Antioxidant flavonoids from the rhizomes of Helminthostachys zeylanica

Huang, Yu‐Ling; Yeh, Pei-Yu; Shen, Chien‐Chang; Chen, Chien-Chih

doi:10.1016/j.phytochem.2003.09.009

Cited by 74 publications

(99 citation statements)

References 6 publications

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“…Four flavonoids, ugonins A-D were isolated from rhizomes [58,59]. Moreover, ugonins E-T were isolated from root as antioxidant and anti-inflammatory activity by Huang [60,61]. Additionally, ugonin K promoted osteoblastic differentiation and mineralization via activating of p38 MAPK and ERK pathway [54].…”

Section: Bioactivities Of H Zeylanica Extractsmentioning

confidence: 99%

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Mitsunaga

Yamauchi

2015

J Wood Sci

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Controlling melanogenesis is important for maintaining the good health and cosmetic appearance of a human body. This study aims to search the active compounds from natural products exhibiting the melanogenesis modulating activity and elucidate the mechanism underlying the observed activity. Two novel quercetin glycosideswere isolated and identified from Helminthostachys zeylanica roots 50 % ethanol extract. Compound 1 exhibited intracellular melanogenesis stimulatory activity, while 2 showed no effect even the structural similarity. To understand the structure-activity relationships, twelve quercetin glycosides and seven methylquercetins were synthesized from rutin as starting material. As the result of bioassay using synthesized nineteen quercetin derivatives in B16 melanoma cells, some quercetin-3-O-b-D-glucopyranosides stimulated the intracellular melanogenesis. On the other hand, synthesized 3-O-methylquercetin 12 and 3,4 0 ,7-Otrimethylquercetin 15 increased both intra and extracellular melanin contents with no cytotoxicity. Compoud 15 increased the phosphorylated p38 mitogen-activated protein kinase (MAPK) and microphthalmia-associated transcription factor (MITF) which regulates the expression of tyrosinase, TRP-1 and TRP-2. While 12 enhanced the expression of the melanogenic enzymes without involving the MITF, as evidenced by its lack of any stimulation of the expression of MITF and p-p38 MAPK. This result indicates that 12 may stimulate the expression of tyrosinase, TRP-1, and TRP-2 by stimulating currently unidentified transcriptional factors and/or by regulating the degradation of melanogenic enzymes.

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Section: Bioactivities Of H Zeylanica Extractsmentioning

confidence: 99%

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Mitsunaga

Yamauchi

2015

J Wood Sci

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“…Estudos químicos com samambaias e espécies afi ns foram realizados por diversos autores (Arai et al, 1992;Imperato, 1990;Camps et al, 1990;Marco et al, 1993, Zhou et al, 1998Tsuzuki et al, 2001;Huang et al, 2003), bem como estudos farmacológicos (Suffredini et al, 1999;Bresciani et al, 2003).…”

Section: Introductionunclassified

Estudo farmacognóstico do caule e raízes de Microgramma squamulosa (Kaulf.) Sota (Polypodiaceae)

Suffredini¹,

Bacchi²,

Kraus³

2008

Rev. bras. farmacogn.

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“…C-NMR data of 2 with those of ugonin T 3) showed that the two compounds were extremely similar, except for the ring C signals. Moreover, the chemical shifts of C-2 (δ C 147.9), C-3 (δ C 137.4) and C-4 in 2 were comparable with those of the flavonol ugonin F, 2) while the molecular weight of 2 was 16 mass units less than that of ugonin T. Based on the above evidence, the structure of compound 2 (neougonin B) was unambiguously elucidated as 4″,5″-dihydro-3,5,3′,4′-tetrahydroxy-4″,4″,5″-trimethylfurano[2″,3″:6,7] flavonol.…”

Section: Resultsmentioning

confidence: 76%

Anti-inflammatory Prenylated Flavonoids from <i>Helminthostachys zeylanica</i>

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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1) The rhizomes of H. zeylanica are used in a popular antipyretic and anti-inflammatory Chinese herbal medicine known as "Daodi-Ugon." 1,2) This plant has also been shown to exhibit hepatoprotective activity.3,4) Numerous bioactive flavonoids containing prenyl or geranyl groups have been isolated from the rhizomes of H. zeylanica.2-6) Our current systematic phytochemical investigation of this plant led to the isolation of two new prenylflavonoids, neougonins A (1) and B (2), along with nine known flavonoids (Fig. 1). In addition, compound 1 showed significant inhibition of nitric oxide (NO) production with an IC 50 value of 3.32 µM. We report herein the isolation, structural elucidation and biological evaluation of the isolated compounds. Results and DiscussionThe dried whole plants of H. zeylanica were extracted with 95% EtOH, and the concentrated extract was suspended in water and partitioned with EtOAc. The EtOAc fraction was subjected to repeated column chromatography (MCI CHP 20P, 75-150 µm), and octadecyl silica (ODS)) and semi-preparative HPLC to yield two new prenylated flavonoids, neougonins A (1) and B (2), together with nine known flavonoids.Compound 1 was isolated and purified as a yellow amorphous powder. A molecular ion peak at m/z 424.1887 in the high resolution-electron ionization (HR-EI)-MS indicated a molecular formula of C 25 H 28 O 6 , corresponding to 12 degrees of unsaturation. The IR spectrum of 1 showed the presence of hydroxy (ν max 3407 cm ) and carbonyl (ν max 1637 cm −1 ) groups. The UV spectrum showed a disparate course of spectra with maxima at 230 (sh) nm, 298 (sh) nm. Generally, the spectra corresponded to the π π* and n π* electronic transitions of the flavanone skeleton.

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Antioxidant flavonoids from the rhizomes of Helminthostachys zeylanica

Cited by 74 publications

References 6 publications

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Estudo farmacognóstico do caule e raízes de Microgramma squamulosa (Kaulf.) Sota (Polypodiaceae)

Anti-inflammatory Prenylated Flavonoids from <i>Helminthostachys zeylanica</i>

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