Lupane Triterpenoids from <i>Maytenus</i> Species

Núñez, Marvin J.; Reyes, Carolina; Jiménez, Ignacio A.; Moujir, Laila; Bazzocchi, Isabel L.

doi:10.1021/np058016w

Cited by 47 publications

(18 citation statements)

References 20 publications

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“…Next, these fractions were separated by repeated CC, which led to the isolation of ten compounds in total. Previous literature has reported that 3-epi-betulinic acid (1) [34], oleanolic acid (3) [35,36], and erythrodiol (6) [37] exhibit significant antitumor activities. According to our results, these three compounds exerted high cytotoxicities against both HO-8910 and SMMC-7721 cell lines.…”

Section: Bioassay-oriented Fractionation and Compound Isolationmentioning

confidence: 99%

Cytotoxic Activities of Extracts and Compounds from Viscum coloratum and its Transformation Products by Rhodobacter sphaeroides

Guan-e

Chen

Zhang

et al. 2008

Appl Biochem Biotechnol

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The bioassay-oriented fractionation of mistletoe crude extracts (MCEE) using 75% ethanol and culture products of mistletoe transformed by Rhodobacter sphaeroides, a photosynthetic bacterium (PSBT), revealed that the high cytotoxic activities were due to the petroleum ether extracts (PEs) and the acid-precipitated proteins from the aqueous extracts (AQs) of MCEE and PSBT. The isolated triterpenes may account for the activities of the PEs of MCEE and PSBT, respectively. Extraction of MCEE using petroleum ether led to the isolation of 3-epi-betulinic acid (1), betulonic acid (2), oleanolic acid (3), and beta-amyrin acetate (4), while petroleum ether extraction of PSBT led to the isolation of 1,3,4,betulinic acid (5), erythrodiol (6), and (3beta)-olean-12-ene-3,23-diol (7). The PE of PSBT exerted higher cytotoxicity than the PE of MCEE, which was due to the different triterpene contents of these two extracts. The cytotoxic activities of all compounds were tested, and the results revealed that compounds 1, 2, 3, 5, 6, and 7 contributed significantly to the cytotoxicities of both PEs. The AQ of the PSBT exerted almost the same cytotoxic activity and lower toxicity compared to the AQ of the MCEE. These findings indicate that mistletoe products biotransformed by R. sphaeroides could be used to treat cancers, since they have lower toxicities and higher antitumor activities compared to standard treatments.

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Section: Bioassay-oriented Fractionation and Compound Isolationmentioning

confidence: 99%

Cytotoxic Activities of Extracts and Compounds from Viscum coloratum and its Transformation Products by Rhodobacter sphaeroides

Guan-e

Chen

Zhang

et al. 2008

Appl Biochem Biotechnol

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“…The studies demonstrated that the principles of biological interest are associated to fl avonoids, sesquiterpenes, alkaloids and pentacyclic triterpenes (PCTT) (Bruning & Wagner, 1978;Oliveira et al, 2006). Among the PCTT isolated from species of Celastraceae, friedelane, oleanane, lupane, taraxerane, ursane, dammarane and baccharane series represent the main constituents (Nuñez et al, 2005). Some of these compounds present pharmacological effects, like antitumoral (González et al, 2000) and antispermatogenic (Vieira Filho et al, 2002) activities.…”

Section: Introductionmentioning

confidence: 99%

Maytenus salicifolia Reissek, Celastraceae: triterpenes isolated from stems and antioxidant property of extracts from aerial parts

Magalhães¹,

Ferrari²,

Guimarâes³

et al. 2011

Rev. bras. farmacogn.

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Six pentacyclic triterpenes were isolated from hexane extract of stems of Maytenus salicifolia Reissek, Celastraceae: 30-hydroxyfriedelan-3-one (1), 3,16-dioxofriedelane (2), friedeline (3), lupeol (4), betuline (5) and lup-20(29)-en-3,30-diol (6). The structure each one was established on the basis of detailed 1 H and 13 C NMR spectral investigation and by comparison with the respective literature values. For compound 1, the complete 2D NMR (HMBC, HMQC and NOESY) spectral data were herein reported for the first time. Compounds 1, 2, 5 and 6 were isolated for the first time from this plant. Antioxidant activity is described for some extracts from species of the Celastraceae family, then, the extracts from aerial parts of M. salicifolia were evaluated in relation to antioxidant potential using the DPPH method. Compared to quecertin, the AcEt extract (EAF) from leaves, AcEt (EAPF) and MeOH (EMPF) from pulp fruit and AcEt (EAT) and MeOH (EMT) from stems showed significant antioxidant property.

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“…In our research group, we have previously reported several lupane triterpenoids from Maytenus species as being of interest as inhibitors of nitric oxide and prostaglandin E2, as well as possessing antimicrobial and cytotoxic activities (Núñez et al, 2005: Reyes et al, 2006 …”

Section: Resultsmentioning

confidence: 99%

Phytochemical profile of the stems of Aeonium lindleyi

Kennedy¹

2012

Rev. bras. farmacogn.

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Aeonium species are plants rich in phenols and terpenoids and have been widely used in the Canary folk medicine. Following our project concerning bioactive compounds from Macaronesian region, a phytochemical study was carried out to investigate the constituents of the stems of Aeonium lindleyi Webb & Berthel.,Crassulaceae. Air dried and chopped stems of this plant were extracted with ethanol in a Soxhlet apparatus and the total extract was chromatographed on silica gel to afford sixteen known compounds including, one sterol, four lupane triterpenes and eleven phenolic compounds. Their structures were elucidated by means of 1 H-and 13 C-NMR spectroscopic studies and comparison of their spectral data with values in the literature. Both group of isolated metabolites are known by their diverse biological activities and they have been described as antioxidant, cytotoxic, anti-inflammatory. Our results contribute to the knowledge of A. lindleyi as a potential source of bioactive compounds.

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Lupane Triterpenoids from Maytenus Species

Cited by 47 publications

References 20 publications

Cytotoxic Activities of Extracts and Compounds from Viscum coloratum and its Transformation Products by Rhodobacter sphaeroides

Cytotoxic Activities of Extracts and Compounds from Viscum coloratum and its Transformation Products by Rhodobacter sphaeroides

Maytenus salicifolia Reissek, Celastraceae: triterpenes isolated from stems and antioxidant property of extracts from aerial parts

Phytochemical profile of the stems of Aeonium lindleyi

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