β-Phenylethylamines and the isoquinoline alkaloids

Engineering biosynthesis of the anticancer alkaloid noscapine in yeast

“…Secoberberines such as 5 ′ and 7 are structurally unique and are currently commercially inaccessible. Thus, few studies have been conducted on secoberberine-based drug development 39 40 41 42 43 44 45 46 . In addition, the structure of 7 synthesized by CYP82X1 has not been confirmed due to the lack of authentic standards and limited quantity of the compound achieved in the in vitro investigations 47 .…”

“…Noscapine is a phthalideisoquinoline alkaloid synthesized from L -tyrosine through scoulerine 36 , and the biosynthesis scheme involves multiple types of alkaloids, including 1-benzylisoquinoline, protoberberine and secoberberine alkaloids 37 38 . Among them, secoberberine alkaloids exhibit a unique structural scaffold, but their pharmacological activities are less investigated than alkaloids such as 1-benzylisoquinoline, protoberberine or phthalideisoquinoline alkaloids 39 40 41 42 43 44 45 46 , which may be due to limited access to these molecules.…”

RhI/RhIII catalyst-controlled divergent aryl/heteroaryl C–H bond functionalization of picolinamides with alkynes

“…It is important to note that the isoquinoline moiety forms the core of many biologically active molecules. 14 In this study microwave heating was generally applied since it dramatically reduced reaction times (from 24 h to just 1 h) while preserving the high site-selectivity, as exemplified in the isolation of 2 in 90% yield. Both electron-donating and electron-withdrawing substituents at either the pyridine ( 14–15 , 54 and 62%) or the diarylacetylene 15 ( 11–12 , 61% and 63%) coupling partners were well tolerated.…”

Simultaneous quantification of 11 isoquinoline alkaloids in Corydalis impatiens (Pall.) Fisch by HPLC

“…The contents of the 11 alkaloids are shown in Table 4. It was found that capnoidine (1), bicuculline (3), protopine (4), isoapocavidine (5), cavidine (7), and ochotensimine (9) are six major alkaloid components of C. impatiens, while the contents of apocavidine (6), tetrahydroepiberberine (8), and tetrahydrocorysamine (11) are relatively lower, and the N = 3). c) LOQ (S/N = 10).…”

“…In previous chemical composition study of C. impatiens , 11 alkaloids (capnoidine, chelianthifoline, bicuculline, protopine, isoapocavidine, apocavidine, cavidine, tetrahydroepiberberine, ochotensimine, tetrahydrocoptisine, and tetrahydrocorysamine) had been isolated and identified . These compounds belong to isoquinoline alkaloids and had been reported to show a wide variety of biological and pharmacological activities such as anti‐inflammatory , antimicrobial , antitumor , antibacterial , antimalaria , anti‐hepatitis B virus , and antileukemic . Similarly, tetrahydrocoptisine showed significant anticholinesterase and antiplasmodial activities .…”