ent-Rosane diterpenoids from Euphorbia milii showing an Epstein–Barr virus lytic replication assay

Abstract

Thirteen new ent-rosane diterpenoids were bioassay-guided isolated from the aerial parts of Euphorbia milii evaluating by Epstein–Barr virus lytic replication assay.

Euphorbia Diterpenes: An Update of Isolation, Structure, Pharmacological Activities and Structure–Activity Relationship

“…Most of the studied species contained both polycyclic and macrocyclic diterpenes and included E. lathyris [ 31 ], E. stracheyi [ 32 ], E. royleana [ 33 ], E. antiquorum [ 34 ], E. kansuensis [ 35 , 36 ], E. prolifera [ 37 ], E. peplus [ 38 ], E. aellenii [ 39 ], E. pilosa [ 40 ], E. saudiarabica [ 28 ], E. marginata [ 41 ], E. neriifolia [ 42 ], E. resinifera [ 43 ], E. pekinensis [ 44 ], E. hylonoma [ 45 ], E. milii [ 46 ], E. wallichii [ 47 ], and E. ebracteolata [ 48 ]. While others contained only macrocyclic diterpenes like E. esula [ 49 ], E. helioscopia [ 50 ], E. yinshanica [ 51 ], E. grandicornis [ 52 ], and E. kansui [ 53 ].…”

“…Within the review period, over 200 different polycyclic diterpenes were described, including abietanes ( 1 – 5 ) [ 38 , 68 ], atisane ( 6 ) [ 35 ], cembranes ( 7 – 9 ) [ 33 , 44 ]; ent -abietanes ( 10 – 28 ) [ 34 , 38 , 47 , 59 ], ent -atisanes ( 29 – 41 ) [ 32 , 33 ], ent -labdanes ( 68 – 72 ) [ 38 , 51 ], ent -isopimaranes ( 42 – 64 ) [ 43 , 45 , 69 , 70 ], ent -kauranes ( 65 – 67 ) [ 33 ], ent -rosanes ( 73 – 87 ) [ 45 , 46 , 71 ], gaditanone ( 88 ) [ 27 ], and kaurane ( 247 ) [ 31 , 66 ]. Atisanes and cembranes were the least dominant subclasses, as only one new atisane, atisane-3-oxo-16 α ,17-diol ( 6 ) [ 35 ], from E. kansuensis and three cembranes diterpenes, euphopane C ( 7 ) from E. pekinensis [ 44 ], euphoroylean A ( 8 ), and B ( 9 ) from E. royleana [ 33 ], were isolated.…”

“…Chemical investigation of E. neriifolia led to the isolation of ent -rosane diterpenoids, euphominoid E ( 73 ) [ 71 ], while studies on E. hylonoma afforded ent-rosa-1(10), 15-dien-2-one ( 74 ) [ 45 ]. Others included euphominoid A–L ( 75 – 87 ) isolated from E. milii [ 46 ]. Rosane diterpenoids, such as 18-hydroxyhugorosenone, were previously isolated from E. ebracteolata.…”

“…Cytotoxic, inhibition of NO [35,36] E. kansui ingenane (n = 15), jatrophane (n = 8) Cytotoxic effect, antiproliferative [53,65] E. kopetdaghi Other Cytotoxic [25] E. lathyris ingenane (n = 1), lathyrane (n = 8), tigliane (n = 1) Inhibitory of NO [31,66] E. marginata ingol (n = 20), Multidrug reversal activity [41] E. micractina jatrophane (n = 2) Anti-HIV-1 replication ability [67] E. milii ent-rosane (n = 16) Inhibitory (anti-EBV lytic replication [46] E.neriifolia abietane n = 2), ent-abietane (n = 9), ent-isopimarane (n = 12), ent-rosane (n = 1), ingol (n = 5), rosane (n = 2)…”

“…In this review we have collected information about the occurrence, isolation, structure and biological activities of Euphorbia diterpenes between the years 2013 and 2020, as summarized in Table 2 alongside Figures 1-15. Within the review period, over 200 different polycyclic diterpenes were described, including abietanes (1-5) [38,68], atisane (6) [35], cembranes (7)(8)(9) [33,44]; ent-abietanes (10-28) [34,38,47,59], ent-atisanes (29-41) [32,33], ent-labdanes (68-72) [38,51], ent-isopimaranes [43,45,69,70], ent-kauranes (65-67) [33], ent-rosanes (73-87) [45,46,71], gaditanone (88) [27], and kaurane (247) [31,66]. Atisanes and cembranes were the least dominant subclasses, as only one new atisane, atisane-3-oxo-16α, 17-diol (6) [35], from E. kansuensis and three cembranes diterpenes, euphopane C ( 7) from E. pekinensis [44], euphoroylean A (8), and B ( 9) from E. royleana [33], were isolated.…”