Cytotoxic Indole Diterpenoids from a -Derived Fungus Sp. PQJ-1

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2023 Oct 28

PMID 37894482

Authors

Wenxing Li

Guohui Yi

Kaiwen Lin

Guangying Chen

Yang Hui

Wenhao Chen

Affiliations

Soon will be listed here.

Abstract

Two new indole diterpene derivatives, 5-hydroxy--aflatrem () and 14-hydroxy--aflatrem (), along with one known analogue, 14-(,-dimethl--valyloxy)paspalinine (), were isolated from the fermentation broth of the fungus sp. PQJ-1 derived from . The structures of the new compounds were elucidated from spectroscopic data and ECD spectroscopic analyses. All the compounds (-) were evaluated for their cytotoxicity against A549, Hela, Hep G2, and MCF-7 cell lines. Compounds and exhibited selective inhibition against Hela cells. Further studies showed that significantly induced apoptosis and suppressed migration and invasion in Hela cells. Moreover, could up-regulate pro-apoptotic genes BAX and Caspase-3 and down-regulate anti-apoptotic genes Bcl-xL and XIXP.

References

Ma Y, Ma W, Zhou Z, Huang X, Jiang X, Du K . Synthesis of 8-Fluoroneocryptolepine and Evaluation for Cytotoxic Activity against AGS Cancer Cells. J Nat Prod. 2022; 85(4):963-971. DOI: 10.1021/acs.jnatprod.1c01078. View

Corsello M, Kim J, Garg N . Indole diterpenoid natural products as the inspiration for new synthetic methods and strategies. Chem Sci. 2017; 8(9):5836-5844. PMC: 5618777. DOI: 10.1039/c7sc01248a. View

Elmore S . Apoptosis: a review of programmed cell death. Toxicol Pathol. 2007; 35(4):495-516. PMC: 2117903. DOI: 10.1080/01926230701320337. View

Zheng C, Bai M, Zhou X, Huang G, Shao T, Luo Y . Penicilindoles A-C, Cytotoxic Indole Diterpenes from the Mangrove-Derived Fungus Eupenicillium sp. HJ002. J Nat Prod. 2018; 81(4):1045-1049. DOI: 10.1021/acs.jnatprod.7b00673. View

Karon K, Lapkowski M, Dobrowolski J . ECD spectroelectrochemistry: A review. Spectrochim Acta A Mol Biomol Spectrosc. 2021; 250:119349. DOI: 10.1016/j.saa.2020.119349. View

Kumar P, Nagarajan A, Uchil P . Analysis of Cell Viability by the MTT Assay. Cold Spring Harb Protoc. 2018; 2018(6). DOI: 10.1101/pdb.prot095505. View

Gardner D, Welch K, Lee S, Cook D, Riet-Correa F . Tremorgenic Indole Diterpenes from Ipomoea asarifolia and Ipomoea muelleri and the Identification of 6,7-Dehydro-11-hydroxy-12,13-epoxyterpendole A. J Nat Prod. 2018; 81(7):1682-1686. DOI: 10.1021/acs.jnatprod.8b00257. View

Zhou G, Sun C, Hou X, Che Q, Zhang G, Gu Q . Ascandinines A-D, Indole Diterpenoids, from the Sponge-Derived Fungus HDN15-152. J Org Chem. 2021; 86(3):2431-2436. DOI: 10.1021/acs.joc.0c02575. View

Kong F, Fan P, Zhou L, Ma Q, Xie Q, Zheng H . Penerpenes A-D, Four Indole Terpenoids with Potent Protein Tyrosine Phosphatase Inhibitory Activity from the Marine-Derived Fungus Penicillium sp. KFD28. Org Lett. 2019; 21(12):4864-4867. DOI: 10.1021/acs.orglett.9b01751. View

10.

Xu W, Gavia D, Tang Y . Biosynthesis of fungal indole alkaloids. Nat Prod Rep. 2014; 31(10):1474-87. PMC: 4162825. DOI: 10.1039/c4np00073k. View

11.

Xu L, Hai P, Zhang S, Xiao J, Gao Y, Ma B . Prenylated Indole Diterpene Alkaloids from a Mine-Soil-Derived Tolypocladium sp. J Nat Prod. 2019; 82(2):221-231. DOI: 10.1021/acs.jnatprod.8b00589. View

12.

Yu J, Wang J, Liu S, Yin C, Tang D, Li Y . 7-Methoxy-13-dehydroxypaxilline: New indole diterpenoid from an endophytic fungus sp. Nb 19. Nat Prod Res. 2022; 38(1):103-111. DOI: 10.1080/14786419.2022.2107639. View

13.

Li W, Lei X, Yan X, Qin Y, Chen G, Li S . Hainanxylogranolides A-F: New Limonoids isolated from the seeds of Hainan mangrove plant Xylocarpus granatum. Fitoterapia. 2022; 165:105407. DOI: 10.1016/j.fitote.2022.105407. View

14.

Fan Y, Wang Y, Liu P, Fu P, Zhu T, Wang W . Indole-diterpenoids with anti-H1N1 activity from the aciduric fungus Penicillium camemberti OUCMDZ-1492. J Nat Prod. 2013; 76(7):1328-36. DOI: 10.1021/np400304q. View

15.

Sun C, Liu X, Sun N, Zhang X, Shah M, Zhang G . Cytotoxic Nitrobenzoyl Sesquiterpenoids from an Antarctica Sponge-Derived . J Nat Prod. 2022; 85(4):987-996. DOI: 10.1021/acs.jnatprod.1c01118. View

16.

Gatenby W, Munday-Finch S, Wilkins A, Miles C . Terpendole M, a novel indole-diterpenoid isolated from Lolium perenne infected with the endophytic fungus Neotyphodium lolii. J Agric Food Chem. 1999; 47(3):1092-7. DOI: 10.1021/jf980767z. View

17.

Li W, Zhou X, Ji S, Wang Y, Sun Z, Huang Z . Two new lactam derivatives from a derived fungus PQJ-2. Nat Prod Res. 2022; 38(3):372-378. DOI: 10.1080/14786419.2022.2122964. View

18.

Li C, Gloer J, Wicklow D, Dowd P . Thiersinines A and B: novel antiinsectan indole diterpenoids from a new fungicolous Penicillium species (NRRL 28147). Org Lett. 2002; 4(18):3095-8. DOI: 10.1021/ol026424a. View

19.

Sun K, Li Y, Guo L, Wang Y, Liu P, Zhu W . Indole diterpenoids and isocoumarin from the fungus, Aspergillus flavus, isolated from the prawn, Penaeus vannamei. Mar Drugs. 2014; 12(7):3970-81. PMC: 4113809. DOI: 10.3390/md12073970. View

20.

Chaiyosang B, Kanokmedhakul K, Yodsing N, Boonlue S, Yang J, Wang Y . Three new indole diterpenoids from KKU-CT2. Nat Prod Res. 2021; 36(19):4973-4981. DOI: 10.1080/14786419.2021.1914613. View