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

Abstract

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.

Hepatoprotective Effect of Ugonin M, A Helminthostachys zeylanica Constituent, on Acetaminophen-Induced Acute Liver Injury in Mice

“…The crude extract of HZ demonstrated hepatoprotective effects in the traditional use and was proven in previous reports [ 14 , 15 ]. Phytochemical research has reported that HZ is abundant in flavonoids [ 18 , 19 , 20 , 22 , 23 ]. Ugonin M, one of the major flavonoid components of HZ [ 34 ], exhibited both in vitro [ 19 , 23 ] and in vivo [ 24 ] antioxidant and anti-inflammatory activities.…”

“…Current studies used the crude extracts of HZ to evaluate the anti-inflammatory effects through in vivo hepatotoxicity [ 14 , 15 ] and acute lung injury models [ 16 ]. Several unique flavonoids isolated from HZ were reported to possess a variety of biological activities including antioxidant activities [ 17 , 18 ], anti-inflammatory activities [ 17 , 19 , 20 , 21 , 22 , 23 , 24 ], melanogenesis inhibitory activities [ 25 , 26 ]; neuroprotection [ 27 ], antiosteoporosis [ 23 , 28 , 29 ], anti-cancer [ 30 , 31 ], and immunomodulatory effects [ 32 ]; and prevention of neointimal hyperplasia and migration [ 33 ].…”

Phytochemicals from fern species: potential for medicine applications

“…Different prenylated flavonoids have been isolated from Helminthostachys zeylanica (L.) Hook., Fig. 19 Prenylated flavonoids from Helminthostachys zeylanica (Huang et al 2010a, b, c) including the new molecules neougonins A and B, and the previously-described ugonin D,2-(3,4-dihydroxyphenyl)-6-((2,2-dimethyl-6-methylene cyclohexyl)methyl)-5,7-dihydroxy-chroman-4-one, ugonins E, J, L, and S, 4″a,5″,6″,7″,8″,8″a-hexahydro-5,3′,4′-trihydroxy-5″,5″,8″a-trimethyl-4H-chromeno [2″,3″:7,6]flavone, 4″a,5″,6″,7″,8″,8″a-hexahydro-5, 3′,4′-trihydroxy-5″,5″,8″atrimethyl-4H-chromeno[2″, 3″:7,8] flavone, and ugonin N (Su et al 2016). Besides flavonoids, the new peroxy fatty acids thermalic acids A, and B, have been isolated from O. thermal (Dong et al 2016).…”

Natural Antidiabetic of Tunjuk Langit (Helminthostachys zeylanica) Rhizome Extracts

“…Talang Mamak tribe in Riau use H. zeylanica to treat inflammation, dysentery, cataracts, early-stage tuberculosis, syphilis, diabetic, and malaria. 2 H. zeylanica contains saponins, flavonoids, stilbenes and phenolics and shows various biological activities such as antioxidant, 3,4,5 anti-inflammation, 6,7,8 anti-osteoporotic, 9 and antihyperuricemia. 10 Furthermore, phenolics and flavonoids inhibit α-glucosidase enzyme which is responsible in glucose levels.…”