Published November 30, 2021
| Version v1
Journal article
Restricted
Naturally occurring physalins from the genus Physalis: A review
Authors/Creators
- 1. Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100193, China
Description
Wu, Jiangping, Zhao, Jianping, Zhang, Tao, Gu, Yucheng, Khan, Ikhlas A., Zou, Zhongmei, Xu, Qiongming (2021): Naturally occurring physalins from the genus Physalis: A review. Phytochemistry (112925) 191: 1-25, DOI: 10.1016/j.phytochem.2021.112925, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112925
Files
Restricted
The record is publicly accessible, but files are restricted. <a href="https://zenodo.org/account/settings/login?next=https://zenodo.org/records/8257643">Log in</a> to check if you have access.
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:C975531D7073E356E267013CEE34FFAC
References
- Abdel Moneim, A.E., Bauomy, A.A., Diab, M.M., Shata, M.T., Al-Olayan, E.M., El- Khadragy, M.F., 2014. The protective effect of Physalis peruviana L. against cadmium-induced neurotoxicity in rats. Biol. Trace Elem. Res. 160, 392-399. https://doi.org/10.1007/s12011-014-0066-9.
- Araki, Y., Nakazaki, A., Nishikawa, T., 2021. Biomimetic synthesis of the CDE ring moiety of Physalins, complex 13,14-Secosteroids. Org. Lett. 23, 989-994. https://doi. org/10.1021/acs.orglett.0c04198.
- Bastos, G.N., Santos, A.R., Ferreira, V.M., Costa, A.M., Bispo, C.I., Silveira, A.J., Do Nascimento, J.L., 2006. Antinociceptive effect of the aqueous extract obtained from roots of Physalis angulata L. on mice. J. Ethnopharmacol. 103, 241-245. https://doi. org/10.1016/j.jep.2005.08.008.
- Benjamin, B.D., Mulchandani, N.B., 1979. Isolation of physalin D, a 13,14-seco -16,24, cyclo -steroid from tissue cultures of Physalis minima. Planta Med. 37, 88-90. https:// doi.org/10.1055/s-0028-1097305.
- Brustolim, D., Vasconcelos, J.F., Freitas, L.A., Teixeira, M.M., Farias, M.T., Ribeiro, Y.M., Tomassini, T.C., Oliveira, G.G., Pontes-de-Carvalho, L.C., Santos, R., Soares, M.B., 2010. Activity of physalin F in a collagen-induced arthritis model. J. Nat. Prod. 73, 1323-1326. https://doi.org/10.1021/np900691.
- Bunsho Makino, M.K., Kito, Kpji, et al., 1995. New physalins possessing an additioonal carbon-carbon bond from Physalis alkekengi var franchetii. Tetrahedron 51, 12529-12538. https://doi.org/10.1016/0040-4020(95)00807-k.
- Cabrera, R., Recule, F., 2018. Unusual clinical presentations of malignant melanoma: a review of clinical and histologic features with special emphasis on dermatoscopic findings. Am. J. Clin. Dermatol. 19, 15-23. https://doi.org/10.1007/s40257-018- 0373-6.
- Castro, D.P., Moraes, C.S., Gonzalez, M.S., Ribeiro, I.M., Tomassini, T.C., Azambuja, P., Garcia, E.S., 2012. Physalin B inhibits trypanosoma cruzi infection in the gut of rhodnius prolixus by affecting the immune system and microbiota. J. Insect Physiol. 58, 1620-1625. https://doi.org/10.1016/j.jinsphys.2012.10.001.
- Chang, J.C., Lin, C.C., Wu, S.J., Lin, D.L., Wang, S.S., Miaw, C.L., Ng, L.T., 2008. Antioxidative and hepatoprotective effects of Physalis peruviana extract against acetaminophen-induced liver injury in rats. Pharm. Biol. 46, 724-731. https://doi. org/10.1080/13880200802215768.
- Chao, C., Zhang, Z.F., Berthiller, J., Boffetta, P., Hashibe, M., 2006. NAD(P)H:quinone oxidoreductase 1 (NQO1) Pro187Ser polymorphism and the risk of lung, bladder, and colorectal cancers: a meta-analysis. Cancer Epidemiol. Biomark. Prev. 15, 979-987. https://doi.org/10.1158/1055-9965.EPI-05-0899.
- Chen, R., Liang, J.Y., Yang, F., Liu, R., 2006. Chemical constituents from Physalis alkekengi and structural revision of physalin G. Chin. J. Nat. Med. 5, 186-189.
- Chen, L.X., He, H., Qiu, F., 2011. Natural withanolides: an overview. Nat. Prod. Rep. 28, 705-740. https://doi.org/10.1039/c0np00045k.
- Choudhary, M.I., Yousaf, S., Ahmed, S., Yasmeen, K., 2005. Antileishmanial physalins from Physalis minima. Chem. Biodivers. 2, 1164-1173. https://doi.org/10.1002/ cbdv.200590086.
- Choudhary, M.I., Yousuf, S., Samreen Ahmed, S., Atta-Ur-Rahman, 2007. New leishmanicidal physalins from Physalis minima. Nat. Prod. Res. 21, 877-883. https:// doi.org/10.1080/14786410701315147.
- da Silva, R.R., da Silva, B.J., Rodrigues, A.P., Farias, L.H., da Silva, M.N., Alves, D.T., Bastos, G.N., do Nascimento, J.L., Silva, E.O., 2015. In vitro biological action of aqueous extract from roots of Physalis angulata against Leishmania (Leishmania) amazonensis. BMC Compl. Alternative Med. 15, 1-10. https://doi.org/10.1186/ s12906-015-0717-1.
- Damu, A.G., Kuo, P.C., Su, C.R., Kuo, T.H., Chen, T.H., Bastow, K.F., Lee Damu, A.G., Kuo, P.C., Su, C.R., Kuo, T.H., Chen, T.H., Bastow, K.F., Lee, K.H., Wu, T.S., 2007. Isolation, structures, and structure-cytotoxic activity relationships of withanolides and physalins from Physalis angulata. J. Nat. Prod. 70, 1146-1152. https://doi.org/ 10.1021/np0701374.
- de Andrade, M.F., de Almeida, V.D., de Souza, L.M.S., Paiva, D.C.C., Andrade, C.M., de Medeiros Fernandes, T.A.A., 2018. Involvement of neutrophils in chagas disease pathology. Parasite Immunol. 40, e12593 https://doi.org/10.1111/pim.12593.
- Dkhil, M.A., Al-Quraishy, S., Diab, M.M., Othman, M.S., Aref, A.M., Abdel Moneim, A.E., 2014. The potential protective role of Physalis peruviana L. fruit in cadmium-induced hepatotoxicity and nephrotoxicity. Food Chem. Toxicol. 74, 98-106. https://doi. org/10.1016/j.fct.2014.09.013.
- do Espirito Santo, R.F., Lima, M.D.S., Juiz, P.J.L., Opretzka, L.C.F., Nogueira, R.C., Ribeiro, I.M., Tomassini, T.C.B., Soares, M.B.P., Villarreal, C.F., 2019. Physalis angulata concentrated ethanolic extract suppresses nociception and inflammation by modulating cytokines and prostanoids pathways. Nat. Prod. Res. 1-5 https://doi. org/10.1080/14786419.2019.1705812.
- Dujardin, J.C., 2006. Risk factors in the spread of leishmaniases: towards integrated monitoring? Trends Parasitol. 22, 4-6. https://doi.org/10.1016/j.pt.2005.11.004.
- Fang, C.S., Yang, Y.J., 2015. Study on anti-tumor activities of Physalins B in vitro. Journal of Guangzhou University of Traditional Chinese Medicine 32, 652-656.
- Gao, C., Li, R., Zhou, M., Yang, Y., Kong, L., Luo, J., 2018. Cytotoxic withanolides from Physalis angulata. Nat. Prod. Res. 32, 676-681. https://doi.org/10.1080/ 14786419.2017.1338281.
- Garcia, E.S., Castro, D.P., Ribeiro, I.M., Tomassini, T.C., Azambuja, P., 2006. Trypanosoma rangeli: effects of physalin B on the immune reactions of the infected larvae of rhodnius prolixus. Exp. Parasitol. 112, 37-43. https://doi.org/10.1016/j. exppara.2005.09.003.
- Guimaraes, E.T., Lima, M.S., Santos, L.A., Ribeiro, I.M., Tomassini, T.B., Ribeiro dos Santos, R., dos Santos, W.L., Soares, M.B., 2009. Activity of physalins purified from Physalis angulata in in vitro and in vivo models of cutaneous leishmaniasis. J. Antimicrob. Chemother. 64, 84-87. https://doi.org/10.1093/jac/dkp170.
- Han, H.Y., Wang, X.H., Wang, N.L., Ling, M.T., Wong, Y.C., Yao, X.S., 2008. Lignans isolated from campylotropis hirtella (Franch.) Schindl. decreased prostate specific antigen and androgen receptor expression in LNCaP cells. J. Agric. Food Chem. 56, 6928-6935. https://doi.org/10.1021/jf800476r.
- Han, H.Y., Qiu, L., Wang, X.H., Qiu, F., Wong, Y.C., Yao, X.S., 2011. Physalins A and B inhibit androgen-independent prostate cancer cell growth through activation of cell apoptosis and downregulation of androgen receptor expression. Biol. Pharm. Bull. 34, 1584-1588. https://doi.org/10.1248/bpb.34.1584.
- Hao, H., Zang, L.H., Feng, Y.S., Chen, L.X., Kang, N., Tashiro, S., Onodera, S., Qiu, F., Ikejima, T., 2013. Physalin A induces apoptosis via p53-Noxa-mediated ROS generation, and autophagy plays a protective role against apoptosis through p38-NFκ B survival pathway in A375-S2 cells. J. Ethnopharmacol. 148, 544-555. https:// doi.org/10.1016/j.jep.2013.04.051.
- Helvaci, S., Kokdil, G., Kawai, M., Duran, N., Duran, G., Guvenc, A., 2010. Antimicrobial activity of the extracts and physalin D from Physalis alkekengi and evaluation of antioxidant potential of physalin D. Pharm. Biol. 48, 142-150. https://doi.org/ 10.3109/13880200903062606.
- Hsu, C.C., Wu, Y.C., Farh, L., Du, Y.C., Tseng, W.K., Wu, C.C., Chang, F.R., 2012. Physalin B from Physalis angulata triggers the NOXA-related apoptosis pathway of human melanoma A375 cells. Food Chem. Toxicol. 50, 619-624. https://doi.org/10.1016/j. fct.2011.12.017.
- Hu, X.F., Zhang, Q., Zhang, P.P., Sun, L.J., Liang, J.C., Morris-Natschke, S.L., Chen, Y., Lee, K.H., 2018. Evaluation of in vitro/in vivo anti-diabetic effects and identification of compounds from Physalis alkekengi. Fitoterapia 127, 129-137. https://doi.org/ 10.1016/j.fitote.2018.02.015.
- Huang, M., He, J.X., Hu, H.X., Zhang, K., Wang, X.N., Zhao, B.B., Lou, H.X., Ren, D.M., Shen, T., 2020. Withanolides from the genus Physalis: a review on their phytochemical and pharmacological aspects. J. Pharm. Pharmacol. 72, 649-669. https://doi.org/10.1111/jphp.13209.
- Jacobo-Herrera, N.J., Bremner, P., Marquez, N., Gupta, M.P., Gibbons, S., Munoz, E., Heinrich, M., 2006. Physalins from Witheringia solanacea as modulators of the NF- κ B cascade. J. Nat. Prod. 69, 328-331. https://doi.org/10.1021/np050225t.
- Januario, A.H., Filho, E.R., Pietro, R.C., Kashima, S., Sato, D.N., Franca, S.C., 2002. Antimycobacterial physalins from Physalis angulata L. (Solanaceae). Phytother Res. 16, 445-448. https://doi.org/10.1002/ptr.939.
- Ji, L., Yuan, Y.L., Luo, L.P., Chen, Z., Ma, X.Q., Ma, Z.J., Cheng, L., 2012. Physalins with anti-inflammatory activity are present in P hysalis alkekengi var. franchetii and can function as michael reaction acceptors. Steroids 77, 441-447. https://doi.org/ 10.1016/j.steroids.2011.11.016.
- Ji, M.S., Lee, K.M., Lee, H.J., Ji, H.Y., Chu, W.N., 2019. Physalin A regulates the Nrf2 pathway through ERK and p38 for induction of detoxifying enzymes. BMC Compl. Alternative Med. 19, 101-105. https://doi.org/10.1186/s12906-019-2511-y.
- Kang, N., Jian, J.F., Cao, S.J., Zhang, Q., Mao, Y.W., Huang, Y.Y., Peng, Y.F., Qiu, F., Gao, X.M., 2016. Physalin A induces G2/M phase cell cycle arrest in human non-small cell lung cancer cells: involvement of the p38 MAPK/ROS pathway. Mol. Cell. Biochem. 415, 145-155. https://doi.org/10.1007/s11010-016-2686-1.
- Kawai, M., Matsuura, T., 1970. The structure of physalin C : a bitter principle of Physalis Alkekengi var. Franchetii. Tetrahedron 26, 1743-1745. https://doi.org/10.1016/ s0040-4020(01)93024-8.
- Kawai, M., Matsuura, T., Kyuno, S., Matsuki, H., Saito, K., 1987. A new physalin from Physalis alkekengi: structure of physalin L. Phytochemistry 26, 3313-3317. https:// doi.org/10.1016/S0031-9422(00)82495-4.
- Kawai, M.O.T., Nakanishi, M., Matsuura, T., Butsucan, Y., Mori, Y., Harada, K., Suzuki, M., Kawai, T., Matsuura, 1988. Structure of physalin M isolated from Physalis alkekengi var. francheti. Bull. Chem. Soc. Jpn. 61, 2696-2698. https://doi.org/ 10.1246/bcsj.61.2696.
- Kawai, M., Ogura, T., Butsugan, Y., Taga, T., Hayashi, M., 1991. Benzilic acid rearrangement-type reaction of physalins to neophysalins - structural revision of one of the dehydration products of physalin A. Tetrahedron 47, 2103-2110. https://doi. org/10.1016/s0040-4020(01)96121-6.
- Kawai, M., Ogura, T., Makino, B., Matsumoto, A., Hayashi, M., 1992. Physalins N and O from Physalis alkekengi. Phytochemistry 31, 4299-4302. https://doi.org/10.1016/ 0031-9422(92)80462-N.
- Kawai, M.M.A., Makino, B., Mori, H., Ogura, T., Butsugan, Y., Ogawa, K., Hayashi, M., 1993. ChemInform Abstract: the structure of physalin P, a neophysalin from Physalis alkekengi. Bull. Chem. Soc. Jpn. 66, 1299-1300. https://doi.org/10.1002/ chin.199332226.
- Kawai, M., Yamamoto, T., Makino, B., Yamamura, H., Araki, S., Butsugan, Y., Saito, K., 2001. The structure of physalin T from Physalis alkekengi var. franchetti. J. Asian Nat. Prod. Res. 3, 199-205. https://doi.org/10.1080/10286020108041391.
- Krebs, E.E., Gravely, A., Nugent, S., Jensen, A.C., DeRonne, B., Goldsmith, E.S., Kroenke, K., Bair, M.J., Noorbaloochi, S., 2018. Effect of opioid vs nonopioid medications on pain-related function in patients with chronic back pain or hip or knee osteoarthritis pain: the SPACE randomized clinical trial. J. Am. Med. Assoc. 319, 872-882. https://doi.org/10.1001/jama.2018.0899.
- Kuo, P.C., Kuo, T.H., Damu, A.G., Su, C.R., Lee, E.J., Wu, T.S., Shu, R., Chen, C.M., Bastow, K.F., Chen, T.H., Lee, K.H., 2006. Physanolide A, a novel skeleton steroid, and other cytotoxic principles from Physalis angulata. Org. Lett. 8, 2953-2956. https://doi.org/10.1021/ol060801s.
- Li, P., Sheng, X., Wang, X.Z., Zhang, J.H., Bao, C.H., He, Y.L., Ding, R., 1996. Effect of physalin B on chemiluminescence and H2O2 production of activated polymorphonuclear leukocyte. Chin. J. Pathophysiol. 12, 626-628.
- Li, Y.Z., Pan, Y.M., Huang, X.Y., Wang, H.S., 2008. Withanolides from Physalis alkekengi var. franchetii. Helv. Chim. Acta 91, 2284-2291.
- Li, K., Diao, Y.P., Wang, M.D., Yang, S.S., Zhang, H.L., Huang, S.S., Yang, H., 2010. Chemical constituents of the fruits of physalis alkekengi L. Var. franchetii (mast.) Makino. Chin. J. Org. Chem. 30, 128-131.
- Li, X., Zhang, C., Wu, D., Tang, L., Cao, X., Xin, Y., 2012a. In vitro effects on intestinal bacterium of physalins from Physalis alkekengi var. Franchetii. Fitoterapia 83, 1460-1465. https://doi.org/10.1016/j.fitote.2012.08.011.
- Li, X.L., Zhang, C.L., Wu, D.C., Tang, L., Cao, X.J., Xin, Y., 2012b. In vitro effects on intestinal bacterium of physalins from Physalis alkekengi var. Francheti. Fitoterapia 83, 1460-1465. https://doi.org/10.1016/j.fitote.2012.08.011.
- Li, X., Zhao, J.P., Yang, M., Liu, Y.L., Li, Z.C., Li, R.Y., Li, X.R., Li, N., Xu, Q.M., Khan, I. A., Yang, S.L., 2014. Physalins and withanolides from the fruits of Physalis alkekengi L. var. franchetii (Mast.) Makino and the inhibitory activities against human tumor cells. Phytochem. Lett. 10, 95-100. https://doi.org/10.1016/j.phytol.2014.08.004.
- Li, A.L., Chen, B.J., Li, G.H., Zhou, M.X., Li, Y.R., Ren, D.M., Lou, H.X., Wang, X.N., Shen, T., 2018. Physalis alkekengi L. var. franchetii (Mast.) Makino: an ethnomedical, phytochemical and pharmacological review. J. Ethnopharmacol. 210, 260-274. https://doi.org/10.1016/j.jep.2017.08.022.
- Lima Mda, S., Evangelista, A.F., Santos, G.G., Ribeiro, I.M., Tomassini, T.C., Pereira Soares, M.B., Villarreal, C.F., 2014. Antinociceptive properties of physalins from Physalis angulata. J. Nat. Prod. 77, 2397-2403. https://doi.org/10.1021/np5003093.
- Lin, Y.H., Hsiao, Y.H., Ng, K.L., Kuo, Y.H., Lim, Y.P., Hsieh, W.T., 2020. Physalin A attenuates inflammation through down-regulating c-Jun NH2 kinase phosphorylation/Activator Protein 1 activation and up-regulating the antioxidant activity. Toxicol. Appl. Pharmacol. 402, 115115. https://doi.org/10.1016/j. taap.2020.115115.
- Ma, Y.M., Han, W., Li, J., Hu, L.H., Zhou, Y.B., 2015. Physalin B not only inhibits the ubiquitin-proteasome pathway but also induces incomplete autophagic response in human colon cancer cells. Acta Pharmacol. Sin. 36, 517-527. https://doi.org/ 10.1038/aps.2014.157.
- Magalhaes, H.I.F., Veras, M.L., Pessoa, O.D.L., Silveira, E.R., Moraes, M.O., Pessoa, C., Costa-Lotufo, L.V., 2006. Preliminary investigation of structure-activity relationship of cytotoxic physalins. Lett. Drug Des. Discov. 3, 9-13.
- Makino, B., Kawai, M., Iwata, Y., Yamamura, H., Butsugan, Y., Ogawa, K., Hayashi, M., 1995a. Physalins possessing an endoperoxy structure from Physalis alkekengi var Franchetii - structural revision of physalin K. Bull. Chem. Soc. Jpn. 68, 219-226. https://doi.org/10.1246/bcsj.68.219.
- Makino, B., Kawai, M., Kito, K., Yamamura, H., Butsugan, Y., 1995b. New physalins possessing an additional carbon-carbon bond from Physalis alkekengi var Franchetii. Tetrahedron 51, 12529-12538. https://doi.org/10.1002/chin.199611236.
- Makino, B., Kawai, M., Ogura, T., Nakanishi, M., Yamamura, H., Butsugan, Y., 1995c. Structural revision of physalin H isolated from Physalis angulata. J. Nat. Prod. 58, 1668-1674. https://doi.org/10.1021/np50125a004.
- Matsuura, T., Kawai, M., Nakashima, R., Butsugan, Y., 1970. Structures of physalin A and physalin B, 13,14-seco -16,24-cyclo -steroids from Physalis alkekengi var. Francheti. J. Chem. Soc. Perkin. Transactions 15, 664-670. https://doi.org/10.1039/ j39700000664.
- Meira, C.S., Guimaraes, E.T., Bastos, T.M., Moreira, D.R., Tomassini, T.C., Ribeiro, I.M., Dos Santos, R.R., Soares, M.B., 2013. Physalins B and F, seco -steroids isolated from Physalis angulata L., strongly inhibit proliferation, ultrastructure and infectivity of Trypanosoma cruzi. Parasitology 140, 1811-1821. https://doi.org/10.1017/ S0031182013001297.
- Men, R.Z., Li, N., Ding, W.J., Hu, Z.J., Ma, Z.J., Cheng, L., 2014. Unprecedent aminophysalin from Physalis angulata. Steroids 88, 60-65. https://doi.org/10.1016/ j.steroids.2014.06.016.
- Misico, R.I., Nicotra, V.E., Oberti, J.C., Barboza, G., Gil, R.R., Burton, G., 2011. Withanolides and Related Steroids. Springer Vienna.
- Olmstead, R.G., Bohs, L., Abdel Migid, H., Santiago-Valentin, E., Garcia, V.F., Collier, S. M., 2008. A molecular phylogeny of the Solanaceae. Taxon 57, 1159-1181. https:// doi.org/10.1002/tax.574010.
- Othman, M.S., Nada, A., Zaki, H.S., Abdel Moneim, A.E., 2014. Effect of physalis peruviana L. on cadmium-induced testicular toxicity in rats. Biol. Trace Elem. Res. 159, 278-287. https://doi.org/10.1007/s12011-014-9955-1.
- Ozawa, M., Morita, M., Hirai, G., Tamura, S., Kawai, M., Tsuchiya, A., Oonuma, K., Maruoka, K., Sodeoka, M., 2013. Contribution of cage-shaped structure of physalins to their mode of action in inhibition of TNF- κ B activation. ACS Med. Chem. Lett. 4, 730-735. https://doi.org/10.1021/ml400144e.
- P´erez-Castorena, A.L., Luna, M., Martinez, M., Maldonado, E., 2012. New sucrose esters from the fruits of Physalis solanaceus. Carbohydr. Res. 352, 211-214. https://doi. org/10.1016/j.carres.2012.02.003.
- Pinto, L.A., Meira, C.S., Villarreal, C.F., Vannier-Santos, M.A., de Souza, C.V., Ribeiro, I. M., Tomassini, T.C., Galvao-Castro, B., Soares, M.B., Grassi, M.F., 2016. Physalin F, a seco -steroid from Physalis angulata L., has immunosuppressive activity in peripheral blood mononuclear cells from patients with HTLV1-associated myelopathy. Biomedecine & pharmacotherapie 79, 129-134. https://doi.org/10.1016/j. biopha.2016.01.041.
- Qiu, L., Jiang, Z.H., Liu, H.X., Chen, L.X., Yao, X.S., Qiu, F., 2008a. A pair of 3-epimeric physalins from Physalis alkekengi L. var. franchetii. J. Asian Nat. Prod. Res. 10, 881-885. https://doi.org/10.1080/10286020802144735.
- Qiu, L., Zhao, F., Jiang, Z.H., Chen, L.X., Zhao, Q., Liu, H.X., Yao, X.S., Qiu, F., 2008b. Steroids and flavonoids from Physalis alkekengi var. franchetii and their inhibitory effects on nitric oxide production. J. Nat. Prod. 71, 642-646. https://doi.org/ 10.1021/np700713r.
- Ramachandra, L. Row, Sambi, K., Reddy Subrahmanya, N., Sarma, T.J., 1980. New physalins from Physalis angulata and Physalis lancifolia. Structure and reactions of physalins D, I, G and K. Phytochemistry 19, 1175-1181. https://doi.org/10.1016/ 0031-9422(80)83078-0.
- Rastrelli, M., Tropea, S., Rossi, C.R., Alaibac, M., 2014. Melanoma: epidemiology, risk factors, pathogenesis, diagnosis and classification. In Vivo: International Journal of In Vivo Research 28, 1005-1012.
- Reiko Sunayama, M.K., Kaoru Umehara, Akira Ueno, 1993. Physalin and neophysalins from Physalis alkekengi var. franchetii and their differentiation inducing activity. Phytochemistry 34, 529-533. https://doi.org/10.1016/0031-9422(93)80040-Y.
- Row, L.R., Sarma, N.S., Reddy, K.S., Matsuura, T., Nakashima, R., 1978. The structure of Physalins F and J from Physalis angulata and P. Lancifolia. Phytochemostry 17, 1647-1650. https://doi.org/10.1016/S0031-9422(00)94660-0.
- S´a, M.S., Menezes, M., Krettli, A.U., Ribeiro, I.M., Soares, M., 2011. Antimalarial activity of physalins B, D, F, and G. J. Nat. Prod. 74, 2269-2272. https://doi.org/10.1021/ np200260f.
- Sattler, S., Kennedy-Lydon, T., Sattler, S., 2017. The Role of the Immune System beyond the Fight against Infection. Springer International Publishing.
- Shan, Z., Cai, S., Yu, J., Zhang, Z., Vallecillo, T.G.M., Serafini, M.J., Thomas, A.M., Pham, N.Y.N., Bellampalli, S.S., Moutal, A., Zhou, Y., Xu, G.B., Xu, Y.M., Luo, S., Patek, M., Streicher, J.M., Gunatilaka, A.A.L., Khanna, R., 2019. Reversal of peripheral neuropathic pain by the small-molecule natural product physalin F via block of CaV2.3 (R-type) and CaV2.2 (N-type) voltage-gated calcium channels. ACS Chem. Neurosci. 10, 2939-2955. https://doi.org/10.1021/acschemneuro.9b00166.
- Silva, B.J.M.D., Pereira, S., Rodrigues, A., Nascimento, J.L.M.D., Silva, E.O., 2018. In vitro antileishmanial effects of Physalis angulata root extract on Leishmania infantum. J. Integr. Med. 16, 404-410. https://doi.org/10.1016/j.joim.2018.08.004.
- Soares, M.B., Bellintani, M.C., Ribeiro, I.M., Tomassini, T.C., Santos, R., 2003. Inhibition of macrophage activation and lipopolysaccaride-induced death by seco -steroids purified from Physalis angulata L. Eur. J. Pharmacol. 459, 107-112. https://doi.org/ 10.1016/S0014-2999(02)02829-7.
- Soares, M.B., Brustolim, D., Santos, L.A., Bellintani, M.C., Paiva, F.P., Ribeiro, Y.M., Tomassini, T.C., Santos, R., 2006. Physalins B, F and G, seco -steroids purified from Physalis angulata L., inhibit lymphocyte function and allogeneic transplant rejection. Int. Immunopharm. 6, 408-414. https://doi.org/10.1016/j.intimp.2005.09.007.
- Sun, C.P., Qiu, C.Y., Yuan, T., Nie, X.F., Sun, H.X., Zhang, Q., Li, H.X., Ding, L.Q., Zhao, F., Chen, L.X., Qiu, F., 2016. Antiproliferative and anti-inflammatory withanolides from Physalis angulata. J. Nat. Prod. 79, 1586-1597. https://doi.org/ 10.1021/acs.jnatprod.6b00094.
- Sun, C.P., Oppong, M.B., Zhao, F., Chen, L.X., Qiu, F., 2017a. Unprecedented 22,26-seco physalins from Physalis angulata and their anti-inflammatory potential. Org. Biomol. Chem. 15, 8700-8704. https://doi.org/10.1039/c7ob02205k.
- Sun, C.P., Qiu, C.Y., Zhao, F., Kang, N., Chen, L.X., Qiu, F., 2017b. Physalins V-IX, 16,24- cyclo -13,14-seco withanolides from Physalis angulata and their antiproliferative and anti-inflammatory activities. Sci. Rep. 7, 4057. https://doi.org/10.1038/s41598- 017-03849-9.
- Sun, J.L., Jiang, Y.J., Cheng, L., 2019a. Two new physalin derivatives from Physalis alkekengi L. var. franchetii (Mast.) Makino. Nat. Prod. Res. 1-4 https://doi.org/ 10.1080/14786419.2019.1619724.
- Sun, J.L., Jiang, Y.J., Ding, W.J., Cheng, L., Ma, Z.J., 2019b. Physalinol A, a 1,10-seco - physalin with an epidioxy from Physalis alkekengi L. var. franchetii (Mast.) Makino. Tetrahedron Lett. 60, 1330-1332. https://doi.org/10.1016/j.tetlet.2019.04.003.
- Tahrani, A.A., Piya, M.K., Kennedy, A., Barnett, A.H., 2010. Glycaemic control in type 2 diabetes: targets and new therapies. Pharmacol. Ther. 125, 328-361. https://doi. org/10.1016/j.pharmthera.2009.11.001.
- Vieira, A.T., Pinho, V., Lepsch, L.B., Scavone, C., Ribeiro, I.M., Tomassini, T., Santos, R., Soares, M.B., Teixeira, M.M., Souza, D.G., 2005. Mechanisms of the anti-inflammatory effects of the natural secosteroids physalins in a model of intestinal ischaemia and reperfusion injury. Br. J. Pharmacol. 146, 244-251. https://doi.org/ 10.1038/sj.bjp.0706321.
- Wang, A., Wang, S., Zhou, F., Li, P., Wang, Y., Gan, L., Lin, L., 2018. Physalin B induces cell cycle arrest and triggers apoptosis in breast cancer cells through modulating p53-dependent apoptotic pathway. Biomedecine & pharmacotherapie 101, 334-341. https://doi.org/10.1016/j.biopha.2018.02.094.
- Wang, L., Gu, J., Zong, M., Zhang, Q., Li, H., Li, D., Mou, X., Liu, P., Liu, Y., Qiu, F., Zhao, F., 2021. Anti-inflammatory action of physalin A by blocking the activation of NF- κ B signaling pathway. J. Ethnopharmacol. 267, 113490. https://doi.org/ 10.1016/j.jep.2020.113490.
- Williams, C., 2002. Amlodipine prevents angina, not atherosclerosis. Pharmacotherapy 22, 400-401. https://doi.org/10.1592/phco.22.5.400.33195.
- Wu, S.J., Ng, L.T., Huang, Y.M., Lin, D.L., Wang, S.S., Huang, S.N., Lin, C.C., 2005. Antioxidant activities of Physalis peruviana. Biol. Pharm. Bull. 28, 963-966. https:// doi.org/10.1248/bpb.28.963.
- Wu, Y., Zheng, Y., Chen, N., Luan, L., Liu, X., 2011. Plasma pharmacokinetics and tissue distribution study of physalin D in rats by ultra-pressure liquid chromatography with tandem mass spectrometry. J. Chromatogr. B 879, 443-448. https://doi.org/ 10.1371/journal.pone.0040727.
- Wu, S.Y., Leu, Y.L., Chang, Y.L., Wu, T.S., Kuo, P.C., Liao, Y.R., Teng, C.M., Pan, S.L., 2012. Physalin F induces cell apoptosis in human renal carcinoma cells by targeting NF- κ B and generating reactive oxygen species. PloS One 7, e40727.
- Wu, J.P., Li, X., Zhao, J.P., Wang, R.J., Xia, Z.F., Li, X.R., Liu, Y.L., Xu, Q.M., Khan, I.A., Yang, S.L., 2018a. Anti-inflammatory and cytotoxic withanolides from Physalis minima. Phytochemistry 155, 164-170. https://doi.org/10.1016/j. phytochem.2018.08.009.
- Wu, J.P., Xia, Z.F., Liu, Y.L., Li, X.R., Xu, Q.M., Yang, S.L., 2018b. Study on steroidal chemical constituents of Physalis minima. Chin. Tradit. Herb. Drugs 49, 62-68.
- Wu, J.P., Zhang, T., Si, J.G., Xu, Q.M., Gu, Y.C., Yang, S.L., Zou, Z.M., 2020. Five new 5,6-β -epoxywithanolides from Physalis minima. Fitoterapia 140, 104413. https://doi. org/10.1016/j.fitote.2019.104413.
- Xiang, D., Zou, J., Zhu, X., Chen, X., Luo, J., Kong, L., Zhang, H., 2020. Physalin D attenuates hepatic stellate cell activation and liver fibrosis by blocking TGF- β/Smad and YAP signaling. Phytomedicine 78, 153294. https://doi.org/10.1016/j. phymed.2020.153294.
- Xu, W.X., Chen, J.C., Liu, J.Q., Wang, Y.F., 2013. Three new physalins from Physalis alkekengi var. franchetii. Natur. Prod. & Bioprosp. 3, 103-106. https://doi.org/ 10.1007/s13659-013-0021-z.
- Yang, Y.J., Sha, G.W., Nie, Y., Xie, L., 2015. Experimental study on anti-inflammatory and antibacterial effects of physalin B. E. Pharmacy. Today 25, 167-168.
- Yang, B.Y., Xia, Y.G., Pan, J., Liu, Y., Wang, Q.H., Kuang, H.X., 2016. Phytochemistry and biosynthesis of δ -lactone withanolides. Phytochemistry Rev. 15, 771-797. https://doi.org/10.1007/s11101-015-9420-6.
- Yang, Y.K., Xie, S.D., Xu, W.X., Nian, Y., Liu, X.L., Peng, X.R., Ding, Z.T., Qiu, M.H., 2016. Six new physalins from Physalis alkekengi var. franchetii and their cytotoxicity and antibacterial activity. Fitoterapia 112, 144-152. https://doi.org/10.1016/j. fitote.2016.05.010.
- Yu, Y.J., Sun, L.J., Ma, L., Li, J.Y., Hu, L.H., Liu, J.W., 2010. Investigation of the immunosuppressive activity of Physalin H on T lymphocytes. Int. Immunopharm. 10, 290-297. https://doi.org/10.1016/j.intimp.2009.11.013.
- Zhang, W.N., Tong, W.Y., 2016. Chemical constituents and biological activities of plants from the genus Physalis. Chem. Biodivers. 13, 48-65. https://doi.org/10.1002/ cbdv.201400435.
- Zhang, J., Schulz, W.A., Li, Y., Wang, R., Zotz, R., Wen, D., Siegel, D., Ross, D., Gabbert, H.E., Sarbia, M., 2003. Association of NAD(P)H: quinone oxidoreductase 1 (NQO1) C609T polymorphism with esophageal squamous cell carcinoma in a German caucasian and a northern Chinese population. Carcinogenesis 24, 905-909. https://doi.org/10.1093/carcin/bgg019.
- Zhang, S., Li, J., Yang, S.L., Li, X.R., Xu, Q.M., 2017. Antischistosomal activity of physalins against Schistosomajaponicum. Acta Chinese Medicine and Pharmacology 45, 25-28.
- Zhang, Q., Hu, X.F., Xin, M.M., Liu, H.B., Sun, L.J., Morris-Natschke, S.L., Chen, Y., Lee, K.H., 2018. Antidiabetic potential of the ethyl acetate extract of Physalis alkekengi and chemical constituents identified by HPLC-ESI-QTOF-MS. J. Ethnopharmacol. 225, 202-210. https://doi.org/10.1016/j.jep.2018.07.007.
- Zhang, Q., Xu, N., Hu, X., Zheng, Y., 2020. Anti-colitic effects of physalin B on dextran sodium sulfate-induced BALB/c mice by suppressing multiple inflammatory signaling pathways. J. Ethnopharmacol. 259, 112956. https://doi.org/10.1016/j. jep.2020.112956.
- Zhao, Z.D., Yang, Y.J., Xia, L., Liu, W.H., Li, S.L., Lin, J., 2018. Research progress on physalin B. Chinese Traditional Patent Medicine 40, 1580-1584.
- Zhao, N., Feng, X.C., Pan, G.X., Qiu, F., 2020. Research progress on pharmacological actions of physalin A. Drug Evaluation Research 43, 340-344.
- Zheng, Y., Chen, Y., Ren, Y., Luan, L., Wu, Y., 2012. An ultra-pressure liquid chromatography-tandem mass spectrometry method for the simultaneous determination of three physalins in rat plasma and its application to pharmacokinetic study of Physalis alkekengi var. franchetii (Chinese lantern) in rats. J. Pharmaceut. Biomed. 58, 94-101. https://doi.org/10.1016/j.jpba.2011.09.012.
- Zheng, Y., Chen, J., Liu, L., Liang, X., Hong, D., 2016. In vivo pharmacokinetics of and tissue distribution study of physalin B after intravenous administration in rats by liquid chromatography with tandem mass spectrometry. Biomed. Chromatogr. 30, 1278-1284. https://doi.org/10.1002/bmc.3678.
- Zhu, F.F., Dai, C.Y., Fu, Y.F., Loo, J.F.C., Xia, D.J., Gao, S.P., Ma, Z.J., Chen, Z., 2016. Physalin A exerts anti-tumor activity in non-small cell lung cancer cell lines by suppressing JAK/STAT3 signaling. Oncotarget 7, 9463-9477. https://doi.org/ 10.18632/oncotarget.7051.