Planta Med 2016; 82(09/10): 872-876
DOI: 10.1055/s-0042-102885
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Peniphenylanes A–G from the Deep-Sea-Derived Fungus Penicillium fellutanum HDN14-323

Zhenzhen Zhang
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, P. R. China
,
Wenqiang Guo
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, P. R. China
,
Xueqian He
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, P. R. China
,
Qian Che
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, P. R. China
,
Tianjiao Zhu
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, P. R. China
,
Qianqun Gu
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, P. R. China
,
Dehai Li
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, P. R. China
› Author Affiliations
Further Information

Publication History

received 21 August 2015
revised 01 February 2016

accepted 03 February 2016

Publication Date:
22 March 2016 (online)

Abstract

Seven new 6-methylsaligenin derivatives, including the trimeric peniphenylanes A–B (12) and dimeric peniphenylanes C–G (37), together with four known biogenetically related compounds (811) were discovered from the extract of the deep-sea-derived fungus Penicillium fellutanum HDN14-323. The structures of the new compounds were established through extensive analysis. Their cytotoxic activity against HeLa, HL-60, and HCT-116 cell lines was evaluated, with compound 4 exhibiting the best activity against the HeLa cell line (IC50 = 9.3 µM).

Supporting Information

 
  • References

  • 1 Manohar CS, Raghukumar C. Fungal diversity from various marine habitats deduced through culture-independent studies. FEMS Microbiol Lett 2013; 341: 69-78
  • 2 Skropeta D. Deep-sea natural products. Nat Prod Rep 2008; 25: 1131-1166
  • 3 Wang YT, Xue YR, Liu CH. A brief review of bioactive metabolites derived from deep-sea fungi. Mar Drugs 2015; 68: 9745-9749
  • 4 Skropeta D, Wei L. Recent advances in deep-sea natural products. Nat Prod Rep 2014; 31: 999-1025
  • 5 Wu GW, Sun XH, Yu GH, Wang W, Zhu TJ, Gu QQ, Li DH. Cladosins A–E, hybrid polyketides from a deep-sea-derived fungus, Cladosporium sphaerospermum . J Nat Prod 2014; 77: 270-275
  • 6 Guo WQ, Peng JX, Zhu TJ, Gu QQ, Keyzers RA, Li DH. Sorbicillamines A–E, nitrogen containing sorbicillinoids from the deep-sea derived fungus Penicillium sp. F23-2. J Nat Prod 2013; 76: 2106-2112
  • 7 Wu GW, Ma HY, Zhu TJ, Li J, Gu QQ, Li DH. Penilactones A and B, two novel polyketides from antarctic deep-sea derived fungus Penicillium crustosum PRB-2. Tetrahedron 2012; 68: 9745-9749
  • 8 Li DH, Cai SX, Zhu TJ, Wang FP, Xiao X, Gu QQ. Three new sorbicillin trimers, trisorbicillinones B, C and D, from a deep ocean sediment derived fungus, Phialocephala sp. FL30 r. Tetrahedron 2010; 66: 5101-5106
  • 9 Bogan LE, Wolk SK. Synthesis of and assignment of carbon- 13 NMR resonances to m-cresol novolak dimers. Macromolecules 1992; 25: 161-165
  • 10 Singh V, Samanta B, Kane VV. Molecular complexity from aromatics: synthesis and photoreaction of endo-tricyclo[5.2.2.02,6]undecanes. Formal total syntheses of (±)-coriolin. Tetrahedron 2000; 56: 7785-7795
  • 11 Thomas E, Brion JD, Peyrat JF. Synthesis and preliminary biological evaluation of new antiproliferative aromatic analogues of 1α,25-dihydroxyvitamin D3. Eur J Med Chem 2014; 86: 381-393
  • 12 Suzuki M, Sugiyama T, Watanabe M, Murayama T, Yamashita K. Synthesis and absolute configuration of pyriculol. Agric Biol Chem 1987; 51: 1121-1127
  • 13 Liu M, Hansen PE, Lin XK. Bromophenols in marine algae and their bioactivities. Mar Drugs 2011; 9: 1273-1292
  • 14 Chen L, Fang YC, Zhu TJ, Gu QQ, Zhu WM. Gentisyl alcohol derivatives from the marine-derived fungus Penicillium terrestre . J Nat Prod 2008; 71: 66-70
  • 15 Malak LG, Ibrahim MA, Bishay DW, Abdel-baky AM, Moharram AM, Tekwani B, Cutler SJ, Ross SA. Antileishmanial metabolites from Geosmithia langdonii . J Nat Prod 2014; 77: 1987-1991
  • 16 Hayashi J, Sekine T, Deguchi S, Lin Q, Horie S, Tsuchiya S, Yano S, Watanabe K, Ikegami F. Phenolic compounds from Gastrodia rhizome and relaxant effects of related compounds on isolated smooth muscle preparation. Phytochemistry 2002; 59: 513-519
  • 17 Zhang ZC, Su G, Lin J, Wu H, Xie XD. Two new neuroprotective phenolic compounds from Gastrodia elata . J Asian Nat Prod Res 2013; 15: 619-623
  • 18 Noda N, Kobayashi Y, Miyahara K, Fukahori S. 2, 4-Bis(4-hydroxybenzyl)phenol from Gastrodia elata . Phytochemistry 1995; 39: 1247-1248
  • 19 Taguchi H, Yosioka I, Yamasaki K, Kim IH. Studies on the constituents of Gastrodia elata Blume. Chem Pharm Bull (Tokyo) 1981; 29: 55-62
  • 20 Fu GM, Yu BY, Zhu DN. Two novel phloroglucinol derivatives from Euphorbia ebracteolata hayata. J Asian Nat Prod Res 2006; 8: 149-153
  • 21 Li N, Wang KJ, Chen JJ, Zhou J. Phenolic compounds from the rhizomes of Gastrodia elata . J Asian Nat Prod Res 2007; 9: 373-377
  • 22 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63
  • 23 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990; 82: 1107-1112