz, H-5), 7.42 (1H, d, J = 8.0 Hz, H-8), 7.28 (1H, dd, J = 8.0, 7.8 Hz, H-7), and 7.00 (1H, dd, J = 8.0, 7.8 Hz, H-6), as well as δ H 7.56 (1H, d, J = 8.0 Hz, H-5′), 7.29 (1H, d, J = 8.0 Hz, H-8′), 7.19 (1H, dd, J = 8.0, 7.8 Hz, H-7′), and 6.97 (1H, dd, J = 8.0, 7.8 Hz, H-6′), revealed the presence of two 1,2,3,4-tetra-substituted benzene rings.…”

“…Previous chemical investigation of C. anisum-olens yielded various compounds, containing alkaloids, lignans, cyclic peptides, and coumarins, which exhibited diverse biological activities, such as hypolipidemic, anti-HIV, and human monoamine oxidase inhibitory activities. − Our rudimentary biological activity evaluation data indicated that the crude extract of the fruits of C. anisum-olens possessed a remarkable anti-HIV-1 effect holding an EC 50 value of 8.27 μg/mL in vitro .…”

Natural α-Glucosidase and Protein Tyrosine Phosphatase 1B Inhibitors: A Source of Scaffold Molecules for Synthesis of New Multitarget Antidiabetic Drugs

“…Eighteen different alkaloids able to inhibit both PTP1B and α-glucosidase were extracted from Clausena anisum-olens [ 66 ] ( Table 11 ).…”

“…Eighteen different alkaloids able to inhibit both PTP1B and α-glucosidase were extracted from Clausena anisum-olens [66] (Table 11). It is interestingly to observe that among all carbazole, Clausenanisine A (224) exhibited the lowest IC 50 values on both targets, suggesting that the carbazole moiety bearing a fivemembered cyclic ether, a methoxy group, and a short aliphatic chain represents a promising lead structure for developing new MLDs active on both PTP1B and α-glucosidase.…”

Artapilosines A and B, Unusual Phenanthrene Derivatives Related to Aporphine Alkaloids from Artabotrys pilosus

“…Our experimental data suggested that the 85% EtOH extract of A. pilosus stems and leaves showed anti-HIV-1 activity in vitro , having an EC 50 value of 7.18 μg/mL. As an ongoing program to explore compounds from tropical medicinal plants or tropical fruits with novel molecular structures and potential pharmacological activities in China, − a phytochemical study on the chemical constituents from A. pilosus was performed and resulted in the isolation of two unusual phenanthrene derivatives related to aporphine alkaloids, artapilosines A ( 1 ) and B ( 2 ), as well as two biogenetically related known aporphine alkaloids, (−)-anonaine ( 3 ) and (−)- N -acetylanonaine ( 4 ). , Artapilosine A ( 1 ) represents the first example of a new series of phenanthrene derivatives with an uncommon dihydroacephenanthrylene system in its unprecedented carbon skeleton, in which the six-membered nitrogen-containing heterocyclic structure in the aporphine class alkaloid was replaced by a unique five-membered carbocyclic ring. This is the first report in which a new carbon–carbon bond between C-5 and C-6a in 1 was formed and the nitrogen atom of N-6 was lost in a typical aporphine alkaloid.…”