Kopetdaghinanes, pro-apoptotic hemiacetialic cyclomyrsinanes from Euphorbia kopetdaghi

Riahi, Farhad; Dashti, Nasrin; Ghanadian, Mustafa; Aghaei, Mahmoud; Faez, Farough; Jafari, Seyyed Mehdi; Zargar, Narges

doi:10.1016/j.fitote.2020.104636

Cited by 9 publications

(11 citation statements)

References 25 publications

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“…The newly reported diterpenoids structures led to new information about their biological activities and their biogenesis in plants. Plants newly investigated within this time frame were E. kopetdaghi [ 25 ], E. sanctae-catharinae [ 26 ], E. gaditana [ 27 ], E. saudiarabica [ 28 ], and E. glomerulans [ 29 ].…”

Section: Occurrence Of Euphorbia Diterpenesmentioning

confidence: 99%

“…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 ). Anticancer, chemoreversal abilities, and anti-inflammatory activities were the most-studied biological studies.…”

Section: Occurrence Of Euphorbia Diterpenesmentioning

confidence: 99%

“…This skeletal structure had not been previously identified [ 104 ]. Phytochemical investigations of the aerial extracts of E. kopetdaghi yielded previously undescribed cyclomyrsinol diterpenoids, named kopetdaghinane A ( 381 ) and B ( 382 ) [ 25 ], which were found to possess an oxidation pattern of a new tetrahydrofuran pattern having a hemiacetal group. This was the first report of cyclomyrsinol diterpenes from this species.…”

Section: Lower Diterpenesmentioning

confidence: 99%

“…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)…”

Section: Occurrence Of Euphorbia Diterpenesmentioning

confidence: 99%

“…For instance, meroterpenoids including fischernolide A-D (311-314) [30] and fischeriana A (315) [30] were isolated from E. fischeriana for the first time in this species. Two abietane-type diterpenoids 1α,9β-dihydroxy-ent-abieta-8(14),13(15)-dien-16,12-olide (4) and 1α-hydroxy-14-oxo-ent-abieta-8,13(15)-dien-16,12-olide (5) together with ent-abietanetype (17)(18)(19)(20)(21)(22)(23)(24)(25)(26), ingol-type (165-169) and rosane-type (337-338) diterpenenoids were isolated from E. neriifolia [68]. A previous study by Baloch et al [85] reported the isolation of ten ingenane-type diterpenes from the latex of E. cauducifolia (Syn.…”

Section: Meroterpenoidsmentioning

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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