Isolation and Identification of Triterpenoids from Rosa laevigata var. leiocapus and Evaluation of Their Anti-SARS-COV-2 Activity
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    Abstract:

    To understand the triterpenoids from Rosa laevigata var. leiocapus and their SARS-CoV-2 inhibitory activities, 15 compounds were isolated from the 95% EtOH extract by using chromatographic separation techniques, such as silica gel, Sephadex LH-20 and pre-HPLC. On the basis of spectral data, their structures were identified as laevigaterpene A (1), 2α, 23-dihydroxy oleanolic acid (2), 1β-hydroxyeuscaphic acid (3), 3β-(p-hydroxytranscin-namoyloxy)olean-12-en-28-oic acid (4), 3β-trans-p-coumaroyloxy-2α-hydroxy oleanolic acid (5), 2α, 3α-dihydroxyo-lean-12-en-28-oic acid (6), pomolic acid (7), lup-3β-ol-28-carboxylate (8), 2α, 3α, 19α, 23-tetrahydroxyurs-12-en-28-oic acid (9), acetyl-11α-methoxy-β-boswellic acid (10), arjunic acid (11), 2α, 3α, 19α-trihydroxy-28-norurs-12-ene (12), euscaphic acid (13), 2α, 19α-dihydroxy-3-oxo-12-ursen-28-oic acid (14), and oleanolic acid (15). Compounds 1-15 were obtained from this species at first time. Moreover, compounds4,10 and 12 were isolated from Rosa at first time. Compounds 8 and15 exhibited strong inhibitory effects on SARS-CoV-2 Mpro, with IC50 of (6.74±0.33) and (5.19±0.25) μmol/L, respectively, showing potential anti-SARS-CoV-2 activity.

    Reference
    [1] LIU X G, LI J L, GAO P Y, et al. Recent advances in research on edible Rosa laevigata Michx. [J]. Food Sci, 2013, 34(11): 392-398. 刘学贵, 李佳骆, 高品一, 等. 药食两用金樱子的研究进展[J]. 食品科学, 2013, 34(11): 392-398. doi: 10.7506/spkx1002-6630-201311081.
    [2] HOU S P, HOU M N. Research progress in chemical constituents of Rosa L. Plants [J]. Chem Bioeng, 2021, 38(1): 11-16. 侯少平, 侯敏娜. 蔷薇属植物化学成分研究进展[J]. 化学与生物工程, 2021, 38 (1): 11-16. doi: 10.3969/j.issn.1672-5425.2021.01.003.
    [3] GU Z P, ZHANG S M, LIU D. Development and utilization of the resources of Rosa laevigata Michx. [J]. Chin Wild Plant Res, 1994(4): 30-32. 顾志平, 张曙明, 刘东. 金樱子资源的开发利用[J]. 中国野生植物资源, 1994(4): 30-32.
    [4] LIN F H, PENG Y H, CHAI S F, et al. Comparative study on the quality of Rosa laevigata var. Leiocarpus and Rosa laevigata Michx. [J]. J Guangdong Pharmaceut Univ, 2010, 26(4): 345-347. 林芳花, 彭永宏, 柴素芬, 等. 光果金樱子和金樱子质量比较研究[J]. 广东药学院学报, 2010, 26(4): 345-347. doi: 10.3969/j.issn.1006-8783.2010.04.005.
    [5] WANG Y Q, CHEN B Y. New taxa of Guangdong plants [J]. J Trop Subtrop Bot, 1995, 3(1): 29-33. 王英强, 陈邦余. 广东植物新类群[J]. 热带亚热带植物学报, 1995, 3(1): 29-33.
    [6] GAO P Y, WANG M, LIU X G, et al. Triterpenes from the fruits of Rosa laevigata with acetylcholinesterase and Aβ-aggregation inhibitory activities [J]. RSC Adv, 2016, 6(3): 2431-2435. doi: 10.1039/C5RA21590K.
    [7] XIAO C J, ZHOU X L, HAN B Y, et al. Chemical constituents from rhizome of Isodon adenantha [J]. Nat Prod Res Dev, 2013, 25(3): 333-337. 肖朝江, 周星利, 韩冰洋, 等. 腺花香茶菜地下根茎化学成分研究[J]. 天然产物研究与开发, 2013, 25(3): 333-337. doi: 10.3969/j.issn.1001-6880.2013.03.010.
    [8] SUN J H, GAN C L, HUANG J, et al. Determination of triterpenoids and phenolic acids from Sanguisorba officinalis L. by HPLC-ELSD and its application [J]. Molecules, 2021, 26(15): 4505. doi: 10.3390/molecules26154505.
    [9] WANG H S, DAI H F, WANG P, et al. Chemical constituents from litters of Casuarina equisetifolia and their biological activity [J]. Nat Prod Res Dev, 2018, 30(3): 390-395. 王海生, 戴好富, 王佩, 等. 木麻黄凋落物化学成分及其生物活性的研究[J]. 天然产物研究与开发, 2018, 30(3): 390-395. doi: 10.16333/j.1001-6880.2018.3.008.
    [10] SEO C, LEE J E, LEE J A, et al. Acylated triterpenoids, flavonoids, and lignans isolated from the stems of Tetracera loureiri [J]. Chem Nat Compd, 2019, 55(2): 386-389. doi: 10.1007/s10600-019-02699-3.
    [11] JIANG X H, LIU Z B, HUO H Z, et al. Triterpenoids from Salvia bowleyana [J]. Guihaia, 2021, 41(7): 1097-1103. 蒋小华, 刘章彬, 霍华珍, 等. 南丹参三萜类化学成分的研究[J]. 广西植物, 2021, 41(7): 1097-1103. doi: 10.11931/guihaia.gxzw202002042.
    [12] NAM J H, JUNG H J, TAPONDJOU L A, et al. The anti-hyperlipi-demic effect and constituents of the 19α-hydroxyursane-type triterpe-noid fraction obtained from the leaves of Rubus crataegifolius [J]. Nat Prod Sci, 2007, 13(2): 152-159.
    [13] MA X M, DI D L, SHI Y P. Triterpenoids and steroids from Ixeridium gracile [J]. Chem Nat Compd, 2008, 44(3): 399-401. doi: 10.1007/s10600-008-9078-z.
    [14] LI X H, SHEN D D, LI N, et al. Bioactive triterpenoids from Sym-plocos chinensis [J]. J Asian Nat Prod Res, 2003, 5(1): 49-56. doi: 10.1080/1028602031000080469.
    [15] WANG F, HUA H M, WANG S M, et al. Chemical constituents from frankincense [J]. Chin Trad Herb Drugs, 2011, 42(7): 1293-1296. 王峰, 华会明, 王淑美, 等. 乳香的化学成分研究[J]. 中草药, 2011, 42(7): 1293-1296.
    [16] PONOU B K, TEPONNO R B, RICCIUTELLI M, et al. Novel 3-oxo- and 3, 24-dinor-2, 4-secooleanane-type triterpenes from Terminalia ivorensis A. Chev. [J]. Chem Biodiv, 2011, 8(7): 1301-1309. doi: 10.1002/cbdv.201000145.
    [17] HAN Y F, PAN J, GAO K, et al. Sesquiterpenes, nortriterpenes and other constituents from Ligularia tongolensis [J]. Chem Pharm Bull, 2005, 53(10): 1338-1341. doi: 10.1248/cpb.53.1338.
    [18] ZHENG G H, PIAO H S. Study on chemical constituents from Potentilla supina [J]. Chin Trad Herb Drugs, 2012, 43(7): 1285-1288. 郑光海, 朴惠顺. 朝天委陵菜化学成分研究[J]. 中草药, 2012, 43(7): 1285-1288.
    [19] ZHAO J, GAO W Y, DUAN H Q, et al. Study on chemical constituents of Geum japonicum [J]. Chin Trad Herb Drugs, 2008, 39(7): 978-981. 赵晶, 高文远, 段宏泉, 等. 日本路边青的化学成分研究[J]. 中草药, 2008, 39(7): 978-981. doi: 10.3321/j.issn:0253-2670.2008.07.007.
    [20] KISHIKAWA A, AMEN Y, SHIMIZU K. Anti-allergic triterpenes isolated from olive milled waste [J]. Cytotechnology, 2017, 69(2): 307-315. doi: 10.1007/s10616-016-0058-z.
    [21] LI H Y, LIU G M, LIU F, et al. Research of ursolic acid and similar pentacyclic triterpenoid [J]. J Hunan Univ Technol, 2009, 23(5): 18-21. 李宏杨, 刘国民, 刘飞, 等. 熊果酸及五环三萜同类物的研究进展[J]. 湖南工业大学学报, 2009, 23(5): 18-21. doi: 10.3969/j.issn.1673-9833.2009.05.005.
    [22] SHEN X J, ZHAO H M, ZHAO L, et al. Research progress on oleanolic acid research [J]. Guangzhou Chem Ind, 2019, 47(24): 16-19. 沈晓静, 赵红梅, 赵蕾, 等. 齐墩果酸研究进展[J]. 广州化工, 2019, 47(24): 16-19. doi: 10.3969/j.issn.1001-9677.2019.24.011.
    [23] JOO H E, LEE H J, SHIN E A, et al. c‐Jun N‐terminal kinase-dependent endoplasmic reticulum stress pathway is critically involved in arjunic acid induced apoptosis in non‐small cell lung cancer cells [J]. Phytotherapy Res, 2016, 30(4): 596-603. doi: 10.1002/ptr.5563.
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敖卓仪,关晓娴,吴杰伟.光果金樱子三萜类化合物的分离鉴定与抗SARS-CoV-2活性评价[J].热带亚热带植物学报,2023,31(6):879~885

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  • Received:February 26,2023
  • Online: November 24,2023
  • Published: November 20,2023
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