Seco-pimarane diterpenoids and androstane steroids from an endophytic Nodulisporium fungus derived from Cyclosorus parasiticus

Xiaoli Yang; Ping Wu; Jinghua Xue; Hanxiang Li; Xiaoyi Wei

doi:10.1016/j.phytochem.2023.113679

Seco-pimarane diterpenoids and androstane steroids from an endophytic Nodulisporium fungus derived from Cyclosorus parasiticus

Phytochemistry. 2023 Jun:210:113679. doi: 10.1016/j.phytochem.2023.113679. Epub 2023 Apr 12.

Authors

Xiaoli Yang¹, Ping Wu², Jinghua Xue³, Hanxiang Li³, Xiaoyi Wei⁴

Affiliations

¹ Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement and Guangdong Provincial Key Laboratory of Digital Botanical Garden and Public Science, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou, 510650, People's Republic of China; University of Chinese Academy of Sciences, Yuquanlu 19A, Beijing, 100049, People's Republic of China.
² Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement and Guangdong Provincial Key Laboratory of Digital Botanical Garden and Public Science, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou, 510650, People's Republic of China; University of Chinese Academy of Sciences, Yuquanlu 19A, Beijing, 100049, People's Republic of China. Electronic address: wuping@scbg.ac.cn.
³ Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement and Guangdong Provincial Key Laboratory of Digital Botanical Garden and Public Science, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou, 510650, People's Republic of China.
⁴ Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement and Guangdong Provincial Key Laboratory of Digital Botanical Garden and Public Science, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou, 510650, People's Republic of China; University of Chinese Academy of Sciences, Yuquanlu 19A, Beijing, 100049, People's Republic of China. Electronic address: wxy@scbg.ac.cn.

PMID: 37059288
DOI: 10.1016/j.phytochem.2023.113679

Abstract

Five previously undescribed specialized metabolites, including three 9,11-seco-pimarane diterpenoids, nodulisporenones A-C, and two androstane steroids, nodulisporisterones A and B, together with previously described ergosterol derivatives, dankasterone A and demethylincisterol A₃, were isolated from solid cultures of the endophytic fungus Nodulisporium sp. SC-J597. Their structures including absolute configurations were elucidated by extensive spectroscopic analysis and theoretical calculations of electronic circular dichroism spectra. Among them, nodulisporenones A and B are the first examples of seco-pimarane diterpenoids that is cyclized to form an unprecedented diterpenoid lactone scaffold and nodulisporisterones A and B represent the first normal C₁₉ androstane steroids of fungal origin. Nodulisporisterone B exhibited potent inhibitory effect on the production of NO in LPS-stimulated RAW264.7 macrophages (IC₅₀ = 2.95 μM). This compound, together with the two known ergosterol derivatives, also displayed cytotoxicity against A549, HeLa, HepG2 and MCF-7 cancer cell lines with IC₅₀ values of 5.2-16.9 μM.

Keywords: Androstane; Cyclosorus parasiticus; Endophyte; Isopimarane; Nodulisporium; Thelypteridaceae; Xylariaceae.

MeSH terms

Abietanes* / chemistry
Androstanes
Diterpenes* / chemistry
Ergosterol
Fungi
Humans
Molecular Structure
Steroids

Substances

Abietanes
Steroids
Diterpenes
Androstanes
Ergosterol