A new tetracyclic diterpenoid from the seeds of <i>Euphorbia lathyris</i>

Ma, Lie‐Feng; Zhang, Yue; Zhang, Xuan; Chen, Meng-Jia; Zhan, Zha‐Jun; Shan, Wei‐Guang

doi:10.1177/1747519819901101

Cited by 5 publications

(10 citation statements)

References 25 publications

(33 reference statements)

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“…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.…”

Section: Higher Diterpenesmentioning

confidence: 99%

“…The previous unreported diterpenoids, considered as 18 (or 19)-norditerpenoids of the ent -isopimaranes skeleton, were isolated for the first time from E. neriifolia [ 73 ]. Furthermore, an unusual tetracyclic diterpenoid named eupholathone ( 343 ) [ 66 ] was isolated from E. lathyris and described for the first time in the genus. Besides, previously undescribed euphnerin A ( 337 ) and euphnerin B ( 338 ) [ 71 ] isolated from the stems of E. neriifolia were found to possess a spirocyclic carbon skeleton rarely found among rosane diterpenoids.…”

Section: Higher Diterpenesmentioning

confidence: 99%

“…Rings A and B are usually trans-configured, while rings B and C are cis-configured. Lathyrane diterpenes were isolated from the seed extracts of E. lathyris ( 247 – 248 ) [ 31 , 66 ], root extracts of E. stracheyi ( 249 – 261 ) [ 32 ], whole-plant extracts of E. royleana ( 262 – 295 ) [ 33 ], and aerial extracts of E. antiquorum ( 296 – 299 ) [ 34 ]. Other records described the isolation of lathyrane diterpenes from E. kansuensis ( 300 – 301 ) [ 35 ], E. lathyris ( 302 – 307 ) [ 103 ], and E. antiquorum ( 308 – 310 ) [ 56 ].…”

Section: Lower Diterpenesmentioning

confidence: 99%

“…In general, tigliane-type diterpenes contain a double bond between the C-1 and C-2 in ring A, and another double bond in their B-ring [ 58 ]. Tigliane ( 339 – 346 ) [ 52 , 57 , 66 , 71 , 102 ], myrsinol ( 347 – 352 ) [ 58 , 74 ] , paraliane ( 353 – 361 ) [ 49 , 72 ], pepluane ( 362 – 365 ) [ 72 ], presegetane ( 366 – 368 ) [ 49 ], cyclomyrsinol ( 369 – 370 ) [ 39 ] and daphnane ( 371 – 373 ) [ 40 , 53 ] were found dominant in Euphorbia 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%

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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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