Three new diterpenoids from Euphorbia peplus

Abstract

Three new diterpenoids (1-3) (two abietane type diterpenoids and a paralianone type diterpenoid), together with four known compounds (4-7) were isolated from the whole plants of Euphorbia peplus. Their structures were elucidated through spectroscopic analysis and physicochemical characteristics. The cytotoxic activities of compounds 1-7 against five human tumor cell lines were evaluated, however, they were inactive at the concentration of 40 μM. The compound 3 enhanced lysosomal biogenesis with Lyso Tracker staining

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 ].…”

“…Of this, E. esula [ 49 ] had the highest number of isolated diterpenes ( n = 44), of which the majority were jatrophane and lathyrane diterpenes, followed by E. royleana [ 33 ] ( n = 36). Others were E. neriifolia [ 42 ], ( n = 32), E. lathyris ( n = 21) [ 31 ] ( n = 28), E. kansui [ 53 ] ( n = 23), E. stracheyi [ 32 ] ( n = 22), E. peplus [ 38 ] ( n = 22), E. antiquorum [ 34 ], ( n = 21) and E. marginata [ 41 ] ( n = 20). While other species reported only one or two diterpenes such as E. gaditana [ 27 ] ( n = 1), E. kopetdaghi [ 25 ] ( n = 2), E. aellenii [ 39 ] ( n = 2), E. pilosa ( n = 2) and E. grandicornis ( n = 2) ( Table 1 ).…”

“…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.…”

“…Few other Euphorbia species investigated within the review period were reported to contain ent -abietane diterpenoids. Three previously undescribed abietane-type diterpenes; 11,12-didehydro-8 α ,14-dihydro-7-oxo-helioscopinolide A ( 1 ) and 8 β -acetyl-paralianone D ( 2 ) isolated from the acetone extracts of E. peplus [ 38 ] differed from retusolides A-F previously isolated from E. retusa [ 81 ] and ent-abietane diterpenoids from the roots of E. guyoniana [ 82 ], which had a cyclopropane at C-4. The compound: 11,12-didehydro-8 α ,14-dihydro-7-oxo-helioscopinolide A ( 1 ) differed from helioscopinolides and secohelioscopinolides previously isolated from E. formosana only by the hydroxyl group at C-7 [ 83 ].…”

Jatrophane Diterpenoids from the Seeds of Euphorbia peplus with Potential Bioactivities in Lysosomal-Autophagy Pathway

“…Recently, our group discovered ingenane type diterpenoids 20-deoxyingenol and its analogues from E. peplus, possessing activity to promote lysosome biogenesis, limit amyloid plaque formation in APP/SP1 mice's brain, which suggested that the potential of these compounds for the treatment of Alzheimer disease [10]. The subsequent phytochemical studies of the plants of the genus Euphorbia led to isolation of several novel diterpenoids with significant bioactivities [11][12][13][14][15][16]. In our continuing efforts to uncover structurally novel diterpenes capable of inducing lysosomal biogenesis, four new jatrophane type diterpenoids euphopepluanones F − K (1 − 4), along with eight known diterpenoids (5 − 12) were obtained from the seed of E. peplus (Fig.…”