Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe

doi:10.1007/s13659-022-00356-x

应用天然产物 ›› 2022, Vol. 12 ›› Issue (5): 32-32.DOI: 10.1007/s13659-022-00356-x

• ORIGINAL ARTICLE • 上一篇下一篇

Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe

Lin Zhou, Subiy Akbar, Meng-Xi Wang, He-Ping Chen, Ji-Kai Liu

School of Pharmaceutical Sciences, South-Central Minzu University, 430074 Wuhan, China

收稿日期:2022-05-02 修回日期:2022-07-05 出版日期:2022-10-24 发布日期:2022-10-12
通讯作者: He-Ping Chen,E-mail:chenhp@mail.scuec.edu.cn;Ji-Kai Liu,E-mail:liujikai@mail.scuec.edu.cn
基金资助:
The authors thank the National Natural Science Foundation of China (grant numbers 21961142008,22177138) for fundings.

Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe

Lin Zhou, Subiy Akbar, Meng-Xi Wang, He-Ping Chen, Ji-Kai Liu

School of Pharmaceutical Sciences, South-Central Minzu University, 430074 Wuhan, China

Received:2022-05-02 Revised:2022-07-05 Online:2022-10-24 Published:2022-10-12
Contact: He-Ping Chen,E-mail:chenhp@mail.scuec.edu.cn;Ji-Kai Liu,E-mail:liujikai@mail.scuec.edu.cn
Supported by:
The authors thank the National Natural Science Foundation of China (grant numbers 21961142008,22177138) for fundings.

摘要/Abstract

摘要： Chemical investigation on the medicinal fungus Ganoderma australe led to the identification of ten new nor-lanostane triterpenes, namely two hexa-nor ones, ganoaustratetraenones A (1) and B (2), five penta-nor ones, ganoaustraldehydes A–E (3–7), and three tetra-nor ones ganoaustrenoic acids A–C (8–10). The chemical structures along with the absolute configurations were determined by extensive spectroscopic analysis of 1D & 2D NMR and HRESIMS data. The postulated biosynthesis pathways of these compounds were proposed. Ganoaustraldehydes A (3) and B (4) showed moderate inhibition against nitric oxide production in RAW264.7 macrophage cells with the respective IC₅₀ values of 32.5, 34.2 μM (the IC₅₀ of positive control pyrrolidine dithiocarbamate was 20.0 μM).

关键词: Basidiomycete, Ganoderma australe, Nor-lanostane, Structural determination, Anti-NO production

Abstract: Chemical investigation on the medicinal fungus Ganoderma australe led to the identification of ten new nor-lanostane triterpenes, namely two hexa-nor ones, ganoaustratetraenones A (1) and B (2), five penta-nor ones, ganoaustraldehydes A–E (3–7), and three tetra-nor ones ganoaustrenoic acids A–C (8–10). The chemical structures along with the absolute configurations were determined by extensive spectroscopic analysis of 1D & 2D NMR and HRESIMS data. The postulated biosynthesis pathways of these compounds were proposed. Ganoaustraldehydes A (3) and B (4) showed moderate inhibition against nitric oxide production in RAW264.7 macrophage cells with the respective IC₅₀ values of 32.5, 34.2 μM (the IC₅₀ of positive control pyrrolidine dithiocarbamate was 20.0 μM).

Key words: Basidiomycete, Ganoderma australe, Nor-lanostane, Structural determination, Anti-NO production

Lin Zhou, Subiy Akbar, Meng-Xi Wang, He-Ping Chen, Ji-Kai Liu. Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe[J]. 应用天然产物, 2022, 12(5): 32-32.

Lin Zhou, Subiy Akbar, Meng-Xi Wang, He-Ping Chen, Ji-Kai Liu. Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe[J]. Natural Products and Bioprospecting, 2022, 12(5): 32-32.

参考文献

1. Kladar NV, Gavarić NS, Božin BN. Ganoderma: insights into anticancer effects. Eur J Cancer Prev. 2016;25(5):462–71.
2. Boh B, Berovic M, Zhang J, Zhi-Bin L. Ganoderma lucidum and its pharmaceutically active compounds. Biotechnol Annu Rev. 2007;13:265–301.
3. Amaral AE, Carbonero ER, Rita de Cássia GS, Kadowaki MK, Sassaki GL, Osaku CA, Gorin PAJ, Iacomini M. An unusual water-soluble β-glucan from the basidiocarp of the fungus Ganoderma resinaceum. Carbohydr Polym. 2008;72(3):473–8.
4. Peng XR, Liu JQ, Han ZH, Yuan XX, Luo HR, Qiu MH. Protective effects of triterpenoids from Ganoderma resinaceum on H2O2-induced toxicity in HepG2 cells. Food Chem. 2013;141(2):920–6.
5. Zhao ZZ, Chen HP, Huang Y, Li ZH, Zhang L, Feng T, Liu JK. Lanostane triterpenoids from fruiting bodies of Ganoderma leucocontextum. Nat Prod Bioprospect. 2016;6:103–9.
6. Baby S, Johnson AJ, Govindan B. Secondary metabolites from Ganoderma. Phytochemistry. 2015;114:66–101.
7. Paterson RRM. Ganoderma—a therapeutic fungal biofactory. Phytochemistry. 2006;67(18):1985–2001.
8. Niedermeyer THJ, Jira T, Lalk M, Lindequist U. In vitro bone inducing effects of Lentinula edodes (shiitake) water extract on human osteoblastic cell cultures. Nat Prod Bioprospect. 2013;3:137–40.
9. Peng X, Qiu M. Meroterpenoids from Ganoderma species: a review of last five years. Nat Prod Bioprospect. 2018;8:137–49.
10. Guo JC, Yang L, Ma QY, Ge YZ, Kong FD, Zhou LM, Zhang F, Xie QY, Yu ZF, Dai HF, Zhao YX. Triterpenoids and meroterpenoids with α-glucosidase inhibitory activities from the fruiting bodies of Ganoderma australe. Bioorg Chem. 2021;117:105448.
11. León F, Valencia M, Rivera A, Nieto I, Quintana J, Estévez F, Bermejo J. Novel cytostatic lanostanoid triterpenes from Ganoderma australe. Helv Chim Acta. 2003;86:3088–95.
12. Isaka M, Chinthanom P, Mayteeworakoon S, Laoteng K, Choowong W, Choeyklin R. Lanostane triterpenoids from cultivated fruiting bodies of the basidiomycete Ganoderma australe. Nat Prod Res. 2018;32:1044–9.
13. Jain AC, Gupta SK. The isolation of lanosta-7, 9 (11), 24-trien-3β, 21-diol from the fungus Ganoderma australe. Phytochemistry. 1984;23:686–7.
14. Zhang JJ, Dong Y, Qin FY, Yan YM, Cheng YX. Meroterpenoids and alkaloids from Ganoderma australe. Nat Prod Res. 2021;35:3226–32.
15. Zhang JJ, Dong Y, Qin FY, Cheng YX. Australeols A- F, neuroprotective meroterpenoids from Ganoderma australe. Fitoterapia. 2019;134:250–5.
16. Nishitoba T, Sato H, Sakamura S. Triterpenoids from the fungus Ganoderma lucidum. Phytochemistry. 1987;26:1777–84.
17. Zhao XR, Huo XK, Dong PP, Wang C, Huang SS, Zhang BJ, Zhang HL, Deng S, Liu KX, Ma XC. Inhibitory effects of highly oxygenated lanostane derivatives from the fungus Ganoderma lucidum on P-glycoprotein and α-glucosidase. J Nat Prod. 2015;78:1868–76.
18. Kikuchi T, Kanomi S, Murai Y, Kadota S, Tsubono K, Ogita Z-I. Lanostane triterpenes from the fruiting bodies of Ganoderma lucidum and their inhibitory effects on adipocyte differentiation in 3T3-L1 Cells. Chem Pham Bull. 1986;34(10):4030–6.
19. Wang WF, Xiao H, Zhong JJ. Biosynthesis of a novel ganoderic acid by expressing CYP genes from Ganoderma lucidum in Saccharomyces cerevisiae. Appl Microbiol Biotechnol. 2022;106(2):523–34.
20. Zhou L, Guo LL, Isaka M, Li ZH, Chen HP. Triterpenes from the fungus Ganoderma australe. J Fungi. 2022;8(5):503.

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Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe

Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe

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