Biodiversity Literature Repository

Submit to community
Liberated Data
Published January 31, 2020 | Version v1
Journal article Restricted

Phytochemical and biological studies on rare and endangered plants endemic to China. Part XIV. Structurally diverse terpenoids from the twigs and needles of the endangered plant Picea brachytyla

Creators

  • 1. ∗ & Department of Natural Products Chemistry, School of Pharmacy, Fudan University, Shanghai, 201203, PR China

Description

Jiang, Wei, Xiong, Juan, Zang, Yi, Li, Junmin, Osman, Ezzat E.A., Li, Jing-Ya, Zhou, Yu-Bo, Li, Jia, Hu, Jin-Feng (2020): Phytochemical and biological studies on rare and endangered plants endemic to China. Part XIV. Structurally diverse terpenoids from the twigs and needles of the endangered plant Picea brachytyla. Phytochemistry (112161) 169: 1-11, DOI: 10.1016/j.phytochem.2019.112161, URL: http://dx.doi.org/10.1016/j.phytochem.2019.112161

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:FFD1FFF8A922FFEE5A26FF93EF6AFF86

Has part
Figure: 10.5281/zenodo.8293828 (DOI)
Figure: 10.5281/zenodo.8293830 (DOI)
Figure: 10.5281/zenodo.8293832 (DOI)
Figure: 10.5281/zenodo.8293834 (DOI)
Figure: 10.5281/zenodo.8293837 (DOI)
Figure: 10.5281/zenodo.8293839 (DOI)

References

  • Anjaneyulu, V., Satyanarayana, P., Viswanadham, K.N., Jyothi, V.G., Nageswara Rao, K., Padhika, P., 1999. Triterpenoids from Mangifera indica. Phytochemistry 50, 1229-1236.
  • Ayer, W.A., Macaulay, J.B., 1987. Metabolites of the honey mushroom, Armillaria mellea. Can. J. Chem. 65, 7-14.
  • Bleif, S., Hannemann, F., Lisurek, M., von Kries, J.P., Zapp, J., Dietzen, M., Antes, I., Bernhardt, R., 2011. Identification of CYP106A2 as a regioselective allylic bacterial diterpene hydroxylase. Chembiochem 12, 576-582.
  • Bohlmann, F., Zdero, C., Schwarz, H., 1975. Naturally occurring terpene derivatives, XLVII. On a new sesquiterpene from Tanaceturm balsumita L.ssp. balsamitoides (Schultz Bip.) Grierson. Chem. Ber. 108, 1369-1372.
  • Cambie, R.C., Mander, L.N., Bose, A.K., Manhas, M.S., 1964. Rotatory dispersion and circular dichroism studies of some α -tetralones. Tetrahedron 20, 409-416.
  • Cheung, H.T.A., Miyase, T., Lenguyen, M.P., Smal, M.A., 1993. Further acidic constituents and neutral components of Pinus massoniana resin. Tetrahedron 49, 7903-7915.
  • Chu, K.Y., Lin, Y., Hendel, A., Kulpa, J.E., Brownsey, R.W., Johnson, J.D., 2010. ATPcitrate lyase reduction mediates palmitate-induced apoptosis in pancreatic beta cells. J. Biol. Chem. 285, 32606-32615.
  • Davis, D.C., Hoch, D.G., Wu, L., Abegg, D., Martin, B.S., Zhang, Z.-Y., Adibekian, A., Dai, M., 2018. Total synthesis, biological evaluation, and target identification of rare Abies sesquiterpenoids. J. Am. Chem. Soc. 140, 17465-17473.
  • Deb, D.K., Chen, Y., Sun, J., Wang, Y., Li, Y.C., 2017. ATP-citrate lyase is essential for high glucose-induced histone hyperacetylation and fibrogenic gene up-regulation in mesangial cells. Am. J. Physiol. Renal. Physiol. 313, 423-429.
  • DeFronzo, R.A., Ferrannini, E., Zimmet, P., Alberti, G., 2015. International Textbook of Diabetes Mellitus, fourth ed. Jonh Wiley & Sons, Ltd., Chichester.
  • Dorenkamp, M., Muller, J.P., Shanmuganathan, K.S., Schulten, H., Muller, N., Loffler, I., Muller, U.A., Wolf, G., Bohmer, F.-D., Godfrey, R., Waltenberger, J., 2018. Hyperglycaemia-induced methylglyoxal accumulation potentiates VEGF resistance of diabetic monocytes through the aberrant activation of tyrosine phosphatase SHP-2/ SRC kinase signalling axis. Sci. Rep. 8, 14684.
  • Forster, P.G., Ghisalberti, E.L., Jefferies, P.R., 1985. Labdane diterpenes from an Acacia species. Phytochemistry 24, 2991-2993.
  • Fu, L.-G., Jin, J.-M., 1992. China Plant Red Data Book: Rare and Endangered Plants. Science Press, Beijing and New York.
  • Granchi, C., 2018. ATP citrate lyase (ACLY) inhibitors: an anti-cancer strategy at the crossroads of glucose and lipid metabolism. Eur. J. Med. Chem. 157, 1276-1291.
  • Handa, M., Murata, T., Kobayashi, K., Selenge, E., Miyase, T., Batkhuu, J., Yoshizaki, F., 2013. Lipase inhibitory and LDL anti-oxidative triterpenes from Abies sibirica. Phytochemistry 86, 168-175.
  • Hanson, J.R., 1991. Wagner- Meerwein rearrangements. Comp. Org. Syn. 3, 705-719.
  • Hieda, T., Mikami, Y., Obi, Y., Kisaki, T., 1983. Microbial transformation of the labdanes, cis -abienol and sclareol. Agric. Biol. Chem. 47, 243-250.
  • Hjortness, M.K., Riccardi, L., Hongdusit, A., Ruppe, A., Zhao, M., Kim, E.Y., Zwart, P.H., Sankaran, B., Arthanari, H., Sousa, M.C., De Vivo, M., Fox, J.M., 2018. Abietane-type diterpenoids inhibit protein tyrosine phosphatases by stabilizing an inactive enzyme conformation. Biochemi 57, 5886-5896.
  • Hlubucek, J.R., Aasen, A.J., Almqvist, S.-O., Enzell, C.R., 1974. Synthesis of 14,15-bisnor- 8-hydroxylabd-11E -en-13-one, a new tobacco constituent. Acta Chem. Scand. B 28, 131-132.
  • Hu, C.-L., Xiong, J., Gao, L.-X., Li, J., Zeng, H., Zou, Y., Hu, J.-F., 2016a. Diterpenoids from the shed trunk barks of the endangered plant Pinus dabeshanensis and their PTP1B inhibitory effects. RSC Adv. 6, 60467-60478.
  • Hu, C.-L., Xiong, J., Li, J.-Y., Gao, L.-X., Wang, W.-X., Cheng, K.-J., Yang, G.-X., Li, J., Hu, J.-F., 2016b. Rare sesquiterpenoids from the shed trunk barks of the critically endangered plant Abies beshanzuensis and their bioactivities. Eur. J. Org. Chem. 2016, 1832-1835.
  • Hu, C.-L., Xiong, J., Wang, P.-P., Ma, G.-L., Tang, Y., Yang, G.-X., Li, J., Hu, J.-F., 2017. Diterpenoids from the needles and twigs of the cultivated endangered pine Pinus kwangtungensis and their PTP1B inhibitory effects. Phytochem. Lett. 20, 239-245.
  • Ibrahim, M.A., Na, M., Oh, J., Schinazi, R.F., McBrayer, T.R., Whitaker, T., Doerksen, R.J., Newman, D.J., Zachos, L.G., Hamann, M.T., 2013. Significance of endangered and threatened plant natural products in the control of human disease. Proc. Natl. Acad. Sci. U.S.A. 110, 16832-16837.
  • Karlberg, A.-T., Bohlinder, K., Boman, A., Hacksell, U., Hermansson, J., Jacobsson, S., Nilsson, J.L.G., 1988. Identification of 15-hydroperoxyabietic acid as a contact allergen in Portuguese colophony. J. Pharm. Pharmacol. 40, 42-47.
  • Koerner, S.K., Hanai, J.-I., Bai, S., Jernigan, F.E., Oki, M., Komaba, C., Shuto, E., Sukhatme, V.P., Sun, L., 2017. Design and synthesis of emodin derivatives as novel inhibitors of ATP-citrate lyase. Eur. J. Med. Chem. 126, 920-928.
  • Li, S., Qin, C., Cui, S., Xu, H., Wu, F., Wang, J., Su, M., Fang, X., Li, D., Jiao, Q., Zhang, M., Xia, C., Zhu, L., Wang, R., Li, J., Jiang, H., Zhao, Z., Li, J.-Y., Li, H., 2019. Discovery of a natural-product-derived preclinical candidate for once-weekly treatment of type 2 diabetes. J. Med. Chem. 62, 2348-2361.
  • Lopez-Pujol, J., Zhang, F.-M., Ge, S., 2006. Plant biodiversity in China: richly varied, endangered, and in need of conservation. Biodivers. Conserv. 15, 3983-4026.
  • Machumi, F., Samoylenko, V., Yenesew, A., Derese, S., Midiwo, J.O., Wiggers, F.T., Jacob, M.R., Tekwani, B.L., Khan, S.I., Walker, L.A., Muhammad, I., 2010. Antimicrobial and antiparasitic abietane diterpenoids from the roots of Clerodendrum eriophyllum. Nat. Prod. Commun. 5, 853-858.
  • Matsunami, K., Otsuka, H., Takeda, Y., 2010. Structural revisions of blumenol C glucoside and byzantionoside B. Chem. Pharm. Bull. 58, 438-441.
  • Miyase, T., Ueno, A., Takizawa, N., Kobayashi, H., Oguchi, H., 1987. Studies on the glycosides of Epimedium grandiflorum Morr. var. thunbergianum (Miq.) NAKAI. II. Chem. Pharm. Bull. 35, 3713-3719.
  • Munesada, K., Siddiqui, H.L., Suga, T., 1992. Biologically active labdane-type diterpene glycosides from the root-stalks of Gleichenia japonica. Phytochemistry 31, 1533-1536.
  • Newman, D.J., Cragg, G.M., 2016. Natural products as sources of new drugs from 1981 to 2014. J. Nat. Prod. 79, 629-661.
  • Nguyen, H.X., Nguyen, M.T.T., Nguyen, N.T., Awale, S., 2017. Chemical constituents of propolis from Vietnamese Trigona minor and their antiausterity activity against the PANC-1 human pancreatic cancer cell line. J. Nat. Prod. 80, 2345-2352.
  • Ohmoto, T., Kanatani, K., Yamaguchi, K., 1987. Constituent of pollen. XIII. Constituents of Cedrus deodara loud. (2). Chem. Pharm. Bull. 35, 229-234.
  • Ohtsu, H., Tanaka, R., Matsunaga, S., Tokuda, H., Nishino, H., 1999. Anti-tumor-promoting rearranged abietane diterpenes from the leaves of Larix kaempferi. Planta Med. 65, 664-666.
  • Park, K.-J., Subedi, L., Kim, S.-Y., Lee, K.-R., 2018. Anti-inflammatory terpenoid derivatives from the twigs of Syringa oblata var. dilatata. Phytochem. Lett. 27, 183-186.
  • Paton, D.M., 2017. Bempedoic acid. ATP-citrate lyase inhibitor, AMPK activator, treatment of hypercholesterolemia. Drug Future 42, 201-208.
  • Qiu, Y., Liu, Y., Kang, M., Yi, G., Huang, H., 2013. Spatial and temporal population genetic variation and structure of Nothotsuga longibracteata (Pinaceae), a relic conifer species endemic to subtropical China. Genet. Mol. Biol. 36, 598-607.
  • Raldugin, V.A., Grishko, V.V., Kukina, T.P., Druganov, A.G., Shakirov, M.M., 2005. 18- Succinyloxyabieta-8,11,13-triene as a new component from green shoots of the Siberian fir. Russ. Chem. Bull., Int. Ed. 54, 1747-1748.
  • Ryu, Y.B., Jeong, H.J., Kim, J.H., Kim, Y.M., Park, J.-Y., Kim, D., Naguyen, T.T.H., Park, S.-J., Chang, J.S., Park, K.H., Rho, M.-C., Lee, W.S., 2010. Biflavonoids from Torreya nucifera displaying SARS-CoV 3CL pro inhibition. Bioorg. Med. Chem. 18, 7940-7947.
  • Snatzke, G., 1965. Circular dichroismus-X: modifizierung der octantenregel fur α,β - ungesattigte ketone: cisoide enone, dienone und arylketone. Tetrahedron 21, 439-448.
  • Sun, L., Wang, P., Xu, L., Gao, L., Li, J., Piao, H., 2019. Discovery of 1,3-diphenyl-1H - pyrazole derivatives containing rhodanine-3-alkanoic acid groups as potential PTP1B inhibitors. Bioorg. Med. Chem. Lett 29, 1187-1193.
  • Tanaka, R., Ohtsu, H., Matsunaga, S., 1997. Abietane diterpene acids and other constituents from the leaves of Larix kaempferi. Phytochemistry 46, 1051-1057.
  • Tanaka, R., Wada, S., Kinouchi, Y., Tokuda, H., Matsunaga, S., 2004. A new seco -abietane-type diterpene from the stem bark of Picea glehni. Planta Med. 70, 877-880.
  • The Plant List, 2013. Version 1.1. A working list for all plant species. http://www. theplantlist.org/1.1/browse/G/Pinaceae/, Accessed date: 26 April 2019.
  • Tu, W.-C., Qi, Y.-Y., Ding, L.-F., Yang, H., Liu, J.-X., Peng, L.-Y., Song, L.-D., Gong, X., Wu, X.-D., Zhao, Q.-S., 2019. Diterpenoids and sesquiterpenoids from the stem bark of Metasequoia glyptostroboides. Phytochemistry 161, 86-96.
  • van Beek, T.A., Claassen, F.W., Dorado, J., Godejohann, M., Sierra-Alvarez, R., Wijnberg, J.B.P.A., 2007. Fungal biotransformation products of dehydroabietic acid. J. Nat. Prod. 70, 154-159.
  • Wang, B., Ju, J., He, X.-F., Yuan, T., Yue, J.-M., 2010. Three new terpenoids from Pinus yunnanensis. Helv. Chim. Acta 93, 490-496.
  • Wang, W., Li, X.-C., Ali, Z., Khan, I.A., 2009. Two new C13 nor-isoprenoids from the leaves of Casearia sylvestris. Chem. Pharm. Bull. 57, 636-638.
  • Wang, W.-L., Chen, X.-Y., Gao, Y., Gao, L.-X., Sheng, L., Zhu, J., Xu, L., Ding, Z.-Z., Zhang, C., Li, J.-Y., Li, J., Zhou, Y.-B., 2017. Benzo[c][1,2,5]thiadiazole derivatives: a new class of potent Src homology-2 domain containing protein tyrosine phosphatase-2 (SHP2) inhibitors. Bioorg. Med. Chem. Lett 27, 5154-5157.
  • Wu, L., Li, Y.-L., Li, S.-M., Yang, X.-W., Xia, J.-H., Zhou, L., Zhang, W.-D., 2010. Systematic phytochemical investigation of Abies spectabilis. Chem. Pharm. Bull. 58, 1646-1649.
  • Xiong, J., Hong, Z.-L., Xu, P., Zou, Y. Yu, S.-B., Yang, G.-X., Hu, J.-F., 2016. ent -Abietane diterpenoids with anti-neuroinflammatory activity from the rare Chloranthaceae plant Chloranthus oldhamii. Org. Biomol. Chem. 14, 4678-4689.
  • Xiong, J., Wang, L.-J., Qian, J., Wang, P.-P., Wang, X.-J., Ma, G.-L., Zeng, H., Li, J., Hu, J.- F., 2018. Structurally diverse sesquiterpenoids from the endangered ornamental plant Michelia shiluensis. J. Nat. Prod. 81, 2195-2204.
  • Yang, W., Zhao, W., Xiao, J., Li, R., Zhang, P., Kissimova-Skarbek, K., Schneider, E., Jia, W., Ji, L., Guo, X., Shan, Z., Liu, J., Tian, H., Chen, L., Zhou, Z., Ji, Q., Ge, J., Chen, G., Brown, J., 2012. Medical care and payment for diabetes in China: enormous threat and great opportunity. PLoS One 7, e39513.
  • Yang, X.-W., Feng, L., Li, S.-M., Liu, X.-H., Li, Y.-L., Wu, L., Shen, Y.-H., Tian, J.-M., Zhang, X., Liu, X.-R., Wang, N., Liu, Y., Zhang, W.-D., 2010. Isolation, structure, and bioactivities of abiesadines A-Y, 25 new diterpenes from Abies georgei Orr. Bioorg. Med. Chem. 18, 744-754.
  • Zhao, Q.-Q., Song, Q.-Y., Jiang, K., Li, G.-D., Wei, W.-J., Li, Y., Gao, K., 2015. Spirochensilides A and B, two new rearranged triterpenoids from Abies chensiensis. Org. Lett. 17, 2760-2763.
  • Zheng, W.-J., Fu, L.-G., 1978. Flora of China, vol. 7. Science Press, Beijing, pp. 32-211.
  • Zhu, F., Qin, C., Tao, L., Liu, X., Shi, Z., Ma, X., Jia, J., Tan, Y., Cui, C., Lin, J., Tan, C., Jiang, Y., Chen, Y., 2011. Clustered patterns of species origins of nature-derived drugs and clues for future bioprospecting. Proc. Natl. Acad. Sci. U.S.A. 108, 12943-12948.