Clerodane Diterpenoids from Callicarpa hypoleucophylla and Their Anti-Inflammatory Activity

被引:16
作者
Lin, Yu-Chi [1 ]
Lin, Jue-Jun [1 ]
Chen, Shu-Rong [1 ]
Hwang, Tsong-Long [2 ,3 ,4 ,5 ]
Fang, Shu-Yen [2 ]
Korinek, Michal [2 ,3 ,4 ]
Chen, Ching-Yeu [6 ]
Lin, Yun-Sheng [7 ]
Wu, Tung-Ying [7 ,8 ]
Yen, Ming-Hong [9 ]
Wang, Chih-Hsin [10 ]
Cheng, Yuan-Bin [1 ,11 ,12 ]
机构
[1] Kaohsiung Med Univ, Coll Pharm, Ctr Nat Prod Res & Dev, Grad Inst Nat Prod, Kaohsiung 80708, Taiwan
[2] Chang Gung Univ, Grad Inst Nat Prod, Grad Inst Biomed Sci, Coll Med, Taoyuan 33302, Taiwan
[3] Chang Gung Univ Sci & Technol, Res Ctr Ind Human Ecol, Res Ctr Chinese Herbal Med, Coll Human Ecol, Taoyuan 33302, Taiwan
[4] Chang Gung Univ Sci & Technol, Grad Inst Hlth Ind Technol, Coll Human Ecol, Taoyuan 33302, Taiwan
[5] Chang Gung Mem Hosp, Dept Anesthesiol, Taoyuan 33302, Taiwan
[6] Tzu Hui Inst Technol, Dept Phys Therapy, Pingtung 92641, Taiwan
[7] Meiho Univ, Dept Biol Sci & Technol, Pingtung 912009, Taiwan
[8] Meiho Univ, Dept Food Sci & Nutr, Pingtung 912009, Taiwan
[9] Kaohsiung Med Univ, Sch Pharm, Coll Pharm, Kaohsiung 80708, Taiwan
[10] Kaohsiung Armed Forces Gen Hosp, Div Pharm, Zuoying Branch, Kaohsiung 81342, Taiwan
[11] Natl Sun Yat Sen Univ, Dept Marine Biotechnol & Resources, Kaohsiung 80424, Taiwan
[12] Kaohsiung Med Univ Hosp, Dept Med Res, Kaohsiung 80708, Taiwan
来源
MOLECULES | 2020年 / 25卷 / 10期
关键词
Callicarpa hypoleucophylla; clerodane diterpenoid; anti-inflammatory activity; CHEMICAL-CONSTITUENTS; CYTOTOXIC DITERPENES; HUMAN NEUTROPHILS; ELASTASE RELEASE; LEAVES; NUDIFLORA; AMERICANA; ACID;
D O I
10.3390/molecules25102288
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Plants of the genus Callicarpa are known to possess several medicinal effects. The constituents of the Taiwan endemic plant Callicarpa hypoleucophylla have never been studied. Therefore, C. hypoleucophylla was selected for our phytochemical investigation. Two new clerodane-type diterpenoids, named callihypolins A (1) and B (2), along with seven known compounds were isolated from the leaves and twigs of the Lamiaceae plant C. hypoleucophylla and then characterized. The structures of compounds 1 and 2 were elucidated by spectroscopic data analysis, specifically, two-dimension nuclear magnetic resonance (NMR). The anti-inflammatory activity of compounds 1-9 based on the suppression of superoxide anion generation and elastase release was evaluated. Among the isolates, compounds 2-4 showed anti-inflammatory activity (9.52-32.48% inhibition at the concentration 10 mu m) by suppressing superoxide anion generation and elastase release. Our findings not only expand the description of the structural diversity of the compounds present in plants of the genus Callicarpa but also highlight the possibility of developing anti-inflammatory agents from Callicarpa endemic species.
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页数:10
相关论文
共 40 条
[1]   Three new cholinesterase-inhibiting cis-clerodane diterpenoids from Otostegia limbata [J].
Ahmad, VU ;
Khan, A ;
Farooq, U ;
Kousar, F ;
Khan, SS ;
Nawaz, SA ;
Abbasi, MA ;
Choudhary, MI .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (04) :378-381
[2]   Four new diterpenoids from Ballota limbata [J].
Ahmad, VU ;
Farooq, U ;
Abbaskhan, A ;
Hussain, J ;
Abbasi, MA ;
Nawaz, SA ;
Choudhary, ML .
HELVETICA CHIMICA ACTA, 2004, 87 (03) :682-689
[3]   Isolation, Identification and Activities of Natural Antioxidants from Callicarpa kwangtungensis Chun [J].
Cai, Hao ;
Xie, Zhiyong ;
Liu, Guanghui ;
Sun, Xiuman ;
Peng, Guangtian ;
Lin, Baoqin ;
Liao, Qiongfeng .
PLOS ONE, 2014, 9 (03)
[4]   Cytotoxic Clerodane Diterpenes from Zuelania guidonia [J].
Calderon, Carlos ;
De Ford, Christian ;
Castro, Victor ;
Merfort, Irmgard ;
Murillo, Renato .
JOURNAL OF NATURAL PRODUCTS, 2014, 77 (03) :455-463
[5]   Isolation and identification of mosquito bite deterrent terpenoids from leaves of American (Callicarpa americana) and Japanese (Callicarpa japonica) beautyberry [J].
Cantrell, CL ;
Klun, JA ;
Bryson, CT ;
Kobaisy, M ;
Duke, SO .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (15) :5948-5953
[6]   Anti-inflammatory and cytotoxic diterpenes from formosan Polyalthia longifolia var. pendula [J].
Chang, Fang-Rong ;
Hwang, Tsong-Long ;
Yang, Yu-Liang ;
Li, Chia-En ;
Wu, Chin-Chung ;
Issa, Hamad H. ;
Hsieh, Wen-Bin ;
Wu, Yang-Chang .
PLANTA MEDICA, 2006, 72 (14) :1344-1347
[7]   Diterpenes from Grangea maderaspatana [J].
Chang, Fang-Rong ;
Huang, Shih-Ting ;
Liaw, Chih-Chuang ;
Yen, Ming-Hong ;
Hwang, Tsong-Long ;
Chen, Ching-Yeu ;
Hou, Ming-Feng ;
Yuan, Shyng-Shiou ;
Cheng, Yuan-Bin ;
Wu, Yang-Chang .
PHYTOCHEMISTRY, 2016, 131 :124-129
[8]   Inhibitory effects of 16-hydroxycleroda-3,13(14)E-dien-15-oic acid on superoxide anion and elastase release in human neutrophils through multiple mechanisms [J].
Chang, Han-Lin ;
Chang, Fang-Rong ;
Chen, Jin-Shan ;
Wang, Hui-Po ;
Wu, Yi-Hsiu ;
Wang, Chien-Chiao ;
Wu, Yang-Chang ;
Hwang, Tsong-Long .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2008, 586 (1-3) :332-339
[9]   seco-Abietane Diterpenoids, a Phenylethanoid Derivative, and Antitubercular Constituents from Callicarpa pilosissima [J].
Chen, Jih-Jung ;
Wu, Hung-Ming ;
Peng, Chien-Fang ;
Chen, Ih-Sheng ;
Chu, Shih-Der .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (02) :223-228
[10]   Randainins A-D, Based on Unique Diterpenoid Architectures, from Callicarpa randaiensis [J].
Cheng, Ho-Hsi ;
Cheng, Yuan-Bin ;
Hwang, Tsong-Long ;
Kuo, Yao-Haur ;
Chen, Chung-Hsiung ;
Shen, Ya-Ching .
JOURNAL OF NATURAL PRODUCTS, 2015, 78 (08) :1823-1828