First <i>seco</i>-C Oleananes from Nature

Román, Luisa U.; Guerra-Ramı́rez, Diana; Morán, Gerardo; Martínez, Iván; Hernández, José Falcón; Cerda-Garcı́a-Rojas, Carlos M.; Torres-Valencia, J. Martı́n; Joseph‐Nathan, Pedro

doi:10.1021/ol036107j

Cited by 17 publications

(14 citation statements)

References 31 publications

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“…However, their chemical composition has been reported, which helped us to explain their effects. Stevia pilosa and Stevia eupatoria extracts have compounds such as luteolin, quercetin, β-sitosterol, stigmasterol [11], seco-triterpenes [17], and longipinenes [18]. Luteolin has shown cellular arrest and apoptosis induction in many types of cancer cell lines, such as prostate cancer (PC-3), liver cancer (SMMC7721), colon cancer (COLO205), and cervical cancer (HeLa) [19].…”

Section: Discussionmentioning

confidence: 99%

Stevia Eupatoria and Stevia Pilosa Extracts Inhibit the Proliferation and Migration of Prostate Cancer Cells

et al. 2020

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Background and Objectives: Prostate cancer is the second most harmful disease in men worldwide and the number of cases is increasing. Therefore, new natural agents with anticancer potential should be examined and the response of existing therapeutic drugs must be enhanced. Stevia pilosa and Stevia eupatoria are two species that have been widely used in traditional medicine, but their effectiveness on cancer cells and their interaction with antineoplastic drugs have not been studied. The aim of this study was to evaluate the anticancer activity of Stevia pilosa methanolic root extract (SPME) and Stevia eupatoria methanolic root extract (SEME) and their effect, combined with enzalutamide, on prostate cancer cells. Materials and Methods: The study was conducted on a human fibroblast cell line, and on androgen-dependent (LNCaP) and androgen-independent (PC-3) prostate cancer cell lines. The cell viability was evaluated using a Trypan Blue exclusion test for 48 h, and the migration by a wound-healing assay for 24, 48, and 72 h. Results: The results indicate that SPME and SEME were not cytotoxic at concentrations less than 1000 μg/mL in the human fibroblasts. SPME and SEME significantly reduced the viability and migration of prostate cancer cells in all concentrations evaluated. The antiproliferative effect of the Stevia extracts was higher in cancer cells than in normal cells. The enzalutamide decreased the cell viability in all concentrations tested (10–50 µM). The combination of the Stevia extracts and enzalutamide produced a greater effect on the inhibition of the proliferation and migration of cancer cells than the Stevia extracts alone, but not of the enzalutamide alone. Conclusion: The results indicate that SPME and SEME have an inhibitory effect on the viability and migration of prostate cancer cells and do not interfere with the enzalutamide anticancer effect. The data suggest that Stevia extracts may be a potential source of molecules for cancer treatment.

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Section: Discussionmentioning

confidence: 99%

Stevia Eupatoria and Stevia Pilosa Extracts Inhibit the Proliferation and Migration of Prostate Cancer Cells

et al. 2020

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“…Sasanquol (108) was isolated from sasanqua oil, obtained from the seeds of Camellia sasanqua. 86 Compounds 109-115 showed potent inhibitory effects of the induction of Epstein-Barr virus early antigen induced by the tumor promoter 12-O-tetradecanoylphorbol 13-acetate.…”

Section: Triterpenes Derived From Processes Of Cyclization Of S or Osmentioning

confidence: 99%

Unusually cyclized triterpenes: occurrence, biosynthesis and chemical synthesis

et al. 2009

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The biosynthetic origin of most of triterpenes lies in cascade cyclizations and rearrangements of the acyclic precursors squalene (S) and 2,3-oxidosqualene (OS), processes leading to tetra- and pentacyclic triterpene skeleta. Apart from these, a number of triterpenoid structures derived from cyclization processes, that are different from those leading to tetra- and pentacyclic triterpenes, are also found in Nature. We have defined these processes as unusual cyclizations, and grouped them in three blocks, namely, incomplete cyclizations of the corresponding S-derived precursors, cyclizations of S or OS towards polycyclic triterpenes and subsequent cleavage of the preformed ring systems, and two independent cyclizations of the S- or OS-derived precursor. Apart from the molecules obtained from intact organisms, we will also consider the compounds obtained from in vitro cyclizations promoted by enzyme systems. After establishing which compounds could unambiguously be grouped under the term 'unusually cyclized triterpenes', this review moves on to the advances achieved in this kind of structure during the last ten years. These advances are presented in three parts. The first one presents the structure and biological properties of the unusual triterpenes reported in the last decade. The second part considers the main biosynthetic pathways which justify the formation of these triterpenes from their corresponding acyclic precursors. Finally, we look at the achievements made in different synthetic strategies directed at some of these molecules. One hundred and twenty-three references are cited.

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“… [69] Closely related seco ‐labdane 67 was isolated shortly after by Robinson and co‐workers from Koanophyllon conglobatum [70] . Interestingly, 67 bears both a ketone and a vinyl group across the 7,8 bond fission, possibly suggesting a biosynthetic Grob fragmentation to effect B‐ring cleavage [71–74] . This motif is also present in 68 , isolated in 1998 from the flowering plant Fleischmannia microstemon [75] …”

Section: Isolation and Bioactivitymentioning

confidence: 96%

seco‐Labdanes: A Study of Terpenoid Structural Diversity Resulting from Biosynthetic C−C Bond Cleavage

Grant

Brimble

2021

Chemistry A European J

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The cleavage of a C−C bond is a complexity generating process, which complements oxidation and cyclisation events in the biosynthesis of terpenoids. This process leads to increased structural diversity in a cluster of related secondary metabolites by modification of the parent carbocyclic core. In this review, we highlight the diversifying effect of C−C bond cleavage by examining the literature related to seco‐labdanes—a class of diterpenoids arising from such C−C bond cleavage events.

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First seco-C Oleananes from Nature

Cited by 17 publications

References 31 publications

Stevia Eupatoria and Stevia Pilosa Extracts Inhibit the Proliferation and Migration of Prostate Cancer Cells

Stevia Eupatoria and Stevia Pilosa Extracts Inhibit the Proliferation and Migration of Prostate Cancer Cells

Unusually cyclized triterpenes: occurrence, biosynthesis and chemical synthesis

seco‐Labdanes: A Study of Terpenoid Structural Diversity Resulting from Biosynthetic C−C Bond Cleavage

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