Biodiversity Literature Repository

Submit to community
Liberated Data
Published June 30, 2020 | Version v1
Journal article Restricted

Kadanguslactones A-E, further oxygenated terpenoids from Kadsura angustifolia fermented by a symbiotic endophytic fungus, Penicillium ochrochloron SWUKD4.1850

Description

Qin, Dan, Shen, Weiyun, Gao, Tiancong, Zuo, Shihao, Song, Hongchuan, Xu, Jieru, Yu, Baohong, Peng, Yajun, Guo, Jiali, Tang, Wenwen, Dong, Jinyan (2020): Kadanguslactones A-E, further oxygenated terpenoids from Kadsura angustifolia fermented by a symbiotic endophytic fungus, Penicillium ochrochloron SWUKD4.1850. Phytochemistry (112335) 174: 1-10, DOI: 10.1016/j.phytochem.2020.112335, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112335

Files

Restricted

The record is publicly accessible, but files are restricted. Log in to check if you have access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:7D5AFFA9FB77C7620D37D5786317EF65

Has part
Figure: 10.5281/zenodo.8294835 (DOI)
Figure: 10.5281/zenodo.8294837 (DOI)
Figure: 10.5281/zenodo.8294839 (DOI)
Figure: 10.5281/zenodo.8294843 (DOI)
Figure: 10.5281/zenodo.8294845 (DOI)
Figure: 10.5281/zenodo.8294847 (DOI)
Figure: 10.5281/zenodo.8294849 (DOI)

References

  • Aly, A.H., Debbab, A., Proksch, P., 2011. Fungal endophytes: unique plant inhabitants with great promises. Appl. Micribiol. Biotechnol. 90, 1829-1845.
  • Borges, W.S., Borges, K.B., Bonato, P.S., Said, S., Pupo, M.T., 2009. Endophytic fungi: natural products, enzymes and biotransformation reactions. Curr. Org. Chem. 13, 1137-1163.
  • Cui, J.L., Zhang, Y.Y., Vijayakumar, V., Zhang, G., Wang, M.L., Wang, J.H., 2018. Secondary metabolite accumulation associates with ecological succession of endophytic fungi in Cynomorium songaricum rupr. J. Agric. Food Chem. 66, 5499-5509.
  • Dong, J.Y., Chen, Y.G., Song, H.C., Zhu, Y.H., Zhou, Y.P., Li, L., He, Y.P., Cao, J., Zhang, K.Q., 2007. Hydroxylation of the triterpenoid nigranoic acid by the fungus Gliocladium roseum YMF1.00133. Chem. Biodivers. 4, 112-117.
  • Gao, X.M., Pu, J.X., Huang, S.X., Lu, Y., Lou, L.G., Li, R.T., Xiao, W.L., Chang, Y., Sun, H.D., 2008. Kadcoccilactones A-J, triterpenoids from Kadsura coccinea. J. Nat. Prod. 71, 1182-1188.
  • Hayashi, N., Ujihara, T., 2017. Conformations of Flavan-3-ols in water: analysis using density functional theory. J. Nat. Prod. 80, 319-327.
  • He, F., Pu, J.X., Huang, S.X., Wang, Y.Y., Xiao, W.L., Li, L.M., Liu, J.P., Zhang, H.B., Li, Y., Sun, H.D., 2010. Schinalactone A, a new cytotoxic triterpenoid from Schisandra sphenanthera. Org. Lett. 12, 1208-1211.
  • He, F., Li, X.Y., Yang, G.Y., Li, X.N., Luo, X., Zou, J., Li, Y., Xiao, W.L., Sun, H.D., 2012. Nortriterpene constituents from Schisandra sphenanthera. Tetrahedron 68, 440-446.
  • Huang, Q., An, H.M., Song, H.C., Mao, H.Q., Shen, W.Y., Dong, J.Y., 2015. Diversity and biotransformative potential of endophytic fungi associated with the medicinal plant Kadsura angustifolia. Res. Microbiol. 166, 45-55.
  • Huang, S.X., Han, Q.B., Lei, C., Pu, J.X., Xiao, W.L., Yu, J.L., Yang, L.M., Xu, H.X., Zheng, Y.T., Sun, H.D., 2008. Isolation and characterization of miscellaneous terpenoids of Schisandra chinensis. Tetrahedron 64, 4260-4267.
  • Huang, S.X., Yang, L.B., Xiao, W.L., Lei, C., Liu, J.P., Lu, Y., Weng, Z.Y., Li, L.M., Li, R.T., Yu, J.L., Zheng, Q.T., Sun, H.D., 2007. Wuweizidilactones A-F: novel highly oxygenated nortriterpenoids with unusual skeletons isolated from Schisandra chinensis. Chem. Eur J. 13, 4816-4822.
  • Jia, M., Chen, L., Xin, H.L., Zheng, C.J., Rahman, K., Han, T., Qin, L.P., 2016. A friendly relationship between endophytic fungi and medicinal plants: a systematic review. Front. Microbiol. 7, 906.
  • Kharwar, R.N., Mishra, A., Gond, S.K., Stierle, A., Stierle, D., 2011. Conformations of Flavan-3-ols in water: analysis using density functional theory. Nat. Prod. Rep. 28, 1208-1228.
  • Kim, H.M., Ryu, B., Lee, J.S., Choi, J.B., Jang, D.S., 2015. Schisandrosides A-D, dibenzocyclooctadiene lignan glucosides from the roots of Schisandra chinensis. Chem. Pharmaceut. Bull. 63, 746-751.
  • Lee, H.S., Kim, M.R., Park, Y., Park, H.J., Chang, U.J., Kim, S.Y., Suh, H.J., 2012. Ermenting red ginseng enhances its safety and efficacy as a novel skin care anti-aging ingredient: in vitro and animal study. J. Med. Food 15, 1015-1023.
  • Lei, C., Huang, S.X., Xiao, W.L., Ma, Y.B., Chen, J.J., Pu, J.X., Sun, H.D., 2010. Bisnortriterpenoids possessing an 18-nor-schiartane skeleton from Schisandra propinqua var. propinqua. Planta Med. 76, 1611-1615.
  • Lei, C., Pu, J.X., Huang, S.X., Chen, J.J., Liu, J.P., Yang, L.B., Ma, Y.B., Xiao, W.L., Li, X.N., Sun, H.D., 2009. A class of 18 (13→14)-abeo-schiartane skeleton nortriterpenoids from Schisandra propinqua var. propinqua. Tetrahedron 65, 164-170.
  • Li, R.T., Han, Q.B., Zheng, Y.T., Wang, R.R., Yang, L.M., Lu, Y., Sang, S.Q., Zheng, Q.T., Zhao, Q.S., Sun, H.D., 2005. Structure and anti-HIV activity of micrandilactones B and C, new nortriterpenoids possessing a unique skeleton from Schisandra micrantha. Chem. Commun. 23, 2936-2938.
  • Li, R.T., Xiang, W., Li, S.H., Lin, Z.W., Sun, H.D., 2004. Lancifodilactones B-E, new nortriterpenes from Schisandra lancifolia. J. Nat. Prod. 67, 94-97.
  • Miyake, Y., Fukumoto, S., Okada, M., Sakaida, K., Nakamura, Y., Osawa, T., 2005. Antioxidative catechol lignans converted from sesamin and sesaminol triglucoside by culturing with Aspergillus. J. Agric. Food Chem. 53, 22-27.
  • Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paull, K., Vistica, D., 1991. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J. Natl. Cancer Inst. 83, 757-766.
  • Nakano, D., Kwak, C.J., Fujii, K., Ikemura, K., Satake, A., Ohkita, M., 2006. Sesamin metabolites induce an endothelial nitric oxide-dependent vasorelaxation through their antioxidative property-independent mechanisms: possible involvement of the metabolites in the antihypertensive effect of sesamin. J. Pharmacol. Exp. Therapeut. 318, 328-335.
  • Peng, W., Ding, F., Jiang, Y.T., Peng, Y.K., 2014. Bioavailability and activity of natural food additive triterpenoids as influenced by protein. J. Agric. Food Chem. 62, 2271-2283.
  • Petrini, O., 1991. In: Andrews, J., Hirano, S. (Eds.), Microbial Ecology of Leaves. Springer- Verlag, New York, pp. 179-497.
  • Pimentel, M.R., Molina, G., Dionisio, A.P., Marostica Junior, M.R., Pastore, G.M., 2010. The use of endophytes to obtain bioactive compounds and their application in biotransformation process. Biotechnol. Res. Int. 2011 576286.
  • Prado, S., Li, Y.Y., Nay, B., 2012. In: Atta-ur-Rahman (Ed.), Studies in Natural Products Chemistry. Elsevier, The Netherlands, pp. 249-296.
  • Qin, D., Shen, W.Y., Wang, J.Q., Han, M.J., Chai, F.N., Duan, X.X., Yan, X., Guo, J.L., Gao, T.C., Zuo, S.H., Dong, J.Y., 2019. Enhanced production of unusual triterpenoids from Kadsura angustifolia fermented by a symbiont endophytic fungus, Penicillium s p. SWUKD4.1850. Phytochemistry 158, 56-66.
  • Shi, Y.M., Xiao, W.L., Pu, J.X., Sun, H.D., 2015. Triterpenoids from the Schisandraceae family: an update. Nat. Prod. Rep. 32, 367-410.
  • Shen, Y.C., Lin, Y.C., Chiang, M.Y., Sheau, F.Y., Cheng, Y.B., Liao, C.C., 2005. Kadsuphilactones A and B, two new triterpene dilactones from Kadsura philippinensis. Org. Lett. 7, 3307-3310.
  • Song, Q.Y., Jiang, K., Zhao, Q.Q., Gao, K., Jin, X.J., Yao, X.J., 2013. Eleven new highly oxygenated triterpenoids from the leaves and stems of Schisandra chinensis. Org. Biomol. Chem. 11, 1251-1258.
  • Sun, H.D., Qiu, S.X., Lin, L.Z., Wang, Z.Y., Lin, Z.W., Pengsuparp, T., 1996. Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase. J. Nat. Prod. 59, 525-527.
  • Sun, R., Song, H.C., Wang, C.R., Shen, K.Z., Xu, Y.B., Gao, Y.X., 2011. Compounds from Kadsura angustifolia with anti-HIV activity. Bioorg. Med. Chem. Lett 21, 961-965.
  • Wang, L., Qin, D., Zhang, K., Huang, Q., Liu, S., Han, M.J., Dong, J.Y., 2017. Metabolites from the co-culture of nigranoic acid and Umbelopsis dimorpha SWUKD3. 1410, an endophytic fungus from Kadsura angustifolia. Nat. Prod. Res. 31, 1414-1421.
  • Wu, T., Wang, N., Zhang, Y., Xu, X., 2013. Advances in the study on microbial fermentation and transformation of traditional Chinese medicine. Afr. J. Microbiol. Res. 7, 1644-1650.
  • Xia, Y.G., Yang, B.Y., Kuang, H.X., 2015. Schisandraceae triterpenoids: a review. Phytochemistry Rev. 14, 155-187.
  • Xiao, W.L., Li, R.T., Huang, S.X., Pu, J.X., Sun, H.D., 2008. Triterpenoids from the Schisandraceae family. Nat. Prod. Rep. 25, 871-891.
  • Xiao, W.L., Wu, Y.L., Shang, S.Z., He, F., Luo, X., Yang, G.Y., Pu, J.X., Chen, G.Q., Sun, H.D., 2010b. Four new nortriterpenoids from Schisandra lancifolia. Helv. Chim. Acta 93, 1975-1981.
  • Xiao, W.L., Yang, S.Y., Yang, L.M., Yang, G.Y., Wang, R.R., Zhang, H.B., Zhao, W., Pu, J.X., Lu, Y., Zheng, Y.T., Sun, H.D., 2010a. Chemical constituents from the leaves and stems of Schisandra rubriflora. J. Nat. Prod. 73, 221-225.
  • Xue, Y.B., Yang, J.H., Li, X.N., Du, X., Pu, J.X., Xiao, W.L., 2011. Henrischinins A-C: three new triterpenoids from Schisandra henryi. Org. Lett. 13, 1564-1567.
  • Yang, Y.H., Sun, R., Song, H.C., Xu, Y.B., Yang, P., Dong, Y.Y., Shen, Z.K., Wang, A.R., Chen, Y.G., Dong, J.Y., 2012. Microbial transformation of the triterpene nigranoic acid in Trichoderma sp. Phytochem. Lett. 5, 123-127.
  • Zhang, J.P., Wang, G.W., Tian, X.H., Yang, Y.X., Liu, Q.X., Chen, L.P., Li, H.L., Zhang, W.D., 2015. The genus Carpesium: a review of its ethnopharmacology, phytochemistry and pharmacology. J. Ethnopharmacol. 163, 173-191.
  • Zhang, S., Won, Y.K., Ong, C.N., Shen, H.M., 2005. Anti-cancer potential of sesquiterpene lactones: bioactivity and molecular mechanisms. Curr. Med. Chem. 5, 239-249.
  • Zhou, M., Liu, Y., Song, J., Peng, X.G., Cheng, Q., Cao, H., Xiang, M., Ruan, H.L., 2016. Schincalide A, a schinortriterpenoid with a tricyclo [5.2. 1.01, 6] decane-bridged system from the stems and leaves of Schisandra incarnate. Org. Lett. 18, 4558-4561.
  • Zhou, M., Zhang, R.H., Wang, M., Xu, G.B., Liao, S.G., 2017. Prodrugs of triterpenoids and their derivatives. Eur. J. Med. Chem. 131, 222-236.