A New Fatty Acid Glycoside Compound in Munronia Pinnata

doi:10.6023/cjoc202310019

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1348-1356.DOI: 10.6023/cjoc202310019 Previous Articles Next Articles

矮陀陀中一个新的脂肪酸苷类化合物

刘培源^a^,^b, 韦玉璐^b, 宋静茹^b, 颜小捷^b, 卢凤来^b, 陈月圆^b, 羊学荣^b^,^*(), 李典鹏^b^,^c^,^*()

a 桂林医学院药学院广西桂林 541004
b 广西壮族自治区中国科学院广西植物研究所广西植物功能物质与资源持续利用重点实验室广西桂林 541006
c 广西中医药大学中药壮瑶药创新药物教育部工程研究中心广西南宁 530200

收稿日期:2023-10-22 修回日期:2023-11-28 发布日期:2023-12-15
基金资助:
广西自然科学基金(2020GXNSFBA297055); 广西科技基础条件与人才计划(桂科AA21196009); 国家重点研发项目(2022YFD1600302); 国家自然科学基金(U20A2004); 广西科学院基础研究基金(CQZ-C-1901); 桂林创新平台与人才计划(20210102-3); 广东省重点领域研究发展计划(2020B1111110003)

A New Fatty Acid Glycoside Compound in Munronia Pinnata

Peiyuan Liu^a^,^b, Yulu Wei^b, Jingru Song^b, Xiaojie Yan^b, Fenglai Lu^b, Yueyuan Cheng^b, Xuerong Yang^b(), Dianpeng Li^b^,^c()

a School of Pharmacy, Guilin Medical University, Guilin, Guangxi 541004
b Guangxi Key Laboratory of Plant Functional Phytochemicals and Sustainable Utilization, Guangxi Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy Sciences, Guilin, Guangxi 541006
c Engineering Research Center of Innovative Traditional Chinese, Zhuang and Yao Materia Medica, Ministry of Education, Guangxi University of Chinese Medicine, Nanning, Guangxi 530200

Received:2023-10-22 Revised:2023-11-28 Published:2023-12-15
Contact: * E-mail: yxrxl@sina.cn; ldp@gxib.cn
Supported by:
Natural Science Foundation of Guangxi(2020GXNSFBA297055); Guangxi Science and Technology Base and Talent Project (Guike AA21196009); National Key Research and Development Program(2022YFD1600302); National Natural Science Foundation of China(U20A2004); Basic Research Fund of Guangxi Academy of Sciences(CQZ-C-1901); Guilin Innovation Platform and Talent Plan(20210102-3); Key Area Research and Development Program of Guangdong Province(2020B1111110003)

1. .pdf(4098KB)

Abstract

The chemical constituents of the aerial parts of Munronia pinnata W. Theobald were investigated by using chro- matographic techniques. Ten compounds were isolated from the 95% ethanol extract of Munronia pinnata. Their structures were identified as munrofatty A (1), 2-[[6-O-((2E)-6R-hydroxy-2,6-dimethyl-2,7-octadienoyl)-β-D-glucopyranosyl]oxy]-2- methylpropanoic acid (2), kaempferol-3-O-(6-O-trans-p-coumaroyl)-β-D-glucopyranoside (3), castanoside A (4), kaempferol- 3-O-(6''-O-cis-pcoumaroyl)-β-D-glucopyranoside (5), aurantiamide acetate (6), blumenol A (7), grasshopper ketone (8), curcusinol (9) and loliolide (10) through detailed analyses of various technical means, including MS, IR, 1D- and 2D-NMR spectroscopic methods, quantum calculation methods and other technical means. Compound 1 is a new compound, while NMR data of compound 2 are presented for the first time. Compound 1 was evaluated for cytotoxicity against HCT116, A549, HepG2, MCF7 and MDAMB cells, and was non-toxic to the tested cells at a concentration of 160 μmol/L.

Key words: meliaceae, Munronia pinnata, munrofatty A, structural identification

Cite this article

Peiyuan Liu, Yulu Wei, Jingru Song, Xiaojie Yan, Fenglai Lu, Yueyuan Cheng, Xuerong Yang, Dianpeng Li. A New Fatty Acid Glycoside Compound in Munronia Pinnata[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1348-1356.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 29

[1]	Editorial Board of Flora Reipublicae Popularis Sinicae Flora Reipublicae Popularis Sinicae, Vol. 43(3), Science Press, Beijing, 1997, p. 57. (in Chinese)
	(中国科学院中国植物志编辑委员会, 中国植物志, 43卷第三册, 科学出版社, 北京, 1997, p. 57.)
[2]	Qi S. H. Ph.D. Dissertation, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 2003. (in Chinese)
	(漆淑华, 博士论文, 中国科学院昆明植物研究所, 昆明, 2003.)
[3]	Su L.; Huang L. Z.; Cai Y. J. Youjiang Med. Univ. Natl. 2021, 43, 741. (in Chinese)
	(苏玲, 黄丽贞, 蔡毅, 右江民族医学院学报, 2021, 43, 741.)
[4]	Qi S. H.; Wu D. G.; Chen L.; Ma Y. B.; Luo X. D. J. Agric. Food Chem. 2003, 51, 6949. doi: 10.1021/jf030292y
[5]	Yan Y.; Zhang J. X.; Huang T.; Mao X. Y.; Gu W.; He H. P.; Di Y. T.; Li S. L.; Chen D. Z.; Zhang Y.; Hao X. J. J. Nat. Prod. 2015, 78, 811. doi: 10.1021/np501057f
[6]	Wei D. W.; Li L. F.; Zeng X. R.; Yu Y. H.; Wang Z. Y.; Cheng H. S. Southwest China J. Agric. Sci. 2012, 25, 153. (in Chinese)
	(韦德卫, 黎柳锋, 曾宪儒, 于永浩, 曾涛, 王助引, 陈海珊, 西南农业学报, 2012, 25, 153.)
[7]	Ge Y. H.; Zhang J. X.; Mu S. Z.; Chen Y.; Yang F. M.; Lu Y.; Hao X. J. Tetrahedron 2012, 68, 566. doi: 10.1016/j.tet.2011.11.003
[8]	Qi S. H.; Chen L.; Wu D. G.; Ma Y. B.; Luo X. D. Tetrahedron 2003, 59, 4193. doi: 10.1016/S0040-4020(03)00573-8
[9]	Cai X. H.; Luo X. D.; Zhou J.; Hao X. J. J. Integr. Plant Biol. 2006, 48, 1126. doi: 10.1111/jipb.2006.48.issue-9
[10]	Li X. L.; He Q. X.; Zhang F. L.; Zhao Y. L.; Liu K. C.; Jing S. P. Nat. Prod. Bioprospect. 2012, 2, 76. doi: 10.1007/s13659-012-0001-8
[11]	Yang X. R.; Tanaka N.; Tsuji D.; Lu F. L.; Yan X. J.; Itoh K.; Li D. P.; Kashiwada Y. Tetrahedron 2019, 75, 130779. doi: 10.1016/j.tet.2019.130779
[12]	Yang X. R.; Liu P. Y.; Wei Y. L.; Song J. R.; Yan X. J.; Jiang X. H.; Li J. X.; Li X. Q.; Li D. P.; Lu F. L. Molecules 2023, 28, 6839. doi: 10.3390/molecules28196839
[13]	Huang Y. L.; Tanaka T.; Matsuo Y.; Kouno I.; Li D. P.; Nonaka G. Heterocycles 2011, 83, 2327.
[14]	Fiorentino A.; D'Abrosca B.; Pacifico S.; Mastellone C.; Piscopo V.; Monaco P. J. Agric. Food Chem. 2006, 54, 9593.
[15]	Rodriguez A. D. Magn. Reson. Chem. 1992, 30, 980.
[16]	Kurz M.; Schmieder P.; Kessler H. Angew. Chem., nt. Ed. Engl. 1991, 30, 1331.
[17]	Zhu G.; Live D.; Bax A. J. Am. Chem. Soc. 1993, 104, 355. doi: 10.1021/ja00365a093
[18]	Ning D. S.; Fu Y. X.; Li L. C.; Zou Z. Q.; Pan Z. H. Chin. J. Org. Chem. 2023, 43, 1594. (in Chinese)
	(宁德生, 符毓夏, 李连春, 邹芷琪, 潘争红, 有机化学, 2023, 43, 1594.)
[19]	Iwai T.; Kubota T.; Kobayashi J. J. Nat. Prod. 2014, 77, 1544.
[20]	He W.; Jiang Y.; Zhao M. B.; Zeng K. W.; Tu P. F. J. Asian Nat. Prod. Res. 2017, 19, 660.
[21]	Takido M.; Fukuhara K.; Yamanouchi S.; Takahashi S. Phytochemistry 1983, 22, 224.
[22]	Han Y.; Zhang A. H.; Sun H.; Zhang Y. Z.; Meng X. C.; Yan G. L.; Liu L.; Wang X. J. J. Sep. Sci. 2017, 40. 2182.
[23]	Li G.; Pan Z. H.; Li H. Y.; Fu Y. X.; Li L. C.; Yu L. L.; Ning D. S. Guangxi Plant 2021, 41, 1080. (in Chinese)
	(李根, 潘争红, 李海云, 符毓夏, 李连春, 于玲玲, 宁德生, 广西植物, 2021, 41, 1080.)
[24]	Xu J. Z.; Zeng S. S.; Qu H. Chin. Tradit. Herb. Drugs 2010, 41, 1424. (in Chinese)
	(徐金钟, 曾珊珊, 瞿海, 中草药, 2010, 41, 1424.)
[25]	Wu C. H.; Chen Y.; Li X. X.; Liu L. L.; Wang T.; Zhang Y. Chin. J. Med. Chem. 2014, 24, 211. (in Chinese)
	(吴春华, 陈玥, 李晓霞, 刘丽丽, 王涛, 张祎, 中国药物化学杂志, 2014, 24, 211.)
[26]	Xiao H.; Guo Y. P.; Li Z. Z.; Sun S. W.; Wang H.; Lv C. Y.; Zhang Y. H.; Wang W. Chin. Tradit. Herb. Drugs 2002, 53, 4937. (in Chinese)
	(肖寒, 郭友朋, 李治周, 孙世伟, 王惠, 吕超艺, 张英华, 王威, 中草药, 2002, 53, 4937.)
[27]	Wang T. M.; Wang K. J.; Tang J.; Li N. J. Chin. Chem. Soc. 2009, 56, 882.
[28]	Kimura J.; Maki N. J. Nat. Prod. 2002, 65, 58.
[29]	Yang X. R.; Tanaka N.; Song J. R.; Lu F. L.; Yan X. J.; Li J. X.; Zhao X. Y.; Kashiwada Y.; Li D. P. J. Asian Nat. Prod. Res. 2022, 24, 1027.

No.	1			2
No.	δ_C (type)	δ_H (J in Hz)		δ_C (type)	δ_H (J in Hz)
1 2 3 4 5 6 7 8 9 10 11 12 1' 2' 3' 4' 5' 6' 1'' 2'' 3'' 4''	169.9 (C) 125.9 (C) 140.5 (CH) 143.3 (CH) 128.6 (CH) 38.1 (CH₂) 40.1 (CH) 71.9 (CH) 40.6 (CH₂) 175.2 (CH) 12.6 (CH₃) 14.1 (CH₃) 99.9 (CH) 71.8 (CH) 78.3 (CH) 75.3 (CH) 75.5 (CH) 65.2 (CH₂) 179.0 (C) 80.4 (C) 24.6 (CH₃) 26.9 (CH₃)	— — 7.22 (d, J=11.3 Hz) 6.13 (dd, J=14.9, 11.3 Hz) 6.42~6.52 (m) 2.05~2.14 (m) 2.37~2.43 (m) 1.66~1.74 (m) 3.99 (dt, J=4.4, 4.1 Hz) 2.43~2.49 (m) — 1.92 (s) 0.93 (s) 4.55 (d, J=7.8 Hz) 3.28~3.30 (m) 3.41 (dd, J=9.0, 9.0 Hz) 3.25~3.28 (m) 3.52 (ddd, J=9.6, 7.3, 2.1 Hz) 4.18 (dd, J=11.8, 7.3 Hz) 4.48 (dd, J=11.8, 2.1 Hz) — — 1.51 (s) 1.46 (s)		169.5 (C) 128.4 (C) 144.4 (CH) 24.5 (CH₂) 41.8 (CH₂) 73.6 (C) 146.0 (CH) 112.4 (CH₂) 12.4 (CH₃) 27.8 (CH₃) — — 99.9 (CH) 71.8 (CH) 78.3 (CH) 75.3 (CH) 75.5 (CH) 65.2 (CH₂) 179.5 (C) 80.2 (C) 27.0 (CH₃) 24.6 (CH₃)	— — 6.81 (tq, J=7.7, 1.4 Hz) 2.16~2.32 (m) 1.57~1.63 (m) — 5.92 (dd, J=17.3, 10.8 Hz) 5.06 (dd, J=10.8, 1.5 Hz) 5.23 (dd, J=17.3, 1.5 Hz) 1.82 (s) 1.28 (s) — — 4.54 (d, J=7.8 Hz) 3.24~3.30 (m) 3.37~3.43 (m) 3.24~3.30 (m) 3.51 (ddd, J=9.5, 7.2, 2.1 Hz) 4.16 (dd, J=11.8, 7.3 Hz) 4.45 (dd, J=11.8, 2.1 Hz) — — 1.50 (s) 1.46 (s)

No.	1			2
No.	δ_C (type)	δ_H (J in Hz)		δ_C (type)	δ_H (J in Hz)
1 2 3 4 5 6 7 8 9 10 11 12 1' 2' 3' 4' 5' 6' 1'' 2'' 3'' 4''	169.9 (C) 125.9 (C) 140.5 (CH) 143.3 (CH) 128.6 (CH) 38.1 (CH₂) 40.1 (CH) 71.9 (CH) 40.6 (CH₂) 175.2 (CH) 12.6 (CH₃) 14.1 (CH₃) 99.9 (CH) 71.8 (CH) 78.3 (CH) 75.3 (CH) 75.5 (CH) 65.2 (CH₂) 179.0 (C) 80.4 (C) 24.6 (CH₃) 26.9 (CH₃)	— — 7.22 (d, J=11.3 Hz) 6.13 (dd, J=14.9, 11.3 Hz) 6.42~6.52 (m) 2.05~2.14 (m) 2.37~2.43 (m) 1.66~1.74 (m) 3.99 (dt, J=4.4, 4.1 Hz) 2.43~2.49 (m) — 1.92 (s) 0.93 (s) 4.55 (d, J=7.8 Hz) 3.28~3.30 (m) 3.41 (dd, J=9.0, 9.0 Hz) 3.25~3.28 (m) 3.52 (ddd, J=9.6, 7.3, 2.1 Hz) 4.18 (dd, J=11.8, 7.3 Hz) 4.48 (dd, J=11.8, 2.1 Hz) — — 1.51 (s) 1.46 (s)		169.5 (C) 128.4 (C) 144.4 (CH) 24.5 (CH₂) 41.8 (CH₂) 73.6 (C) 146.0 (CH) 112.4 (CH₂) 12.4 (CH₃) 27.8 (CH₃) — — 99.9 (CH) 71.8 (CH) 78.3 (CH) 75.3 (CH) 75.5 (CH) 65.2 (CH₂) 179.5 (C) 80.2 (C) 27.0 (CH₃) 24.6 (CH₃)	— — 6.81 (tq, J=7.7, 1.4 Hz) 2.16~2.32 (m) 1.57~1.63 (m) — 5.92 (dd, J=17.3, 10.8 Hz) 5.06 (dd, J=10.8, 1.5 Hz) 5.23 (dd, J=17.3, 1.5 Hz) 1.82 (s) 1.28 (s) — — 4.54 (d, J=7.8 Hz) 3.24~3.30 (m) 3.37~3.43 (m) 3.24~3.30 (m) 3.51 (ddd, J=9.5, 7.2, 2.1 Hz) 4.16 (dd, J=11.8, 7.3 Hz) 4.45 (dd, J=11.8, 2.1 Hz) — — 1.50 (s) 1.46 (s)

矮陀陀中一个新的脂肪酸苷类化合物

A New Fatty Acid Glycoside Compound in Munronia Pinnata

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 29

Related Articles 3

Recommended Articles

Metrics

Comments

[1]	Desheng Ning, Yuxia Fu, Lianchun Li, Zhiqi Zou, Zhenghong Pan. A New Monoterpene-Phenylpropanoid from Illicium difengpi [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1591-1595.
[2]	Zhang Wenbo, Shi Danshu, Zhang Chunzhen, Yu Zhiguo. Two New Rhabduscin Analogues from Xenorhabdus bovienii SN52 [J]. Chin. J. Org. Chem., 2017, 37(4): 996-999.
[3]	ZHANG Jun-Tao, FENG Jian-Peng, CHEN Jie, CAO Xiao-Ping*. Progress in Research of Malyngamides [J]. Chin. J. Org. Chem., 2008, 28(06): 964-974.