Anti-influenza sesquiterpene from the roots of Reynoutria japonica

Nguyen Xuan Nhiem, Phan Van Kiem, Chau Van Minh, Nguyen Thi Hoai, Ho Viet Duc, Bui Huu Tai, Tran Hong Quang, Hoang Le Tuan Anh, Sang Gu Yeo, Jae Hyoung Song, Doo Sung Cheon, Moon Ho Park, Hyun Jeong Ko, Seung Hyun Kim

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

One new flavonol glycoside, 4′-O-methylmyricitrin 3′-O-β-D-glucopyranoside (1), one new sesquiterpene, reynoudiol (11), as well as the 12 known compounds (2-10, 12-14) quercetin 3-O-methyl ether (2), quercitrin (3), isorhamnetin 3-α-L-rhamnopyranoside (4), tamarixetin 3-α-L-rhamnopyranoside (5), myricitrin (6), 4′-O-methylmyricitrin (7), isorhamnetin 3-O-β-D-xylopyranosyl (1→2)-O-β-D- glucopyranoside (8), isorhamnetin 3-O-β-D-apiofuranosyl-(1→2)-O- β-D-glucopyranoside (9), (+)-catechin (10), 7-drimene-3,11,12-triol (12), clovane-2β,9α-diol (13), and α-cadinol (14), were isolated from the methanol extract of Reynoutria japonica roots. Based on in vitro screening of the anti-influenza activity of the isolated compounds, reynoudiol showed significantly higher activity than that of oseltamivir phosphate at the same concentration, and did not induce any detectable cytopathic effect in MDCK cells. The CC50 of reynoudiol was above 50 μM and could inhibit influenza virus infection with an IC50 of 0.29 ± 0.01 μM. The therapeutic index (TI) of reynoudiol against influenza infection was 172.4, and thus, this compound can be potentially used to treat oseltamivir-resistant influenza virus infection.

Original languageEnglish
Pages (from-to)315-318
Number of pages4
JournalNatural Product Communications
Volume9
Issue number3
Publication statusPublished - 2014 Jan 1

Fingerprint

Reynoutria japonica
isorhamnetin
Sesquiterpenes
influenza
sesquiterpenoids
Human Influenza
Orthomyxoviridae
Oseltamivir
Virus Diseases
infection
quercitrin
glycols
cytopathogenicity
catechin
flavonols
quercetin
Madin Darby Canine Kidney Cells
inhibitory concentration 50
glycosides
Catechin

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Plant Science
  • Complementary and alternative medicine

Cite this

Nhiem, N. X., Kiem, P. V., Minh, C. V., Hoai, N. T., Duc, H. V., Tai, B. H., ... Kim, S. H. (2014). Anti-influenza sesquiterpene from the roots of Reynoutria japonica. Natural Product Communications, 9(3), 315-318.
Nhiem, Nguyen Xuan ; Kiem, Phan Van ; Minh, Chau Van ; Hoai, Nguyen Thi ; Duc, Ho Viet ; Tai, Bui Huu ; Quang, Tran Hong ; Anh, Hoang Le Tuan ; Yeo, Sang Gu ; Song, Jae Hyoung ; Cheon, Doo Sung ; Park, Moon Ho ; Ko, Hyun Jeong ; Kim, Seung Hyun. / Anti-influenza sesquiterpene from the roots of Reynoutria japonica. In: Natural Product Communications. 2014 ; Vol. 9, No. 3. pp. 315-318.
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Nhiem, NX, Kiem, PV, Minh, CV, Hoai, NT, Duc, HV, Tai, BH, Quang, TH, Anh, HLT, Yeo, SG, Song, JH, Cheon, DS, Park, MH, Ko, HJ & Kim, SH 2014, 'Anti-influenza sesquiterpene from the roots of Reynoutria japonica', Natural Product Communications, vol. 9, no. 3, pp. 315-318.

Anti-influenza sesquiterpene from the roots of Reynoutria japonica. / Nhiem, Nguyen Xuan; Kiem, Phan Van; Minh, Chau Van; Hoai, Nguyen Thi; Duc, Ho Viet; Tai, Bui Huu; Quang, Tran Hong; Anh, Hoang Le Tuan; Yeo, Sang Gu; Song, Jae Hyoung; Cheon, Doo Sung; Park, Moon Ho; Ko, Hyun Jeong; Kim, Seung Hyun.

In: Natural Product Communications, Vol. 9, No. 3, 01.01.2014, p. 315-318.

Research output: Contribution to journalArticle

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AU - Nhiem, Nguyen Xuan

AU - Kiem, Phan Van

AU - Minh, Chau Van

AU - Hoai, Nguyen Thi

AU - Duc, Ho Viet

AU - Tai, Bui Huu

AU - Quang, Tran Hong

AU - Anh, Hoang Le Tuan

AU - Yeo, Sang Gu

AU - Song, Jae Hyoung

AU - Cheon, Doo Sung

AU - Park, Moon Ho

AU - Ko, Hyun Jeong

AU - Kim, Seung Hyun

PY - 2014/1/1

Y1 - 2014/1/1

N2 - One new flavonol glycoside, 4′-O-methylmyricitrin 3′-O-β-D-glucopyranoside (1), one new sesquiterpene, reynoudiol (11), as well as the 12 known compounds (2-10, 12-14) quercetin 3-O-methyl ether (2), quercitrin (3), isorhamnetin 3-α-L-rhamnopyranoside (4), tamarixetin 3-α-L-rhamnopyranoside (5), myricitrin (6), 4′-O-methylmyricitrin (7), isorhamnetin 3-O-β-D-xylopyranosyl (1→2)-O-β-D- glucopyranoside (8), isorhamnetin 3-O-β-D-apiofuranosyl-(1→2)-O- β-D-glucopyranoside (9), (+)-catechin (10), 7-drimene-3,11,12-triol (12), clovane-2β,9α-diol (13), and α-cadinol (14), were isolated from the methanol extract of Reynoutria japonica roots. Based on in vitro screening of the anti-influenza activity of the isolated compounds, reynoudiol showed significantly higher activity than that of oseltamivir phosphate at the same concentration, and did not induce any detectable cytopathic effect in MDCK cells. The CC50 of reynoudiol was above 50 μM and could inhibit influenza virus infection with an IC50 of 0.29 ± 0.01 μM. The therapeutic index (TI) of reynoudiol against influenza infection was 172.4, and thus, this compound can be potentially used to treat oseltamivir-resistant influenza virus infection.

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Nhiem NX, Kiem PV, Minh CV, Hoai NT, Duc HV, Tai BH et al. Anti-influenza sesquiterpene from the roots of Reynoutria japonica. Natural Product Communications. 2014 Jan 1;9(3):315-318.