Diterpenes inhibiting NO production from Euphorbia helioscopia

New Bioactive Macrocyclic Diterpenoids from Euphorbia helioscopia

“…Diterpenoids are particularly rich and diversified in Euphorbia species, from which more than 650 diterpenoids have been isolated and identified, including jatrophanes, lathyranes, ingenanes, tiglianes, abietanes, kauranes, pimaranes, daphnanes, casbbanes, myrsinanes, and so on . Many of them possessed significant biological activities, including cytotoxic, antimicrobial, anti‐inflammatory, and pesticidal activities . In particular, some ingenol and phorbol esters are potent and promising diterpenoids that are under clinical investigation .…”

Heliosterpenoids A and B, two Novel Jatrophane-Derived Diterpenoids with a 5/6/4/6 Ring System from Euphorbia helioscopia

“…The IR spectrum suggested the presence of ester carbonyl (1743 cm −1 ), carbonyl (1715 cm −1 ), α , β -unsaturated keton (1675 cm −1 ) as well as a characteristic band for the aromatic ring (1602 and 1454 cm −1 ) functionalities. Based on those known jatrophane-skeleton diterpenoids with acyloxy groups from E. helioscopia 5, 9, 12–14 , 1 H and 13 C NMR resonances of 1 showed a set of typical signals for polyesterified jatrophane-type diterpene nature as well (Table 1). The 1 H NMR spectrum of 1 in CDCl 3 implied a benzoyl group [ δ H 8.05 (2 H, dd, J  = 7.8, 1.2 Hz, H-2′ and H-6′), 7.60 (1 H, t, J  = 7.8 Hz, H-4′), and 7.47 (2 H, t, J  = 7.8 Hz, H-3′ and H-5′)], a pair of cis olefinic protons [ δ H 6.45 (1 H, dd, J  = 10.2, 2.4 Hz, H-7), and 5.86 (1 H, d, J  = 10.2 Hz, H-8)] and two oxygenated methine protons [ δ H 5.62 (1 H, d, J  = 1.8 Hz, H-14), and 5.26 (1 H, dd, J  = 7.2, 2.4 Hz, H-3)].…”

“…2, was deduced from the interpretation of the NOESY spectrum, together with comparison with the large variety of known jatrophane diterpenes, in which all the five membered ring is trans -fused with the 12-membered macro-ring forming the skeleton, and H-4 is α -oriented and C-15 substituted group is β -oriented based on a biogenetic point of view 5, 14–17 . Besides, the NOE difference experiments of 1 were also performed to give further data for the relative configuration determination (Supporting Information).…”

Therapeutic Potential of Essential Oils Focusing on Diterpenes

“…The antioxidant capacities of EOs are a common concern for those bearing active hydroxyl group (−OH) in their structures as they can scavenge ROS (Bakkali et al ., 208). In vitro and in vivo studies have revealed the potential antioxidant capacities of some important diterpenes, such as carnosol, carnosic acid (600 mg/kg) (Ortuño et al ., ; Carvalho et al ., ), rosmadial, rosmarinic acid (Pérez‐Fons et al ., ; Petiwala and Johnson, ), lobocompactols A and B (IC 50 : 17.80–59.06 μM) (Minh et al ., ), foliol, linearol (5 μM), sidol (10 μM) (González‐Burgos et al ., ), and jatrophane diterpenes (Chen et al ., ). However, Pérez‐Fons et al .…”

“…() observed an effect on phospholipid membranes by diterpenes obtained from Rosmarinus officinalis that was thought to be the result of changes in the membrane permeability. The most common modes of antioxidant activities are the antiradical (Ayinampudi et al ., ), inhibition of lipid peroxidant (Ortuño et al ., ), and ROS and nitric oxide radical (NO ● ) production (Chen et al ., ). It has also been postulated that for that concentration‐dependent antioxidant and cytotoxic activity of EOs (Bakkali et al ., ) that at low concentrations, EOs show antioxidant activity (cytoprotectivity), while at high concentration, they may act as cytotoxic (pro‐oxidant) agents.…”