New Lycopodium alkaloids from Lycopodium obscurum

Abstract

Abstract:Three new Lycopodium alkaloids, obscurumines C-E (1-3), along with nine known compounds, were isolated from the club moss Lycopodium obscurum L. Structures of the new compounds were determined on the basis of their spectroscopic analysis and the relative configurations of 1 were established by X-ray crystallographic analysis. All the new isolates were tested for the acetylcholinesterase (AChE) inhibitory activity.

PIDA/I2-Mediated α- and β-C(sp3)–H Bond Dual Functionalization of Tertiary Amines

“…Next, the robustness of this strategy was evaluated in the syntheses of Lycopodium alkaloids, obscurumine C ( 13 ) and obscurumine O ( 17 ), which are well-known for their unique 6/6/6/6 fused skeletons and 1,6-dihydropyridine-2,3-dione moieties. Biogenetically, these alkaloids might be derived from lycopodine ( 11 ) via the action of oxidase.…”

New Lycopodine-Type Alkaloids from <i>Lycopodium carinatum</i>

“…Other isolated compounds from the crude alkaloidal fraction were lycopodine, 31) lycocarinatine A, 28) 12-epi-lycodoline N-oxide, 32) lycofoline, 30) anhydrolycodoline, 30) obscurumine C, 33) gnidioidine, 30) malycorin B, 29) fawcettimine, 34) lycoposerramine-C, 35) lycoposerramine-D, 35) lycoposerramine-P, 35) phlegmariurine A, 22) phlegmariurine B, 36) huperzine A, 5) huperzine C, 37) 13N-formyl huperzine A, 38) lycodoline, 32,39) and Chemical Conversion of Lycopocarinamine A (1) into Lycopocarinamine B (2) To a solution of lycopocarinamine A (1, 1.0 mg) in MeOH (0.5 mL) was added freshly prepared ether solution of CH 2 N 2 (excess). The mixture was stirred for 1 h at room temperature.…”

Obscurinin A, a unique Lycopodium alkaloid possessing an 8/6/6/6/5 pentacyclic system isolated from Lycopodium obscurum L.

“…Lycopodium obscurum L. is a traditional Chinese medicinal herb used for centuries to treat various ailments such as contusions, dysmenorrhea, quadriplegia, and arthritic pain. 23 From 2000 to 2023, chemical investigations on this plant have identified twenty-one new Lycopodium alkaloids, 23–28 including twelve alkaloids reported by our research group. As part of our ongoing efforts to explore structurally diverse and biologically interesting Lycopodium alkaloids, 23,26 we focused our research on L. obscurum collected from Yunnan, China.…”

“…23 From 2000 to 2023, chemical investigations on this plant have identified twenty-one new Lycopodium alkaloids, 23–28 including twelve alkaloids reported by our research group. As part of our ongoing efforts to explore structurally diverse and biologically interesting Lycopodium alkaloids, 23,26 we focused our research on L. obscurum collected from Yunnan, China. This effort resulted in the isolation of obscurinin A ( 1 ), a novel Lycopodium alkaloid with an unprecedented 8/6/6/6/5 ring system (Fig.…”