New halimane and clerodane diterpenoids from Croton cnidophyllus

doi:10.1007/s13659-023-00386-z

应用天然产物 ›› 2023, Vol. 13 ›› Issue (3): 21-21.DOI: 10.1007/s13659-023-00386-z

New halimane and clerodane diterpenoids from Croton cnidophyllus

Xun Wei, Jia-Luo Huang, Hua-Hua Gao, Fang-Yu Yuan, Gui-Hua Tang, Sheng Yin

School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, 510006, People’s Republic of China

收稿日期:2023-05-09 出版日期:2023-06-24 发布日期:2023-07-18
通讯作者: Gui-Hua Tang,E-mail:tanggh5@mail.sysu.edu.cn;Sheng Yin,E-mail:yinsh2@mail.sysu.edu.cn
基金资助:
This work was supported by the National Natural Science Foundation of China (No. 82273804), the Science and Technology Program of Guangzhou, China (No. 202201011613), the Southern Marine Science and Engineering Guangdong Laboratory (Zhuhai) (No. SML2021SP301), the Open Program of Shenzhen Bay Laboratory (No. SZBL2021080601007), the Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program (No. 2017BT01Y093), and the Guangdong Basic and Applied Basic Research Foundation, China (No. 2021B1515140062).

New halimane and clerodane diterpenoids from Croton cnidophyllus

Xun Wei, Jia-Luo Huang, Hua-Hua Gao, Fang-Yu Yuan, Gui-Hua Tang, Sheng Yin

School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, 510006, People’s Republic of China

Received:2023-05-09 Online:2023-06-24 Published:2023-07-18
Contact: Gui-Hua Tang,E-mail:tanggh5@mail.sysu.edu.cn;Sheng Yin,E-mail:yinsh2@mail.sysu.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (No. 82273804), the Science and Technology Program of Guangzhou, China (No. 202201011613), the Southern Marine Science and Engineering Guangdong Laboratory (Zhuhai) (No. SML2021SP301), the Open Program of Shenzhen Bay Laboratory (No. SZBL2021080601007), the Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program (No. 2017BT01Y093), and the Guangdong Basic and Applied Basic Research Foundation, China (No. 2021B1515140062).

摘要/Abstract

摘要： Three new halimane furanoditerpenoids (1-3) and three new clerodane furanoditerpenoids (4-6), along with seven known terpenoids including four pimarane diterpenoids (7-10) and three norisoprenoids (11-13) were isolated from the 95% EtOH extracts of the plants of Croton cnidophyllus. The 2D structures including absolute configuration of new furanoditerpenoids (1-6) were elucidated by analysis of their HRMS and NMR data as well as comparison of experimental and calculated ECD curves. Bioassay revealed that two compounds (8 and9) possessed certain inhibitory effects against NO production stimulated by LPS, with IC₅₀ values of 19.00±1.76 and 21.61±1.11 μM, respectively.

关键词: Euphorbiaceae, Croton cnidophyllus, Furanoditerpenoids, Anti-inflammatory activity

Abstract: Three new halimane furanoditerpenoids (1-3) and three new clerodane furanoditerpenoids (4-6), along with seven known terpenoids including four pimarane diterpenoids (7-10) and three norisoprenoids (11-13) were isolated from the 95% EtOH extracts of the plants of Croton cnidophyllus. The 2D structures including absolute configuration of new furanoditerpenoids (1-6) were elucidated by analysis of their HRMS and NMR data as well as comparison of experimental and calculated ECD curves. Bioassay revealed that two compounds (8 and9) possessed certain inhibitory effects against NO production stimulated by LPS, with IC₅₀ values of 19.00±1.76 and 21.61±1.11 μM, respectively.

Key words: Euphorbiaceae, Croton cnidophyllus, Furanoditerpenoids, Anti-inflammatory activity

Xun Wei, Jia-Luo Huang, Hua-Hua Gao, Fang-Yu Yuan, Gui-Hua Tang, Sheng Yin. New halimane and clerodane diterpenoids from Croton cnidophyllus[J]. 应用天然产物, 2023, 13(3): 21-21.

Xun Wei, Jia-Luo Huang, Hua-Hua Gao, Fang-Yu Yuan, Gui-Hua Tang, Sheng Yin. New halimane and clerodane diterpenoids from Croton cnidophyllus[J]. Natural Products and Bioprospecting, 2023, 13(3): 21-21.

参考文献

1 Wang R, Fan RZ, Ni FQ, Sang J, Xie XL, Luo SY, Tang GH, Yin S. 19-nor-, 20-nor-, and tetranor-halimane-type furanoditerpenoids from Croton crassifolius. J Nat Prod. 2020;83:255-67.
2 Hu R, Huang JL, Yuan FY, Wei X, Zou MF, Tang GH, Li W, Yin S. Crotonianoids A-C, three unusual tigliane diterpenoids from the seeds of Croton tiglium and their anti-prostate cancer activity. J Org Chem. 2022;87:9301-6.
3 Cui JJ, Ji KL, Liu HC, Zhou B, Liu QF, Xu CH, Ding J, Zhao JX, Yue JM. Cytotoxic tigliane diterpenoids from Croton damayeshu. J Nat Prod. 2019;82:1550-7.
4 Krebs HC, Ramiarantsoa H. Clerodane diterpenes of Croton hovarum. Phytochemistry. 1997;45:379-81.
5 Qi JJ, Zhou JS, Zhang Y, Fan YY, Zhou B, Liu HC, Zhao JX, Yue JM. Sublyratins A-O, labdane-type diterpenoids from Croton sublyratus. J Nat Prod. 2021;84:2971-80.
6 Santos HS, Barros FWA, Albuquerque MRJR, Bandeira PN, Pessoa C, Braz-Filho R, Monte FJQ, Leal-Cardoso JH, Lemos TLG. Cytotoxic diterpenoids from Croton argyrophylloides. J Nat Prod. 2009;72:1884-7.
7 Moura VLA, Monte FJO, Filho RB. A new casbane-type diterpenoid from Croton nepetaefolius. J Nat Prod. 1990;53:1566-71.
8 Baccelli C, Navarro I, Block S, Abad A, Morel N, Quetin-Leclercq J. Vasorelaxant activity of diterpenes from Croton zambesicus and synthetic trachylobanes and their structure-activity relationships. J Nat Prod. 2007;70:910-7.
9 Roengsumran S, Achayindee S, Petsom A, Pudhom K, Singtothong P, Surachetapan C, Vilaivan T. Two new cembranoids from Croton oblongifolius. J Nat Prod. 1998;61:652-4.
10 Kitazawa E, Ogiso A, Takahashi S, Aiya S, Kurabayashi M, Kuwano H, Hata T, Tamura C. Plaunol A and B, new anti-ulcer diterpenelactones from Croton sublyratus. Tetrahedron Lett. 1979;20:1117-20.
11 Rakotonandrasana OL, Raharinjato FH, Rajaonarivelo M, Dumontet V, Martin MT, Bignon J, Rasoanaivo P. Cytotoxic 3,4-seco-Atisane diterpenoids from Croton barorum and Croton goudotii. J Nat Prod. 2010;73:1730-3.
12 Wang GC, Li JG, Li GQ, Xu JJ, Wu X, Ye WC, Li YL. Clerodane diterpenoids from Croton crassifolius. J Nat Prod. 2012;75:2188-92.
13 Terefe EM, Okalebo FA, Derese S, Muriuki J, Rotich W, Mas-Claret E, Sadgrove N, Padilla-González GF, Prescott TAK, Siddique H, Langat MK. Constituents of Croton megalocarpus with potential anti-HIV activity. J Nat Prod. 2022;85:1861-6.
14 Adelekan AM, Prozesky EA, Hussein AA, Ureña LD, van Rooyen PH, Liles DC, Meyer JJM, Rodríguez B. Bioactive diterpenes and other constituents of Croton steenkampianus. J Nat Prod. 2008;71:1919-22.
15 Thongtan J, Kittakoop P, Ruangrungsi N, Saenboonrueng J, Thebtaranonth Y. New antimycobacterial and antimalarial 8,9-secokaurane diterpenes from Croton kongensis. J Nat Prod. 2003;66:868-70.
16 Liu CP, Xu JB, Zhao JX, Xu CH, Dong L, Ding J, Yue JM. Diterpenoids from Croton laui and their cytotoxic and antimicrobial activities. J Nat Prod. 2014;77:1013-20.
17 Jiang ZY, Liu CJ, Niu Q, Yan XY, Xiao D, Zhang HL, Huang CQ, Shi SL, Zuo AX, He HP. In vitro hypoglycemic diterpenoids from the roots of Croton yunnanensis. J Nat Prod. 2023;86:199-208.
18 Li B, Hans-Joachim E. Croton. Flora China. 2008;11:258-64.
19 Yuan FY, Tang ZY, Huang D, Li W, Wu SQ, Huang JL, Yan XL, Fan RZ, Tang GH, Yin S. Tigliane and rhamnofolane glycosides from Euphorbia wallichii prevent oxidative stress-induced neuronal death in PC-12 cells. Bioorg Chem. 2022;128: 106103.
20 Wu SQ, Fan RZ, Yuan FY, Li W, Huang D, Li S, Tang GH, Huang ZS, Yin S. Euphylonoids A and B, two highly modified jatrophane diterpenoids with potent lipid-lowering activity from Euphorbia hylonoma. Org Lett. 2022;24:8854-8.
21 Zou MF, Pan YH, Hu R, Yuan FY, Huang D, Tang GH, Li W, Yin S. Highly modified nor-clerodane diterpenoids from Croton yanhuii. Fitoterapia. 2021;153: 104979.
22 Krebs HC, Ramiarantsoa H. Clerodane diterpenes and other constituents of Croton hovarum. Phytochemistry. 1996;41:561-3.
23 Maslovskaya LA, Savchenko AI, Gordon VA, Reddell PW, Pierce CJ, Parsons PG, Williams CM. EBC-316, 325-327, and 345: New pimarane diterpenes from Croton insularis found in the Australian rainforest. Aust J Chem. 2015;68:652-9.
24 Itokawa H, Ichihara Y, Takeya K, Morita H, Motidome M. Diterpenes from Croton Salutaris. Phytochemistry. 1991;30(12):4071-3.
25 Ravindranath N, Ravinder Reddy M, Ramesh C, Ramu R, Prabhakar A, Jagadeesh B, Das B. New lathyrane and podocarpane diterpenoids from Jatropha curcas. Chem Pharm Bull. 2004;52:608-11.
26 Chao CH, Cheng JC, Shen DY, Wu TS. Anti-hepatitis C virus dinorditerpenes from the roots of Flueggea virosa. J Nat Prod. 2014;77:22-8.
27 Kim KH, Lee KH, Choi SU, Kim YH, Lee KR. Terpene and phenolic constituents of Lactuca indica L. Arch Pharm Res. 2008;31:983-8.
28 Kisiel W, Michalska K, Szneler E. Norisoprenoids from aerial parts of Cichorium pumilum. Biochem Syst Ecol. 2004;32:343-6.

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New halimane and clerodane diterpenoids from Croton cnidophyllus

New halimane and clerodane diterpenoids from Croton cnidophyllus

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