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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

Ping Hai
1   Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, China
,
Yunqing He
2   Faculty of Materials and Chemical Engineering, Yibin University, Yibin, China
,
Ruirui Wang
3   School of Pharmaceutical Sciences, Yunnan University of Chinese Medicine, Kunming, China
,
Jian Yang
4   State 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
2   Faculty of Materials and Chemical Engineering, Yibin University, Yibin, China
,
Xudong Wu
2   Faculty of Materials and Chemical Engineering, Yibin University, Yibin, China
,
Nie Chen
2   Faculty of Materials and Chemical Engineering, Yibin University, Yibin, China
,
Li Ye
2   Faculty of Materials and Chemical Engineering, Yibin University, Yibin, China
,
Rongtao Li
1   Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, China
› InstitutsangabenGefördert durch: the Key Project at Central Government Level: the ability establishment of sustainable use for valuable Chinese medicine resources 2060302
Gefördert durch: the Scientific and technological innovation project of China Academy of Chinese Medical Sciences CI2021A01809
Gefördert durch: the Scientific and technological innovation project of China Academy of Chinese Medical Sciences CI2021A04005
Gefördert durch: the Fundamental Research Funds for the Central public welfare research institutes ZZXT201906
Gefördert durch: the Startup Project supported by Yibin University 2021QH03
Gefördert durch: National Natural Science Foundation of China 21702181
Gefördert durch: National Natural Science Foundation of China 22067012
Gefördert durch: National Natural Science Foundation of China 82060637
Gefördert durch: the Yunnan Innovation Team, the Higher Educational Key Laboratory for New drugs for Viral Respiratory Diseases (Chinese Traditional Medicine) of Yunnan Province 2019HC018
Gefördert durch: the Key Lab of Process Analysis and Control of Sichuan Universities GCFX2021004
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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

Supporting Information

    General experimental procedures, calculation details, HRESIMS, and 1D, and 2D NMR spectrum of compounds 1~15, are included in Supporting Information.

  • Ergänzendes Material


Publikationsverlauf

Eingereicht: 06. März 2022

Angenommen nach Revision: 03. August 2022

Accepted Manuscript online:
03. August 2022

Artikel online veröffentlicht:
08. Dezember 2022

© 2022. Thieme. All rights reserved.

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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