Published June 30, 2021
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Antifeedant, cytotoxic, and anti-inflammatory neo-clerodane diterpenoids in the peltate glandular trichomes and fresh leaves of Ajuga forrestii
- 1. ** & * & State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, & University of Chinese Academy of Sciences, Beijing, 100049, PR China
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Wang, Ying, Liu, Yan-Chun, Li, Wen-Yuan, Guo, Kai, Liu, Yan, Li, Sheng-Hong (2021): Antifeedant, cytotoxic, and anti-inflammatory neo-clerodane diterpenoids in the peltate glandular trichomes and fresh leaves of Ajuga forrestii. Phytochemistry (112731) 186: 1-9, DOI: 10.1016/j.phytochem.2021.112731, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112731
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References
- Amano, T., Nishida, R., Kuwahara, Y., 1997. Ajugatakasins A and B, new diterpenoids from Ajuga decumbens, and feeding stimulative activity of related neoclerodane analogs toward the turnip sawfly. Biosci. Biotechnol. Biochem. 61, 1518-1522. https://doi.org/10.1271/bbb.61.1518.
- Ambr´osio, S.R., Oki, Y., Heleno, V.C.G., Chaves, J.S., Nascimento, P.G.B.D., Lichston, J. E., Constantino, M.G., Varanda, E.M., Costa, F.B.D., 2008. Constituents of glandular trichomes of Tithonia diversifolia: relationships to herbivory and antifeedant activity. Phytochemistry 69, 2052-2060. https://doi.org/10.1016/j. phytochem.2008.03.019.
- Andersen-Ranberg, J., Kongstad, K.T., Nielsen, M.T., Jensen, N.B., Pateraki, I., Bach, S.S., Hamberger, B., Zerbe, P., Staerk, D., Bohlmann, J., Moller, B.L., Hamberger, B., 2016. Expanding the landscape of diterpene structural diversity through stereochemically controlled combinatorial biosynthesis. Angew. Chem. Int. Ed. 55, 2142-2146. https://doi.org/10.1002/ange.201510650.
- Casteel, D.A., 1992. Peroxy natural products. Nat. Prod. Rep. 9, 289-312. https://doi. org/10.1039/NP9920900289.
- Chen, T., Diao, Q.Y., Yu, H.Z., Jiao, C.L., Ruan, J., 2018. Phytochemical, cytotoxic and chemotaxonomic study on Ajuga forrestii Diels (Labiatae). Nat. Prod. Res. 32, 977-981. https://doi.org/10.1080/14786419.2017.1371161.
- Chen, X.Y., Berim, A., Dayan, F.E., Gang, D.R., 2017. A (-)-kolavenyl diphosphate synthase catalyzes the first step of salvinorin A biosynthesis in Salvia divinorum. J. Exp. Bot. 68, 1109-1122 doi: org/10.1093/jxb/erw493.
- Coll, J., Tandron ´, Y.A., 2006. Isolation and identification of neo -clerodane diterpenes from Ajuga nipponensis Makino. Nat. Prod. Commun. 1, 183-189. https://doi.org/ 10.1177/1934578X0600100302.
- Corea, G., Fattorusso, C., Fattorusso, E., Lanzotti, V., 2005. Amygdaloidins A-L, twelve new 13 α- OH jatrophane diterpenes from Euphorbia amygdaloides L. Tetrahedron 61, 4485-4494. https://doi.org/10.1016/j.tet.2005.02.031.
- Fan, G., Zhi, D., Ren, H., Li, Z., Hu, Q., Liu, Y., Zhang, Z., Fei, D., 2016. A New succinate derivative from Ajuga decumbens. Nat. Prod. Commun. 11, 497-498. https://doi.org/ 10.1177/1934578X1601100420.
- Gershenzon, J., Mabry, T.J., 1984. Sesquiterpene lactones from a Texas population of Helianthus maximiliani. Phytochemistry 23, 1959-1966. https://doi.org/10.1016/ S0031-9422(00)84950-X.
- Guo, P., Li, Y., Jin, D., Xu, J., He, Y., Zhang, L., Guo, Y., 2012. Neo -clerodane diterpenes from Ajuga ciliata and their inhibitory activities on LPS-induced NO production. Phytochem. Lett. 83, 1409-1414. https://doi.org/10.1016/j.phytol.2012.05.014.
- Guo, P., Li, Y., Xu, J., Liu, C.Z., Ma, Y.G., Guo, Y.Q., 2011. Bioactive neo -clerodane diterpenoids from the whole plants of Ajuga ciliata Bunge. J. Nat. Prod. 74, 1575-1583. https://doi.org/10.1021/np2001557.
- Happyana, N., Agnolet, S., Muntendam, R., Van Dam, A., Schneider, B., Kayser, O., 2013. Analysis of cannabinoids in laser-microdissected trichomes of medicinal Cannabis sativa using LCMS and cryogenic NMR. Phytochemistry 87, 51-59. https://doi.org/ 10.1016/j.phytochem.2012.11.001.
- He, G.X., Liang, X.L., Ouyang, W., Yi, G.Q., Li, Y.Y., Zhao, J.P., Ikhlas, K., 2013. Chemical constituents from Ajuga nipponensis. J. Chin. Med. Mater. 36, 1950-1953. https:// doi.org/10.13863/j.issn1001-4454.2013.12.026.
- Herz, W., Kumar, N., Blount, J.F., 1980. A thiol-containing ester side chain in a sesquiterpene lactone from Eupatorium mikanioides. Absolute configuration of deacetyleupaserrin and its congeners. J. Org. Chem. 45, 489-493. https://doi.org/ 10.1021/jo01291a023.
- Hsu, W.H., Lin, B.Z., Leu, J.D., Lo, P.H., Yu, H.Y., Chen, C.T., Tu, Y.H., Lin, Y.L., Lee, Y.J., 2020. Involvement of 8-O-acetylharpagide for Ajuga taiwanensis mediated suppression of senescent phenotypes in human dermal fibroblasts. Sci. Rep. 10, 19731. https://doi.org/10.1038/s41598-020-76797-6.
- Israili, Z.H., Lyoussi, B., 2009. Ethnopharmacology of the plants of genus Ajuga. Pak. J. Pharm. Sci. 22, 425-462.
- Johnson, M.A., Croteau, R., 1984. Biosynthesis of ascaridole: iodide peroxidase-catalyzed synthesis of a monoterpene endoperoxide in soluble extracts of Chenopodium ambrosioides fruit, 235, 254-966. https://doi.org/10.1016/0003-9861(84)90274-1.
- Li, C.H., Liu, Y., Hua, J., Luo, S.H., Li, S.H., 2014. Peltate glandular trichomes of Colquhounia seguinii harbor new defensive clerodane diterpenoids. J. Integr. Plant Biol. 56, 928-940. https://doi.org/10.1111/jipb.12242.
- Liu, D.Z., Liu, J.K., 2013. Peroxy natural products. Nat. Prod. Bioprospect. 3, 161-206. https://doi.org/10.1007/s13659-013-0042-7.
- Liu, W., Song, Z., Wang, H., Yang, X., Guo, Y., 2020. Diterpenoids as potential anti-inflammatory agents from Ajuga pantantha. Bioorg. Chem. 101, 103966. https://doi. org/10.1016/j.bioorg.2020.103966.
- Liu, Y., Jing, S.X., Luo, S.H., Li, S.H., 2019. Non-volatile natural products in plant glandular trichomes: chemistry, biological activities and biosynthesis. Nat. Prod. Rep. 36, 626-665. https://doi.org/10.1039/C8NP00077H.
- Lu, X., Zhang, L., Zhang, F., Jiang, W., Shen, Q., Zhang, L., Lv, Z., Wang, G., Tang, K.X., 2013. AaORA, a trichome-specific AP2/ERF transcription factor of Artemisia annua, is a positive regulator in the artemisinin biosynthetic pathway and in disease resistance to B otrytis cinerea. New Phytol. 198, 1191-1202. https://doi.org/ 10.1111/nph.12207.
- Luan, F., Han, K., Li, M., Zhang, T., Liu, D., Yu, L., Lv, H., 2019. Ethnomedicinal uses, phytochemistry, pharmacology, and toxicology of species from the genus Ajuga L.: a systematic review. Am. J. Chin. Med. 47, 959-1003. https://doi.org/10.1142/ S0192415X19500502.
- Luo, S.H., Luo, Q., Niu, X.M., Xie, M.J., Zhao, X., Schneider, B., Gershenzon, J., Li, S.H., 2010. Glandular trichomes of Leucosceptrum canum harbor defensive sesterterpenoids. Angew. Chem. Int. Ed. 49, 4471-4475. https://doi.org/10.1002/ ange.201000449.
- Min, Z., Wang, S., Zheng, Q., Wu, B., Mizuno, M., Tanaka, T., Inuma, M., 1989. Four new insect antifeedant neo -clerodane diterpenoids, ajugacumbins A,B,C and D, from Ajuga decumbens. Chem. Pharm. Bull. 37, 2505-2508. https://doi.org/10.1248/ cpb.37.2505.
- Ni, B., Dong, X., Fu, J., Yin, X., Lin, L., Xia, Z., Zhao, Y., Xue, D., Yang, C., Ni, J., 2015. Phytochemical and biological properties of Ajuga decumbens (Labiatae): a review. Trop. J. Pharmaceut. Res. 14, 1525-1536. https://doi.org/10.4314/tjpr.v14i8.28.
- Norris, M.D., Perkins, M.V., 2016. Structural diversity and chemical synthesis of peroxide and peroxide-derived polyketide metabolites from marine sponges. Nat. Prod. Rep. 33, 861-880. https://doi.org/10.1039/C5NP00142K.
- Ono, M., Furusawa, C., Ozono, T., Oda, K., Yasuda, S., Okawa, M., Kinjo, J., Ikeda, T., Miyashita, H., Yoshimitsu, H., 2011. Four new iridoid glucosides from Ajuga reptans. Chem. Pharm. Bull. 59, 1065-1068. https://doi.org/10.1248/cpb.59.1065.
- Peters, R.J., 2010. Two rings in them all: the labdane-related diterpenoids. Nat. Prod. Rep. 27, 1521-1530. https://doi.org/10.1039/c0np00019a.
- Qing, X., Yan, H.M., Ni, Z.Y., Vavricka, C.J., Zhang, M.L., Shi, Q.W., Gu, Y.C., Kiyota, H., 2017. Chemical and pharmacological research on the plants from genus Ajuga. Heterocycl. Commun. 23, 245-268. https://doi.org/10.1515/hc-2017-0064.
- Ramanandraibe, V., Martin, M.T., Rakotondramanana, D.L., Mambu, L., Ramanitrahasimbola, D., Labaied, M., Grellier, P., Rasoanaivo, P., Frappier, F., 2005. Pseudoguanolide sesquiterpene lactones from Vernoniopsis caudata and their in vitro antiplasmodial activities. J. Nat. Prod. 68, 800-803. https://doi.org/10.1021/ np0401866.
- Ravindranath, N., Ramesh, C., Kishore, K.H., Murty, U.S., Das, B., 2003. Clerodendrone, a novel hydroquinone diterpenoid from Clerodendrum indicum. J. Chem. Res. 2003, 440-441. https://doi.org/10.3184/030823403103174452.
- Riaz, N., Nawaz, S.A., Mukhtar, N., Malik, A., Chaudhary, M.I., 2007. Isolation and enzyme-inhibition studies of the chemical constituents from Ajuga bracteosa. Chem. Biodivers. 4, 72-83. https://doi.org/10.1002/cbdv.200790008.
- Scheerer, J.R., Lawrence, J.F., Wang, G.C., Evans, D.A., 2007. Asymmetric synthesis of salvinorin A, a potent κ opioid receptor agonist. J. Am. Chem. Soc. 129, 8968-8969. https://doi.org/10.1021/ja073590a.
- Senel, Gulcan, Akcin, Oznur, Ergen, Ozyurt, Sabri, M., 2011. Petiole anatomy of some lamiaceae taxa. Pakistan J. Bot. 43, 1437-1443.
- Shimomura, H., Sashida, Y., Ogawa, K., 1989a. Neo -clerodane diterpenes from Ajuga ciliata var. villosior. Chem. Pharm. Bull. 37, 988-992. https://doi.org/10.1248/ cpb.37.988.
- Shimomura, H., Sashida, Y., Ogawa, K., 1989b. Neo -clerodane diterpenes from Ajuga nipponensis. Chem. Pharm. Bull. 37, 354-357. https://doi.org/10.1248/cpb.37.354.
- Shimomura, H., Sashida, Y., Ogawa, K., 1989c. Neo -clerodane diterpenes from Ajuga decumbens. Chem. Pharm. Bull. 37, 996-998. https://doi.org/10.1248/cpb.37.996.
- Shikishima, Y., Takaishi, Y., Honda, G., Ito, M., Takeda, Y., Tori, M., Takaoka, S., Kodzhimatov, O.K., Ashurmetov, O., 2002. Sesquiterpenes from Ferula penninervis. J. Nat. Prod. 65, 1897-1903. https://doi.org/10.1021/np020014d.
- Venditti, A., Frezza, C., Maggi, F., Lupidi, G., Bramucci, M., Quassinti, L., Giuliani, C., Cianfaglione, K., Papa, F., Serafini, M., Bianco, A., 2016. Phytochemistry, micromorphology and bioactivities of Ajuga chamaepitys (L.) Schreb. (Lamiaceae, Ajugoideae): two new harpagide derivatives and an unusual iridoid glycosides pattern. Fitoterapia 113, 35-43. https://doi.org/10.1016/j.fitote.2016.06.016.
- Wang, A.G., Lu, Y., Feng, X.Z., 1994. Chemical constituents of Ajuga forrestii Diels. Acta Pharm. Sin. 29, 899-904. https://doi.org/10.16438/j.0513-4870.1994.12.004.
- Wang, H.J., Teng, X.F., Zhang, Y.T., Gu, Q., He, L., 2020. Diterpenoids from the whole plants of Ajuga nipponensis and their inhibition of rankl-induced osteoclastogenesis. Chem. Biodivers. 18, e2000780 https://doi.org/10.1002/cbdv.202000780.
- Wu, Z.Y., Li, X.W., 2005. Flora of China, pp. 72-73.
- Xie, Z., Fan, C., Zhu, Z., 2014. The Compilation of Chinese Herbal Medicines,
- Xiong, Y., Qu, W., Sun, J.B., Wang, M.H., Liang, J.Y., 2013. Eudesmane sesquiterpenoid lactones and abietane diterpenoids from Ajuga forrestii Diels. Phytochem. Lett. 6, 457-460. https://doi.org/10.1016/j.phytol.2013.05.017.