Published June 30, 2021 | Version v1
Journal article Restricted

Meroterpenoids from the leaves of Psidium guajava (guava) cultivated in Korea using MS/MS-based molecular networking

  • 1. * & Korea Bioactive Natural Material Bank, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, 151-742, Republic of

Description

Ryu, Byeol, Cho, Hyo Moon, Zhang, Mi, Lee, Ba Wool, Doan, Thi Phuong, Park, Eun Jin, Lee, Hee Ju, Oh, Won Keun (2021): Meroterpenoids from the leaves of Psidium guajava (guava) cultivated in Korea using MS/MS-based molecular networking. Phytochemistry (112723) 186: 1-12, DOI: 10.1016/j.phytochem.2021.112723, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112723

Files

Restricted

The record is publicly accessible, but files are restricted to users with access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:7210FF88FF95010FFFE8FF84FF84FFCC

References

  • Chang, C.H., Hsieh, C.L., Wang, H.E., Peng, C.C., Chyau, C.C., Peng, R.Y., 2013. Unique bioactive polyphenolic profile of guava (Psidium guajava) budding leaf tea is related to plant biochemistry of budding leaves in early dawn. J. Sci. Food Agric. 93 (4), 944-954. https://doi.org/10.1002/jsfa.5832.
  • Chen, N.H., Zhang, Y.B., Huang, X.J., Jiang, L., Jiang, S.Q., Li, G.Q., Li, Y.L., Wang, G.C., 2016. Drychampones A-C: three meroterpenoids from Dryopteris championii. J. Org. Chem. 81 (19), 9443-9448. https://doi.org/10.1021/acs.joc.6b01720.
  • Fu, H.Z., Luo, Y.M., Li, C.J., Yang, J.Z., Zhang, D.M., 2010. Psidials A-C, three unusual meroterpenoids from the leaves of Psidium guajava. L. Org. Lett. 12 (4), 656-659. https://doi.org/10.1021/ol9024869.
  • Gutierrez, R.M.P., Mitchell, S., Solis, R.V., 2008. Psidium guajava: a review of its traditional uses, phytochemistry and pharmacology. J. Ethnopharmacol. 117 (1), 1-27. https://doi.org/10.1016/j.jep.2008.01.025.
  • Hou, J.Q., Fan, C.L., Pei, X., Zhang, P.L., Deng, F., Jiang, W.Q., Wang, G.C., Zhang, X.Q., Ye, W.C., Wang, H., 2019. Psiguadiols A-J, rearranged meroterpenoids as potent PTP1B inhibitors from Psidium guajava. J. Nat. Prod. 82 (12), 3267-3278. https:// doi.org/10.1021/acs.jnatprod.9b00333.
  • Huang, C.S., Yin, M.C., Chiu, L.C., 2011. Antihyperglycemic and antioxidative potential of Psidium guajava fruit in streptozotocin-induced diabetic rats. Food Chem. Toxicol. 49 (9), 2189-2195. https://doi.org/10.1016/j.fct.2011.05.032.
  • Kim, H.W., Park, E.J., Cho, H.M., An, J.P., Chin, Y.W., Kim, J., Sung, S.H., Oh, W.K., 2020. Glucose uptake-stimulating galloyl ester triterpenoids from Castanopsis sieboldii. J. Nat. Prod. 83 (10), 3093-3101. https://doi.org/10.1021/acs. jnatprod.0c00645.
  • Lee, A.R., Cho, H.M., Park, E.J., Zhang, M., Doan, T.P., Lee, B.W., Cho, K.A., Oh, W.K., 2020. Metabolite profiling of rambutan (Nephelium lappaceum L.) seeds using UPLCqTOF-MS/MS and senomorphic effects in aged human dermal fibroblasts. Nutrients 12 (5), 1430. https://doi.org/10.3390/nu12051430.
  • Lee, S., Km, Y.S., Choi, H.K., Cho, S.K., 2011. Determination of the volatile components in the fruits and leaves of guava plants (Psidium guajava L.) grown on Jeju island, South Korea. J. Essent. Oil Res. 23 (6), 52-56. https://doi.org/10.1080/ 10412905.2011.9712282.
  • Liu, J., Jiang, L.-R., Liu, M.-F., 2016. Unusual meroterpenoids from leaves of Psidium guajava. Chem. Nat. Compd. 51 (1), 37-70. https://doi.org/10.1007/s10600-016- 1548-0.
  • Oh, W.K., Lee, C.H., Lee, M.S., Bae, E.Y., Sohn, C.B., Oh, H., Kim, B.Y., Ahn, J.S., 2005. Antidiabetic effects of extracts from Psidium guajava. J. Ethnopharmacol. 96 (3), 411-415. https://doi.org/10.1016/j.jep.2004.09.041.
  • Okuda, T., Yoshida, T., Hatano, T., Yazaki, K., Ikegami, Y., Shingu, T., 1987. Guavins A, C and D, complex tannins from Psidium guajava. Chem. Pharm. Bull. 35 (1), 443-446. https://doi.org/10.1248/cpb.35.443.
  • L, S. d. M. Paz, W.H.P., de Oliveira, R.N., Heerdt, G., Angolini, C.F.F., Silva, V.R., Santos, L.S., Soares, M.B.P., Bezerra, D.P., Morgon, N.H., Almeida, J., da Silva, F.M. A., Costa, E.V., Koolen, H.H.F., 2019. Structure-based molecular networking for the target discovery of oxahomoaporphine and 8-oxohomoaporphine alkaloids from Duguetia surinamensis J. Nat. Prod. 82 (8), 2220-2228. https://doi.org/10.1021/acs. jnatprod.9b00287.
  • Pluskal, T., Castillo, S., Villar-Briones, A., Oresic, M., 2010. MZmine 2: modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data. Bmc Bioinformatics 11, 395. https://doi.org/10.1186/1471- 2105-11-395.
  • Prabu, G.R., Gnanamani, A., Sadulla, S., 2006. Guaijaverin - a plant flavonoid as potential antiplaque agent against Streptococcus mutans. J. Appl. Microbiol. 101 (2), 487-495. https://doi.org/10.1111/j.1365-2672.2006.02912.x.
  • Saltiel, A.R., Kahn, C.R., 2001. Insulin signalling and the regulation of glucose and lipid metabolism. Nature 414 (6865), 799-806. https://doi.org/10.1038/414799a.
  • Shen, S.C., Cheng, F.C., Wu, N.J., 2008. Effect of guava (Psidium guajava Linn.) leaf soluble solids on glucose metabolism in type 2 diabetic rats. Phytother. Res. 22 (11), 1458-1464. https://doi.org/10.1002/ptr.2476.
  • Tang, G.H., Dong, Z., Guo, Y.Q., Cheng, Z.B., Zhou, C.J., Yin, S., 2017. Psiguajadials A-K: unusual psidium meroterpenoids as phosphodiesterase-4 inhibitors from the leaves of Psidium guajava. Sci. Rep. 7 (1), 1047. https://doi.org/10.1038/s41598-017- 01028-4.
  • Ukwueze, S.E., Osadebe, P.O., Okoye, F.B., 2015. A new antibacterial benzophenone glycoside from Psidium guajava (Linn.) leaves. Nat. Prod. Res. 29 (18), 1728-1734. https://doi.org/10.1080/14786419.2014.1003188.
  • Wang, L., Liu, Y., Luo, Y., Huang, K., Wu, Z., 2018. Quickly screening for potential alphaglucosidase inhibitors from guava leaves tea by bioaffinity ultrafiltration coupled with HPLC-ESI-TOF/MS method. J. Agr. Food Chem. 66 (6), 1576-1582. https://doi. org/10.1021/acs.jafc.7b05280.
  • Wang, M.X., Carver, J.J., Phelan, V.V., Sanchez, L.M., Garg, N., Peng, Y., Nguyen, D.D., Watrous, J., Kapono, C.A., Luzzatto-Knaan, T., Porto, C., Bouslimani, A., Melnik, A. V., Meehan, M.J., Liu, W.T., Criisemann, M., Boudreau, P.D., Esquenazi, E., Sandoval-Calderon, M., Kersten, R.D., Pace, L.A., Quinn, R.A., Duncan, K.R., Hsu, C. C., Floros, D.J., Gavilan, R.G., Kleigrewe, K., Northen, T., Dutton, R.J., Parrot, D., Carlson, E.E., Aigle, B., Michelsen, C.F., Jelsbak, L., Sohlenkamp, C., Pevzner, P., Edlund, A., McLean, J., Piel, J., Murphy, B.T., Gerwick, L., Liaw, C.C., Yang, Y.L., Humpf, H.U., Maansson, M., Keyzers, R.A., Sims, A.C., Johnson, A.R., Sidebottom, A. M., Sedio, B.E., Klitgaard, A., Larson, C.B., Boya, C.A., Torres-Mendoza, D., Gonzalez, D.J., Silva, D.B., Marques, L.M., Demarque, D.P., Pociute, E., O' Neill, E.C., Briand, E., Helfrich, E.J.N., Granatosky, E.A., Glukhov, E., Ryffel, F., Houson, H., Mohimani, H., Kharbush, J.J., Zeng, Y., Vorholt, J.A., Kurita, K.L., Charusanti, P., McPhail, K.L., Nielsen, K.F., Vuong, L., Elfeki, M., Traxler, M.F., Engene, N., Koyama, N., Vining, O.B., Baric, R., Silva, R.R., Mascuch, S.J., Tomasi, S., Jenkins, S., Macherla, V., Hoffman, T., Agarwal, V., Williams, P.G., Dai, J.Q., Neupane, R., Gurr, J., Rodriguez, A.M.C., Lamsa, A., Zhang, C., Dorrestein, K., Duggan, B.M., Almaliti, J., Allard, P.M., Phapale, P., Nothias, L.F., Alexandrovr, T., Litaudon, M., Wolfender, J.L., Kyle, J.E., Metz, T.O., Peryea, T., Nguyen, D.T., VanLeer, D., Shinn, P., Jadhav, A., Muller, R., Waters, K.M., Shi, W.Y., Liu, X.T., Zhang, L.X., Knight, R., Jensen, P.R., Palsson, B.O., Pogliano, K., Linington, R.G., Gutierrez, M., Lopes, N.P., Gerwick, W.H., Moore, B.S., Dorrestein, P.C., Bandeira, N., 2016.
  • Yang, J.L., Ha, T.K.Q., Lee, B.W., Kim, J., Oh, W.K., 2017. PTP1B inhibitors from the seeds of Iris sanguinea and their insulin mimetic activities via AMPK and ACC phosphorylation. Bioorg Med Chem Lett 27 (22), 5076-5081. https://doi.org/ 10.1016/j.bmcl.2017.09.031.
  • Yang, J.Y., Sanchez, L.M., Rath, C.M., Liu, X., Boudreau, P.D., Bruns, N., Glukhov, E., Wodtke, A., de Felicio, R., Fenner, A., Wong, W.R., Linington, R.G., Zhang, L., Debonsi, H.M., Gerwick, W.H., Dorrestein, P.C., 2013. Molecular networking as a dereplication strategy. J. Nat. Prod. 76 (9), 1686-1699. https://doi.org/10.1021/ np400413s.
  • Yang, X.L., Hsieh, K.L., Liu, J.K., 2007. Guajadial: an unusual meroterpenoid from guava leaves Psidium guajava. Org. Lett. 9 (24), 5135-5138. https://doi.org/10.1021/ ol702537q.
  • Yang, X.W., Li, Y.P., Su, J., Ma, W.G., Xu, G., 2016. Hyperjapones A-E, terpenoid polymethylated acylphloroglucinols from Hypericum japonicum. Org. Lett. 18 (8), 1876-1879. https://doi.org/10.1021/acs.orglett.6b00650.