Three ent-trachylobane diterpenes from the leaf exudates of Psiadia punctulata

Juma, Bernard F.; Midiwo, Jacob O.; Yenesew, Abiy; Waterman, Peter G.; Heydenreich, Matthias; Peter, Martin G.

doi:10.1016/j.phytochem.2006.04.007

Cited by 9 publications

(13 citation statements)

References 5 publications

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“…The chemistry of the diterpenes of this exudate could explain the cited activities [10]. As shown in previous works, the exudate from leaves of P. punctulata indeed is comprised of terpenoids, among them diterpenes from the classes of kauranes and trachylobanes [9,11,12]. Kauranes have already been reported for several families of higher plants and some of them have been cited as anti-inflammatory, antibacterial, antifungal, antitumor, and cytotoxic agents [13].…”

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confidence: 73%

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Study of Anti-Tuberculosis Activity Behaviour of Natural Kaurane and Trachylobane Diterpenes Compared with Structural Properties Obtained by Theoretical Calculations

Soares

Cabral

Martins

et al. 2017

Natural Product Communications

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A set of seven diterpenes, three kauranes and four trachylobanes, isolated from the African plant Psiadia punctulata were assayed against Mycobacterium tuberculosis and reached activity comparable with cycloserine, a second line drug used to treat tuberculosis (TB). Several structural properties of those diterpenes, such as lipophilicity, HOMO and LUMO energies, charge density, and intramolecular hydrogen bond (IHB) formation, were obtained by theoretical calculations and compared with their activities. Peculiar correlations were observed, especially between activity, lipophilicity and IHB formation.

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confidence: 73%

“…Psiadia punctulata (DC) Vatke is an African, erect round-topped shrub whose leaves are covered by an exudate, mainly when they are young [9,10]. This exudate seems to be responsible for the plant's drought resistance and also for the grazing-deterrent effect which makes browsing herbivores like giraffes and goats avoid it, even during severe drought [10,11].…”

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confidence: 99%

Study of Anti-Tuberculosis Activity Behaviour of Natural Kaurane and Trachylobane Diterpenes Compared with Structural Properties Obtained by Theoretical Calculations

Soares

Cabral

Martins

et al. 2017

Natural Product Communications

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“…It is reported that P. punctulata is usually avoided by some herbivore animals even during severe drought conditions. An exudate, rich in pharmacologically active secondary metabolites, is potentially responsible for its unpalatable nature and drought resistance (Midiwo et al 2003;Juma et al 2001;Juma et al 2006). We thus hypothesize that one important impact of the presence of O. ficus-indica on native diversity occurs Significance of the differences between the invaded and adjacent uninvaded plots was tested using a permutation test with 1000 permutations through affecting grazing and browsing patterns by herbivores.…”

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confidence: 99%

The invasive Opuntia ficus-indica homogenizes native plant species compositions in the highlands of Eritrea

Tesfay

Kreyling

2020

Biol Invasions

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Invasion by exotic species is recognized as one of the major threats to biodiversity. The effects of invasion by Opuntia ficus-indica (Cactaceae) on the species diversity, richness and composition of invaded communities were studied at three sites in the highlands of Eritrea, East Africa. This paper investigates whether the presence of O. ficus-indica causes a negative effect on the native biodiversity in a region rarely studied so far. The vegetation in invaded and uninvaded plots with similar habitat conditions was sampled and differences in the species composition, diversity and richness were compared between the plots. The overall plant species composition differed significantly with invasion by O. ficus-indica. The invasion by O. ficus-indica also led to a significant homogenization of community compositions. The species richness and Shannon diversity index did not differ significantly between the invaded and uninvaded plots. Nevertheless, we still detected species with significantly lower occurrence in the invaded plots (Psiadia punctulata), but also species which preferred invaded plots (Plectranthus hadiensis). We conclude that O. ficus-indica exerts a negligible effect on the species diversity and richness but that it affects species composition and that there are species which suffer due to its presence. Due to the continuous pressure of the invasion by O. ficus-indica on the species composition and dry climates, further homogenization in the native species diversity is to be expected in the future for the highlands of Eritrea.

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“…1 These compounds have been largely cited as cytotoxic, antitumoral, genotoxic, antiinflammatory, antibacterial, antifungal and moluscidal. [2][3][4] On the other hand, trachylobane is found in some species of Euphorbiaceae, 5 Annonaceae, 6 Asteraceae, 7 Lamiaceae 8 and Leguminosae. 9 Although the biological activities of trachylobane compounds are poorly investigated, they are cited to possess vasorelaxant and cytotoxic properties.…”

Section: Introductionmentioning

confidence: 99%

“…The cytotoxicity of the compounds 1, 3, 4, 6-11 against a small panel of cancer cell lines was evaluated ( Figure 1). (1)(2)(3)(4)(5)(6)(7) and chemical derivatives of compound 1 (8)(9)(10)(11) were attributed to two oxymethylene groups attached to a quaternary carbon. In addition, the presence of the shielded doublets at d 0.58 (d, J = 7.5 Hz, H-12) and 0.83 (dd, J = 7.5 and 2.4 Hz, H-13) of a tetrasubstituted cyclopropane ring suggested that 1 belongs to the trachylobane series.…”

Section: Introductionmentioning

confidence: 99%

Trachylobane and kaurane diterpenes from Croton floribundus spreng

Uchôa¹,

Silva²,

Silveira³

et al. 2013

Quím. Nova

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Recebido em 20/7/12; aceito em 16/12/12; publicado na web em 14/5/13A new trachylobane diterpene ent-trachyloban-18,19-diol (1) was isolated from root bark of Croton floribundus, along with known diterpenes ent-trachyloban-19-oic acid (2), 15b-hydroxy-ent-trachyloban-19-oic acid (3), ent-trachyloban-19-ol (4), ent-kaur-16-en-19-oic acid (5), ent-kaur-16-ene-6a,19-diol (6) and ent-16a-hydroxykaur-11-en-19-oic acid (7). ent-trachyloban-18,19-diol (1) was submitted to derivatization reactions affording four new compounds (8)(9)(10)(11). Cytotoxic activity of diterpenes 1, 3, 4, 7-11 against three human cancer cell lines was evaluated. No compounds showed cytotoxic potential with IC 50 values greater than 25 mg/mL. Compound 6 was evaluated against five human cancer cell lines, showing moderate effect against three cancer cell lines, MDA-MB-435, with IC 50 values of 14.32, 13.47 and 12.1 mg/mL, respectively.Keywords: diterpenes; Croton floribundus; Euphorbiaceae. INTRODUCTIONTrachylobane and kaurene are diterpenoids biosynthetically derived from the monocyclic membrane. Kaurenes have been reported in several families of higher plants, with kaurenoic acid and its natural derivatives found particularly in the Asteraceae and Euphorbiaceae families. 1 These compounds have been largely cited as cytotoxic, antitumoral, genotoxic, antiinflammatory, antibacterial, antifungal and moluscidal. [2][3][4] On the other hand, trachylobane is found in some species of Euphorbiaceae, 5 Annonaceae, 6 Asteraceae, 7 Lamiaceae 8 and Leguminosae. 9 Although the biological activities of trachylobane compounds are poorly investigated, they are cited to possess vasorelaxant and cytotoxic properties. 10As part of an investigative effort to find bioactive diterpenoids in native species from Northeastern Brazil flora, this study reports the phytochemical investigation of the root bark of Croton floribundus Spreng., a tree with ethnobotanical use in the treatment of syphilis and ulcers.11 In this work, the new ent-trachyloban-18,19-diol (1) is reported, along with the known ent-trachyloban-19-oic acid (2), 12 ent-15b-hydroxytrachyloban-19-oic acid (3), 13 ent-trachyloban-19--ol (4), 12 ent-kaur-16-en-19-oic acid (5), 14 ent-kaur-16-en-6a,19-diol (6) 15 and ent-16a-hydroxykaur-11-en-19-oic acid (7). 16 ent-trachyloban-18,19-diol 1 was derivatized to the diacetate, dimethoxyl and diallyl derivatives 8-10, respectively. In addition, an unusual oxidized product 11 was obtained by oxidation with PCC and chromic acid. The cytotoxicity of the compounds 1, 3, 4, 6-11 against a small panel of cancer cell lines was evaluated (Figure 1). Vol. 36,No. 6 were attributed to two oxymethylene groups attached to a quaternary carbon. In addition, the presence of the shielded doublets at d 0.58 (d, J = 7.5 Hz, H-12) and 0.83 (dd, J = 7.5 and 2.4 Hz, H-13) of a tetrasubstituted cyclopropane ring suggested that 1 belongs to the trachylobane series. RESULTS AND DISCUSSIONChemical shifts and comparative analysis of BB and DEPT- 13C NMR spectra revealed 20 lines...

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Three ent-trachylobane diterpenes from the leaf exudates of Psiadia punctulata

Cited by 9 publications

References 5 publications

Study of Anti-Tuberculosis Activity Behaviour of Natural Kaurane and Trachylobane Diterpenes Compared with Structural Properties Obtained by Theoretical Calculations

Study of Anti-Tuberculosis Activity Behaviour of Natural Kaurane and Trachylobane Diterpenes Compared with Structural Properties Obtained by Theoretical Calculations

The invasive Opuntia ficus-indica homogenizes native plant species compositions in the highlands of Eritrea

Trachylobane and kaurane diterpenes from Croton floribundus spreng

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