Jatrophane Diterpenoids from <i>Euphorbia glomerulans</i>

Hasan, Aobulikasimu; Liu, Ge-yu; Hu, Rui; Aisa, Haji Akber

doi:10.1021/acs.jnatprod.8b00507

Cited by 24 publications

(18 citation statements)

References 29 publications

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“…The presence of an isobutanoyloxy moiety at C-8 rather than at C-7 had a positive effect on the modulation of drug accumulation in the MCF-7/ADR cells by comparing the substituents and RF values of 314, 315, and 316. Furthermore, with the comparison of the biological results of 307, 309, and 311 to those of 308, 310, and 318, it was demonstrated that favorable following trend in activity at C-8 is: benzoyloxy group [ H & hydroxy group (Hasan et al 2019). Remy and Litaudon (2019) have published a review on anti-CHIKV activity of eighty diterpenoids covering the years 2011 to 2019.…”

Section: Mdr Reversing Activitymentioning

confidence: 99%

Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

et al. 2020

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Diterpene compounds specially macrocyclic ones comprising jatrophane, lathyrane, terracinolide, ingenane, pepluane, paraliane, and segetane skeletons occurring in plants of the Euphorbiaceae family are of considerable interest in the context of natural product drug discovery programs. They possess diverse complex skeletons and a broad spectrum of therapeutically relevant biological activities including anti-inflammatory, anti-chikungunya virus, anti-HIV, cytotoxic, and multidrug resistance-reversing activities as well as curative effects on thrombotic diseases. Among macrocyclic diterpenes of Euphorbia, the discovery of jatrophane and modified jatrophane diterpenes with a wide range of structurally unique polyoxygenated polycyclic derivatives and as a new class of powerful inhibitors of P-glycoprotein has opened new frontiers for research studies on this genus. In this review, an attempt has been made to give in-depth coverage of the articles on the naturally occurring jatrophanes and rearranged jatrophane-type diterpenes isolated from species belonging to the Euphorbiaceae family published from 1984 to March 2019, with emphasis on the biogenesis, isolation methods, structure, biological activity, and structureactivity relationship.

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Section: Mdr Reversing Activitymentioning

confidence: 99%

Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

et al. 2020

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“…In addition to these signals, the 13 C NMR spectrum displayed four methyls ( δ C 20.7, 23.1, 24.0 and 25.2), one sp 3 methylene ( δ C 52.3), one sp 2 methylene ( δ C 114.2), five sp 3 methines ( δ C 42.8, 47.7, 65.2, 72.7 and 81.0), two sp 2 methines ( δ C 133.1 and 136.1), three sp 3 quaternary carbons ( δ C 49.6, 79.1 and 85.2) and three sp 2 quaternary carbons ( δ C 138.0, 204.9 and 213.2). These signals account for 19 carbons, indicating the absence of one carbon signal that may be attributed to conformational exchange of the jatrophane type diterpenoid molecule [ 17 , 18 ]. The spectroscopic data of 1 was similar to (2 S *,3 S *,4 R *,5 R *,7 S *,8 R *,13 S *,15 R *)-5,7,8-triacetoxy-3-benzoyloxy-15-hydroxyjatropha-6(17),11 E -diene-9,14-dione ( 5 ) [ 17 ] except for the presence of signals responsible for an hydroxy group ( δ H 2.33) and an additional oxygenated quaternary carbon ( δ C 79.1), the absence of the proton signal at C-2.…”

Section: Resultsmentioning

confidence: 99%

Jatrophane Diterpenoids from the Seeds of Euphorbia peplus with Potential Bioactivities in Lysosomal-Autophagy Pathway

Ding

et al. 2021

Nat. Prod. Bioprospect.

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Euphopepluanones F − K (1 − 4), four new jatrophane type diterpenoids were isolated from the seeds of Euphorbia peplus, along with eight known diterpenoids (5 − 12). Their structures were established on the basis of extensive spectroscopic analysis and X-ray crystallographic experiments. The new compounds 1 − 4 were assessed for their activities to induce lysosomal biogenesis through LysoTracker Red staining. Compound 2 significantly induced lysosomal biogenesis. In addition, compound 2 could increase the number of LC3 dots, indicating that it could activate the lysosomal-autophagy pathway. Graphic Abstract

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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%

“…The cytotoxic evaluation of jatrophane diterpenoids isolated from the acetone extracts of E. glomerulans on multidrug-resistant breast cancer cells (MCF-7/ADR) was found to overexpress the P-glycoprotein (P-gp) with varying chemoreversal abilities and with reduced cytotoxicity activity. Euphoglomeruphane K ( 233 ) and L ( 234 ) showed better MDR reversal activity, with IC 50 values of 5.00 μM and 5.10 μM, respectively, compared to verapamil, the positive control, with IC 50 value of 4.70 μM [ 29 ].…”

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

confidence: 99%

“…Melanin synthesis activity, inhibitory (α-glucosidase), inhibitory (NO production) [34,[54][55][56] E. dracunculoides tigliane (n = 1), myrsinol (n = 2) Cytotoxic [57,58] E. ebracteolata rosane (n = 5) Lipase inhibitory [48] E. esula jatrophane (n = 41) Antimalarial [34,59] E. fischeriana ent-abietane (n = 4), meroterpenoid (n = 5), tigliane (n = 5) Cytotoxic [30,[60][61][62][63] E. gaditana gaditanone (n = 1) Not evaluated [27] E. glomerulans jatrophane (n = 17) MDR-chemoreversal [29] E. grandicornis tigliane (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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Jatrophane Diterpenoids from Euphorbia glomerulans

Cited by 24 publications

References 29 publications

Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

Jatrophane Diterpenoids from the Seeds of Euphorbia peplus with Potential Bioactivities in Lysosomal-Autophagy Pathway

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

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