Ent-kauren-19-oic acid derivatives from the stem bark of Croton pseudopulchellus Pax

Langat, Moses K.; Crouch, Neil R.; Pohjala, Leena; Tammela, Päivi; Smith, Peter J.; Mulholland, Dulcie A.

doi:10.1016/j.phytol.2012.03.002

Cited by 22 publications

(18 citation statements)

References 19 publications

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“…These signals agree with the report of Somova et al 26 & Langat et al 15 on kaurenoid isolation and characterisation. The DEPT-135 pulse sequence produces eight methene (CH 2 ) carbons with a total of 22 carbon atoms.…”

Section: Characterization Of 14-acetoxo-12-oxokaur-16-en--19-oic Acidsupporting

confidence: 93%

“…Subsequently, eluted with different polarity of acetone-ethyl acetate solvent system. The fractions were collected from the column, purified by PTLC to give five compounds (1) (60mg), (2) (62.1mg), (3) (52mg), (4) (108mg), and (5) (62mg) from F [8][9][10][11][12][13][14][15][16][17][18][19] (100mg), F 75-87 (87mg), F 52-64 (80mg), F 20-28 (310mg), and F [35][36][37][38][39][40][41][42][43][44][45] (74mg), respectively.…”

Section: Maceration and Liquid-liquid Extractionmentioning

confidence: 99%

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Diterpenoids of Alepidea Amatymbica Eckl. & Zeyh: Studies of Their Cytotoxic, Antimicrobial, and Lipoxygenase Inhibitory Activities

Okoli¹

2017

MOJBOC

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Alepidea amatymbica, an herbaceous plant with a broad ethnomedicinal application among the native of Eastern and Southern Africa. The isolation of diterpenoids from A. amatymbica and evaluation of their biological activities, based on the ethnomedicinal information, was the primary focus of this investigation. Five bioassay guided isolated diterpenoids: ent-13-hydroxy-16-kauren-19-oic acid (1), 16-hydroxy-kaur-6-en-19-oic acid (2), 14-acetoxy ent-kaur-16-en-19-oic acid (3), 14-oxokaur-16-en-19-oic acid (4), and 14-acetoxo-12-oxokaur-16-en-19-oic acid (5) were screened in vitro for their anti-inflammatory, cytotoxicity, and antimicrobial. The diterpenoids were isolated and purified using open column chromatography, PTLC, and characterised with FTIR, NMR, and HRMS EI. The diterpenoids were not cytotoxicity on the normal cell but showed a significant effect of cancer cell lines. 14-acetoxo-12-oxokaur-16-en-19-oic acid showed a high inhibitory effect on lipoxygenase with an EC 50 of 19.10±3.15µg/ ml compared to standard indomethacin with EC 50 of 17.22±5.48µg/ml. Among the diterpenes isolated and tested, 14-oxokaur-16-en-19-oic acid and 14-acetoxo-12-oxokaur-16-en-19-oic acid showed significant antibiotic activities against bacteria (MIC 125µg/ml) compared to gentamycin. Consequently, the antibiotic activity is structurally linked to the positions of acetate and oxo groups at C-14 and C-12 which enhances the activity of the diterpenoids. The in-vitro biological activities confirmed that the diterpenoids are sources of treatment and management of inflammationrelated diseases, justifying its traditional applications.

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Section: Characterization Of 14-acetoxo-12-oxokaur-16-en--19-oic Acidsupporting

confidence: 93%

Section: Maceration and Liquid-liquid Extractionmentioning

confidence: 99%

Diterpenoids of Alepidea Amatymbica Eckl. & Zeyh: Studies of Their Cytotoxic, Antimicrobial, and Lipoxygenase Inhibitory Activities

Okoli¹

2017

MOJBOC

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“…In this study, twenty-two compounds were isolated from the roots of C. megalocarpoides including twelve new ent-clerodane diterpenoids (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12), a new abietane diterpenoid (13), the known crotocorylifuran (4 a) [7] (l " Fig. 1), the two known abietane diterpenoids, isolophanthin A [8] and abietic acid [9], four known ent-trachylobane diterpenoids, ent-3α,18-dihydroxytrachylobane [10], ent-trachyloban-18-ol [10], ent-trachyloban-18-oic acid [10,11], ent-3α-hydroxytrachyloban-18-al [12] and the triterpenoids, lupeol [13] and acetyl aleurotolic acid [14,15]. Compound 1 was isolated as a colourless oil and was determined to have a molecular formula of C 21 H 28 O 5 from HR-ESI-MS.…”

Section: Resultsmentioning

confidence: 99%

New ent-Clerodane and Abietane Diterpenoids from the Roots of Kenyan Croton megalocarpoides Friis & M. G. Gilbert

et al. 2016

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The roots of the endangered medicinal plant Croton megalocarpoides collected in Kenya were investigated and twenty-two compounds isolated. Among them were twelve new ent-clerodane (1-12) and a new abietane (13) diterpenoids, alongside the known crotocorylifuran (4 a), two known abietane and four known ent-trachylobane diterpenoids, and the triterpenoids, lupeol and acetyl aleurotolic acid. The structures of the compounds were determined using NMR, HRMS and ECD. The isolated compounds were evaluated against a series of microorganisms (fungal and bacteria) and also against Plasmodium falciparum, however no activity was observed.

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“…120 Leaves are applied by Tanzanians to their chest for chest ailments. 125 Quantitative assessment of anti-plasmodial activity in vitro was determined via the parasite lactate dehydrogenase assay using a modied method described by Makler et al 126 Compound 54, the major constituent was tested in duplicate against the chloroquine sensitive (CQS) strain of P. falciparum (D10) and showed weak activity against the P. falciparum (CQS) D10 strain. 125 Quantitative assessment of anti-plasmodial activity in vitro was determined via the parasite lactate dehydrogenase assay using a modied method described by Makler et al 126 Compound 54, the major constituent was tested in duplicate against the chloroquine sensitive (CQS) strain of P. falciparum (D10) and showed weak activity against the P. falciparum (CQS) D10 strain.…”

Section: Kaurene Diterpenesmentioning

confidence: 99%

“…125 Quantitative assessment of anti-plasmodial activity in vitro was determined via the parasite lactate dehydrogenase assay using a modied method described by Makler et al 126 The activity of some of the compounds was not reported in this study (Fig. 57,120-124 Langat et al isolated two new ent-kauren-19-oic acid derivatives; compounds 50-51 together with the known compounds; 52-55, 60, eudesm-4(15)-ene-1b,6a-diol (102), (À)-7-epivaleran-4-one (103), germacra-4(15),5E,10(14)-trien-9b-ol (104) and acetyl aleuritolic acid (105) from the hexane and methylene chloride extracts of the stem bark of this plant.…”

Section: Pentacyclic Triterpenoidsmentioning

confidence: 99%

The chemistry and bioactivity of Southern African flora I: a bioactivity versus ethnobotanical survey of alkaloid and terpenoid classes

et al. 2015

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As a whole, the African continent is highly endowed with a huge floral biodiversity. Natural products which have been isolated from plants growing in this region have shown interesting chemical structures with diverse biological activities, which could serve as a starting point for drug discovery. In this study, a literature survey led to the collection of 864 secondary metabolites from 101 plant species from 57 plant families. A correlation between the known biological activities of isolated compounds and the ethnobotanical uses of the plants has been attempted. This review is a survey of the bioactivities of alkaloids and terpenoids which have been isolated from Southern African flora versus the ethnobotanical uses of the plants used in Southern African traditional medicine.

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Ent-kauren-19-oic acid derivatives from the stem bark of Croton pseudopulchellus Pax

Cited by 22 publications

References 19 publications

Diterpenoids of Alepidea Amatymbica Eckl. & Zeyh: Studies of Their Cytotoxic, Antimicrobial, and Lipoxygenase Inhibitory Activities

Diterpenoids of Alepidea Amatymbica Eckl. & Zeyh: Studies of Their Cytotoxic, Antimicrobial, and Lipoxygenase Inhibitory Activities

New ent-Clerodane and Abietane Diterpenoids from the Roots of Kenyan Croton megalocarpoides Friis & M. G. Gilbert

The chemistry and bioactivity of Southern African flora I: a bioactivity versus ethnobotanical survey of alkaloid and terpenoid classes

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