Fortuneicyclidins A and B, Pyrrolizidine Alkaloids with a 7-Azatetracyclo[5.4.3.0.0^2,8]tridecane Core, from Cephalotaxus fortunei

Abstract

Fortuneicyclidins A (1) and B (2), a pair of epimeric pyrrolizidine alkaloids containing an unprecedented 7-azatetracyclo­[5.4.3.0.02,8]­tridecane core, were isolated from the seeds of Cephalotaxus fortunei, along with two biogenetically relative known analogues, 3 and 4. The structures were determined by multiple spectral techniques and chemical derivatization methods. Compound 1 showed inhibitory activity against α-glucosidase.

Cephalotaxine-type and homoerythrina-type alkaloids with antiproliferative effects from Cephalotaxus fortunei

“…The obtained known alkaloids were identified as cephalofortine F ( 4 ), 19 cephalofortuneine ( 5 ), 18 2-epicephalofortuneine ( 6 ), 23 3-epiwilsonine ( 7 ), 24 wilsonine ( 8 ), 18 epischelhammercine B ( 9 ), 25 fortunine ( 10 ), 22 fortuneicyclidin A ( 12 ), 20 cephalocyclidin A ( 14 ), 21 cephalofortine B ( 16 ), 19 cephalotines A ( 18 ) and B ( 19 ), 22 4-hydrocephalotaxine ( 20 ), 23 cephalotine D ( 21 ), 22 epicephalotaxine ( 22 ), 26 cephalotaxine ( 23 ), 27 acetylcephalotaxine ( 24 ), 22 cephalofortine A ( 25 ), 19 11-hydroxycephalotaxine ( 26 ), 19 (−)-cephalezomine H ( 27 ), 19,28 cephalezomine H ( 28 ), 28,29 demethylcephalotaxinone ( 29 ), 25 drupacine ( 30 ), 30 hainanensine ( 31 ) 31 and cephalancetine C ( 32 ) 32 via comparison of the reported spectroscopic data. It deserved to be mentioned that 14 and its hydrochloride salt ( 14a ) were respectively obtained during the isolation.…”

“…The 1 H and 13 C NMR data showed that compound 11 might be the reduction product of fortuneicyclidin A (12) at C-11, which it was proved by the following 2D NMR data. 20 The planar structure of 11 was established by its 1 H-1 H COSY and HMBC experiments (Fig. 2).…”

Classifying natural products from plants, fungi or bacteria using the COCONUT database and machine learning

“…3). In details, the fungal epicospirocin 1 [33], penicimeroterpenoid A [34], beetleane A [35], funiculolide D [36], and fusoxypenes A [37], the bacterial vertirhodin A [38], bosamycin A [39], and dumulmycin [40], and the plant fortuneicyclidin A [41], meloyunnanine A [42], hyperfol B [43], pegaharmol A [44], hunzeylanine A [45], mucroniferal A [46], perovsfolin A [47], horienoid A [48], and erythrivarine J [49] were correctly classified. On the other hand, the fungal rhizolutin [50] and myxadazoles A [51] and the bacterial marinoterpin A [52] were misclassified.…”

Classifying Natural Products from Plants, Fungi or Bacteria using the COCONUT Database and Machine Learning

“…Among 20 recently reported NPs from plants, fungi, or bacteria, 17 were correctly assigned to their origin, while only two were misassigned (Table 3, Figure 3). In details, the fungal epicospirocin 1, [33] penicimeroterpenoid A, [34] beetleane A, [35] funiculolide D, [36] and fusoxypenes A, [37] the bacterial vertirhodin A, [38] bosamycin A, [39] and dumulmycin, [40] and the plant fortuneicyclidin A, [41] meloyunnanine A, [42] hyperfol B, [43] pegaharmol A, [44] hunzeylanine A, [45] mucroniferal…”