A New Abietane Diterpenoid from <i>Plectranthus bishopianus</i><scp>Benth</scp>.

Syamasundar, K. V.; Guvvala, Vinodh; Srinivas, K. V. N. S.; Srinivasulu, B.

doi:10.1002/hlca.201100425

Cited by 9 publications

(3 citation statements)

References 5 publications

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“…The petroleum ether-soluble phase contained four ent -clerodane diterpenes: a new compound, ornatin B methyl ester ( 5 ), and three known compounds, ornatin D ( 6 ), 12 11 R *-acetoxykolavenic acid ( 7 ), 14 and 11 R *-acetoxy-2-oxokolavenic acid ( 8 ). 14 Four known abietane diterpenes, 6β,7α-dihydroxyroyleanone ( 9 ), 29 , 30 6β-hydroxy-7α-methoxyroyleanone ( 10 ), 31 7α-acetoxy-6β-hydroxyroyleanone ( 11 ), 29 and coleon U ( 13 ), 18 , 32 were isolated from C. forsteri “Marginatus”, whereas two known ent -kaurane diterpenes, ent -15-oxokaur-16-en-19-oic acid ( 14 ) 33 and xylopinic acid ( 15 ), 34 were isolated from P. ciliatus . These compounds were identified by spectroscopic data and comparison with the literature.…”

Section: Resultsmentioning

confidence: 99%

Diterpenes Isolated from Three Different Plectranthus Sensu Lato Species and Their Antiproliferative Activities against Gynecological and Glioblastoma Cancer Cells

Gáborová,

Vágvölgyi,

Tayeb

et al. 2024

ACS Omega

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Fourteen diterpenes were isolated from methanol extracts of the aerial parts ofColeus comosus,Coleus forsteri "Marginatus", and Plectranthus ciliatus. The compounds belong to the abietane (1−4, 9−11, and 13), ent-clerodane (5−8), and entkaurane (14, 15) classes. Three new compounds were isolated from C. comosus, including 3-O-acetylornatin G (2), 3,12-di-Oacetylornatin G (3), ornatin B methyl ester (5), and ornatin F (4), for which we proposed a revised structure. The structures of the compounds were determined by comprehensive spectroscopic data analysis. The isolated diterpenes were examined in silico for their physicochemical and early ADME properties. Their antiproliferative effects were determined in vitro using human breast (MDA-MB-231 and MCF-7), cervical (HeLa), and glioblastoma (U-87 MG) cancer cell lines. The royleanone-and hydroquinone-type abietane diterpenes (9−13)exhibited the most potent antiproliferative activity against all cancer cell lines tested, particularly against glioblastoma cells, with IC 50 values ranging from 1.1 to 15.6 μM.

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Section: Resultsmentioning

confidence: 99%

Diterpenes Isolated from Three Different Plectranthus Sensu Lato Species and Their Antiproliferative Activities against Gynecological and Glioblastoma Cancer Cells

Gáborová,

Vágvölgyi,

Tayeb

et al. 2024

ACS Omega

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“…Extraction of plant material at room temperature under sonication has also been described in several studies, e.g., the aerial parts of C. forsteri ‘Marginatus’ [ 38 ] and C. madagascariensis [ 54 ] were extracted with methanol in an ultrasonic bath. Moreover, the leaves of C. bishopianus were extracted with hot methanol [ 36 , 37 ], the aerial parts of C. maculosus subsp. edulis with hot benzene [ 104 ], and the aerial parts of C. lanuginosus were extracted by percolation with diethyl ether [ 23 ].…”

Section: Occurrence and Isolation Of Abietane Diterpenesmentioning

confidence: 99%

Abietane Diterpenes of the Genus Plectranthus sensu lato

2021

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Plectranthus (Lamiaceae), which—according to the latest systematic revision—includes three separate genera (Coleus, Plectranthus sensu stricto, and Equilabium), is a genus widely used in traditional medicine—mainly in the treatment of various ailments of the digestive tract, respiratory tract, and skin. Many species of Plectranthus s.l. have been shown to produce phenolic compounds and terpenes. Diterpenes, especially those of the abietane class, are the most studied group of secondary metabolites found in Plectranthus s.l., which is characterized by a significant structural diversity arising from the oxygenation and further rearrangement of the basic tricyclic abietane skeleton to a complete aromatization of the ring system. This review summarizes the known information on abietane diterpenes, showing their structures, sources, and biosynthesis. A classification of these compounds into nine groups, according to the arrangement of their ring C, is used. Royleanones, spirocoleons, and hydroquinones are the largest classes of abietane diterpenes, covering more than 70% of all the compounds reviewed.

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“…In another study, parviflorone D ( Salim et al, 2008 ) was isolated from an acetonic extract of P. ecklonii , together with the diterpene sugiol ( de Albuquerque et al, 2007 ) and mixtures of ursolic acid (UA) ( Lukhoba et al, 2006 ) with oleanolic acid (OA) ( Dellar et al, 1996 ) and ß-sitosterol ( Gaspar-Marques et al, 2008 ) with stigmasterol ( Narukawa et al, 2001 ) ( Simões et al, 2010 ). Meanwhile, the compounds OA ( Dellar et al, 1996 ), ß-sitosterol ( Gaspar-Marques et al, 2008 ), and stigmasterol ( Narukawa et al, 2001 ) have also been isolated in Plectranthus bishopianus Benth., but from a methanolic extract ( Syamasundar et al, 2012 ).…”

Section: Isolated Compounds From Plectranthus Ecklonii Benthmentioning

confidence: 99%

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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A New Abietane Diterpenoid from Plectranthus bishopianusBenth.

Cited by 9 publications

References 5 publications

Diterpenes Isolated from Three Different Plectranthus Sensu Lato Species and Their Antiproliferative Activities against Gynecological and Glioblastoma Cancer Cells

Diterpenes Isolated from Three Different Plectranthus Sensu Lato Species and Their Antiproliferative Activities against Gynecological and Glioblastoma Cancer Cells

Abietane Diterpenes of the Genus Plectranthus sensu lato

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

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