Citation: Zhou Shuai-Zhen, Tang Chun-Ping, Ke Chang-Qiang, Yao Sheng, Lin Ge, Ye Yang. Three new dimeric diterpenes from Rhododendron molle[J]. Chinese Chemical Letters, ;2017, 28(6): 1205-1209. doi: 10.1016/j.cclet.2017.02.020 shu

Three new dimeric diterpenes from Rhododendron molle

Zhou Shuai-Zhen ^a,b ,
Tang Chun-Ping ^a,b ,
Ke Chang-Qiang ^a,b ,
Yao Sheng ^a,b ,
Lin Ge ^b,c ,
Ye Yang ^a,b,d,,

a.
State Key Laboratory of Drug Research, and Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
b.
SIMM-CUHK Joint Research Laboratory for Promoting Globalization of Traditional Chinese Medicines between Shanghai Institute of Materia Medica, Chinese Academy of Sciences and The Chinese University of Hong Kong, China
c.
School of Biomedical Sciences, The Chinese University of Hong Kong, Hong Kong, China
d.
School of Life Science and Technology, ShanghaiTech University, Shanghai 201203, China

Corresponding author: Ye Yang, yye@mail.shcnc.ac.cn
Received Date: 22 November 2016
Revised Date: 5 January 2017
Accepted Date: 28 February 2017
Available Online: 4 June 2017

Figures(3)

Birhodomolleins A-C (1-3), three novel diterpenoids dimerized from two grayanane diterpenes through an oxygen bridge, were isolated from the flowers of Rhododendron molle. Their structures were elucidated by interpretation of their 1D and 2D NMR and other spectroscopic data. Birhodomollein A (1) contains a rare chloro-substitution on one of the grayanane moieties. These are the first examples of dimeric diterpenes from the Ericaceae family.
- Rhododendron molle,
- Ericaceae,
- Dimeric diterpene,
- Grayanane,
- Birhodomolleins A-C
1. [1]
  Editorial Committee of Flora of China, Flora of China 14, Science Press or Missouri Botanical Garden Press, Beijing or St. Louis, 2005, pp. 242-517.
2. [2]
  Li Y., Liu Y.B., Zhang J.J.. Antinociceptive grayanoids from the roots of Rhododendron molle[J]. J. Nat. Prod., 2015,78:2887-2895. doi: 10.1021/acs.jnatprod.5b00456
3. [3]
  Zhang H.P., Wang L.Q., Qin G.W.. Grayanane diterpenoids from the leaves of Craiobiodendron yunnanense[J]. Bioorg. Med. Chem., 2005,13:5289-5298. doi: 10.1016/j.bmc.2005.06.006
4. [4]
  Editorial Committee of Flora of China, Flora of China (Zhongguo zhiwuzhi), vol. 57, Science Press, Beijng, 1994, pp. 367-369(in Chinese).
5. [5]
  Li C.J., Wang L.Q., Chen S.N., Qin G.W.. Diterpenoids from the fruits of Rhododendron molle[J]. J. Nat. Prod., 2000,63:1214-1217. doi: 10.1021/np000009e
6. [6]
  Chen S.N., Zhang H.P., Wang L.Q., Bao G.H., Qin G.W.. Diterpenoids from the flowers of Rhododendron molle[J]. J. Nat. Prod., 2004,67:1903-1906. doi: 10.1021/np040012o
7. [7]
  Bao G.H., Wang L.Q., Cheng K.F., Qin G.W.. One new diterpene glucoside from the roots of Rhododendron molle[J]. Chin. Chem. Lett., 2002,13:955-956.
8. [8]
  Bao G.H., Wang L.Q., Cheng K.F.. Diterpenoid and phenolic glycosides from the roots of Rhododendron molle[J]. Planta Med., 2003,69:434-439. doi: 10.1055/s-2003-39716
9. [9]
  Zhong G.H., Hu M.Y., Wei X.Y.. Grayanane diterpenoids from the flowers of Rhododendron molle with cytotoxic activity against a Spodoptera frugiperda cell line[J]. J. Nat. Prod., 2005,68:924-926. doi: 10.1021/np049645t
10. [10]
  Wang S.J., Lin S., Zhu C.G.. Highly acylated diterpenoids with a new 3, 4-secograyanane skeleton from the flower buds of Rhododendron molle[J]. Org. Lett., 2010,12:1560-1563. doi: 10.1021/ol1002797
11. [11]
  Li Y., Liu Y.B., Zhang J.J.. Mollolide A a diterpenoid with a new 1, 10:2, 3-disecograyanane skeleton from the roots of Rhododendron molle[J]. Org. Lett., 2013,15:3074-3077. doi: 10.1021/ol401254e
12. [12]
  Zhou S.Z., Yao S., Tang C.P.. Diterpenoids from the flowers of Rhododendron molle[J]. J. Nat. Prod., 2014,77:1185-1192. doi: 10.1021/np500074q
13. [13]
  Li Y., Liu Y.B., Liu Y.L.. Mollanol A, a diterpenoid with a new C-nor-Dhomograyanane skeleton from the fruits of Rhododendron molle[J]. Org. Lett., 2014,16:4320-4323. doi: 10.1021/ol5020653
14. [14]
  Zhang M., Liu J.M., Zhao J.L.. Two new diterpenoids from the endophytic fungus Trichoderma sp.Xy24 isolated from mangrove plant Xylocarpus granatum[J]. Chin. Chem. Lett., 2016,27:957-960. doi: 10.1016/j.cclet.2016.02.008
15. [15]
  Wu Z.Y., Li H.Z., Wang W.G.. Lyonin A a new 9, 10-Secograyanotoxin from Lyonia ovalifolia[J]. Chem. Biodivers., 2011,8:1182-1187. doi: 10.1002/cbdv.v8.6
16. [16]
  Li T., Wang B., de Voogd N.J.. Two new diterpene alkaloids from the South China Sea Sponge Agelas aff. Nemoechinata[J]. Chin. Chem. Lett., 2016,27:1048-1051. doi: 10.1016/j.cclet.2016.05.017
17. [17]
  Ohta T., Hikino H.. Carbon-13 NMR spectra of ericaceous toxins[J]. Org. Mag. Res., 1979,12:445-449. doi: 10.1002/(ISSN)1097-458X
1. [1]
  Ling-Hao Zhao , Hai-Wei Yan , Jian-Shuang Jiang , Xu Zhang , Xiang Yuan , Ya-Nan Yang , Pei-Cheng Zhang . Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy. Chinese Chemical Letters, 2024, 35(5): 108863-. doi: 10.1016/j.cclet.2023.108863
2. [2]
  Deli Chen , Jiawen Li , Xudong Xu , Zhaocui Sun , Yun Yang , Minghui Xu , Hanqiao Liang , Junshan Yang , Hui Meng , Guoxu Ma , Jianhe Wei . Plant-microbial interactions inspired the discovery of novel sesquiterpenoid dimeric skeletons of hidden natural products from Hibiscus tiliaceus. Chinese Chemical Letters, 2024, 35(10): 109451-. doi: 10.1016/j.cclet.2023.109451
3. [3]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
4. [4]
  Jiao Li , Chenyang Zhang , Chuhan Wu , Yan Liu , Xuejian Zhang , Xiao Li , Yongtao Li , Jing Sun , Zhongmin Su . Defined organic-octamolybdate crystalline superstructures derived Mo₂C@C as efficient hydrogen evolution electrocatalysts. Chinese Chemical Letters, 2024, 35(6): 108782-. doi: 10.1016/j.cclet.2023.108782
5. [5]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
6. [6]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
7. [7]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
8. [8]
  Chen Li , Ziyuan Zhao , Shouyun Yu . Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides. Chinese Chemical Letters, 2024, 35(6): 109128-. doi: 10.1016/j.cclet.2023.109128
9. [9]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
10. [10]
  Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C₆₀-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
11. [11]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
12. [12]
  Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO₂ via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
13. [13]
  Jiajun Wang , Guolin Yi , Shengling Guo , Jianing Wang , Shujuan Li , Ke Xu , Weiyi Wang , Shulai Lei . Computational design of bimetallic TM₂@g-C₉N₄ electrocatalysts for enhanced CO reduction toward C₂ products. Chinese Chemical Letters, 2024, 35(7): 109050-. doi: 10.1016/j.cclet.2023.109050
14. [14]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775
15. [15]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
16. [16]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
17. [17]
  Kaihui Huang , Boning Feng , Xinghua Wen , Lei Hao , Difa Xu , Guijie Liang , Rongchen Shen , Xin Li . Effective photocatalytic hydrogen evolution by Ti3C2-modified CdS synergized with N-doped C-coated Cu2O in S-scheme heterojunctions. Chinese Journal of Structural Chemistry, 2023, 42(12): 100204-100204. doi: 10.1016/j.cjsc.2023.100204
18. [18]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
19. [19]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
20. [20]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(844)
HTML views(25)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142