Triterpenoids from the roots ofRubus parvifolius

Choi, Yoon Soo; Son, Kun Ho; Chul, Jae

doi:10.1007/bf02876860

Cited by 12 publications

(5 citation statements)

References 8 publications

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“…Six ursane triterpenoids were isolated for the first time from the calyxes of F. ananassa and were tested for inhibition of melanogenesis in B16-F10 mouse melanoma cells. pomolic acid (4) (Fraga et al 2006), fupenzic acid (5) (Zhang et al 2006) and euscaphic acid (6) (Choi et al 1991 proton signals in the gHMBC spectrum. This indicated that the position of the ketone was C-2.…”

Section: Introductionmentioning

confidence: 97%

Triterpenoids fromFragaria ananassacalyx and their inhibitory effects on melanogenesis in B16-F10 mouse melanoma cells

Song

Cho

Im³

et al. 2013

Natural Product Research

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Column chromatographic technology was applied to isolate six purified ursane triterpenoids from the calyx of Fragaria ananassa and they were identified on the basis of spectroscopic methods to be ursolic acid (1), pomolic acid (2), 2-oxo-pomolic acid (3), 3-O-acetyl pomolic acid (4), fupenzic acid (5) and euscaphic acid (6). This is the first study in which these compounds have been isolated from the calyx of F. ananassa. Compared to a well-known inhibitor, α-arbutin, compounds 2-6 showed a significant decrease in intracellular melanin content in B16-F10 cells, and in culture media melanin.

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Section: Introductionmentioning

confidence: 97%

Triterpenoids fromFragaria ananassacalyx and their inhibitory effects on melanogenesis in B16-F10 mouse melanoma cells

Song

Cho

Im³

et al. 2013

Natural Product Research

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“…Similar to compounds 1 and 3 , the MS 3 spectrum of U5 also readily yielded an ion at m/z 407 by the elimination of HCOOH (46 Da). Therefore, compound U5 was also proposed to be a 3β‐OH derivative and was tentatively proposed as corosolic acid …”

Section: Resultsmentioning

confidence: 99%

“…Rubus parvifolius L., a widely used medicinal plant, is composed of abundant ursane‐type triterpenoids . HPLC/ESI‐MS n was performed to analyze ursane‐type triterpenoids from the EtOAc extract of Rubus parvifolius L. To obtain an efficient separation, chromatographic conditions were optimized as described above.…”

Section: Resultsmentioning

confidence: 99%

“…Triterpene acids 1–4 (Scheme ) were isolated from Rubus parvifolius L. All of the structures were fully characterized by a direct comparison of their 1D and 2D NMR data with those reported in literature . HPLC‐grade methanol and acetonitrile were purchased from Merck Co. (Darmstadt, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…Therefore, compound U5 was also proposed to be a 3β-OH derivative and was tentatively proposed as corosolic acid. [19] CONCLUSIONS A facile method based on HPLC coupled with ESI tandem mass spectrometry was established for the differentiation of common diastereoisomeric ursane-type triterpenoids at the C-3 position.…”

Section: Identification Of Unknown Compound U5mentioning

confidence: 99%

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Differentiation of common diastereoisomeric ursane‐type triterpenoids by high‐performance liquid chromatography/tandem mass spectrometry

Gao

Shi

Lū

et al. 2011

Rapid Comm Mass Spectrometry

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A rapid and stable method consisting of high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry was established for the identification and differentiation of common diastereoisomeric ursane-type triterpenoids at the C-3 position. Two characteristic fragment ions, [M-H-H(2) O-CO(2)](-) and [M-H-H(2)O-HCOOH](-) , exhibited significant stereochemical effects and were utilized to distinguish 3-OH epimers. Based on reference standards, the abundance of the fragment ion [M-H-H(2)O-HCOOH](-) in 3β-OH compounds in the MS(3) experiment was dramatically higher compared to [M-H-H(2) O-CO(2)](-); however, for 3α-OH compounds, the product ion [M-H-H(2) O-CO(2)](-) was noted to be higher than [M-H-H(2)O-HCOOH](-). Energy-resolved mass spectrometric experiments were carried out to support the differentiation of these diastereoisomeric triterpenoids at the C-3 position. Using this method, a total of nine ursane-type triterpenoids from a plant crude extract, including four pairs of epimers at the C-3 position, were identified and distinguished rapidly. Furthermore, offline Fourier transform ion cyclotron resonance tandem mass spectrometry was also performed to assign accurate elemental compositions.

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Activity of crude extract ofRubus crataegifolius roots as a potent apoptosis inducer and DNA topoisomerase I inhibitor

et al. 2000

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The effects of methanol extract of Rubus crategifolius roots and its solvent fractions were investigated on the proliferation of MCF-7 human breast carcinoma cells. The methanol extract inhibited the proliferation of MCF-7 cells in a concentration dependent manner. Moreover, their methanol soluble (W-M) fraction had the greatest inhibitory effect on the growth of MCF-7 cells. To evaluate whether the W-M fraction affects on the cell cycle of MCF-7 cells, cells treated with this fraction were analyzed with flow cytometry. The W-M fraction increased G0/G1 phase after 24 h-treatment and induced apoptosis after 48 h-treatment. The hallmark of apoptosis, DNA fragmentation, also appeared by W-M fraction after 48 h-treatment. Furthermore, the methanol extract and its W-M fraction inhibited the activity of the topoisomerase I enzyme in the relaxation assay. From these results, their W-M fraction as well as methanol extract of R. crategifolius roots are necessary for further studies as a potent inhibitor of the growth of cancer cells.

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Triterpenoids from the roots ofRubus parvifolius

Cited by 12 publications

References 8 publications

Triterpenoids fromFragaria ananassacalyx and their inhibitory effects on melanogenesis in B16-F10 mouse melanoma cells

Triterpenoids fromFragaria ananassacalyx and their inhibitory effects on melanogenesis in B16-F10 mouse melanoma cells

Differentiation of common diastereoisomeric ursane‐type triterpenoids by high‐performance liquid chromatography/tandem mass spectrometry

Activity of crude extract ofRubus crataegifolius roots as a potent apoptosis inducer and DNA topoisomerase I inhibitor

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