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

• well-known profuse production of bioactive molecules, Basidiomycota have already been proven to be a valuable source for new anti-infectives [4]. These include a myriad of triterpenoids which have been resourceful in the discovery of potent antimicrobials [5]. Specifically, lanostane triterpenoids are

• bioactive lanostane triterpenoids [9][10]. In addition, the edible European fungus Macrolepiota procera also produced antiproliferative and anti-inflammatory lanostanoid derivatives [11]. Furthermore, triterpenes from Tricholoma pardinum and Fomitopsis betulina (previously known as Piptoporus betulinus

• cytotoxicity assay. Recent structure–activity relationship (SAR) studies have indicated a key role played by the hydroxy group at C-3 in cytotoxic effects of lanostane triterpenoids [23][36]. According to a study by Wang et al. (2023) [36], synthetic derivatives of pachymic acid demonstrated moderate to high

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

• (CYP) superfamily comprises hemethiolate enzymes that perform remarkable regio- and stereospecific oxidative chemistry. As such, CYPs are key agents for the structural and functional tailoring of triterpenoids, one of the largest classes of plant natural products with widespread applications in

• 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

• - and steroid-modifying CYPs across the plant CYPome, present a structure-based summary of their reactions, and highlight recent examples of particular interest to the field. Our review therefore provides a comprehensive up-to-date picture of CYPs involved in the biosynthesis of triterpenoids and

Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation

• Lukáš Ďurina,
• Anna Ďurinová,
• František Trejtnar,
• Ľuboš Janotka,
• Lucia Messingerová,
• Jana Doháňošová,
• Ján Moncol and
• Róbert Fischer

Beilstein J. Org. Chem. 2021, 17, 2781–2786, doi:10.3762/bjoc.17.188

• , triterpenoids, polysaccharides, and alkaloids are responsible for the majority of the activities found in Codonopsis species. Although the polyhydroxylated pyrrolidine alkaloids from C. pilosula possess glycosidase inhibitory activities and they are considered to be anticancer species, their activity against

Phenolic constituents from twigs of Aleurites fordii and their biological activities

• Kyoung Jin Park,
• Won Se Suh,
• Da Hye Yoon,
• Chung Sub Kim,
• Sun Yeou Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2021, 17, 2329–2339, doi:10.3762/bjoc.17.151

• this plant have been used as a Korean traditional medicine for treating sore throat, respiratory illness, constipation, and dieresis [2][3]. Phytochemical investigations of A. fordii reported coumarins, diterpenoid esters, triterpenoids, and tannins [4][5][6][7]. Some phorbol diterpenoids isolated from

Chemical constituents of Chaenomeles sinensis twigs and their biological activity

• Joon Min Cha,
• Dong Hyun Kim,
• Lalita Subedi,
• Zahra Khan,
• Sang Un Choi,
• Sun Yeou Kim and
• Chung Sub Kim

Beilstein J. Org. Chem. 2020, 16, 3078–3085, doi:10.3762/bjoc.16.257

• studies on this plant have reported triterpenoids [2][3][4][5][6][7][8] and phenolic compounds [2][9][10][11][12], and some of them showed anti-inflammatory and neuroprotective [13][14][15], antitumor [2], tissue factor inhibitory [5][9], antibacterial [8], antihemolytic [8], or antipruritic activities

• [11]. As a part of the continuing studies to identify bioactive constituents from the Korean medicinal plants [13][16][17][18][19][20], previous phytochemical investigations on the MeOH extract of the twigs of C. sinensis have led to the isolation and characterization of triterpenoids [13], biphenyls

• against four human tumor cell lines A549, SK-OV-3, SK-MEL-2, and BT549 using a sulforhodamine B (SRB) assay. Of the three lupane-type triterpenoids (9–11), betulin (9) and betulinic acid (10) showed potent cytotoxicity with IC50 values of 4.2–8.7 μM against all four tumor cell lines whereas betulinal (11

Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

• Dong Cai,
• ZhiHua Zhang,
• Yufan Meng,
• KaiLi Zhu,
• LiYi Chen,
• ChangXiang Yu,
• ChangWei Yu,
• ZiYi Fu,
• DianShen Yang and
• YiXia Gong

Beilstein J. Org. Chem. 2020, 16, 798–808, doi:10.3762/bjoc.16.73

• -type pentacyclic triterpenoids, and the synthetic methods studied here can also apply to the modification of structurally similar other triterpenoic acids, but further experimental verification is needed. Results and Discussion The synthetic route to 18β-glycyrrhetinic acid piperazinyl amide 4 was

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• ], triterpenoids [10] and prenylated polyketide meroterpenoids [11][12][13][14][15] isolated from soil, endophytes and marine strains. Of this genus, A. ustus [16], A. calidoustus [17], A. insuetus [17], A. insulicola [18], A. bridgeri [18], A. sclerotiorum [19], A. variecolor [19], A. parasiticus [20], A. oryzae

Genicunolide A, B and C: three new triterpenoids from Euphorbia geniculata

• Alia Farozi,
• Javid A. Banday and
• Shakeel A. Shah

Beilstein J. Org. Chem. 2015, 11, 2707–2712, doi:10.3762/bjoc.11.291

• Alia Farozi Javid A. Banday Shakeel A. Shah Department of Chemistry, National Institute of Technology, Hazratbal, Srinagar-190006, J&K, India, Tel.: +91 9906626635 10.3762/bjoc.11.291 Abstract Three new triterpenoids, designated as genicunolide A (1), B (2) and C (3), along with friedelin (4) and

• . Keywords: Euphorbiaceae; Euphorbia geniculata; friedelin; friedelinol; genicunolide A; B; C; pentacyclic triterpenoids; Introduction Euphorbia (Euphorbiaceae) is a very large and diverse genus of flowering plants comprising of about 2,000 members and is found all over the world, ranging from short annual

• ][9][10][11][12][13]. Triterpenoids which have been reported from various species of Euphorbia include β-amyrin [1], β-amyrin acetate [14][18], cycloeucalenol, obtusifoliol, 24-methylenecycloartan-3-β-ol, β-sitosterol, betulin, erythrodiol, oleanolic acid, β-sitosterol glucoside[15], 29-norcycloart-5

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

• the form of free acids or aglycones, has been noted by its low toxicity, biocompatibility and bioactivity [31][32]. A wide array of papers has been published to report its anti-inflammatory, antiviral, and antitumor effects [33][34]. In recent years, it has been found that triterpenoids can serve as

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

• ; lanostane; oleoresin; triterpenoids; Introduction The genus Abies (Pinaceae) comprises 46 species of evergreen conifers [1]. Most of them are found in temperate and boreal regions of the northern hemisphere. The first phytochemical investigation of Abies species was undertaken 75 years ago by Takahashi [2

• tetraterpenoids from the cortical oleoresin of the tree bark, featuring an unprecedented C40 scaffold [6]. Herein, we describe the further phytochemical study of A. balsamea oleoresin, which led to the isolation and structure elucidation of three 3,4-seco-lanostane-type triterpenoids 1–3, one cycloartane-type

Zanthoxoaporphines A–C: Three new larvicidal dibenzo[de,g]quinolin-7-one alkaloids from Zanthoxylum paracanthum (Rutaceae)

• Fidelis N. Samita,
• Louis P. Sandjo,
• Isaiah O. Ndiege,
• Ahmed Hassanali and
• Wilber Lwande

Beilstein J. Org. Chem. 2013, 9, 447–452, doi:10.3762/bjoc.9.47

• same genus as rich in alkaloids [3][4][5], which constitute the most abundant class of compounds in this genus, while coumarins [6], lignans [3] and triterpenoids, especially limonoids [7], are the minor constituents. Different classes of alkaloids have been found and reported from Zanthoxylum species

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

• of immunotherapy methods. Among the most efficient saponin adjuvants are the components of a complex mixture of triterpenoids extracted from the bark of Quillaja saponaria Molina, which are used in veterinary vaccines [4]. One of the best known products of this origin is the less toxic and more

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

• as important scaffolds for new drug development [3]. The chemistry of oleanane-type triterpenoids has been investigated with particular interest and many relevant biological and pharmacological activities of these derivatives have been reported in the literature, among which are antitumor, antiviral

• triterpenoids bearing a γ-lactone function, either isolated from natural sources or obtained by semisynthesis, have shown interesting biological activities [12][13][14]. From the synthetic point of view, the oxidative 28,13β-lactonization allows the preparation of 12α-hydroxyoleananes with a protected 28

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

• , triterpenoids have been recognized as renewables in supramolecular chemistry and nanoscience [5][6][7][8][9][10]. Even though the nano-sized triterpenic acids are available in abundance from a variety of plants, a major difficulty in their use is their availability in pure form. Occurrence of the pentacyclic

• triterpenoids having a β-amyrin skeleton with certain amounts of α-amyrins is common in nature and has been explained by 1,2-CH3 migration during their biosynthesis [11]. The mixture of the triterpenic acids extractable from Terminalia arjuna contains arjunolic acid as the major component along with asiatic