82
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Sarcanoids A and B, two new lindenane-type sesquiterpenoid dimers from the aerial parts of Sarcandra glabra

, , , , , , & show all
Received 20 Dec 2023, Accepted 01 Jun 2024, Published online: 17 Jun 2024

References

  • Bai B, Ye SX, Yang DP, Zhu LP, Tang GH, Chen YY, Li GQ, Zhao ZM. 2019. Chloraserrtone A, a sesquiterpenoid dimer from Chloranthus serratus. J Nat Prod. 82(2):407–411.
  • Chen ZH, Sun YP, Wang YY, Kong LY, Luo J. 2023. Two new sesquiterpenoids from the roots of Sarcandra glabra. Nat Prod Res. 37(20):3505–3511. doi:10.1080/14786419.2022.2089670.
  • Chi J, Wei SS, Gao HL, Xu DQ, Zhang LN, Yang L, Xu WJ, Luo J, Kong LY. 2019a. Diverse chemosensitizing 8,9-secolindenane-type sesquiterpenoid oligomers and monomers from Sarcandra glabra. J Org Chem. 84(14):9117–9126. doi:10.1021/acs.joc.9b00986.
  • Chi J, Xu WJ, Wei SS, Wang XB, Li JX, Gao HL, Kong LY, Luo J. 2019b. Chlotrichenes A and B, two lindenane sesquiterpene dimers with highly fused carbon skeletons from Chloranthus holostegius. Org Lett. 21(3):789–792.
  • Chu JN, Krishnan P, Lim KH. 2023. A comprehensive review on the chemical constituents, sesquiterpenoid biosynthesis and biological activities of Sarcandra glabra. Nat Prod Bioprospect. 13(1):53. doi:10.1007/s13659-023-00418-8.
  • Cui ZR, Wang YY, Li JX, Chi J, Zhang PP, Kong LY, Luo J. 2022. Natural and pseudonatural lindenane heterodimers from Sarcandra glabra by molecular networking. Org Lett. 24(49):9107–9111. doi:10.1021/acs.orglett.2c03769.
  • Du NN, Bai M, Zhang X, Zhou L, Huang XX, Song SJ. 2022. Coumarins from Sarcandra glabra (Thunb.) Nakai and acetylcholinesterase inhibiting activity. Chem Biodivers. 19(10):e202200558.
  • Guo X, Shen L, Tong YH, Zhang J, Wu G, He Q, Yu SR, Ye XW, Zou LB, Zhang ZZ, et al. 2013. Antitumor activity of caffeic acid 3,4-dihydroxyphenethyl ester and its pharmacokinetic and metabolic properties. Phytomedicine. 20(10):904–912. doi:10.1016/j.phymed.2013.04.002.
  • He RR, Yao XS, Li HY, Dai Y, Duan YH, Li YF, Kurihara H. 2009. The anti-stress effects of Sarcandra glabra extract on restraint-evoked immunocompromise. Biol Pharm Bull. 32(2):247–252. doi:10.1248/bpb.32.247.
  • He XF, Yin S, Ji YC, Su ZS, Geng MY, Yue JM. 2010. Sesquiterpenes and dimeric sesquiterpenoids from Sarcandra glabra. J Nat Prod. 73(1):45–50. doi:10.1021/np9006469.
  • Hu XR, Yang JS, Xu XD. 2009. Three novel sesquiterpene glycosides of Sarcandra glabra. Chem Pharm Bull. 57(4):418–420.
  • Hu XR, Wu HF, Zhang XP, Yang JS, Dai Z, Lin RC, Xu XD. 2013. A new sesquiterpene lactone from Sarcandra glabra. Nat Prod Res. 27(13):1197–1201.
  • Kawabata J, Fukushi Y, Tahara S, Mizutani J. 1990. Shizukaol A, a sesquiterpene dimer from Chloranthus japonicas. Phytochemistry. 29(7):2332–2334. doi:10.1016/0031-9422(90)83065-9.
  • Li JX, Chi J, Tang PF, Sun YP, Lu WJ, Xu WJ, Wang YY, Luo J, Kong LY. 2022. Spirolindemers A and B, lindenane sesquiterpenoid oligomers equipped with oxaspiro[4.5]decane from Chloranthus henryi. Chin J Chem. 40(5):603–608.
  • Li Y, Zhang DM, Li JB, Yu SS, Li Y, Luo YM. 2006. Hepatoprotective sesquiterpene glycosides from Sarcandra glabra. J Nat Prod. 69(4):616–620.
  • Liu J, Wen QY, Tian HR, Zhan BJF, Zhu LP, Yang DP, Zhao ZM. 2023. (±)-Sarcanan A, a pair of new enantiomeric dihydrobenzofuran neolignans from the aerial parts of Sarcandra glabra. Nat Prod Res. 37(15):2480–2485.
  • Liu X, Yang J, Fu J, Xu PL, Xie TG, Bai LP, Jiang ZH, Zhu GY. 2021. Monoterpene-flavonoid conjugates from Sarcandra glabra and their autophagy modulating activities. Bioorg Chem. 112:104830. doi:10.1016/j.bioorg.2021.104830.
  • Luo J, Zhang DY, Tang PF, Wang N, Zhao S, Kong LY. 2024. Chemistry and bioactivity of lindenane sesquiterpenoids and their oligomers. Nat Prod Rep. 41(1):25–58. doi:10.1039/D3NP00022B.
  • Luo YM, Liu AH, Zhang DM, Huang LQ. 2005. Two new triterpenoid saponins from Sarcandra glabra. J Asian Nat Prod Res. 7(6):829–834. doi:10.1080/10286020410001721104.
  • Ma LF, Chen YL, Shan WG, Zhan ZJ. 2020. Natural disesquiterpenoids: an update. Nat Prod Rep. 37(7):999–1030. doi:10.1039/c9np00062c.
  • National pharmacopeia committee. 2015. China pharmacopeia, Vol. 1. Beijing: Chemical Industry. p. 223–224.
  • Ni G, Zhang H, Liu HC, Yang SP, Geng MY, Yue JM. 2013. Cytotoxic sesquiterpenoids from Sarcandra glabra. Tetrahedron. 69(2):564–569. doi:10.1016/j.tet.2012.11.023.
  • Qin YQ, Liu W, Yin R, Xiao PT, Wang ZY, Huang TQ, Liu EH. 2024. New 4′,5′-methylenedioxyflavone derivatives from the whole plant of Sarcandra glabra. Nat Prod Res. 38(2):177–185.
  • Sun YP, Chi J, Zhang LJ, Wang SY, Chen ZH, Zhang H, Kong LY, Luo J. 2022a. Sarglaromatics A − E: a class of naphthalene-like architecture fused norlindenane sesquiterpene dimers from Sarcandra glabra. J Org Chem. 87(6):4323–4332. doi:10.1021/acs.joc.2c00014.
  • Sun YP, Wang YY, Li YQ, Wang SY, Zhang DY, Kong LY, Luo J. 2022b. Sarcaglarone A, a lindenane-monoterpene heterodimer from the seeds of Sarcandra glabra. Org Biomol Chem. 20(46):9222–9227.
  • Tsai YC, Chen SH, Lin LC, Fu SL. 2017. Anti-inflammatory principles from Sarcandra glabra. J Agric Food Chem. 65(31):6497–6505. doi:10.1021/acs.jafc.6b05125.
  • Wang M, Zhao J, Zhao Y, Huang RY, Li G, Zeng X, Li X. 2016. A new coumarin isolated from Sarcandra glabra as potential anti-inflammatory agent. Nat Prod Res. 30(16):1796–1801.
  • Wang P, Luo J, Zhang YM, Kong LY. 2015. Sesquiterpene dimers esterified with diverse small organic acids from the seeds of Sarcandra glabra. Tetrahedron. 71(33):5362–5370. doi:10.1016/j.tet.2015.05.112.
  • Wang P, Li RJ, Liu RH, Jian KL, Yang MH, Yang L, Kong LY, Luo J. 2016. Sarglaperoxides A and B, sesquiterpene-normonoterpene conjugates with a peroxide bridge from the seeds of Sarcandra glabra. Org Lett. 18(4):832–835.
  • Wang Y, Cui Z, Chi J, Tang P, Zhang M, Li J, Li Y, Zhang H, Luo J, Kong L. 2021. Sarcaglarols A − D, lindenane-monoterpene heterodimers from Sarcandra glabra based on molecular networks. Chin J Chem. 39(1):129–136.
  • Wang YY, Chen ZH, Li QR, Cui LT, Chi J, Li JX, Sun YP, Kong LY, Luo J. 2022. Sarglafuran A, a lindenane-type sesquiterpene dimers with unique furan ring from the leaves of Sarcandra glabra. Tetrahedron Lett. 98:153834. doi:10.1016/j.tetlet.2022.153834.
  • Xiao LG, Li P, Yan H, Ni W, He L, Liu HY. 2022. Sarcanolides C − E: three new lindenane sesquiterpenoid dimers with anti-inflammatory activities from Sarcandra glabra. Org Biomol Chem. 20(6):1320–1326.
  • Yaermaimaiti S, Wang P, Luo J, Li RJ, Kong LY. 2016. Sesquiterpenoids from the seeds of Sarcandra glabra and the potential anti-inflammatory effects. Fitoterapia. 111:7–11. 2016 − doi:10.1016/j.fitote.2016.03.020.
  • Yang WQ, Hai P, Xiao H, Gao Y, Tao YH, Miao DR, Wang F. 2018. Glabralides A − C, three novel meroterpenoids from Sarcandra glabra. Tetrahedron. 74(2):341–347. doi:10.1016/j.tet.2017.12.001.
  • Yang XR, Tanaka N, Tsuji D, Lu FL, Yan XJ, Itoh K, Li DP, Kashiwada Y. 2020. Sarcaglabrin A, a conjugate of C15 and C10 terpenes from the aerial parts of Sarcandra glabra. Tetrahedron Lett. 61(25):151916. doi:10.1016/j.tetlet.2020.151916.
  • Zeng YL, Liu JY, Zhang Q, Qin XH, Li ZL, Sun GJ, Jin SR. 2021. The traditional uses, phytochemistry and pharmacology of Sarcandra glabra (Thunb.) Nakai, a Chinese herb with potential for development: review. Front Pharmacol. 12:652926. doi:10.3389/fphar.2021.652926.
  • Zhan ZJ, Ying YM, Ma LF, Shan WG. 2011. Natural disesquiterpenoids. Nat Prod Rep. 28(3):594–629. doi:10.1039/c0np00050g.
  • Zhang DY, Wang XX, Wang YN, Wang M, Zhuang PY, Jin Y, Liu H. 2021. Nine sesquiterpenoid dimers with four unprecedented types of carbon skeleton from Chloranthus henryi var. hupehensis. Org Chem Front. 8(16):4374–4386.
  • Zhao JJ, Guo YQ, Yang DP, Xue X, Liu Q, Zhu LP, Yin S, Zhao ZM. 2016. Chlojaponilactone B from Chloranthus japonicus: suppression of inflammatory responses via inhibition of the NF-κB signaling pathway. J Nat Prod. 79(9):2257–2263.
  • Zhou B, Liu QF, Dalal S, Cassera MB, Yue JM. 2017. Fortunoids A − C, three sesquiterpenoid dimers with different carbon skeletons from Chloranthus fortune. Org Lett. 19(3):734–737.
  • Zhou B, Gong Q, Fu Y, Zhou JS, Zhang HY, Yue JM. 2023. Sarglamides A − E, indolidinoid − monoterpenoid hybrids with anti-neuroinflammatory activity from a Sarcandra species. Org Lett. 25(9):1464–1469. doi:10.1021/acs.orglett.3c00196.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.