New compounds from Rhodiola kirilowii

Wiedenfeld, Helmut; Zych, Monika; Buchwald, Waldemar; Furmanow, Mirosława

doi:10.3797/scipharm.2007.75.29

Cited by 12 publications

(16 citation statements)

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“…Hydroquinone (Compound 37 ) is found in both R. rosea and R. sacra . Meanwhile, two hydroquinone derivatives, α‐arbutin (Compound 38 ) and hydroquinone glucose (Compound 39 ), are isolated from R. sacra . Compound 39 is from R. kirilowii .…”

Section: Chemistry and Quality Controlmentioning

confidence: 99%

“…Notably, these compounds could release a fragrance similar to flowers, which might be the material basis for fragrance. Two most important ingredients, namely tyrosol (Compound 59 ) and its derivative salidroside (Compound 62 ), belong to this class . Actually, they are p ‐hydroxyl derivatives of phenylethyl alcohol, which appear frequently in many Rhodiola species, such as R. crenulata , R. rosea , R. sachalinensis , R. sacra , R. kirilowii , and R. quadrifida .…”

Section: Chemistry and Quality Controlmentioning

confidence: 99%

“…Another isomer, epicatechin gallate (Compound 236 ), is identified as a common ingredient of R. crenulata and R. kirilowii . Epigallocatechin 3‐gallate (Compound 238 ) have found in R. crenulata , R. rosea , R. sachalinensis , R. sacra , and R. kirilowii , indicating its potential as a common chemical marker for Rhodiola plants.…”

Section: Chemistry and Quality Controlmentioning

confidence: 99%

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Rhodiola species: A comprehensive review of traditional use, phytochemistry, pharmacology, toxicity, and clinical study

Tao

Cao

et al. 2019

Medicinal Research Reviews

113

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Rhodiola species, belonging to the family Crassulaceae, have long been used as an adaptogen, tonic, antidepressant, and antistress medicine or functional food in Asia and Europe. Due to the valuable application, the growing demand of Rhodiola species has led to a rapid decrease in resource content. This review aims to summarize the integrated research progress of seven mainstream Rhodiola species. We first outline both traditional and current use of Rhodiola for the treatment of various diseases. A detailed summary and comparison of chemical, pharmacological, toxicological, and clinical studies of various Rhodiola species highlight recent scientific advances and gaps, which gives insights into the understanding of Rhodiola application and would be helpful to improve the situation of biological resources and diversities of Rhodiola plants.

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Section: Chemistry and Quality Controlmentioning

confidence: 99%

Section: Chemistry and Quality Controlmentioning

confidence: 99%

Section: Chemistry and Quality Controlmentioning

confidence: 99%

See 1 more Smart Citation

Rhodiola species: A comprehensive review of traditional use, phytochemistry, pharmacology, toxicity, and clinical study

Tao

Cao

et al. 2019

Medicinal Research Reviews

113

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“…An HMBC correlation from the anomeric H-1 ( δ 5.13) to C-7 ( δ 152.1) established that the para -substituted ring was attached to glucose via an ether link between C-1 ( δ 102.3) and C-7 ( δ 152.1). A literature search and comparison of spectroscopic data identified this fragment as an arbutin moiety ( 4 ) 8. The remaining 21 13 C peaks were clustered into three groups each containing 13 C NMR resonances around δ 121, 110, 146, 140, and 168, which, along with three 2-H singlets at δ 6.98, 7.02, and 7.15, were characteristic of the presence of three galloyl groups.…”

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confidence: 99%

HIV-1 Ribonuclease H Inhibitory Phenolic Glycosides from Eugenia hyemalis

et al. 2008

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Three new galloyl arbutins, hyemalosides A-C (1-3), along with nine known compounds were isolated from the evergreen tree Eugenia hyemalis. The structures of compounds 1-3 were determined by analysis of NMR and MS data. Compounds 1-3 inhibited HIV-1 RNase H in vitro with IC 50 values of 1.46, >18, and 1.19 μM, respectively. However, in a XTT-based cell viability assay using the human T-cell line CEM-SS infected with HIV-1 RT , none of the compounds inhibited the cytopathic effect of HIV-1 infection at the highest dose tested (20 μg/mL).As part of a molecularly targeted screening program to discover drug leads from natural products, we investigated the chemistry of the evergreen tree Eugenia hyemalis L. Cambess (Myrtaceae). The organic extract of the plant showed inhibition of ribonuclease H (RNase H) enzymatic activity in a high-throughput screening assay. 1 RNase H is a second, distinct enzymatic activity of the HIV-1 reverse transcriptase protein. It is a nonspecific nuclease that is responsible for hydrolyzing the RNA strand of a RNA/DNA heteroduplex and allowing the incorporation of viral genetic information into the host cell genome. Because RNase H activity is required for viral infectivity, it is a viable target for screening for potential anti-HIV drugs, and a high-throughput fluorescence resonance energy transfer (FRET) assay 1 was developed for this purpose.Bioassay-guided fractionation of the extract led to the isolation of three new compounds, hyemalosides A-C (1-3), along with nine known compounds. The structures of the nine known compounds were determined on the basis of spectroscopic evidence and comparison with literature values. These were characterized as 2-O-galloylarbutin, 2 4-O-galloylarbutin, 2,6-di-O-galloylarbutin, 3 2,4,6-tri-O-galloylarbutin, 4 1,2,6-tri-O-galloyl-β-D-glucose, 5 kaempferol-3-O-(6-O-galloyl-β-D-glucopyranoside), 6 afzelin 2″-O-gallate, 7 afzelin 3″-Ogallate, 7 and quercitrin. 7 HREIMS of compound 1 showed a peak at m/z 727.1191 [M -H] − consistent with a molecular formula of C 33 H 28 O 19 . The 1 H NMR spectrum showed a proton doublet at δ 5.13 (J = 7.9 Hz) along with six resonances from δ 3.88 to 5.49, which were linked by COSY data and indicated a hexose moiety. Large coupling constants for the sugar ring protons (J = 7.9-9.5 Hz) indicated a series of trans diaxial couplings characteristic of glucose and also revealed that the anomeric oxygen was β-oriented.

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“…It is known for its adaptogenic, antioxidant, cardiovascular-protective and antianoxic properties. Due to its high pharmacological value, salidroside is a candidate drug for the treatment of cardiovascular and cerebrovascular diseases (Liu et al, 2006;Wiedenfeld et al, 2007;Peng et al, 2009;Guo et al, 2010). The low yield of salidroside in R. kirilowii calls for the development of biotechnology methods to improve production of this compound in vitro.…”

Section: Introductionmentioning

confidence: 99%

Tyrosol Glucosyltransferase Activity and Salidroside Production in Natural and Transformed Root Cultures of Rhodiola Kirilowii (Regel) Regel Et Maximowicz

Grech‐Baran¹,

Sykłowska-Baranek²,

Giebułtowicz³

et al. 2013

Acta Biologica Cracoviensia Series Botanica

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The study examined tyrosol glucosyltransferase activity and the efficiency of salidroside production in natural and transformed root cultures of Rhodiola kirilowii (Regel) Regel et Maximowicz. Neither enzyme activity nor salidroside accumulation were detected in natural and transformed root cultures maintained in media without tyrosol. To induce TGase activity in biotransformation reactions, tyrosol was added to natural and transformed root cultures on the day of inoculation. The first peak of TGase activity (0.23 U/μg) was detected on day 9 in natural root culture, accompanied by the highest salidroside content (15.79 mg/g d.w.), but TGase activity was highest (0.27 U/μg) on day 15. In transformed root culture, day 18 showed the highest TGase activity (0.15 U/μg), which coincided with the highest salidroside content (2.4 mg/g d.w.). Based on these results, tyrosol was added to the medium on the days of highest previously detected activity of TGase: day 15 for natural root cultures and day 18 for transformed root cultures. This strategy gave significantly higher yields of salidroside than in the cultures supplemented with tyrosol on the day of inoculation. In natural root culture, salidroside production reached 21.89 mg/g d.w., while precursor feeding in transformed root cultures caused a significant increase in salidroside accumulation to 7.55 mg/g d.w. In all treatments, salidroside production was lower in transformed than in natural root cultures.K Ke ey y w wo or rd ds s: : Rhodiola kirilowii, TGase, salidroside, transformed root culture, biotransformation.

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New compounds from Rhodiola kirilowii

Cited by 12 publications

References 0 publications

Rhodiola species: A comprehensive review of traditional use, phytochemistry, pharmacology, toxicity, and clinical study

Rhodiola species: A comprehensive review of traditional use, phytochemistry, pharmacology, toxicity, and clinical study

HIV-1 Ribonuclease H Inhibitory Phenolic Glycosides from Eugenia hyemalis

Tyrosol Glucosyltransferase Activity and Salidroside Production in Natural and Transformed Root Cultures of Rhodiola Kirilowii (Regel) Regel Et Maximowicz

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