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Previously undescribed pyridyl-steroidal glycoalkaloids and 23S,26R-hydroxylated spirostanoid saponin from the fruits of Solanum violaceum ortega and their bioactivities
Kaunda,Joseph Sakah; Qin,Xu-Jie; Zhu,Hong-Tao; Wang,Dong; Yang,Chong-Ren; Zhang,Ying-Jun
2021
Source PublicationPHYTOCHEMISTRY
ISSN0031-9422
Volume184Pages:112656
AbstractThree previously undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A-C, one rare 23S,26R-hydroxylated spirostanoid saponin, and two steroidal alkaloid aglycones, solanindins A and B, derived from the acid hydrolysis of solanindiosides A-C, were isolated from the fruits of Solanum violaceum, together with five known analogues, including two rare steroidal glycosides, two lignans and a diterpene. Structurally, they comprise a 16 beta-methoxy-23-deoxy-22,26-epimino-cholest-type skeleton moiety, and a 16 beta-methoxy-3,23-dideoxy-22,26-epimino-cholest-3,5-dien derivative. The hitherto undescribed structures were established on the basis of extensive spectroscopic analyses. Configurations of sugar moieties were resolved by chemical derivations. Sol- anindiosides A-C, (22R,23S,25R,26R)-spirost-5-ene-3 beta,23,26 trio13-O-beta-D-xylopyranosyl-(1 -> 3)-beta-D-glucopyr-anoside, solanindins A and B, and (15,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methy1]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol were evaluated for their cytotoxic and antibacterial activities. (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol showed the most potent cytotoxic activity against MCF-7 cells (IC50 = 4.386 +/- 0.098 mu M), while solanindin B displayed some inhibitory effects against Staphylococcus aureus Rosenbach with MIC50 value of 37.32 +/- 0.793 mu M. In addition, (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4- [(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyemethyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol induced dose dependent apoptosis effect in MCF-7 cells.
KeywordSolanum violaceum Solanaceae Glycoalkaloids Solanindiosides A-C 235,26R-hydroxylated spirostanoid saponin Lignans Cytotoxicity Apoptosis Antibacterial Staphylococcus aureus
DOI10.1016/j.phytochem.2021.112656
WOS IDWOS:000631274200010
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/73039
Collection中国科学院昆明植物研究所
Affiliation1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Yunnan, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Chinese Acad Sci, Kunming Inst Bot, Yunnan Key Lab Nat Med Chem, Kunming 650204, Yunnan, Peoples R China
Recommended Citation
GB/T 7714
Kaunda,Joseph Sakah,Qin,Xu-Jie,Zhu,Hong-Tao,et al. Previously undescribed pyridyl-steroidal glycoalkaloids and 23S,26R-hydroxylated spirostanoid saponin from the fruits of Solanum violaceum ortega and their bioactivities[J]. PHYTOCHEMISTRY,2021,184:112656.
APA Kaunda,Joseph Sakah,Qin,Xu-Jie,Zhu,Hong-Tao,Wang,Dong,Yang,Chong-Ren,&Zhang,Ying-Jun.(2021).Previously undescribed pyridyl-steroidal glycoalkaloids and 23S,26R-hydroxylated spirostanoid saponin from the fruits of Solanum violaceum ortega and their bioactivities.PHYTOCHEMISTRY,184,112656.
MLA Kaunda,Joseph Sakah,et al."Previously undescribed pyridyl-steroidal glycoalkaloids and 23S,26R-hydroxylated spirostanoid saponin from the fruits of Solanum violaceum ortega and their bioactivities".PHYTOCHEMISTRY 184(2021):112656.
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