Biodiversity Literature Repository

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

Amomutsaokols A-K, diarylheptanoids from Amomum tsao-ko and their α- glucosidase inhibitory activity

Creators

  • 1. ∗ & State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Yunnan Key Laboratory of & ∗ & University of Chinese Academy of Sciences, Beijing, 100049, PR China

Description

He, Xiao-Feng, Wang, Hui-Mei, Geng, Chang-An, Hu, Jing, Zhang, Xue-Mei, Guo, Yuan-Qiang, Chen, Ji-Jun (2020): Amomutsaokols A-K, diarylheptanoids from Amomum tsao-ko and their α- glucosidase inhibitory activity. Phytochemistry (112418) 177: 1-10, DOI: 10.1016/j.phytochem.2020.112418, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112418

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:FFA27C62FFB1FFEFD1159D37821BC534

Related works

Has part
Figure: 10.5281/zenodo.8296158 (DOI)
Figure: 10.5281/zenodo.8296162 (DOI)
Figure: 10.5281/zenodo.8296164 (DOI)
Figure: 10.5281/zenodo.8296166 (DOI)

References

  • Akiyama, K., Kikuzaki, H., Aoki, T., Okuda, A., Lajis, N.H., Nakatani, N., 2006. Terpenoids and a diarylheptanoid from Zingiber ottensii. J. Nat. Prod. 69, 1637-1640.
  • Alberti, A., Riethmuller, E., Beni, S., 2018. Characterization of diphenylheptanoids: an emerging class of bioactive natural products. J. Pharmaceut. Biomed. 147, 13-34.
  • Alegrio, L.V., Braz-Filho, R., Gottlieb, O.R., 1989. Diarylheptanoids and isoflavonoids from Centrolobium species. Phytochemistry 28, 2359-2362.
  • Ali, M.S., Tezuka, Y., Awale, S., Banskota, A.H., Kadota, S., 2001a. Six new diarylheptanoids from the seeds of Alpinia blepharocalyx. J. Nat. Prod. 64 (3), 289-293.
  • Ali, M.S., Tezuka, Y., Banskota, A.H., Kadota, S., 2001b. Blepharocalyxins C-E, three new dimeric diphenylheptanoids, and related compounds from the seeds of Alpinia blepharocalyx. J. Nat. Prod. 64 (4), 491-496.
  • Bruhn, T., Schaumloffel, A., Hemberger, Y., Bringmann, G., 2014. SpecDis, Version 1.62. University of Wuerzburg, Germany.
  • Changtam, C., de Koning, H.P., Ibrahim, H., Sajid, M.S., Gould, M.K., Suksamrarn, A., 2010. Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species. Eur. J. Med. Chem. 45, 941-956.
  • Chang, W.L., Chen, C.H., Lee, S.S., 1999. Three novel constituents from Curculigo capitulata and revision of C-2 stereochemistry in nyasicoside. J. Nat. Prod. 62, 734-739.
  • Deng, Z.T., Geng, C.A., Yang, T.H., Xiang, C.L., Chen, J.J., 2019. Chepraecoxins A-G, entkaurane diterpenoids with α- glucosidase inhibitory activities from Chelonopsis praecox. Fitoterapia 132, 60-67.
  • Chiba, K., Ichizawa, H., Kawai, S., Nishida, T., 2013. α- Glucosidase inhibition activity by cyclic diarylheptanoids from Alnus sieboldiana. J. Wood Chem. Technol. 33 (1), 44-51.
  • de Fatima, A., Kohn, L.K., Ernesto de Carvalho, J., Pilli, R.A., 2006. Cytotoxic activity of (S)goniothalamin and analogues against human cancer cells. Bioorg. Med. Chem. 14 (3), 622-631.
  • Du, D., Gu, H.W., Djukovic, D., Bettcher, L., Gong, M., Zheng, W., Hu, L.Q., Zhang, X.Y., Zhang, R.K., Wang, D.F., Raftery, D., 2018. Multiplatform metabolomics investigation of anti-adipogenic effects on 3T3-L1 adipocytes by a potent diarylheptanoid. J. Proteome Res. 17 (6), 2092-2101.
  • Du, Z.Y., Liu, R.R., Shao, W.Y., Mao, X.P., Ma, L., Gu, L.Q., Huang, Z.S., Chan, A.S.C., 2006. α -Glucosidase inhibition of natural curcuminoids and curcumin analogs. Eur. J. Med. Chem. 41, 213-218.
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J., 2010. Gaussian 09, Revision C1. Gaussian, Inc., Wallingford, CT.
  • Fuchino, H., Konishi, S., Satoh, T., Yagi, A., Saitsu, K., Tatsumi, T., Tanaka, N., 1996. Chemical evaluation of Betula species in Japan. II. Constituents of Betula platyphylla var. japonica. Chem. Pharm. Bull. 44 (5), 1033-1038.
  • Hong, S.S., Lee, J.H., Choi, Y.H., Jeong, W., Ahn, E.K., Lym, S.H., Oh, J.S., 2015. Amotsaokonal A-C, benzaldehyde and cycloterpenal from Amomum tsao-ko. Tetrahedron Lett. 56, 6681-6684.
  • Jiang, L., Wang, Z., Wang, X., Wang, S., Cao, J., Liu, Y., Wang, Z., Wang, X., Wang, S., Cao, J., Liu, Y., 2020. Exploring the inhibitory mechanism of piceatannol on α -glucosidase relevant to diabetes mellitus. RSC Adv. 10, 4529-4537.
  • Jirasek, P., Amslinger, S., Heilmann, J., 2014. Synthesis of natural and non-natural curcuminoids and their neuroprotective activity against glutamate-induced oxidative stress in HT-22 cells. J. Nat. Prod. 77 (10), 2206-2217.
  • Lee, K.Y., Kim, S.H., Sung, S.H., Kim, Y.C., 2008. Inhibitory constituents of lipopolysaccharide-induced nitric oxide production in BV2 microglia isolated from Amomum tsao-ko. Planta Med. 74 (8), 867-869.
  • Li, C.W., Cui, C.B., 2015. Application of several physicochemical techniques in natural products to elucidate stereochemistry. J. Int. Pharm. Res. 42 (6), 811-828.
  • Li, J., Liao, C.R., Wei, J.Q., Chen, L.X., Zhao, F., Qiu, F., 2011. Diarylheptanoids from Curcuma kwangsiensis and their inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages. Bioorg. Med. Chem. Lett 21, 5363-5369.
  • Li, J., Zhuang, C.L., Tang, H., Sun, P., Zhang, W., 2015. Application of coupling constant based analysis in determining the relative configuration of flexible natural molecules. J. Int. Pharm. Res. 42 (6), 713-725.
  • Lin, X.H., Ji, S., Qiao, X., Hu, H.B., Chen, N., Dong, Y.H., Huang, Y., Guo, D., Tu, P.F., Ye, M., 2013. Density Functional Theory calculations in stereochemical determination of terpecurcumins J- W, cytotoxic terpene conjugated curcuminoids from Curcuma longa L. J. Org. Chem. 78, 11835-11848.
  • Lin, Y.S., Lin, J.H., Chang, C.C., Lee, S.S., 2015. Tetrahydropyran- and tetrahydrofurancontaining diphenylheptanoids from Hedychium coronarium rhizomes. J. Nat. Prod. 78, 181-187.
  • Lv, H.N., She, G.M., 2010. Naturally occurring diphenylheptanoids. Nat. Prod. Commun. 5 (10), 1687-1708.
  • Martin, T.S., Kikuzaki, H., Hisamoto, M., Nakatani, N., 2000. Constituents of Amomum tsao-ko and their radical scavenging and antioxidant activities. J. Am. Oil Chem. Soc. 77 (6), 667-673.
  • Masullo, M., Cerulli, A., Olas, B., Pizza, C., Piacente, S., 2015. Giffonins A- I, antioxidant cyclized diphenylheptanoids from the leaves of the Hazelnut Tree (Corylus avellana), source of the Italian PGI product "Nocciola di Giffoni". J. Nat. Prod. 78, 17-25.
  • Moon, S.S., Cho, S.C., Lee, J.Y., 2005. Tsaokoarylone, a cytotoxic diarylheptanoid from Amomum tsao-ko fruits. Bull. Kor. Chem. Soc. 26 (3), 447-450.
  • Ning, A., Zhang, H.W., Xu, L.Z., Yang, S.L., Zou, Z.M., 2010. New diphenylheptanoids from the rhizome of Alpinia officinarum Hance. Food Chem. 119, 513-517.
  • Reddy, S.P., Chinnababu, B., Venkateswarlu, Y., 2014. First stereoselective and concise synthesis of rhoiptelol C. Helv. Chim. Acta 97, 999-1003.
  • Xu, J., Kang, J., Sun, X.C., Cao, X.R., Rena, K., Lee, D., Ren, Q.H., Li, S., Ohizumi, Y., Guo, Y.Q., 2016. Di- and triterpenoids from the leaves of Casearia balansae and neurite outgrowth promoting effects of PC12 cells. J. Nat. Prod. 79 (1), 170-179.
  • Yan, D.X., Geng, C.A., Yang, T.H., Huang, X.Y., Li, T.Z., Gao, Z., Ma, Y.B., Peng, H., Zhang, X.M., Chen, J.J., 2018. LC-MS guided isolation of diterpenoids from Sapium insigne with α- glucosidase inhibitory activities. Fitoterapia 128, 57-65.
  • Yang, Y., Yue, Y., Yan, R.W., Zou, G.L., 2010. Cytotoxic, apoptotic and antioxidant activity of the essential oil of Amomum tsaoko. Bioresour. Technol. 101, 4205-4211.
  • Yokosuka, A., Mimaki, Y., Sakagami, H., Sashida, Y., 2002. New diarylheptanoids and diarylheptanoid glucosides from the rhizomes of Tacca chantrieri and their cytotoxic activity. J. Nat. Prod. 65, 283-289.
  • Yu, L.Q., Shirai, N., Suzuki, H., Sugane, N., Hosono, T., Nakajima, Y., Kajiwara, M., Takatori, K., 2010. The effect of methanol extracts of tsao-ko (Amomum tsao-ko Crevost et Lemaire) on digestive enzyme and antioxidant activity in vitro, and plasma lipids and glucose and liver lipids in mice. J. Nutr. Sci. Vitaminol. 56, 171-176.
  • Zhang, C.C., Geng, C.A., Huang, X.Y., Zhang, X.M., Chen, J.J., 2019. Antidiabetic stilbenes from peony seeds with PTP1B, α- glucosidase, and DPPIV inhibitory activities. J. Agric. Food Chem. 67, 6765-6772.