Journal of Shandong University (Health Sciences) ›› 2019, Vol. 57 ›› Issue (3): 38-41.doi: 10.6040/j.issn.1671-7554.0.2019.053

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Chemical constituents of Chiloscyphus polyanthus var. rivularis

ZHANG Jiaozhen, LOU Hongxiang   

  1. Key Lab of Chemical Biology(Ministry of Education), Department of Natural Products Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, Shandong, China
  • Published:2022-09-27

Abstract: Objective To study the chemical constituents of Chiloscyphus polyanthus var. rivularis. Methods The chemical constituents were isolated and identified on the basis of various chromatographic methods such as MCI gel, silica gel, Sephadex LH-20 column, and semi-preparation HPLC as well as a combination of their spectroscopic data, such as NMR and HRESIMS. Results Isolation of Chiloscyphus polyanthus var. rivularis afforded five compounds, including two new eudesmane type sesquiterpenoids, which were named (3S,7R,10S)-7-hydroxy-3-methoxy-eudesma-4E-ene(1)and (3S,7R,10S)-7-hydroxy-3-ethyoxyl-eudesma-4E-ene(2), one guaiane type sesquiterpenoid(guaianediol, 3), one labdane-type diterpenoid(nivenolide, 4), and one triterpenoid(betulin, 5). Conclusion Compounds 1 and 2 are previously undescribed and compounds 3-5 are isolated from the plants in genus Chiloscyphus for the first time.

Key words: Bryophytes, Chiloscyphus polyanthus var. rivularis, Eudesmane type sesquiterpenoids, Guaiane type sesquiterpenoid, Diterpenoid, Triterpenoid

CLC Number: 

  • R574
[1] Wellman CH, Osterloff PL, Mohiuddin U. Fragments of the earliest land plants[J]. Nature, 2003, 425(6955): 282-285.
[2] Bowman JL, Kohchi T, Yamato KT, et al. Insights into land plant evolution garnered from the marchantia polymorpha genome[J]. Cell, 2017, 171(2): 287-304.e15.
[3] 吴鹏程. 苔藓植物生物学[M]. 北京: 科学出版社, 1998.
[4] 娄红祥. 苔藓植物化学与生物学[M]. 北京: 北京科学技术出版社, 2006.
[5] Asakawa Y, Ludwiczuk A. Chemical constituents of bryophytes: structures and biological activity[J]. J Nat Prod, 2018, 81(3): 641-660.
[6] Asakawa Y, Ludwiczuk A, Nagashima F. Phytochemical and biological studies of bryophytes[J]. Phytochemistry, 2013, 91: 52-80. doi:10.1016/j.phytochem.2012.04.012.
[7] Asakawa Y. Biologically active compounds from bryophytes[J]. Pure and Applied Chemistry, 2007, 79(4): 557-580.
[8] Zinsmeister HD, Becker H, Eicher T. Bryophytes, a source of biologically active, naturally occurring material?[J]. Angew Chem Int Ed Engl, 1991, 30(2): 130-147.
[9] Guo DX, Zhu RX, Wang XN, et al. Scaparvin A, a novel caged cis-clerodane with an unprecedented C-6/C-11 bond, and related diterpenoids from the liverwort Scapania parva[J]. Org Lett, 2010, 12(19): 4404-4407.
[10] Wang LN, Zhang JZ, Li X, et al. Pallambins A and B, unprecedented hexacyclic 19-nor-secolabdane diterpenoids from the Chinese liverwort Pallavicinia ambigua[J]. Org Lett, 2012, 14(4): 1102-1105.
[11] Zhou JC, Zhang JZ, Cheng AX, et al. Highly rigid labdane-type diterpenoids from a Chinese liverwort and light-driven structure diversification[J]. Org Lett, 2015, 17(14): 3560-3563.
[12] Zhou JC, Zhang JZ, Li RJ, et al. Hapmnioides A-C, rearranged labdane-type diterpenoids from the Chinese liverwort haplomitrium mnioides[J]. Org Lett, 2016, 18(17): 4274-4276.
[13] Han JJ, Zhang JZ, Zhu RX, et al. Plagiochianins A and B, two ent-2, 3-seco-aromadendrane derivatives from the liverwort Plagiochila duthiana[J]. Org Lett, 2018, 20(20): 6550-6553.
[14] Wang YY, Wang LN, Hu ZY, et al. A novel derivative of riccardin D induces cell death through lysosomal rupture in vitro and inhibits tumor growth in vivo[J]. Cancer Lett, 2013, 329(2): 207-216.
[15] Lin ZM, Guo YX, Gao YH, et al. Ent-kaurane diterpenoids from Chinese liverworts and their antitumor activities through michael addition as detected in situ by a fluorescence probe[J]. J Med Chem, 2015, 58(9): 3944-3956.
[16] el Sayed KA, Hamann MT. A new norcembranoid dimer from the red sea soft coral Sinularia gardineri[J]. J Nat Prod, 1996, 59(7): 687-689.
[17] Rojas ET, Rodriguez-Hahn L. Nivenolide, a diterpene lactone from Croton niveus[J]. Phytochemistry, 1978, 17(3): 574-575.
[18] 王晓林, 李良琼, 李美蓉. 扁枝槲寄生化学成分研究(Ⅲ)[J]. 华西药学杂志, 1995, 10(1): 1-3. WANG Xiaolin, LI Liangqiong, LI Meirong. Studies on the chemical constituents of Viscum articulatum Burm.f.(Ⅲ)[J]. West China Journal of Pharmaceutcal Sciences, 1995, 10(1): 1-3.
[19] 高谦.中国苔藓志[M]. 9卷.北京: 科学出版社, 2003.
[20] Ma B, Lu ZQ, Guo HF, et al. Rearranged calamenene and eudesmane sesquiterpenoids from two Chinese liverworts[J]. HCA, 2007, 90(1): 52-57.
[21] Toyota M, Saito T, Asakawa Y. The absolute configuration of eudesmane-type sesquiterpenoids found in the Japanese liverwort Chiloscyphus polyanthos[J]. Phytochemistry, 1999, 51(7): 913-920.
[22] Xie CF, Sun B, Guo DX, et al. Terpenoids from the Chinese liverwort chiloscyphus polyanthus[J]. HCA, 2011, 94(3): 534-538.
[23] Zhang JZ, Qiao YN, Li L, et al. Ent-eudesmane-type sesquiterpenoids from the Chinese liverwort chiloscyphus polyanthus var. rivularis[J]. Planta Med, 2016, 82(11/12): 1128-1133.
[24] Zhang JZ, Wang YJ, Zhu RX, et al. Cyperane and eudesmane-type sesquiterpenoids from Chinese liverwort and their anti-diabetic nephropathy potential[J]. RSC Adv, 2018, 8(68): 39091-39097.
[25] Wu C, Gunatilaka AA, McCabe FL, et al. Bioactive and other sesquiterpenes from Chiloscyphus rivularis[J]. J Nat Prod, 1997, 60(12): 1281-1286.
[26] Harrison LJ, Asakawa Y. Oppositane and chiloscyphane sesquiterpenoids from the liverwort Chiloscyphus pallescens[J]. Phytochemistry, 1991, 30(11): 3806-3807.
[27] Cullmann F, Schmidt A, Schuld F, et al. Lignans from the liverworts Lepidozia incurvata, Chiloscyphus polyanthos and Jungermannia exsertifolia ssp. cordifolia[J]. Phytochemistry, 1999, 52(8): 1647-1650.
[28] Asakawa Y. Chemosystematics of the hepaticae[J]. Phytochemistry, 2004, 65(6): 623-669.
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