Two new myrinsol diterpenoids from Euphorbia dracunculoides Lam.

Wang, Li; Zang, Zhen; Wang, Yufei; Huang, Sheng‐Xiong; Cao, Ping; Zhao, Yong

doi:10.1016/j.cclet.2014.08.005

Cited by 15 publications

(17 citation statements)

References 6 publications

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“…The relative configuration of 13 was assigned to be identical to that of proliferin A due to the high resemblance of all proton signals on core skeleton of them. 32 The relative stereochemistry was further confirmed by ROESY experiment. Thus, euphordraculoin M (13) was established as 5α,7β,15β-Otriacetyl-14α-O-benzoyl-2α-O-isobutyryl-10-hydroxy-14-desoxo-10,18-dihydro-3β-O-propanoylmyrsinol.…”

Section: Accepted Manuscriptmentioning

confidence: 63%

“…(8) 9944 (1) 3609 (1) 1638 (1) 18(1) O (14) 6129 (1) 6130 (1) 2515 (1) 19(1) O (15) 6696 (1) 5221 (1) 1586 (1) 17(1) O (21) 8922 (2) 5666 (1) -351(1) 40(1) O (13) 10382 (1) 6498 (1) 2292 (1) 21(1) O (7) 13353 (1) 4791 (1) 1562 (1) 27(1) O (25) 11120 (1) 2699 (1) 1069 (1) 23(1) O (10) 7920 (1) 4299 (1) 3178 (1) 21(1) O (32) 7413 (2) 3080 (1) 3549 (1) 34(1) O (5) 11018 (1) 5593 (1) 796 (1) 21(1) O (23) 10878 (2) 4324 (1) 487 (1) 31(1) O (34) 5664 (2) 7448 (1) 2671 (1) 31(1) C (22) 7202 (3) 4524 (1) -214(1) 32(1) C …”

Section: Contents Of Supplementary Materialsunclassified

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Structurally diversified diterpenoids from Euphorbia dracunculoides

Wang

Sun

et al. 2015

Tetrahedron

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Section: Accepted Manuscriptmentioning

confidence: 63%

Section: Contents Of Supplementary Materialsunclassified

Structurally diversified diterpenoids from Euphorbia dracunculoides

Wang

Sun

et al. 2015

Tetrahedron

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“…Examples of modified jatrophane diterpenes isolated from Euphorbia species were mysrinanes from E. prolifera ( 316 – 322 ) [ 37 ], paralianones from E. peplus ( 323 – 325 ) [ 38 ], pimaranes from E. stracheyi ( 326 – 328 ) [ 32 ], and premyrsinanes from E. sanctae-catharinae ( 329 – 331 ) [ 26 ]. Others were myrsinol from root extracts of E. prolifera ( 347 – 350 ) [ 74 ] and from the aerial extracts of E. dracunculoides ( 351 – 352 ) [ 58 ], paralianes from E. esula ( 353 ) [ 49 ] and E. peplus ( 354 – 361 ) [ 72 ] and pepluane ( 362 – 365 ) [ 72 ]. Jatrophane diterpenes can be polyacrylate derivatives, with the number of ester groups varying from three, as in guyonianin E, to eight, as in esulatin H. The acyl groups common to jatrophane diterpenes include benzoyl, acetyl, isobutanoyl, or nicotinoyl 2-methylbutanoyl, and propionyl, butanoyl, tigloyl, angeloyl, or cinnamoyl.…”

Section: Lower Diterpenesmentioning

confidence: 99%

“…Contrary to other Euphorbiaceae and Thymelaeaceae diterpenes, tigliane diterpenoids have a 5/7/6/3- tetracyclic ring system containing a five-membered ring A, a seven-membered ring B, a six-membered ring C, and a cyclopropane system D. The core skeleton structure has 20 carbons, including five methylene, five methyl, and nine methine groups, and one quaternary carbon. 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%

“…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%

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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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