Euphopanes A–C, three new diterpenoids from <i>Euphorbia pekinensis</i>

Yan, Xue-Long; Huang, Jia-Luo; Tang, Ya-Qi; Yin, Sheng

doi:10.1080/14786419.2020.1765342

Cited by 10 publications

(10 citation statements)

References 19 publications

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“…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 ].…”

Section: Occurrence Of Euphorbia Diterpenesmentioning

confidence: 99%

“…Abietane diterpenoids; 1 α ,9 β -dihydroxy-ent-abieta-8(14),13(15)-dien-16,12-olide ( 4 ) and 1 α -hydroxy-14-oxo-ent-abieta-8,13(15)-dien-16,12-olide ( 5 ) isolated from E. neriifolia exhibited no antiangiogenic activity (HUVECs migration) with an IC 50 value of >50.00 µg/mL [ 68 ]. Cembrane diterpene euphopane C, from the root extracts of E. pekinensis, displayed cytotoxic activities against C4-24B; C4-2B/ENZR, MDA-MB-231 with IC 50 values of 32.30, 29.30 and >50 µM, respectively, compared to doxorubicin (0.53, 1.06 and 0.78 µM respectively) [ 44 ], while euphoroylean A ( 8 ) and euphoroylean B ( 9 ), from the whole plant extract of E. royleana, showed chemoreversal, combination abilities on Hep-G2/DOX; IC 50 > 50 µM, compared to verapamil [ 33 ]. Euphoractone ( 14 ) from E. fischeriana exhibited cytotoxic on H23; IC 50 = 21.07 mmol/L, H460; IC 50 = 20.91 mmol/L) using cisplatin as a positive control [ 60 ].…”

Section: Pharmacological Activities and Structure–activity Relationship (Sar)mentioning

confidence: 99%

“…All the tested compounds exhibited significant cytotoxic activities against C4-2B/ENZR and C4-2B cell lines, with most of them recording IC 50 values ranging between 14.10 µM to 34.70 µM, with low activity reported for the MDA-MB-231 cell line. Notably, euphopane A ( 170 ), euphopane B ( 16 ) and (12 β )-2,12-dihydroxyisopimara-1,7,15-trien-3-one ( 171 ) displayed the most potent activity against C4-2B cell line, with IC 50 values of 14.30 µM, 16.90 µM, and 15.30 µM, respectively, compared to doxorubicin, with IC 50 values of 0.53, 1.06 and 0.78 µM [ 44 ].…”

Section: Pharmacological Activities and Structure–activity Relationship (Sar)mentioning

confidence: 99%

“…Anti-HIV-1, antiangiogenic activity, anti-influenza, NO inhibitory effects [42,[68][69][70][71][72][73] E. pekinensis cembrane (n = 1), ent-abietane (n = 1), isopimarane (n = 4) Cytotoxic [44] Table 1. Cont.…”

Section: Occurrence Of Euphorbia Diterpenesmentioning

confidence: 99%

“…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.…”

Section: Higher Diterpenesmentioning

confidence: 99%

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

et al. 2021

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Euphorbia species have a rich history of ethnomedicinal use and ethnopharmacological applications in drug discovery. This is due to the presence of a wide range of diterpenes exhibiting great structural diversity and pharmacological activities. As a result, Euphorbia diterpenes have remained the focus of drug discovery investigations from natural products. The current review documents over 350 diterpenes, isolated from Euphorbia species, their structures, classification, biosynthetic pathways, and their structure–activity relationships for the period covering 2013–2020. Among the isolated diterpenes, over 20 skeletal structures were identified. Lathyrane, jatrophane, ingenane, ingenol, and ingol were identified as the major diterpenes in most Euphorbia species. Most of the isolated diterpenes were evaluated for their cytotoxicity activities, multidrug resistance abilities, and inhibitory activities in vitro, and reported good activities with significant half-inhibitory concentration (IC50) values ranging from 10–50 µM. The lathyranes, isopimaranes, and jatrophanes diterpenes were further found to show potent inhibition of P-glycoprotein, which is known to confer drug resistance abilities in cells leading to decreased cytotoxic effects. Structure–activity relationship (SAR) studies revealed the significance of a free hydroxyl group at position C-3 in enhancing the anticancer and anti-inflammatory activities and the negative effect it has in position C-2. Esterification of this functionality, in selected diterpenes, was found to enhance these activities. Thus, Euphorbia diterpenes offer a valuable source of lead compounds that could be investigated further as potential candidates for drug discovery.

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