Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• Chemical exploration of solid-state cultures of the polypore Fomitopsis carnea afforded two new C31 lanostane-type triterpenoid glycosides, forpiniosides B (1) and C (2) together with two known derivatives, namely 3-epipachymic acid (3) and (3α,25S)-3-O-malonyl-23-oxolanost-8,24(31)-dien-26-oic acid (4

• elucidation of two new C31 lanostane-type triterpenoid glycosides (compounds 1 and 2 in Figure 1) together with two known derivatives, namely 3-epipachymic acid (3α-acetoxy-16α-hydroxy-5α-lanost-8,24(31)-dien-21-oic acid (3)) [24] and (3α,25S)-3-O-malonyl-23-oxolanost-8,24(31)-dien-26-oic acid (4) [25

• δC 70.7 (C-3') suggesting the presence of a 3-hydroxy-3-methylglutaroyl moiety in compound 1 [23]. These results illustrated that compound 1 is a C31 lanostane-type triterpenoid glucoside. According to the above results, the C31 lanostane-type triterpenoid moiety of compound 1 was identified to be a

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

• pharmaceuticals, food, cosmetics, and agricultural industries. In this review, we provide a full overview of 149 functionally characterised CYPs involved in the biosynthesis of triterpenoids and steroids in primary as well as in specialised metabolism. We describe the phylogenetic distribution of triterpenoid

• 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

• [7]. Hence, there is considerable interest in CYPs involved in triterpenoid and steroid metabolism in plants not only for improving our understanding of plant specialised metabolism, but also for synthetic biology and chemoenzymatic synthesis. In this review, we will provide an extensive overview of

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

• Jana M. Boysen,
• Nauman Saeed and
• Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

• treatment [75][164]. Helvolic acid Helvolic acid (HA) (23) is a fusidane-type antibiotic that belongs to the triterpenoid class of secondary metabolites. Originally, it was discovered from A. fumigatus but later several other members of the sub phylum Pezizomycotina were also found to be HA producers [165

Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale

• Ken-ichi Nakashima,
• Junko Tomida,
• Tomoe Tsuboi,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 2100–2107, doi:10.3762/bjoc.16.177

• sahnii, syn. Mycoleptodiscus indicus) are members of the Muyocopron genus [10]. Therefore, three azaphilone dimers [11] and a triterpenoid [12] previously isolated from Mycoleptodiscus indicus are now considered to be metabolites of Muyocopron strains. However, little information exists regarding the

Diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside: synthesis, derivatives and antimicrobial activity

• Henryk Myszka,
• Patrycja Sokołowska,
• Agnieszka Cieślińska,
• Andrzej Nowacki,
• Maciej Jaśkiewicz,
• Wojciech Kamysz and
• Beata Liberek

Beilstein J. Org. Chem. 2017, 13, 2310–2315, doi:10.3762/bjoc.13.227

• the obtained compounds are active against Gram-positive bacteria and Candida type fungi. Keywords: antimicrobial activities; D-galactosamine; diosgenin; glycosylation; saponin; tetrachlorophthalimido derivatives; Introduction Saponins are steroid or triterpenoid glycosides found in various plants [1

N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity

• Agata Walczewska,
• Daria Grzywacz,
• Dorota Bednarczyk,
• Małgorzata Dawgul,
• Andrzej Nowacki,
• Wojciech Kamysz,
• Beata Liberek and
• Henryk Myszka

Beilstein J. Org. Chem. 2015, 11, 869–874, doi:10.3762/bjoc.11.97

• . Keywords: antimicrobial activities; D-glucosamine; diosgenin glycosylation; N-alkylation; Introduction Saponins are a group of steroid or triterpenoid glycosides, widely distributed in the plant kingdom [1]. Saponins are characteristic by their foaming properties in aqueous solution, causing them to be

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

• Jun Hu,
• Jindan Wu,
• Qian Wang and
• Yong Ju

Beilstein J. Org. Chem. 2013, 9, 2877–2885, doi:10.3762/bjoc.9.324

• –vis region [25]. CT interactions have been employed to induce the supramolecular interactions between donors and acceptors, and lead to the formation of two-component organogels [26][27][28][29][30]. 18β-Glycyrrhetinic acid (GA, 1), a natural pentacyclic triterpenoid obtained from medicinal plants in

• powerful building blocks for materials development due to their unique rigid molecular structures [35][36][37][38][39][40][41]. In our previous work, we have already reported the synthesis of organogels based on triterpenoid moieties. For example, we designed and studied the one-component organogelation

Lanostane- and cycloartane-type triterpenoids from Abies balsamea oleoresin

• Serge Lavoie,
• Charles Gauthier,
• Jean Legault,
• Sylvain Mercier,
• Vakhtang Mshvildadze and
• André Pichette

Beilstein J. Org. Chem. 2013, 9, 1333–1339, doi:10.3762/bjoc.9.150

• -lanostane triterpenoids 1–3, one new cycloartane triterpenoid 4 along with fourteen known terpenoids. Structure determinations were based on extensive 1D/2D NMR, IR and MS spectroscopic analyses, and comparison with literature data. The isolated compounds were evaluated in vitro for their cytotoxicity

• triterpenoid 4 and fourteen known terpenoids. The antibacterial (E. coli and S. aureus) and cytotoxic (A549, DLD-1 and WS1) activities of the isolated compounds are also reported. Results and Discussion The oleoresin of A. balsamea (1st lot) was fractionated by silica gel column chromatography with hexanes

Recent progress in the discovery of small molecules for the treatment of amyotrophic lateral sclerosis (ALS)

• Allison S. Limpert,
• Margrith E. Mattmann and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2013, 9, 717–732, doi:10.3762/bjoc.9.82

• . Neymotin et al. [64] tested two related compounds, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid-ethylamide (CDDO-EA, 28, Figure 13) and CDDO-trifluoroethylamide (CDDO-TFEA, 29), synthetic triterpenoid analogues derived from oleanolic acid [64] for their ability to activate Nrf2/ARE signaling in cell

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

• Sciences, 142290 Pushchino, Moscow region, Russian Federation 10.3762/bjoc.8.87 Abstract Two new triterpenoid saponins 1 and 2 were isolated from the methanol extract of the roots of Acanthophyllum gypsophiloides Regel. These saponins have quillaic acid or gypsogenin moieties as an aglycon, and both bear

• similar sets of two oligosaccharide chains, which are 3-O-linked to the triterpenoid part trisaccharide α-L-Arap-(1→3)-[α-D-Galp-(1→2)]-β-D-GlcpA and pentasaccharide β-D-Xylp-(1→3)-β-D-Xylp-(1→3)-α-L-Rhap-(1→2)-[β-D-Quip-(1→4)]-β-D-Fucp connected through an ester linkage to C-28. The structures of the

• ; structure; Introduction Triterpenoid saponins [1] occur in many plant species and have a diverse range of properties [2]. Nowadays, a steadily growing number of publications [3][4][5][6][7][8][9][10] are aimed at research on saponins as potential adjuvants, with an urgent demand due to the fast development

Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP): A convenient 2-step procedure towards 12-oxo-28-carboxylic acid derivatives

• Jorge A. R. Salvador,
• Vânia M. Moreira,
• Rui M. A. Pinto,
• Ana S. Leal and
• José A. Paixão

Beilstein J. Org. Chem. 2012, 8, 164–169, doi:10.3762/bjoc.8.17

• : bismuth(III) triflate; δ-hydroxy-γ-lactones; MMPP; oleanolic acid; triterpenoid; Findings The molecular diversity that arises from research into natural products represents a valuable tool for driving drug discovery and development [1][2]. In this context, pentacyclic triterpenoids are currently regarded

• -carboxyl acid function. In fact, 12α-hydroxy-3-oxooleanan-28,13β-olide (2) is a key intermediate in the synthesis of S-0139, an endothelin A receptor antagonist [15]. Moreover, as part of our ongoing work on pentacyclic triterpenoid chemistry [16][17], we recently demonstrated that oleanolic δ-hydroxy-γ

The arene–alkene photocycloaddition

• Ursula Streit and
• Christian G. Bochet

Beilstein J. Org. Chem. 2011, 7, 525–542, doi:10.3762/bjoc.7.61

• the core of Lancifodilactone F [70]. This triterpenoid contains three fused and one spiro cycle and is a very challenging target. Initial attempts to construct the fused seven-, six- and five-membered core were unsuccessful. Introduction of a trimethylsiloxy group on the tether and an oxygen

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