Antimicrobial Acylphloroglucinol Meroterpenoids and Acylphloroglucinols from Dryopteris crassirhizoma

Ping Hai; Yunqing He; Ruirui Wang; Jian Yang; Yuan Gao; Xudong Wu; Nie Chen; Li Ye; Rongtao Li

doi:10.1055/a-1917-7910

Planta Medica, Inhaltsverzeichnis

Planta Med 2023; 89(03): 295-307
DOI: 10.1055/a-1917-7910

Biological and Pharmacological Activity

Original Papers

Antimicrobial Acylphloroglucinol Meroterpenoids and Acylphloroglucinols from Dryopteris crassirhizoma

Autoren

Ping Hai

¹Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, China
Yunqing He

²Faculty of Materials and Chemical Engineering, Yibin University, Yibin, China
Ruirui Wang

³School of Pharmaceutical Sciences, Yunnan University of Chinese Medicine, Kunming, China
Jian Yang

⁴State Key Laboratory Breeding Base of Dao-di Herbs, National Resource Center for Chinese Materia Medical, China Academy of Chinese Medical Sciences, Beijing, China
Yuan Gao

²Faculty of Materials and Chemical Engineering, Yibin University, Yibin, China
Xudong Wu

²Faculty of Materials and Chemical Engineering, Yibin University, Yibin, China
Nie Chen

²Faculty of Materials and Chemical Engineering, Yibin University, Yibin, China
Li Ye

²Faculty of Materials and Chemical Engineering, Yibin University, Yibin, China
Rongtao Li

¹Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, China

Abstract

Ten novel meroterpenoids, dryoptins/11″-epi-dryoptins A~E (1~10) with an unprecedented skeleton consisting of dimeric or trimeric acylphloroglucinols and dehydrotheonelline, two undescribed acylphloroglucinol-nerolidol meroterpenoids (11~12), and ten known acylphloroglucinol derivatives (13~22), were isolated from D. crassirhizoma. The novel structures including absolute configurations were established by comprehensive spectroscopic analyses and quantum chemical electronic circular dichroism (ECD) calculations. A biosynthetic pathway of 1~10 was assumed. The trimeric acylphloroglucinol meroterpenoids 7/8 showed significant antifungal activity against standard Candida albicans with a MIC₅₀ value of 1.61 µg/mL [fluconazole (FLC): 3.41 µg/mL], and when combined with FLC, the principal components 20 and 21 exhibited strong antifungal activities against FLC-resistant C. albicans with MIC₅₀ values of 8.39 and 7.16 µg/mL (FLC: > 100 µg/mL), respectively. Moreover, compounds 2, 5/6, 18, 19, and 21 exhibited inhibitory effects against several pathogenic fungi and bacteria, with MIC₅₀ values of 6.25 ~ 50 µg/mL.

Key words

Dryopteridaceae - Dryopteris crassirhizoma - acylphloroglucinol-meroterpenoid - acylphloroglucinol - Candida albicans - antifungal activity

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Referenzen

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