Preparation of β-cyclodextrin/polysaccharide foams using saponin

• Max Petitjean and
• José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

• ]. The aglycone part is composed of steroid and triterpene molecules [3]. Not only present in plants [4][5], saponins have also been discovered in marine animals, such as sea cucumbers [6] or starfish [7]. Chemical structures of this family are varied [1], so they will show different properties [8

New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling

• Elenilson F. da Silva,
• Krist Helen Antunes Fernandes,
• Denise Diedrich,
• Jessica Gotardi,
• Marcia Silvana Freire Franco,
• Carlos Henrique Tomich de Paula da Silva,
• Ana Paula Duarte de Souza and
• Simone Cristina Baggio Gnoatto

Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161

• drug for its treatment, however, its clinical use has been limited due to its side effects. Here, we designed two new nitroaryl-1,2,3-triazole triterpene derivatives as novel anti-RSV drugs. Their anti-RSV and cytotoxic activity were evaluated in vitro, RSV protein F gene effects by RT-PCR and

• the same region occupied by crystallographic ligands in their complex with IMPDH. The results obtained in this study suggest that compound 8 might be a new anti-RSV candidate. Keywords: antiviral; betulinic acid; bioisosterism; respiratory syncytial virus; triterpene; ursolic acid; Introduction

• scenario, here, we report our aims to develop new triterpene derivatives using a bioisosterism approach with RBV as an IMPDH inhibitor and anti-RSV agent. Results and Discussion Chemistry In this study, we synthesized two new heterocycle-modified triterpene derivatives (compounds 7 and 8) with a 1,2,3

Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants

• Karan Malhotra and
• Jakob Franke

Beilstein J. Org. Chem. 2022, 18, 1289–1310, doi:10.3762/bjoc.18.135

• steroids in plants as a starting point for future research. Keywords: biosynthesis; CYPs; cytochrome P450 monooxygenases; plants; steroid; sterol; triterpene; triterpenoid; Introduction Triterpenoids are a large class of natural products derived from precursors containing 30 carbon atoms and composed of

• other families of the CYP85 clan such as CYP87, CYP85, or CYP90 contain mostly triterpene-modifying CYPs to date. The small clans CYP51 and CYP710 are other important examples of groups with a high preference for triterpenoid substrates. The highly diverse CYP71 clan, in contrast, only contains a few

• triterpene-modifying CYPs, particularly in the families CYP93, CYP712 and CYP705. The CYP72 family (CYP72 clan) also contains several known representatives. In other clans, however, not a single triterpene-modifying CYP has been identified so far, for example CYP97, CYP74, or CYP711. The discovery of

Understanding the role of active site residues in CotB2 catalysis using a cluster model

• Keren Raz,
• Ronja Driller,
• Thomas Brück,
• Bernhard Loll and
• Dan T. Major

Beilstein J. Org. Chem. 2020, 16, 50–59, doi:10.3762/bjoc.16.7

• been reviewed elsewhere [3][10][11][12][13][14][15][16][17]. The first crystal structure of a monoterpene cyclase [18] was reported in 2002. Subsequently, the first crystal structures of a sesquiterpene [19][20] and a triterpene [21] cyclase were published in 1997. Less than a decade ago, the first

New terpenoids from the fermentation broth of the edible mushroom Cyclocybe aegerita

• Frank Surup,
• Florian Hennicke,
• Nadine Sella,
• Maria Stroot,
• Steffen Bernecker,
• Sebastian Pfütze,
• Marc Stadler and
• Martin Rühl

Beilstein J. Org. Chem. 2019, 15, 1000–1007, doi:10.3762/bjoc.15.98

• illudine [11], aromadendrane [12], marasmene [13] and fomannosane [14] type skeletons. Although bovistol could formally be supposed to be a triterpene, it is thought to be derived by a hetero-Diels–Alder reaction of two sesquiterpenes to form a dimeric sesquiterpenoid [15]. In the recently published genome

The direct oxidative diene cyclization and related reactions in natural product synthesis

• Juliane Adrian,
• Leona J. Gross and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200

• ], another triterpene natural product found in Jamaican endemic plant Spathelia glabrescens (Rutaceae) [141]. In 1999, Morimoto and co-workers reported on a stereoselective synthesis of the meso-tris-THF natural product teurilene (82) [142][143] (several previous total syntheses existed [144][145][146][147

• product in 29% yield (Scheme 17). This (supposedly) type B’ ring forming reaction occurred with high stereoselectivity for the trans-isomer and in addition a minor amount of the mono-cyclization product 83 was obtained. Eurylene Eurylene (87) represents yet another oxasqualenoid triterpene, sharing some

Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines

• Eric Buchy,
• Branko Vukosavljevic,
• Maike Windbergs,
• Dunja Sobot,
• Camille Dejean,
• Simona Mura,
• Patrick Couvreur and
• Didier Desmaële

Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109

• triterpene, to a drug led to the formation of a prodrug that spontaneously self-assembled as nanoparticles in water. The advantage of this approach is a very high drug loading into the nanoparticles and the absence of burst release [5]. The proof of concept of this method has been done using gemcitabine (2

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

• Elena A. Khatuntseva,
• Vladimir M. Men’shov,
• Alexander S. Shashkov,
• Yury E. Tsvetkov,
• Rodion N. Stepanenko,
• Raymonda Ya. Vlasenko,
• Elvira E. Shults,
• Genrikh A. Tolstikov,
• Tatjana G. Tolstikova,
• Dimitri S. Baev,
• Vasiliy A. Kaledin,
• Nelli A. Popova,
• Valeriy P. Nikolin,
• Pavel P. Laktionov,
• Anna V. Cherepanova,
• Tatiana V. Kulakovskaya,
• Ekaterina V. Kulakovskaya and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2012, 8, 763–775, doi:10.3762/bjoc.8.87

• triterpene aglycon and showed the positions of the substitutions within the oligosaccharide fragments (Table 1 and Table 2). The ROESY spectra (identical for compounds 1 and 2) disclosed the sequence of the residues in two oligosaccharides and their location at the C-3 and C-28 of the aglycon. Thus, the

• location of GlcA (residue a) at the position 3 of the triterpene was established from the presence of a correlation peak 1a/3Agl (Figure 2 and Figure 3). Correlation peaks 1b/2a and 1c/3a correspond to substitutions of the residue a by terminal b at the position 2 and by terminal c at the position 3

• . Esterification of the position 1 of Fuc (residue d) with the carboxy group of the triterpene was unambiguously shown by the high-field shift of C-1 (94.4 ppm), being indirectly confirmed with the long-range correlation peak in the ROESY spectra 16Agl/3d. The sequence of the other residues was disclosed from the

Synthesis and antiviral activities of spacer-linked 1-thioglucuronide analogues of glycyrrhizin

• Christian Stanetty,
• Andrea Wolkerstorfer,
• Hassan Amer,
• Andreas Hofinger,
• Ulrich Jordis,
• Dirk Claßen-Houben and
• Paul Kosma

Beilstein J. Org. Chem. 2012, 8, 705–711, doi:10.3762/bjoc.8.79

• need for new antiviral compounds. Starting from the natural, antivirally active compound glycyrrhizin, spacer-bridged derivatives were generated with improved antiviral activity against the influenza A virus infection. Simplified analogues of the triterpene saponin glycyrrhizin containing 1-thio-β-D

• cells, wherein the 3-(2-thioethyl)-N-acetylamino- and 3-(2-thioethyl)-thio-linked glucuronide derivatives were effective inhibitors with IC50 values as low as 54 µM. Keywords: antiviral activity; carbenoxolone; glycyrrhizin; influenza A virus; thioglycoside; triterpene; Introduction The triterpene

• saponin glycyrrhizin (GL) and its aglycon glycyrrhetinic acid (GA) are the main triterpene components of licorice roots and harbor various pharmacological activities, including antitumor, anti-inflammatory, antioxidant and antiviral properties [1][2]. The antiviral activities have been reported to be

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

• in the presence of propargyl glycosides and propargyl ethers was developed [41]. Recently, Li et al. reported the gold(I)-catalyzed glycosylation with glycosyl ortho-alkynylbenzoates 73 as donors [42]. This glycosylation protocol was used in an efficient synthesis of a cyclic triterpene

A simple route for renewable nano- sized arjunolic and asiatic acids and self- assembly of arjuna- bromolactone

• Braja G. Bag,
• Partha P. Dey,
• Shaishab K. Dinda,
• William S. Sheldrick and
• Iris M. Oppel

Beilstein J. Org. Chem. 2008, 4, No. 24, doi:10.3762/bjoc.4.24

• self-assembly of nano-sized arjuna-bromolactone are reported. Keywords: arjunolic acid; nanochemistry; renewable; self-assembly; triterpene; Introduction Triterpenes are an important class of plant secondary metabolites derived from C30 precursors [1][2]. More than 100 triterpenoids with different

Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells

• Li-Rong Sun,
• Chen Qing,
• Yan-Li Zhang,
• Shu-Yu Jia,
• Zhong-Rong Li,
• Shen-Ji Pei,
• Ming-Hua Qiu,
• Michael L. Gross and
• Samuel X. Qiu

Beilstein J. Org. Chem. 2007, 3, No. 3, doi:10.1186/1860-5397-3-3

• 10.1186/1860-5397-3-3 Abstract Two new cycloartane-type triterpene glycosides, namely cimicifoetisides A (1) and B (2), along with seven known compounds cimigenol, 25-O-acetylcimigenol, cimigenol 3-O-β-D-xylopyranoside, 12β-hydroxycimigenol 3-O-β-D-xylopyranoside, cimigenol 3-O-α-L-arabinopyranoside, 25

• imported into Western markets. [5] In our continuing search for novel anti-cancer agents from natural products, we found that a methanol extract from the rhizomes of C. foetida exhibited considerable cytotoxicity to human cancer cell lines. To date, more than 30 triterpene glycosides have been isolated

• revealed its identity as a member of the cycloartane group of triterpene glycosides, a characteristic and distinguishable chemical marker of Cimicifuga plants. [6] In the 1H-NMR spectrum (Table 1), the characteristic cyclopropane methylene signals at δH 0.22 and 0.46 (each 1H, d, J = 3.0 Hz); eight methyl