C30 and C31 Triterpenoids and Triterpene Sugar Esters with Cytotoxic Activities from Edible Mushroom Fomitopsis pinicola (Sw. Ex Fr.) Krast

Article abstract of DOI:10.1021/acs.jafc.9b04530

Fomitopsis pinicola (Sw. Ex Fr.) Krast has been commonly used as a health food source and antitumor agent. To uncover bioactive key composition of F. pinicola, in our study, we investigated the chemical constituents of a methanol extract of F. pinicola and thirty-five lanostane-type tritetpenoids; 13 new compounds (1-13) and twenty-two known analogues (14-35) were isolated. Among them, compounds 1-9 were C30 lanostane triterpenoids and triterpene sugar esters, while compounds 10-13 were C31 triterpenoids and triterpene sugar esters. Their structures and absolute configurations were elucidated by extensive 1D, 2D NMR, MS, and IR spectra. Furthermore, cytotoxic activities of all isolates against five human tumor cell lines (HL-60, A549, SMMC-7721, MCF-7, and SW480) were evaluated. The results showed that compounds 12, 14, 17, 18, 22, and 23 displayed cytotoxic effects against five human tumor cell lines with IC₅₀ values ranging from 3.92-28.51 μM. Meanwhile, compounds 9 and 35 exhibited selected inhibitory activities against HL-60, SMMC-7721, and MCF-7 with IC₅₀ values in the range of 13.57-36.01 μM. Furthermore, the flow cytometry analysis revealed that compounds 17, 22, and 35 induced apoptosis in HL-60 cell lines. Their structure-activity relationships were preliminarily reported. These findings indicate the vital role of triterpenoids and their glycosides in explaining antitumor effects of F. pinicola and provide important evidence for further development and utilization of this fungus.

Full text of DOI:10.1021/acs.jafc.9b04530

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Bioactive Constituents, Metabolites, and Functions
C30 and C31 Triterpenoids and Triterpene Sugar Esters with Cytotoxic
Activities from Edible Mushroom Fomitopsis pinicola (Sw. Ex Fr.) Krast
Xing-Rong Peng, Haiguo Su, Junhong Liu, Yanjie Huang,
Xinzhi Yang, Zhongrong Li, Lin Zhou, and Ming-Hua Qiu
J. Agric. Food Chem., Just Accepted Manuscript • DOI: 10.1021/acs.jafc.9b04530 • Publication Date (Web): 30 Aug 2019
Downloaded from pubs.acs.org on August 30, 2019
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C30 and C31 Triterpenoids and Triterpene Sugar Esters with Cytotoxic
Activities from Edible Mushroom Fomitopsis pinicola (Sw. Ex Fr.) Krast
Xing-Rong Peng,† Hai-Guo Su,†,‡ Jun-Hong Liu,†,‡ Yan-Jie Huang,†,‡ Xin-Zhi
Yang,†,‡ Zhong-Rong Li,† Lin Zhou,† and Ming-Hua Qiu*,†
†State Key Laboratory of Phytochemistry and Plant Resources in West China,
Kunming Institute of Botany, Chinese Academy of Science, Kunming 650201,
People’s Republic of China
‡University of the Chinese Academy of Science, Beijing 100049, People’s Republic
of China
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Abstract: Fomitopsis pinicola (Sw. Ex Fr.) Krast has been commonly used as a
health food source and anti-tumor agent. To uncover bioactive key composition of F.
pinicola, in our study, we investigated the chemical constituents of methanol extract
of F. pinicola and thirty-five lanostane-type tritetpenoids, including thirteen new
compounds (1‒13) and twenty-two known analogues (14‒35) were isolated. Among
them, compounds 1‒9 were C30 lanostane triterpenoids and triterpene sugar esters,
while compounds 10‒13 were C31 triterpenoids and triterpene sugar esters. Their
structures and absolute configurations were elucidated by extensive 1D, 2D NMR,
MS and IR spectra. Furthermore, cytotoxic activities of all isolates against five human
tumor cell lines (HL-60, A549, SMMC-7721, MCF-7 and SW480) were evaluated.
The results showed that compounds 12, 14, 17, 18, 22 and 23 displayed cytotoxic
effects against five human tumor cell lines with IC50 values ranging from 3.92‒28.51
μM. Meanwhile, compounds 9 and 35 exhibited selected inhibitory activities against
HL-60, SMMC-7721 and MCF-7 with the IC50 values in the range of 13.57‒36.01
μM. Furthermore, the flow cytometry analysis revealed that compounds 17, 22 and 35
induced apoptosis in HL-60 cell lines. Their structure-activity relationships were
preliminarily reported. These findings indicate the vital role of triterpenoids and their
glycosides in explaining anti-tumor effects of F. pinicola and provide an important
evident for the further development and utilization of this fungus.
Keywords: Polyporaceae, Fomitopsis pinicola, C30 triterpenoids, C31 triterpenoids,
cytotoxic activity
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INTRODUCTION
Recent years, mushroom production has substantially increased. One of reason is
that many mushrooms are health food source due to their plentiful protein, vitamins
and minerals, as well as little fat.1 Another one is that some edible mushroom species,
such as Ganoderma (G. lucidum and G. sinense),2,3 Tricholoma (T. matsutake),4
Stropharia (S. rugosoannulata),5 and Pleurotus (P. eryngii),6 have significant
pharmacological attributs.7
Fomitopsis pinicola (Sw. Ex Fr.) Krast is belonging to Basidiomycetes fungus
and has been widely used as health food and medicinal mushroom in Asia.8 The
extract of F. pinicola was reported to exhibit antioxidant, antitumor in vitro and in
vivo9 and hypoglycemic activities.1 Except for C30 lanostane triterpenoids and their
glycosides, C31 triterpenoids and their glycosides were one of the main constituents
of F. pinicola, and these components displayed anti-bacterial,10 anti-microbal effects11
and inhibition of COX-1 and COX-2.12 Notably, lanostane-type triterpenoids showed
more potent anti-tumor activity in recent years.7 Sun et al13 found that the
tumor-inhibition rate of 3-acetoxyl-lanotane-8,24-dien-21 oic acid was 67.16% at a
dose of 10 mg/kg/d. Furthermore, Bao et al14 confirmed that this compound can
improve immunity of rats. Polyporenic acid B with a C31 skeleton showed
cytotoxicity against the HCT116, A549 and HepG2 cell lines (IC50 values: 8.4, 12.1
and 12.2 μM).15 Lanostane triterpenoids from Tricholoma pardinum, pardinols B and
E‒H showed inhibitory activities against different tumor cell lines to some content.16
Thus, to find out more triterpenoids with cytotoxicity, a systematic
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