Diterpenoids from Plectranthus spp. as Potential Chemotherapeutic Agents via Apoptosis

Śliwiński, Tomasz; Sitarek, Przemysław; Skała, Ewa; Isca, Vera M. S.; Synowiec, Ewelina; Kowalczyk, Tomasz; Bijak, Michał; Rijo, Patrícia

doi:10.3390/ph13060123

Cited by 15 publications

(29 citation statements)

References 36 publications

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“…In 1980, Uchida and colleagues were the first to report the isolation and identification of compounds from P. ecklonii ( Uchida et al, 1980 ). At that time, they detected the presence of the abietane parviflorone F ( Srancikova et al, 2013 ) and ecklonoquinones A ( Śliwiński et al, 2020 ) and B ( Andrade et al, 2018 ). After 40 years of research, the composition of this species is still not completely clear, however, here we have enumerated the compounds discovered thus far ( Table 1 and Figure 3 ).…”

Section: Isolated Compounds From Plectranthus Ecklonii Benthmentioning

confidence: 99%

“…Plant extracts containing vitexin ( Gaspar-Marques et al, 2006 ) (apigenin-8- C - β - d -glucopyranoside) are reported to possess anti-inflammatory, and antioxidant activities ( Borghi et al, 2013 ). Phytochemical studies that have been reported investigating P. ecklonii also include the isolation of two isomeric ortho-quinones, ecklonoquinones A ( Śliwiński et al, 2020 ) and B ( Andrade et al, 2018 ) ( Uchida et al, 1980 ), twelve flavones ( Hawas et al, 2008 ), as well as salvigenin ( Van Zyl et al, 2008 ), cirsimiratin ( Nyila et al, 2012 ) and the corresponding flavanone, 2( S )-4',5-dihydroxy-6,7-dimethoxyflavanone ( Costa et al, 2018 ) ( Uchida et al, 1980 ; Grayer et al, 2003 ). Flavonoids with a 5-hydroxy-6,7-dimethoxy-type substitution in the A-ring, such as salvigenin ( Van Zyl et al, 2008 ), cirsimaritin ( Nyila et al, 2012 ) and cirsiliol ( Uchida et al, 1980 ) flavones, are considered typical in the Labiateae family ( Gaspar-Marques et al, 2006 ).…”

Section: Isolated Compounds From Plectranthus Ecklonii Benthmentioning

confidence: 99%

“…Flavonoids with a 5-hydroxy-6,7-dimethoxy-type substitution in the A-ring, such as salvigenin ( Van Zyl et al, 2008 ), cirsimaritin ( Nyila et al, 2012 ) and cirsiliol ( Uchida et al, 1980 ) flavones, are considered typical in the Labiateae family ( Gaspar-Marques et al, 2006 ). No reference to any bioactivities exercised by ecklonoquinones A ( Śliwiński et al, 2020 ) and B ( Andrade et al, 2018 ) has been found in the literature and therefore they are not discussed in this review.…”

Section: Isolated Compounds From Plectranthus Ecklonii Benthmentioning

confidence: 99%

“…This cytotoxic evaluation showed parviflorone D ( Salim et al, 2008 ) as having high toxicity for RAW 264.7 cells ( Andrade et al, 2018 ). Parviflorone D ( Salim et al, 2008 ) isolated from P. ecklonii showed cytotoxicity against human leukaemia cell lines CCRF-CEM and lung adenocarcinoma cell lines A549, by inducing apoptosis and influencing ROS levels ( Śliwiński et al, 2020 ). In another recent study, parviflorone D ( Salim et al, 2008 ) induced apoptosis in a human H7PX glioma cell line, obtained from brain tumour glioblastoma multiforme cells and demonstrated the highest amount of cytotoxicity against CCRF-CEM and A459 cell lines, when compared to other royleanone abietane diterpenes.…”

Section: Biological Activities Of Isolated Compounds From P Ecklonii Benthmentioning

confidence: 99%

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Plectranthus ecklonii Benth: A Comprehensive Review Into its Phytochemistry and Exerted Biological Activities

et al. 2021

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Ethnopharmacological Relevance:Plectranthus genus (Lamiaceae family) contain several species with acknowledged ethnopharmacological uses, such as, for gastrointestinal and respiratory-related problems, due to their anti-inflammatory, antibacterial and antifungal properties. The bioactivity of isolated medicinal compounds from this genus justifies the increased interest in recent times for species of Plectranthus, placing them in the spotlight for natural product drug development.Aim of the study: To the best of our knowledge, this is the first review on the biological activities of Plectranthus ecklonii Benth. As such, the aim of this review was three-fold: 1) to summarize the chemical compounds isolated from P. ecklonii; 2) to collate the biological activities and mechanisms of action of these compounds from in vitro studies; and 3) to evaluate the documented uses and potential applications of this species, in order to postulate on the direction of pharmaceutical uses of this species.Materials and methods: An extensive database retrieval was performed using the electronic databases Web of Science, PubMed, Google Scholar and ScienceDirect. The search criteria consisted of the keywords “Plectranthus ecklonii”, “Plectranthus ecklonii + review”, “Plectranthus ecklonii + diterpenes” or “Plectranthus ecklonii + abietanes”, “ecklonii + parviflorone D”, searched individually and as combinations. Eligibility criteria were set out and titles in English, Portuguese and Spanish were reviewed, with all references included dating from 1970 to 2021. A total of 169 papers were selected and included. Chemical structures were drawn using ChemDraw 20.0, CID numbers were searched in PubChem and the PRISMA diagram was created using PowerPoint 2012.Results: To date, a total of 28 compounds have been isolated from P. ecklonii, including diterpenes, triterpenes, flavonoids, and hydroxycinnamic acids. Most focused on the antimicrobial action of its constituents, although compounds have demonstrated other bioactivities, namely antioxidant, anti-inflammatory and antitumor. The most recent studies emphasize the diterpenoids, particularly parviflorone D, with the help of nanotechnology.Conclusions: The widespread ethnobotanical and traditional uses of P. ecklonii can be scientifically justified by a range of biological activities, demonstrated by isolated secondary metabolites. These bioactivities showcase the potential of this species in the development of economically important active pharmaceutical ingredients, particularly in anticancer therapy.

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Section: Isolated Compounds From Plectranthus Ecklonii Benthmentioning

confidence: 99%

Section: Isolated Compounds From Plectranthus Ecklonii Benthmentioning

confidence: 99%

Section: Isolated Compounds From Plectranthus Ecklonii Benthmentioning

confidence: 99%

Section: Biological Activities Of Isolated Compounds From P Ecklonii Benthmentioning

confidence: 99%

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Plectranthus ecklonii Benth: A Comprehensive Review Into its Phytochemistry and Exerted Biological Activities

et al. 2021

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“…Phytochemical studies on some species of Plectranthus revealed the presence of a large number of diterpenes and triterpenes [ 10 , 11 ]. Isolated terpenes from Plectranthus species are reported to possess antibacterial [ 12 , 13 , 14 ], antitumoral [ 15 , 16 , 17 , 18 ], antifungal [ 12 , 19 ], insecticidal [ 20 ], and antiplasmodial [ 20 ] activities. Moreover, our group has been focused on the phytochemical study of Plectranthus species and we have reported abietane diterpenoids with diverse bioactivity [ 16 , 17 , 21 , 22 , 23 , 24 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

Preliminary Biological Activity Screening of Plectranthus spp. Extracts for the Search of Anticancer Lead Molecules

et al. 2021

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Plectranthus species (Lamiaceae) have been employed in traditional medicine and this is now validated by the presence of bioactive abietane-type diterpenoids. Herein, sixteen Plectranthus acetonic extracts were prepared by ultrasound-assisted extraction and their biological activity was screened. The antimicrobial activity of each extract was screened against yeasts, and Gram-positive and Gram-negative bacteria. The P. hadiensis and P. mutabilis extracts possessed significant activity against Staphylococcus aureus and Candida albicans (microdilution method). Moreover, all extracts showed antioxidant activity using the DPPH method, with P. hadiensis and P. mutabilis extracts having the highest scavenging activities. Selected by the Artemia salina model, P. hadiensis and P.ciliatus possessed low micromolar anti-proliferative activities in human colon, breast, and lung cancer cell lines. Furthermore, the most bioactive extract of P. hadiensis leaves and the known abietane diterpene, 7α-acetoxy-6β-hydroxyroyleanone isolated from this plant, were tested against the aggressive type triple negative breast cancer (MDA-MB-231S). P. hadiensis extract reduced the viability of MDA-MB-231S cancer cell line cells, showing an IC50 value of 25.6 µg/mL. The IC50 value of 7α-acetoxy-6β-hydroxyroyleanone was 5.5 µM (2.15 µg/mL), suggesting that this lead molecule is a potential starting tool for the development of anti-cancer drugs.

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Determination of fingerprints contents of different extracts and parts of six endemic Salvia taxa by GC–MS: Source species for valuable compounds with drug or drug potential

Akdeniz¹,

Yener

Dincel

et al. 2021

Biomedical Chromatography

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Public use of Salvia species and their importance in the scientific world is continually increasing. It is known that this use and the importance of Salvia species are mostly due to the terpenoid compounds that they contain. In this context, the terpenoid–steroid–flavonoid contents of extracts of six endemic Salvia (S. kurdica, S. pseudeuphratica, S. rosifolia, S. siirtica, S. cerino‐pruinosa var. cerino‐pruinosa and S. cerino‐pruinosa var. elazigensis) species prepared with different solvents were determined by gas chromatography–mass spectrometry. Within the framework of the ingredient analysis, content analysis of the ethanol extracts of the root, branch, leaf and flower parts of the species collected in the same period between 2015 and 2017 years was performed. In general, extracts prepared with chloroform and ethanol were found to contain a wide variety of compounds while petroleum ether extracts were found to contain much less varied compounds. In addition, in general, root extracts are richer in terpenoid compounds than aerial part extracts. Some species can be used as source species in terms of ferruginol, cryptanol, 6,7‐dehydroroyleanone, lup‐(20)29‐ene‐2α‐hydroxy‐3β‐acetate, salvigenin and β‐sitosterol contents (52,114.28, 75,979.08, 101,247.41, 40,071.29, 33,952.13 and 34,010.90 μg analyte/g extract, respectively).

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Diterpenoids from Plectranthus spp. as Potential Chemotherapeutic Agents via Apoptosis

Cited by 15 publications

References 36 publications

Plectranthus ecklonii Benth: A Comprehensive Review Into its Phytochemistry and Exerted Biological Activities

Plectranthus ecklonii Benth: A Comprehensive Review Into its Phytochemistry and Exerted Biological Activities

Preliminary Biological Activity Screening of Plectranthus spp. Extracts for the Search of Anticancer Lead Molecules

Determination of fingerprints contents of different extracts and parts of six endemic Salvia taxa by GC–MS: Source species for valuable compounds with drug or drug potential

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