Two New Labdane Diterpenoids from the Leaves of Callicarpa nudiflora

doi:10.6023/cjoc202212020

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (7): 2567-2571.DOI: 10.6023/cjoc202212020 Previous Articles Next Articles

NOTES

裸花紫珠叶中两个新的半日花烷型二萜

余章昕^a, 蒙玉琴^a, 薛萌琳^a, 李小宝^a, 陈光英^a^,^*(), 韩长日^b^,^*()

^a海南师范大学化学与化工学院热带药用资源化学教育部重点实验室热带药用植物化学海南省重点实验室海口 571158
^b海南科技职业大学药食同源植物资源海南省重点实验室海口 571126

收稿日期:2020-12-15 修回日期:2023-01-29 发布日期:2023-03-07
通讯作者: 陈光英, 韩长日
基金资助:
海南省重点研发项目(ZDYF2022SHFZ286); 海南省重点研发项目(ZDYF2021SHFZ072); 海南省自然科学基金(221MS034); 海南省教育厅项目(Hnky2021-30); 国家自然科学基金(21662012); 海南省院士创新平台(YSPTZX202030); 及中央引导地方科技发展资金(ZY2022HN08)

Two New Labdane Diterpenoids from the Leaves of Callicarpa nudiflora

Zhangxin Yu^a, Yuqin Meng^a, Menglin Xue^a, Xiaobao Li^a, Guangying Chen^a(), Changri Han^b()

^aKey Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158
^bKey Laboratory of Medicinal and Edible Plants Resources of Hainan Province, Hainan Vocational University of Science and Technology, Haikou 571126

Received:2020-12-15 Revised:2023-01-29 Published:2023-03-07
Contact: Guangying Chen, Changri Han
Supported by:
Key R&D Projects in Hainan Province-Social Development(ZDYF2022SHFZ286); Key R&D Projects in Hainan Province-Social Development(ZDYF2021SHFZ072); Hainan Provincial Natural Science Foundation(221MS034); Education Department of Hainan Province(Hnky2021-30); National Natural Science Foundation of China(21662012); Innovation Platform for Academicians of Hainan Province(YSPTZX202030); Central Government Guides Local Science and Technology Development(ZY2022HN08)

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Abstract

Two new labdane diterpenoids 3-oxo-7-hydroxy-8(17),13E-labdadien-15-oic acid (1), 3-oxo-8-hydroxy-13E-lab- den-15-oic acid (2), and five known terpenoids were obtained from the leaves of Callicarpa nudiflora during a systematic phytochemical investigation. The structures were elucidated using comprehensive spectroscopic methods [nuclear magnetic resonance spectroscopy (NMR) and high resolution electrospray ionization mass spectroscopy (HR-ESI-MS)], and the absolute configuration of 1 was established based on single-crystal X-ray diffraction. The inhibitory activity of all the compounds on NO production in lipopolysaccharide-induced (LPS) mouse leukemia cells of monocyte macrophage (RAW 264.7) cells was evaluated. Compounds 1 and 2 showed potential anti-inflammatory activity with IC₅₀values of (10.3±0.3) and (12.7±0.4) μmol/L, respectively.

Key words: C. nudiflora, labdane diterpenes, sesquiterpenes

Cite this article

Zhangxin Yu, Yuqin Meng, Menglin Xue, Xiaobao Li, Guangying Chen, Changri Han. Two New Labdane Diterpenoids from the Leaves of Callicarpa nudiflora[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2567-2571.

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Fig. & Tab. 5

Figure 1. Chemical structures of compounds 1~7

Compd.	IC₅₀/(μmol•L^－1)
1	10.3±0.3
2	12.7±0.4
3	17.2±0.6
4	21.3±0.5
5	13.7±0.4
6	22.2±0.2
7	29.1±0.3
Indomethacin	19.2±0.4

Table 2. Inhibitory activity of compounds 1~7 on NO production in RAW264.7 cells induced by LPS (?x±s, n=3)

Figure 2. Key HMBC and 1H-1H COSY correlations of compounds 1 and 2

Figure 3. NOSEY correlations of compounds 1 and 2

Figure 4. Single-crystal X-ray ORTEP (Oak Ridge thermal ellipsoid plot) drawing of 1

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裸花紫珠叶中两个新的半日花烷型二萜

Two New Labdane Diterpenoids from the Leaves of Callicarpa nudiflora

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[2]	Lu Yongping, Qi Weipeng, Weng Guodong, Zhang Xingxian. Progresses in Total Synthesis of Guaiane Sesquiterpenes and Their Analogues [J]. Chin. J. Org. Chem., 2015, 35(7): 1407-1413.
[3]	SUN, Zhi-Hua, ZHANG, Su, SHI, Jiao, HU, Chang-Qi. Sesquiterpenes from Caragana Intermedia [J]. Chinese Journal of Organic Chemistry, 2004, 24(7): 806-810.