Skip to main content
Erschienen in:

26.10.2022 | Original Paper

Communiferulins, farnesylated coumarins from the roots of Ferula communis and their anti-neuroinflammatory activity

verfasst von: Yuki Yoshino, Naonobu Tanaka, Daisuke Tsuji, Kohji Itoh, Yoshiki Kashiwada

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2023

Einloggen, um Zugang zu erhalten

Abstract

Three new farnesylated coumarins, communiferulins A–C (13), and a farnesylated chromone, ferchromone (4), were isolated from the roots of an Apiaceous plant Ferula communis. Their structures including the relative configurations were elucidated by a combination of spectroscopic analyses and calculations of the NMR data. Communiferulins A–C (13) had dihydrofuran rings fused to C-3 and C-4 of their coumarin moieties, while 3 possessed one additional furan ring. HPLC analyses using a chiral column showed 14 to be racemates, and the absolute configurations of (+)-1, (–)-1, (+)-2, and (–)-2 were deduced by comparison of their ECD spectra with TDDFT-calculated spectra. Communiferulins A (1) and B (2), and ferchromone (4) showed inhibitory activities on IL-1β production from LPS-stimulated microglial cells.
Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Zurück zum Zitat Miski M, Mabry TJ (1985) Daucane esters from Ferula communis subsp. communis. Phytochemistry 24:1735–1741CrossRef Miski M, Mabry TJ (1985) Daucane esters from Ferula communis subsp. communis. Phytochemistry 24:1735–1741CrossRef
2.
Zurück zum Zitat Ahmed AA, Abdel-Razek MH, Nassar MI, Izumi S, Ohta S, Hirata T (2001) An eudesmanolide and a carotene from Ferula sinaica. Phytochemistry 57:513–515CrossRef Ahmed AA, Abdel-Razek MH, Nassar MI, Izumi S, Ohta S, Hirata T (2001) An eudesmanolide and a carotene from Ferula sinaica. Phytochemistry 57:513–515CrossRef
3.
Zurück zum Zitat Laboratoire D, Bodo B, Martin MT, Molho D (1987) Ferulenol and ω-hydroxyferulenol, toxic coumarins from Ferula communis var. genuina. Phytochemistry 26:1613–1615CrossRef Laboratoire D, Bodo B, Martin MT, Molho D (1987) Ferulenol and ω-hydroxyferulenol, toxic coumarins from Ferula communis var. genuina. Phytochemistry 26:1613–1615CrossRef
4.
Zurück zum Zitat Motai T, Daikonya A, Kitanaka S (2013) Sesquiterpene coumarins from Ferula fukanensis and their proinflammatory cytokine gene expression inhibitory effects. Chem Pharm Bull 61:618–623CrossRef Motai T, Daikonya A, Kitanaka S (2013) Sesquiterpene coumarins from Ferula fukanensis and their proinflammatory cytokine gene expression inhibitory effects. Chem Pharm Bull 61:618–623CrossRef
5.
Zurück zum Zitat Afifi FU, Abu-Irmaileh B (2000) Herbal medicine in Jordan with special emphasis on less commonly used medicinal herbs. J Ethnopharmacol 72:101–110CrossRef Afifi FU, Abu-Irmaileh B (2000) Herbal medicine in Jordan with special emphasis on less commonly used medicinal herbs. J Ethnopharmacol 72:101–110CrossRef
6.
Zurück zum Zitat Ahmed AA, Hegazy M-EF, Zellagui A, Rhouati S, Mohamed TA, Sayed AA, Abdella MA, Ohta S, Hirata T (2007) Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species. Phytochemistry 68:680–686CrossRef Ahmed AA, Hegazy M-EF, Zellagui A, Rhouati S, Mohamed TA, Sayed AA, Abdella MA, Ohta S, Hirata T (2007) Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species. Phytochemistry 68:680–686CrossRef
7.
Zurück zum Zitat Choudhary MI, Baig I, Nur-e-Alam M, Shahzad-ul-hussan S, Öndognii P, Bunderya M, Oyun Z, Atta-ur R (2001) New α-glucosidase inhibitors from the Mongolian medicinal plant Ferula mongolica. Helv Chim Acta 84:2409–2416CrossRef Choudhary MI, Baig I, Nur-e-Alam M, Shahzad-ul-hussan S, Öndognii P, Bunderya M, Oyun Z, Atta-ur R (2001) New α-glucosidase inhibitors from the Mongolian medicinal plant Ferula mongolica. Helv Chim Acta 84:2409–2416CrossRef
8.
Zurück zum Zitat Tanaka N, Kashiwada Y (2022) Phytochemical studies on traditional herbal medicines based on the ethnopharmacological information obtained by field studies. J Nat Med 75:762–783CrossRef Tanaka N, Kashiwada Y (2022) Phytochemical studies on traditional herbal medicines based on the ethnopharmacological information obtained by field studies. J Nat Med 75:762–783CrossRef
9.
Zurück zum Zitat Suzuki K, Okasaka M, Kashiwada Y, Takaishi Y, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O, Sekiya M, Ikeshiro Y (2007) Sesquiterpene lactones from the roots of Ferula varia and their cytotoxic activity. J Nat Prod 70:1915–1918CrossRef Suzuki K, Okasaka M, Kashiwada Y, Takaishi Y, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O, Sekiya M, Ikeshiro Y (2007) Sesquiterpene lactones from the roots of Ferula varia and their cytotoxic activity. J Nat Prod 70:1915–1918CrossRef
10.
Zurück zum Zitat Kurimoto S, Suzuki K, Okasaka M, Kashiwada Y, Kodzhimatov OK, Takaishi Y (2012) Sesquiterpene lactone glycosides from the roots of Ferula varia. Chem Pharm Bull 60:913–919CrossRef Kurimoto S, Suzuki K, Okasaka M, Kashiwada Y, Kodzhimatov OK, Takaishi Y (2012) Sesquiterpene lactone glycosides from the roots of Ferula varia. Chem Pharm Bull 60:913–919CrossRef
11.
Zurück zum Zitat Kurimoto S, Suzuki K, Okasaka M, Kashiwada Y, Kodzhimatov OK, Takaishi Y (2012) New sesquiterpene lactone glucosides from the roots of Ferula varia. Phytochemistry Lett 5:729–733CrossRef Kurimoto S, Suzuki K, Okasaka M, Kashiwada Y, Kodzhimatov OK, Takaishi Y (2012) New sesquiterpene lactone glucosides from the roots of Ferula varia. Phytochemistry Lett 5:729–733CrossRef
12.
Zurück zum Zitat Al-Yahya MA, Muhammad I, Mirza HH, El-Feraly FS (1998) Antibacterial constituents from the rhizomes of Ferula communis. Phytotherapy Res 12:335–339CrossRef Al-Yahya MA, Muhammad I, Mirza HH, El-Feraly FS (1998) Antibacterial constituents from the rhizomes of Ferula communis. Phytotherapy Res 12:335–339CrossRef
13.
Zurück zum Zitat Manolakou S, Tzakou O, Yannistsaros A (2013) Volatile constituents of Ferula communis L. subsp. communis growing spontaneously in Greece. Rec Nat Prod 7:54–58 Manolakou S, Tzakou O, Yannistsaros A (2013) Volatile constituents of Ferula communis L. subsp. communis growing spontaneously in Greece. Rec Nat Prod 7:54–58
14.
Zurück zum Zitat Niwa K, Yi R, Tanaka N, Kitaguchi S, Tsuji D, Kim S-Y, Tsogtbaatar A, Bunddulam P, Kojoma M, Kawazoe K, Damdinjav D, Itoh K, Kashiwada Y (2020) Linaburiosides A-D, acylated iridoid glucosides from Linaria buriatica. Phytochemistry 171:112247CrossRef Niwa K, Yi R, Tanaka N, Kitaguchi S, Tsuji D, Kim S-Y, Tsogtbaatar A, Bunddulam P, Kojoma M, Kawazoe K, Damdinjav D, Itoh K, Kashiwada Y (2020) Linaburiosides A-D, acylated iridoid glucosides from Linaria buriatica. Phytochemistry 171:112247CrossRef
15.
Zurück zum Zitat Tanaka N, Yamada K, Shimomoto Y, Tsuji D, Itoh K, Kawazoe K, Damdinjav D, Dorjval E, KashiwadaY, (2020) Lophachinins A-E, abietane diterpenes from a Mongolian traditional herbal medicine Lophanthus chinensis. Fitoterapia 146:104702CrossRef Tanaka N, Yamada K, Shimomoto Y, Tsuji D, Itoh K, Kawazoe K, Damdinjav D, Dorjval E, KashiwadaY, (2020) Lophachinins A-E, abietane diterpenes from a Mongolian traditional herbal medicine Lophanthus chinensis. Fitoterapia 146:104702CrossRef
16.
Zurück zum Zitat Niwa K, Tanaka N, Shimomoto Y, Tsuji D, Kim S-Y, Kojoma M, Itoh K, Chen C-H, Lee K-H, Kashiwada Y (2021) Hyperdioxanes, dibenzo-1,4-dioxane derivatives from the roots of Hypericum ascyron. J Nat Med 75:907–914CrossRef Niwa K, Tanaka N, Shimomoto Y, Tsuji D, Kim S-Y, Kojoma M, Itoh K, Chen C-H, Lee K-H, Kashiwada Y (2021) Hyperdioxanes, dibenzo-1,4-dioxane derivatives from the roots of Hypericum ascyron. J Nat Med 75:907–914CrossRef
17.
Zurück zum Zitat Tanaka N, Niwa K, Kajihara S, Tsuji D, Itoh K, Mamadalieva NZ, Kashiwada Y (2020) C28 terpenoids from Lamiaceous plant Perovskia scrophulariifolia: Their structures and anti-neoroinflammatory activity. Org Lett 22:7667–7670CrossRef Tanaka N, Niwa K, Kajihara S, Tsuji D, Itoh K, Mamadalieva NZ, Kashiwada Y (2020) C28 terpenoids from Lamiaceous plant Perovskia scrophulariifolia: Their structures and anti-neoroinflammatory activity. Org Lett 22:7667–7670CrossRef
18.
Zurück zum Zitat Tanaka N, Yoshino Y, Nakano F, Kurimoto S, Kawazoe K, Tsuji D, Itoh K, Li S-L, Sun H-D, Takaishi Y, Kashiwada Y (2022) Lanicepines A and B, sesquiterpenes with amino acid-derived substituents from the flowering aerial parts of Saussurea laniceps. J Nat Prod 85:1180–1185CrossRef Tanaka N, Yoshino Y, Nakano F, Kurimoto S, Kawazoe K, Tsuji D, Itoh K, Li S-L, Sun H-D, Takaishi Y, Kashiwada Y (2022) Lanicepines A and B, sesquiterpenes with amino acid-derived substituents from the flowering aerial parts of Saussurea laniceps. J Nat Prod 85:1180–1185CrossRef
19.
Zurück zum Zitat Lauro G, Das P, Riccio R, Reddy DS, Bifulco G (2020) DFT/NMR approach for the configuration assignment of groups of stereoisomers by the combination and comparison of experimental and predicted sets of data. J Org Chem 85:3297–3306CrossRef Lauro G, Das P, Riccio R, Reddy DS, Bifulco G (2020) DFT/NMR approach for the configuration assignment of groups of stereoisomers by the combination and comparison of experimental and predicted sets of data. J Org Chem 85:3297–3306CrossRef
20.
Zurück zum Zitat Appendino G, Cravotto G, Palmisano G, Annunziata R (1998) Synthesis of fercoprolone, a degraded prenylated coumarin. Tetrahedron 54:10819–10826CrossRef Appendino G, Cravotto G, Palmisano G, Annunziata R (1998) Synthesis of fercoprolone, a degraded prenylated coumarin. Tetrahedron 54:10819–10826CrossRef
21.
Zurück zum Zitat Pfeffer PE, Valentine KM, Parrish FW (1979) Deuterium-induced differential isotope shift carbon-13 NMR. 1. Resonance reassignments of mono- and disaccharides. J Am Chem Soc 101:1265–1274CrossRef Pfeffer PE, Valentine KM, Parrish FW (1979) Deuterium-induced differential isotope shift carbon-13 NMR. 1. Resonance reassignments of mono- and disaccharides. J Am Chem Soc 101:1265–1274CrossRef
22.
Zurück zum Zitat Miski M, Jakupovic J (1990) Cyclic farnesyl-coumarin and farnesyl-chromone derivatives from Ferula communis subsp. communis. Phytochemistry 29:1995–1998CrossRef Miski M, Jakupovic J (1990) Cyclic farnesyl-coumarin and farnesyl-chromone derivatives from Ferula communis subsp. communis. Phytochemistry 29:1995–1998CrossRef
Metadaten
Titel
Communiferulins, farnesylated coumarins from the roots of Ferula communis and their anti-neuroinflammatory activity
verfasst von
Yuki Yoshino
Naonobu Tanaka
Daisuke Tsuji
Kohji Itoh
Yoshiki Kashiwada
Publikationsdatum
26.10.2022
Verlag
Springer Nature Singapore
Erschienen in
Journal of Natural Medicines / Ausgabe 1/2023
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-022-01657-8