scholarly journals Isolation and synthesis of cryptosanguinolentine (isocryptolepine), a naturally-occurring bioactive indoloquinoline alkaloid

RSC Advances ◽  
2020 ◽  
Vol 10 (32) ◽  
pp. 18978-19002
Author(s):  
Elida N. Thobokholt ◽  
Enrique L. Larghi ◽  
Andrea B. J. Bracca ◽  
Teodoro S. Kaufman

The isolation and properties of the heterocycle are detailed and the diversity of chemical approaches toward the natural product are systematically ordered and reviewed.

Planta Medica ◽  
2017 ◽  
Vol 84 (01) ◽  
pp. 8-19 ◽  
Author(s):  
José Ríos ◽  
Salvador Máñez

AbstractBetulinic acid is a naturally occurring pentacyclic lupane-type triterpenoid usually isolated from birch trees, but present in many other botanical sources. It is found in different plant organs, both as a free aglycon and as glycosyl derivatives. A wide range of pharmacological activities has been described for this triterpenoid, including antiviral and antitumor effects. In addition, several other interesting properties have been identified in the fields of immunity and metabolism, namely antidiabetic, antihyperlipidemic, and anti-inflammatory activities. Taken together, these latter three properties make betulinic acid a highly interesting prospect for treating metabolic syndrome. The present review focuses on the therapeutic potential of this agent, along with several of its semisynthetic derivatives, which could open new frontiers in the use of natural product-based medicines.


Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.


1982 ◽  
Vol 37 (5-6) ◽  
pp. 354-362 ◽  
Author(s):  
Lutz Heide ◽  
Eckhard Leistner

AbstractSeveral prenylated naphthalene derivatives were synthesized and characterized by spectroscopic methods. One of these compounds, 2-methoxycarbonyl-3-prenyl-1,4-naphthoquinone, was detected as a new natural product in the root system of Galium mollugo L. This new natural product is likely to be related to the biosynthesis of mollugin and anthraquinones.


2018 ◽  
Vol 81 (12) ◽  
pp. 2750-2755 ◽  
Author(s):  
A. Jonathan Singh ◽  
Alexander P. Gorka ◽  
Heidi R. Bokesch ◽  
Antony Wamiru ◽  
Barry R. O’Keefe ◽  
...  

1987 ◽  
Vol 40 (11) ◽  
pp. 1901 ◽  
Author(s):  
DP Mcadam ◽  
AMA Perera ◽  
RV Stick

The synthesis of the title compound, isolated from the brown kelp ( Ecklonia radiata ) or the giant clam (Tridacna maxima), is reported. Glycosidation of 1-O-acetyl-2,3,5-tri- O- benzoyl -β-D-ribose, either directly with (S)-1,2-di-O-benzylglycerol or via the derived orthoester with (S)-1,2-O-isopropylideneglycerol, led to two fully protected glycerol β-D- ribofuranosides. Subsequent chemical manipulations led to a common intermediate having a free hydroxy group at C5 of the D-ribose residue. Replacement of this hydroxy group by a chlorine atom allowed the introduction of the dimethylarsinyl group at C5 in a two-step procedure, and removal of protecting groups provided the natural product.


HortScience ◽  
2004 ◽  
Vol 39 (4) ◽  
pp. 817C-817
Author(s):  
Chien Wang*

The objective of this study was to determine if treatment with methyl jasmonate (MJ), a naturally occurring substance, would extend the shelf life of tomato slices, specifically when slices were cut from fruit previously treated with this natural product. Tomatoes were harvested at breaker stage. The fruit were divided into four lots. The first three lots were treated with MJ right after harvest at the breaker stage. Fruit from the first lot were sliced immediately after MJ treatment. Fruit from the second lot were placed at 20 °C and allowed to ripen to red stage before slicing. Fruit from the third lot were treated the same way as those in the second lot except they received an additional MJ treatment just before slicing. Fruit from the fourth lot were placed at 20 °C and allowed to ripen to red stage before MJ treatment and slicing. Each lot also included an untreated control. MJ treatments were carried out in 200-L airtight containers. MJ was spotted onto filter paper at final vapor concentration of 10-5 M. Fruit were cut with a meat slicer to obtain slices with 5-mm thickness. Slices were placed in 1-L clear plastic trays with lids and stored at 5 °C. Samples were transferred daily from 5 to 20 °C for evaluation. Fresh-cut tomatoes treated with MJ and sliced at breaker stage (lot 1) had less decay, better quality, and longer shelf life than the untreated slices. However, no differences were found between the control slices and treated slices at the red stage regardless the time of MJ treatment and whether or not additional MJ treatments were applied (lots 2, 3 & 4). The results indicate that the effectiveness of MJ in reducing decay and maintaining quality is affected by the stages of ripeness of tomatoes and the types of decay.


2018 ◽  
Vol 19 (1) ◽  
pp. 79-86 ◽  
Author(s):  
Zeinab A. Muhammad ◽  
Mohamed A.A. Radwan ◽  
Thoraya A. Farghaly ◽  
Hatem M. Gaber ◽  
Mahmuod M. Elaasser

Background: Several biologically active indole alkaloids have been isolated from marine organisms over the previous few years. Many scientsts interested in synthesis of the marine azepinoindole alkaloids due to their wide range of bioliogical activies. </P><P> Objective: We interested herein to synthesize a new series of some analogues of new naturally occurring azepinoindole alkaloids. </P><P> Method: A novel series of [1,2,4,5]tetrazepino[6,7-b]indoles, Marine natural product Hyrtioreticuline C and D analogues, were synthesized via the reaction of 3-hydrazonoindolin-2-one with hydrzaonoyl chlorides in basic medium. </P><P> Results: The spectral data of the products proved their structure. All new derivatives were tested against two carcinoma cell lines ((A-549 & HepG2)) in comparison with the well-known anticancer standard drug (cisplatin) and two derivatives from the tested compounds showed activity more potent than the reference drug. </P><P> Conclusion: We succeeded in synthesis of new antitumor active azepinoindole alkaloids.


2018 ◽  
Vol 16 (27) ◽  
pp. 5027-5035 ◽  
Author(s):  
Ranjan Kumar Acharyya ◽  
Samik Nanda

Asymmetric total synthesis of naturally occurring γ-butenolide containing [4.4]spiro-tetrahydrofuran lanceolactone A has been reported in this present work. Bimetallic (“Pd–Cu”) cascade cyclization was the crucial reaction employed for the construction of the γ-butenolide framework of the natural product.


2000 ◽  
Vol 78 (5) ◽  
pp. 542-545 ◽  
Author(s):  
Veejendra K Yadav ◽  
Philip Williams ◽  
Michael Benn

The synthesis of N-(4-acetamidobutyl)-N-((Z)-4-hydroxy-3-methyl-2-butenyl) guanidine confirmed this as the structure of the natural product hydroxysmirnovine.Key words: hydroxysmirnovine, synthesis, naturally occurring guanidines.


1994 ◽  
Vol 47 (5) ◽  
pp. 933 ◽  
Author(s):  
R Davis ◽  
RJ Capon

A reinvestigation of the known marine natural product strobilinin has revealed it not to be a single compound (2), but to consist of two naturally occurring geometric isomers, neither of which corresponds to the structure originally assigned. These isomers, (8E,13Z,20Z)- strobilinin (10) and (8Z,13E,20Z)-strobilinin (11), were resolved, characterized and identified as their respective acetate derivatives (6) and (7), and their structures assigned by spectroscopic analysis. It would appear that the absolute stereochemistry of the strobilinins is very likely opposite to that of co-occurring variabilin (1).


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