19456-89-4Relevant articles and documents
Two chromone-secoiridoid glycosides and three indole alkaloid glycosides from Neonauclea sessilifolia
Itoh, Atsuko,Tanahashi, Takao,Nagakura, Naotaka,Nishi, Toyoyuki
, p. 359 - 369 (2003)
From the dried roots of Neonauclea sessilifolia, two new chromone-secoiridoid glycosides, sessilifoside and 7″-O-β-D-glucopyranosylsessilifoside, and three novel indole alkaloid glycosides, neonaucleosides A, B, and C, were isolated along with the main known glycosides, 5-hydroxy-2-methylchromone-7-O-β-D-apiofuranosyl-(1→6)- β-D-glucopyranoside, sweroside, loganin, grandifloroside, and quinovic acid 3β-O-β-D-quinovopyranoside-28-O-β-D-glucopyranoside. The structures of these new glycosides were determined by spectroscopic and chemical means. Neonaucleoside A and its C-3 epimer were prepared from secologanin and tryptamine.
The absolute configuration of vincoside
Mattes,Hutchinson,Springer,Clardy
, p. 6270 - 6271 (1975)
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Strictosidine Synthase Triggered Enantioselective Synthesis of N-Substituted (S)-3,14,18,19-Tetrahydroangustines as Novel Topoisomerase i Inhibitors
Cai, Yunrui,Zhu, Huajian,Alperstein, Zaccary,Yu, Wenjun,Cherkasov, Artem,Zou, Hongbin
, p. 3086 - 3092 (2017)
Monoterpenoid indole alkaloids (MIAs) comprise an important class of molecules for drug discovery, and they have variant carbon skeletons with prominent bioactivities. For instance, in spite of limitations to their use, camptothecins are the only clinically approved topoisomerase I (Top1) inhibitors. The enzyme strictosidine synthase, which is key for MIA biosynthesis, was applied to the enantioselective preparation of three N-substituted (S)-3,14,18,19-tetrahydroangustine (THA) derivatives. These non-camptothecin MIAs were shown to have moderate in vitro HepG2 cytotoxicity and Top1 inhibition activities. The (S)-configured MIAs had stronger cytotoxicity and Top1 inhibition than their chemically synthesized (R)-enantiomers, which aligned with the results of molecular dynamics simulations. A series of N-substituted (S)-THAs were then chemoenzymatically synthesized to investigate structure-activity relationships. The most active analogue observed was the N-(2-Cl benzoyl)-substituted derivative (7i). Insight into the binding mode of 7i and a Top1-DNA covalent complex was investigated by molecular dynamics simulations, which will facilitate future efforts to optimize the Top1 inhibitory activities of non-camptothecin MIAs.
Substrate specificity of strictosidine synthase
McCoy, Elizabeth,Galan, M. Carmen,O'Connor, Sarah E.
, p. 2475 - 2478 (2006)
Strictosidine synthase catalyzes a Pictet-Spengler reaction in the first step in the biosynthesis of terpene indole alkaloids to generate strictosidine. The substrate requirements for strictosidine synthase are systematically and quantitatively examined and the enzymatically generated compounds are processed by the second enzyme in this biosynthetic pathway.
Substrate specificity and diastereoselectivity of strictosidine glucosidase, a key enzyme in monoterpene indole alkaloid biosynthesis
Yerkes, Nancy,Wu, Jia Xin,McCoy, Elizabeth,Galan, M. Carmen,Chen, Shi,O'Connor, Sarah E.
, p. 3095 - 3098 (2008)
Strictosidine glucosidase (SGD) from Catharanthus roseus catalyzes the deglycosylation of strictosidine, an intermediate from which thousands of monoterpene indole alkaloids are derived. The steady-state kinetics of SGD with a variety of strictosidine analogs revealed the substrate preferences of this enzyme at two key positions of the strictosidine substrate. Additionally, SGD from C. roseus turns over both strictosidine and its stereoisomer vincoside, indicating that although this enzyme prefers the naturally occurring diastereomer, the enzyme is not completely diastereoselective. The implications of the substrate specificity of SGD in metabolic engineering efforts of C. roseus are highlighted.
Bacterial biotransformation of 3α(S)-strictosidine to the monoterpenoid indole alkaloid vallesiachotamine
Shen, Zhengwu,Eisenreich, Wolfgang,Kutchan, Toni M.
, p. 293 - 296 (1998)
3α(S)-Strictosidine produced by heterologously expressed strictosidme synthase from Rauwolfia serpentina was used in biotransformation experiments with a series of 22 bacterial strains.All strains tested were found to deglucosylate and rearrange the alkaloid to vallesiachotamine, thereby providing an example of how gene technology and microbial biotransformation can be combined for the biotechnological production of alkaloidal natural products. - Keywords: Rauwolfia serpentina, Spodoptera frugiperda, baculovirus, strictosidine synthase, vallesiachotamine.
Total Synthesis of (-)-Strictosidine and Interception of Aryne Natural Product Derivatives "strictosidyne" and "strictosamidyne"
Anthony, Sarah M.,Tona, Veronica,Zou, Yike,Morrill, Lucas A.,Billingsley, John M.,Lim, Megan,Tang, Yi,Houk,Garg, Neil K.
, p. 7471 - 7479 (2021/05/26)
Monoterpene indole alkaloids are a large class of natural products derived from a single biosynthetic precursor, strictosidine. We describe a synthetic approach to strictosidine that relies on a key facially selective Diels-Alder reaction between a glucosyl-modified alkene and an enal to set the C15-C20-C21 stereotriad. DFT calculations were used to examine the origin of stereoselectivity in this key step, wherein two of 16 possible isomers are predominantly formed. These calculations suggest the presence of a glucosyl unit, also inherent in the strictosidine structure, guides diastereoselectivity, with the reactive conformation of the vinyl glycoside dienophile being controlled by an exo-anomeric effect. (-)-Strictosidine was subsequently accessed using late-stage synthetic manipulations and an enzymatic Pictet-Spengler reaction. Several new natural product analogs were also accessed, including precursors to two unusual aryne natural product derivatives termed "strictosidyne"and "strictosamidyne". These studies provide a strategy for accessing glycosylic natural products and a new platform to access monoterpene indole alkaloids and their derivatives.
A (S)- tetrahydro Angustine derivative and its preparation and use (by machine translation)
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Paragraph 0037; 0038, (2018/05/16)
The present invention provides a (S)- tetrahydro Angustine derivatives and their pharmaceutically acceptable salts, the use of nucleotide synthetase catalytic tryptamine and crack link vomica alkali synthetic nucleotide as the initiator, obtained through a series of structural modification. The invention synthesizes the traditional medicinal chemistry to a sole chiral synthesis of a plurality of works and nuclear compound, such compound has outstanding in vitro topoisomerase I inhibitory activity HepG2 with the in vitro anti-tumor activity, can be in the preparation topoisomerase I inhibitor anti-tumor drug in the application. With the following formula (I) structure of the general formula: . (by machine translation)
