Macrocyclic Diterpenoid Constituents of Euphorbia deflexa, an Endemic Spurge from Greece

Abstract

Euphorbia deflexa, an endemic spurge from Greece, was investigated for the occurrence of its diterpene constituents. Through continuous monitoring by 1H NMR, 22 diterpenoids were isolated, including 16 previously undescribed compounds (euphodeflexins A–P), which belong to the jatrophane, ingenane, segetane, and pepluane diterpene types. Their chemical structures were elucidated through a combination of HRESIMS, NMR spectroscopy, and X-ray data. The isolated diterpenoids were tested against a panel of human cancer cell lines, as well as against two bacterial strains. Compounds 1, 13, and 17 were active against the HeLa cell line with IC50 values 9.9, 9.8, and 5.8 μM, respectively.

Tigliane Diterpenoids with Larvicidal, Antifungal, and α-Glucosidase Inhibitory Activities from Croton damayeshu

“…Comparison of the NMR data of 4 with those of the known compound wikstrocin C revealed the presence of an octanoyl unit in compound 4 , which was verified by the 1 H– 1 H COSY correlations of H-2″/H-3″/H-4″ and H-7″/H-8″ (Figure S41, Supporting Information). Additionally, the characteristic resonances (δ C 167.8 (CO), 128.5 (C), 138.0 (CH), 14.6 (CH 3 ), 12.4 (CH 3 )) for a tiglyl group ,, in 4 were observed. On account of the long-range correlation between H-12 (δ H 5.50, d, J = 10.2 Hz) and C-1′ (δ C 167.8) of the tiglyl moiety in the HMBC spectrum (Figure S40, Supporting Information), which indicated the location of the tiglate at C-12, the octanoate group was then assigned to C-13.…”

“…Comparison of the NMR data of 4 with those of the known compound wikstrocin C 7 revealed the presence of an octanoyl unit in compound 4, which was verified by the 1 H− 1 H COSY correlations of H-2″/H-3″/H-4″ and H-7″/H-8″ (Figure S41, Supporting Information). Additionally, the characteristic resonances (δ C 167.8 (CO), 128.5 (C), 138.0 (CH), 14.6 (CH 3 ), 12.4 (CH 3 )) for a tiglyl group 7,14,15 the HMBC spectrum (Figure S40, Supporting Information), which indicated the location of the tiglate at C-12, the octanoate group was then assigned to C-13. The NMR data of compound 5 (Tables 1 and 2 3 and 4, the NMR data of compound 8 were almost the same as compound 7 except for the observation of a different C-13 substitution pattern; that is, compound 8 contains an unsaturated decanoyl unit at C-13.…”

New Diterpenes with Potential Antitumoral Activity Isolated from Plants in the Years 2017–2022

“…Euphstrachenol C 21 was cytotoxic against the MV4-11 (lymphoblast from human biphenotypic B myelomonocytic leukemia) cancer cell line, with an IC 50 value of 5.92 µM, using the MTT assay and taxol as a positive control (Figure 9). [19] and euphodeflexin L 22 [20].…”

Euphorbiaditerpenoids: isolation, structure, bioactivity, biosynthesis, and synthesis (2013–2021)

“…Euphodeflexins O and P ( 933 and 934 ) from E. deflexa are two pepluanes incorporating a rare aromatic ring. 190 …”

“…Presegetanes possess a 5/9/5 skeleton, while segetanes have a 5/7/6/5 skeleton. Euphorbesulins A–C ( 935–937 ) from E. esula , 111 euphodeflexins M and N ( 938 and 939 ) from E. sieboldiana , 191 and euphodeflexins M and N ( 940 and 941 ) from E. deflexa 190 are seven presegetane diterpenoids, while 942 from E. taurinensis 192 and 943 from E. peplus 193 are two rare segetane diterpenoids.…”