Analysis of chemical constituents of Liquidambaris Fructus

FAN Yiying; CEN Xiangni; LIU Haowen; LIU Pinghuai

doi:10.15886/j.cnki.rdswxb.20240061

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Volume 16 Issue 2

Apr. 2025

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Article Navigation > Journal of Tropical Biology > 2025 > 16(2): 188-195

FAN Yiying, CEN Xiangni, LIU Haowen, LIU Pinghuai. Analysis of chemical constituents of Liquidambaris Fructus[J]. Journal of Tropical Biology, 2025, 16(2): 188-195. doi: 10.15886/j.cnki.rdswxb.20240061

Citation:

FAN Yiying, CEN Xiangni, LIU Haowen, LIU Pinghuai. Analysis of chemical constituents of Liquidambaris Fructus[J]. Journal of Tropical Biology, 2025, 16(2): 188-195. doi: 10.15886/j.cnki.rdswxb.20240061

Analysis of chemical constituents of Liquidambaris Fructus

doi: 10.15886/j.cnki.rdswxb.20240061

School of Chemical Engineering and Technology, Hainan University, Haikou, Hainan 570228, China

Received Date: 2024-04-10
Rev Recd Date: 2024-05-16

Abstract

An attempt was made to analyze the chemical constituents of Liquidambaris Fructus, the infructescenses of Liquidambaris formosa Hance, for better development and utilization of Liquidambaris Fructus.The constituents were isolated from different polar solvent extracts of Liquidambaris Fructus and purified by column chromatography, Sephadex LH-20, and semi-preparative high-performance liquid chromatography, and the structures of the compounds purified were identified by employing spectroscopy combined with literature. A total of 17 compounds were isolated from the extracts, including 10 triterpenoids（ 1～10 ）, 1 sterol compound（ 12 ）,2 phenolic acids（ 11, 13 ）, and 3 aromatic esters（ 14, 15, 17 ）. These compounds were identified as oleanolic acid（ 1 ）, ursolic acid（ 2 ）, betulinic acid（ 3 ）, methyl 3-oxoolean-12-en-28-oate（ 4 ）, 3-oxo-11,13（18）-oleanadien-28-oic acid（ 5 ）, 3α-hydroxy-lup-20（29）-ene-28-oic acid（ 6 ）,3-oxooleanolic acid（ 7 ）, 3,30-dioxo-lup-20（29）-en-28-oic acid（ 8 ）, 3-epimaslinic acid（ 9 ）, 3, 11-dioxoolean-12-en-28-oic acid（ 10 ）, gallic acid（ 11 ）, β-sitosterol（ 12 ）, 3, 3′-dimethoxy ellagic acid-4′-O-β-D-primeveroside（ 13 ）, Dipentyl phthalate（ 14 ）, cinnamyl cinnamate（ 15 ）, cisdodeca-1,3-diene（ 16 ）, bis（2-ethyloctyl） phthalate（ 17 ）. Compounds 4, 8, 10, 13, 14, 16 and 17 were isolated for the first time from the genus Liquidambaris and compounds 4, 8, 13, and 16 were also isolated from the genus Liquidambar for the first time, which provides references for the in-depth development of these compounds.
- Liquidambaris Fructus,
- chemical constituent,
- spectroscopic technique

References

[1]	李春深.中草药识别与应用[M]. 天津:天津科学技术出版社, 2018.
[2]	孙玉茹,孙友富.路路通内酯的化学结构[J]. 药学学报, 1996, 31(6)::437-440.
[3]	孙玉茹,孙友富.中药路路通化学成分研究[J]. 中草药, 1988, 19(8):6-7.
[4]	OUYANG X, YI S, LU H, et al. Liquidambar formosana hance:a mini-review of chemical constituents and pharmacology[J]. European Journal of Medicinal Plants, 2016, 17(1):1-11.
[5]	LEE T K W, CASTILHO A, CHEUNG V C H, et al.Lupeol targets liver tumor-initiating cells through phosphatase and tensin homolog modulation[J]. Hepatology, 2011,53(1):160-170.
[6]	李春,孙玉茹,孙有富.中药路路通化学成分的研究[J]. 药学学报, 2002, 37(4):263-266.
[7]	ZHANG H X, KANG Y, LI N, et al. Triterpenoids from Liquidambar Fructus induced cell apoptosis via a PI3KAKT related signal pathway in SMMC7721 cancer cells[J]. Phytochemistry, 2020, 171:112228.
[8]	刘盛玲,吕红,田会茹,等.蚊母草提取物通过抑制Runx2活性抗乳腺癌破骨性骨转移作用[J]. 中国实验方剂学杂志, 2022, 28(7):81-87.
[9]	廖圆月,曾璐,肖林林,等.枫香树属植物化学成分研究进展[J]. 亚太传统医药, 2016, 12(14):77-79.
[10]	谢琼臖,钟有添.枫香树叶的研究进展[J]. 赣南医学院学报, 2014, 34(04):651-653.
[11]	余辅松,邓华,赵李妮,等.岭南山竹子树皮化学成分研究(Ⅱ)[J]. 时珍国医国药, 2018, 29(1):7-9.
[12]	马瑶,李进,吉腾飞.阿尔泰瑞香的化学成分研究[J]. 化学工程, 2022, 50(8):13-19.
[13]	王军民,刘思远,杨莹,等.茯神化学成分的研究[J]. 中成药, 2021, 43(10):2728-2732.
[14]
[15]	JOHNS S R, LAMBERTON J A, MORTON T C, et al.Triterpenes of Lantana tiliaefolia. 24-Hydroxy-3-oxours-12-en-28-oic acid, a new triterpene[J]. Australian Journal of Chemistry, 1983, 36(12):2537.
[16]
[17]	陈艳,黄滔,苑春茂,等.小花清风藤化学成分的研究[J]. 中草药, 2015, 46(21):3146-3150.
[18]	SATIRAPHAN M, PAMONSINLAPATHAM P,SOTANAPHUN U, et al. Lupane triterpenes from the leaves of the tropical rain forest tree Hopea odorata Roxb. and their cytotoxic activities[J]. Biochemical Systematics and Ecology, 2012, 44:407-412.
[19]	曹坚,杨健妮,周秀悄,等.黎药海南九节的化学成分研究[J]. 中药材, 2019, 42(6):1297-1300.
[20]	FUKUDA Y, YAMADA T, WADA S I, et al. Lupane and oleanane triterpenoids from the cones of Liquidamber styraciflua[J]. Journal of Natural Products, 2006, 69(1):142-144.
[21]	THU N T H, HOA P T H, DAT N T, et al. Triterpenoids,steroid, and aromatic compounds from Combretum indicum leaves[J]. Vietnam Journal of Chemistry, 2022, 60(5):629-635.
[22]	莫单丹,周小雷,唐炳兰,等.走马风化学成分的研究[J]. 中成药, 2018, 40(10):2219-2221.
[23]	HUNG L K, THANH P D, MINH P N, et al. Flavonoids and phenolics from the whole plant of Macrosolen bidoupensis tangane&V.S. Dang[J]. Vietnam Journal of Chemistry, 2021, 59(1):115-119.
[24]	廖铁松,沈云亨,李影,等.巴西甘菊花化学成分研究(Ⅱ)[J]. 中药材, 2019, 42(11):2551-2556.
[25]	LEE I K, HAN M S, KIM D W, et al. Phenylpropanoid acid esters from Korean propolis and their antioxidant activities[J]. Bioorganic&Medicinal Chemistry Letters,2014, 24(15):3503-3505.
[26]	MELIKYAN G G, MKRTCHYAN D A, LEBEDEVA K V, et al. Synthesis of(±)-cis-tetradec-5-en-4-olide-the racemate of the sex pheromone of the Japanese beetle[J]. Chemistry of Natural Compounds, 1984, 20(1):94-98.
[27]	郑晓珂,董三丽,冯卫生.浅裂鳞毛蕨地上部分化学成分研究[J]. 天然产物研究与开发, 2005, 17(4):434-436.
[28]	周文武.枫香树叶化学成分研究[D]. 昆明:云南大学,2021.
[29]	钟瑞建,付辉政,周国平,等.枫香树叶的化学成分研究[J]. 江西中医药大学学报, 2015, 27(5):55-57.
[30]	武纤雨,冯喜龙,李莉,等.油樟叶中黄酮类物质抑菌效果研究[J]. 生物资源, 2022, 44(04):402-410. 26
[31]	王艺,叶磊,胡攀,等.木芙蓉黄酮类化学成分、药理作用及提取工艺研究进展[J]. 山东化工,2022, 51(12):80-86.
[32]
[33]	穆晓婷,钱平,蒋璐璐,等.路路通酸对乳腺癌MCF-7细胞和宫颈癌C-33A细胞增殖的影响[J]. 实用药物与临床, 2017, 20(03):254-257.
[34]	QIAN P, MU X T, SU B, et al. Identification of the antibreast cancer targets of triterpenoids in Liquidambaris Fructus and the hints for its traditional applications.BMC complementary medicine and therapies[J]. 2020, 20(1):1-5.
[35]	ZHANG P, LI H, CHEN D, et al. Oleanolic acid induces apoptosis in human leukemia cells through caspase activation and poly(ADP-ribose) polymerase cleavage[J]. Acta biochimica et biophysica sinica, 2007, 39(10):803-809.
[36]	ŽIBERNA L,ŠAMEC D, MOCAN A, et al. Oleanolic acid alters multiple cell signaling pathways:implication in cancer prevention and therapy[J]. International journal of molecular sciences, 2017,18(3):643.

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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Analysis of chemical constituents of Liquidambaris Fructus

School of Chemical Engineering and Technology, Hainan University, Haikou, Hainan 570228, China

Received Date: 2024-04-10

Rev Recd Date: 2024-05-16

Key words:

Abstract: An attempt was made to analyze the chemical constituents of Liquidambaris Fructus, the infructescenses of Liquidambaris formosa Hance, for better development and utilization of Liquidambaris Fructus.The constituents were isolated from different polar solvent extracts of Liquidambaris Fructus and purified by column chromatography, Sephadex LH-20, and semi-preparative high-performance liquid chromatography, and the structures of the compounds purified were identified by employing spectroscopy combined with literature. A total of 17 compounds were isolated from the extracts, including 10 triterpenoids（ 1～10 ）, 1 sterol compound（ 12 ）,2 phenolic acids（ 11, 13 ）, and 3 aromatic esters（ 14, 15, 17 ）. These compounds were identified as oleanolic acid（ 1 ）, ursolic acid（ 2 ）, betulinic acid（ 3 ）, methyl 3-oxoolean-12-en-28-oate（ 4 ）, 3-oxo-11,13（18）-oleanadien-28-oic acid（ 5 ）, 3α-hydroxy-lup-20（29）-ene-28-oic acid（ 6 ）,3-oxooleanolic acid（ 7 ）, 3,30-dioxo-lup-20（29）-en-28-oic acid（ 8 ）, 3-epimaslinic acid（ 9 ）, 3, 11-dioxoolean-12-en-28-oic acid（ 10 ）, gallic acid（ 11 ）, β-sitosterol（ 12 ）, 3, 3′-dimethoxy ellagic acid-4′-O-β-D-primeveroside（ 13 ）, Dipentyl phthalate（ 14 ）, cinnamyl cinnamate（ 15 ）, cisdodeca-1,3-diene（ 16 ）, bis（2-ethyloctyl） phthalate（ 17 ）. Compounds 4, 8, 10, 13, 14, 16 and 17 were isolated for the first time from the genus Liquidambaris and compounds 4, 8, 13, and 16 were also isolated from the genus Liquidambar for the first time, which provides references for the in-depth development of these compounds.

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Reference (36)

[1]	李春深.中草药识别与应用[M]. 天津:天津科学技术出版社, 2018.
[2]	孙玉茹,孙友富.路路通内酯的化学结构[J]. 药学学报, 1996, 31(6)::437-440.
[3]	孙玉茹,孙友富.中药路路通化学成分研究[J]. 中草药, 1988, 19(8):6-7.
[4]	OUYANG X, YI S, LU H, et al. Liquidambar formosana hance:a mini-review of chemical constituents and pharmacology[J]. European Journal of Medicinal Plants, 2016, 17(1):1-11.
[5]	LEE T K W, CASTILHO A, CHEUNG V C H, et al.Lupeol targets liver tumor-initiating cells through phosphatase and tensin homolog modulation[J]. Hepatology, 2011,53(1):160-170.
[6]	李春,孙玉茹,孙有富.中药路路通化学成分的研究[J]. 药学学报, 2002, 37(4):263-266.
[7]	ZHANG H X, KANG Y, LI N, et al. Triterpenoids from Liquidambar Fructus induced cell apoptosis via a PI3KAKT related signal pathway in SMMC7721 cancer cells[J]. Phytochemistry, 2020, 171:112228.
[8]	刘盛玲,吕红,田会茹,等.蚊母草提取物通过抑制Runx2活性抗乳腺癌破骨性骨转移作用[J]. 中国实验方剂学杂志, 2022, 28(7):81-87.
[9]	廖圆月,曾璐,肖林林,等.枫香树属植物化学成分研究进展[J]. 亚太传统医药, 2016, 12(14):77-79.
[10]	谢琼臖,钟有添.枫香树叶的研究进展[J]. 赣南医学院学报, 2014, 34(04):651-653.
[11]	余辅松,邓华,赵李妮,等.岭南山竹子树皮化学成分研究(Ⅱ)[J]. 时珍国医国药, 2018, 29(1):7-9.
[12]	马瑶,李进,吉腾飞.阿尔泰瑞香的化学成分研究[J]. 化学工程, 2022, 50(8):13-19.
[13]	王军民,刘思远,杨莹,等.茯神化学成分的研究[J]. 中成药, 2021, 43(10):2728-2732.
[14]
[15]	JOHNS S R, LAMBERTON J A, MORTON T C, et al.Triterpenes of Lantana tiliaefolia. 24-Hydroxy-3-oxours-12-en-28-oic acid, a new triterpene[J]. Australian Journal of Chemistry, 1983, 36(12):2537.
[16]
[17]	陈艳,黄滔,苑春茂,等.小花清风藤化学成分的研究[J]. 中草药, 2015, 46(21):3146-3150.
[18]	SATIRAPHAN M, PAMONSINLAPATHAM P,SOTANAPHUN U, et al. Lupane triterpenes from the leaves of the tropical rain forest tree Hopea odorata Roxb. and their cytotoxic activities[J]. Biochemical Systematics and Ecology, 2012, 44:407-412.
[19]	曹坚,杨健妮,周秀悄,等.黎药海南九节的化学成分研究[J]. 中药材, 2019, 42(6):1297-1300.
[20]	FUKUDA Y, YAMADA T, WADA S I, et al. Lupane and oleanane triterpenoids from the cones of Liquidamber styraciflua[J]. Journal of Natural Products, 2006, 69(1):142-144.
[21]	THU N T H, HOA P T H, DAT N T, et al. Triterpenoids,steroid, and aromatic compounds from Combretum indicum leaves[J]. Vietnam Journal of Chemistry, 2022, 60(5):629-635.
[22]	莫单丹,周小雷,唐炳兰,等.走马风化学成分的研究[J]. 中成药, 2018, 40(10):2219-2221.
[23]	HUNG L K, THANH P D, MINH P N, et al. Flavonoids and phenolics from the whole plant of Macrosolen bidoupensis tangane&V.S. Dang[J]. Vietnam Journal of Chemistry, 2021, 59(1):115-119.
[24]	廖铁松,沈云亨,李影,等.巴西甘菊花化学成分研究(Ⅱ)[J]. 中药材, 2019, 42(11):2551-2556.
[25]	LEE I K, HAN M S, KIM D W, et al. Phenylpropanoid acid esters from Korean propolis and their antioxidant activities[J]. Bioorganic&Medicinal Chemistry Letters,2014, 24(15):3503-3505.
[26]	MELIKYAN G G, MKRTCHYAN D A, LEBEDEVA K V, et al. Synthesis of(±)-cis-tetradec-5-en-4-olide-the racemate of the sex pheromone of the Japanese beetle[J]. Chemistry of Natural Compounds, 1984, 20(1):94-98.
[27]	郑晓珂,董三丽,冯卫生.浅裂鳞毛蕨地上部分化学成分研究[J]. 天然产物研究与开发, 2005, 17(4):434-436.
[28]	周文武.枫香树叶化学成分研究[D]. 昆明:云南大学,2021.
[29]	钟瑞建,付辉政,周国平,等.枫香树叶的化学成分研究[J]. 江西中医药大学学报, 2015, 27(5):55-57.
[30]	武纤雨,冯喜龙,李莉,等.油樟叶中黄酮类物质抑菌效果研究[J]. 生物资源, 2022, 44(04):402-410.	26
[31]	王艺,叶磊,胡攀,等.木芙蓉黄酮类化学成分、药理作用及提取工艺研究进展[J]. 山东化工,2022, 51(12):80-86.
[32]
[33]	穆晓婷,钱平,蒋璐璐,等.路路通酸对乳腺癌MCF-7细胞和宫颈癌C-33A细胞增殖的影响[J]. 实用药物与临床, 2017, 20(03):254-257.
[34]	QIAN P, MU X T, SU B, et al. Identification of the antibreast cancer targets of triterpenoids in Liquidambaris Fructus and the hints for its traditional applications.BMC complementary medicine and therapies[J]. 2020, 20(1):1-5.
[35]	ZHANG P, LI H, CHEN D, et al. Oleanolic acid induces apoptosis in human leukemia cells through caspase activation and poly(ADP-ribose) polymerase cleavage[J]. Acta biochimica et biophysica sinica, 2007, 39(10):803-809.
[36]	ŽIBERNA L,ŠAMEC D, MOCAN A, et al. Oleanolic acid alters multiple cell signaling pathways:implication in cancer prevention and therapy[J]. International journal of molecular sciences, 2017,18(3):643.

Message Board

Analysis of chemical constituents of Liquidambaris Fructus

doi: 10.15886/j.cnki.rdswxb.20240061

Abstract

References

Proportional views

通讯作者: 陈斌, bchen63@163.com

Proportional views

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