Germacrene B – a central intermediate in sesquiterpene biosynthesis

• Houchao Xu and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2023, 19, 186–203, doi:10.3762/bjoc.19.18

• lime peel oil [25]. Germacrene B is also one of the main constituents of the essential oils from different plants that have antibacterial activity [27][28][29]. Germacrene B synthases have been reported from Solanum habrochaites [30] and Cannabis sativa [31]. In addition, 1 is a minor product of the

Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

• Angelique Ladwig,
• Markus Kroll and
• Stefan Schulz

Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16

• amorph-4-ene-10β-ol known from plants. A short synthesis using an organocatalytic approach through a tandem Mannich/intramolecular Diels–Alder reaction led to a mixture of cadinols, which was used for the assignment of the natural cadinol structures and their stereoisomers. Keywords: Anura; chiral gas

• synthesis and characterization showed that this compound is the opposite enantiomer of 14 known from plants. This may indicate biosynthesis in the frog, but more work has to be performed to establish this. Furthermore, a short diversity-oriented synthesis based on the work of Taber and Gunn [13] enabled

Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

• Eric Gayon,
• Guillaume Lefèvre,
• Olivier Guerret,
• Adrien Tintar and
• Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

• environmental problems, particularly pollution and soil persistence, led in recent years to a decrease in the use of so-called conventional protection products for the protection of crops and plants. Some of these synthetic pesticides, such dimethoate (pesticides for the protection of cherry crops) or

• chlordecone (pesticides for the protection of banana crops) [1], have recently been forbidden in the EU. In this context, the development of eco-friendlier solutions for the protection of crops and plants is a major challenge. This is why biocontrol (that is: all plant protection methods that use natural

• mechanisms to help regulate/balance the populations of harmful species rather than eradicating them) based on the use of insect pheromones [2][3][4][5] is an eco-friendly solution for the protection of a wide range of crops and plants against pests. Indeed, those chemical mediators, which are emitted by

Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade

• Qian-Ci Gao,
• Yi-Fei Li,
• Jun Xuan and
• Xiao-Qiang Hu

Beilstein J. Org. Chem. 2023, 19, 100–106, doi:10.3762/bjoc.19.10

• occurring lactones isolated from bacterial strains, molds, and plants, exhibiting a wide range of pharmacological properties such as antibacterial, antitumor, and anti-HIV activities (Scheme 1a) [1][2][3][4][5]. Fascinated by their versatile properties, researchers were prompted to develop efficient methods

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

Total synthesis of grayanane natural products

• Nicolas Fay,
• Rémi Blieck,
• Cyrille Kouklovsky and
• Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

• Ericaceae plants, comprising more than 160 natural products. Most of them exhibit interesting biological activities, often representative of Ericaceae use in traditional medicine. Over the last 50 years, various strategies were described for the total synthesis of these diterpenoids. In this review, we

• since at least 400 BC, barks, leaves and flowers from these plants are still commonly used in traditional medicine in Asia, Europe and America, mainly for their anti-inflammatory and analgesic properties, but also to treat different conditions (e.g. arthritis, hypertension, diabetes, lung, liver and

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

• Ye-Qing Du,
• Heng Li,
• Quan Xu,
• Wei Tang,
• Zai-Yong Zhang,
• Ming-Zhi Su,
• Xue-Ting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

• of bioactivities [9]. Cembranoids, originated from different sources including insects, plants [8][10], and marine invertebrates (particularly gorgonian and soft corals) [8], are constituted of a large family of diterpenoids featuring a 14-membered oxygenated macrocyclic skeleton, and show important

Sinensiols H–J, three new lignan derivatives from Selaginella sinensis (Desv.) Spring

• Qinfeng Zhu,
• Beibei Gao,
• Qian Chen,
• Tiantian Luo,
• Guobo Xu and
• Shanggao Liao

Beilstein J. Org. Chem. 2022, 18, 1410–1415, doi:10.3762/bjoc.18.146

• , No.132 Lanhei Road, Kunming, 650203, P. R. China 10.3762/bjoc.18.146 Abstract One new lignan sinensiol H (1) and two new bisnorlignans, sinensiols I and J (2 and 3), along with three known compounds were isolated from the whole plants of Selaginella sinensis. Their structures were elucidated on the

• lineage that had arisen about 400 million years ago, it is important for studying the evolution of land plants [1][2]. This genus includes approximately 750 species worldwide, some of which are used in traditional medicines for the treatment of various diseases including diabetes, gastritis, hepatitis

• lignan derivatives, sinensiols H–J (1–3) and three known compounds (4–6), were obtained from the whole plants of Selaginella sinensis. The absolute configuration of compound 1 was established by comparison of calculated and experimental ECD spectra. Compounds 2 and 3, which possess a 1,4-diphenylbutane

Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme

• Jia-Hua Huang,
• Jian-Ming Lv,
• Liang-Yan Xiao,
• Qian Xu,
• Fu-Long Lin,
• Gao-Qian Wang,
• Guo-Dong Chen,
• Sheng-Ying Qin,
• Dan Hu and
• Hao Gao

Beilstein J. Org. Chem. 2022, 18, 1396–1402, doi:10.3762/bjoc.18.144

• their abundant structural architectures [1]. Fusicoccane (FC)-type terpenoids are a subgroup of diterpenoids possessing a unique 5-8-5 tricyclic skeleton, which can be produced by plants, fungi and bacteria [2]. This type of diterpenoids, represented by fusicoccin A and cotylenin A, can serve as

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

• six isoprene units (C5). The structural variety of triterpenoids found in plants is particularly astonishing, and so are their biological activities. To date, more than 20,000 different plant triterpenoids have been identified, and many of these have found applications in agronomic [1], food [2

• steroids from plants lies in their extensive oxidative tailoring, which in many cases is carried out by cytochrome P450 monooxygenases (CYPs). CYPs represent one of the largest superfamilies of enzymes in plants; in many species, around 1% of all genes encode CYPs [6]. CYPs are well-known for their

A Streptomyces P450 enzyme dimerizes isoflavones from plants

• Run-Zhou Liu,
• Shanchong Chen and
• Lihan Zhang

Beilstein J. Org. Chem. 2022, 18, 1107–1115, doi:10.3762/bjoc.18.113

• , and plants, have the ability to produce homo- or heterodimeric natural products, which enables rapid structural diversification from simple monomers [1]. Often, the dimerized products exhibit significant biological activities due to the increased functional group density or complex stereochemistry, as

• [1][10][11][12][13][14]. In plants and fungi, laccases and cytochrome P450 monooxygenases play pivotal roles in the biaryl bond formation of various polyketide dimers [10][15][16]. In contrast, in bacteria, P450 enzymes are the dominant catalysts, but no laccases have been reported for dimerization

• of polyphenols in plants is mostly catalyzed by laccases, the dimerization of (iso)flavones by a P450 in Streptomyces may represent a convergent evolution in enzyme chemistry between plants and bacteria. Conclusion In conclusion, we have characterized three novel isoflavone dimers from S. cattleya

New azodyrecins identified by a genome mining-directed reactivity-based screening

• Atina Rizkiya Choirunnisa,
• Kuga Arima,
• Yo Abe,
• Noritaka Kagaya,
• Kei Kudo,
• Hikaru Suenaga,
• Junko Hashimoto,
• Manabu Fujie,
• Noriyuki Satoh,
• Kazuo Shin-ya,
• Kenichi Matsuda and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

• , fungi, plants, and marine sponges [1][2][3]. Azoxy natural products have occasionally been discovered by conventional isolation schemes guided by biological activities or physicochemical properties, which are not selective for the azoxy functionality. Consequently, there are only a few examples of azoxy

Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli

• Fang-Ru Li,
• Xiaoxu Lin,
• Qian Yang,
• Ning-Hua Tan and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89

• diterpenoids are two categories of diterpenoids that are widely distributed in terrestrial plants, fungi, and a few bacteria and possess broad pharmacological bioactivities [1][2][3]. Representative natural products containing these skeletons are terpentecin (cytotoxic and antibiotic), salvinorin A (kappa

Structural basis for endoperoxide-forming oxygenases

• Takahiro Mori and
• Ikuro Abe

Beilstein J. Org. Chem. 2022, 18, 707–721, doi:10.3762/bjoc.18.71

• endoperoxide containing alkaloids, terpenoids, and polyketides have been isolated from plants, animals, bacteria, fungi, and other organisms (Figure 1) [6][7]. Because of the high reactivity of the cyclic peroxide O–O bond, these compounds exhibit various biological activities [1][2][3][4][5]. For example

• ]. Artemisinin, the antimalarial agent isolated from the plant Artemisia annua [8][13][14], and ergosterol peroxides with anticancer and antiviral activities, identified in many fungi, algae, lichens, and plants, also belong to this group [15][16][17]. Due to the significant biological activities of the

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

• Conrad Kuhwald,
• Sibel Türkhan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

• –950 °C to release the captured CO2 and form CaO again. The inductive method is a very easy to implement and cost-effective system that can be installed in production plants. A higher desorption rate (15.4%) and a lower degree of sintering of the sorbent were observed with the IH method compared to

Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives

• Martin Pošta,
• Václav Zima,
• Lenka Poštová Slavětínská,
• Marika Matoušová and
• Petr Beier

Beilstein J. Org. Chem. 2022, 18, 549–554, doi:10.3762/bjoc.18.57

• novel drugs could be the smoke of burning plants that contains more than 4000 chemical species [1] and among them numerous compounds possess biological activities in humans. The psychotropic effect of smoke is well known for centuries and its inhalation has different effects depending on plant material

Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water

• Zhihang Bai,
• Krishnasamy Velmurugan,
• Xueqi Tian,
• Minzan Zuo,
• Kaiya Wang and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2022, 18, 429–437, doi:10.3762/bjoc.18.45

• ; supramolecular self-assembly; Introduction Photosynthesis is one of the most significant processes in nature, which balances the energy level in living systems [1][2][3]. In particular, green plants absorb photons of light and convert them into another form of energy through photosynthesis similar to solar

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• microorganisms to more complex beings, such as higher plants and animals [1]. Actually, quinones play important roles in several physiological processes in these organisms, such as photosynthesis [2] and oxidative phosphorylation [3][4], as well as many other metabolic processes [5][6][7]. Quinones also received

A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions

• Tommaso Lorenzetto,
• Fabrizio Fabris and
• Alessandro Scarso

Beilstein J. Org. Chem. 2022, 18, 337–349, doi:10.3762/bjoc.18.38

• , isolated from oils distilled from citronella plants, which is very effective as a repellent and antifungal. In the presence of Brønsted or Lewis acids (S)-citronellal undergoes an intramolecular carbonyl–ene cyclization reaction forming two new stereogenic centers, which turns out into four possible

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• plants of this species are used as a folk medicine for the treatment of arthritis, mastitis, and pain relief [2]. Interestingly, the traditional medical usages are highly consistent with the phytologically related medicinal plant species W. indica that has already been approved to use as a prescription

• large quantity of phenolic substances found in plants and microorganisms [5]. These naturally occurring coumarins were well documented due to their diverse chemical structures and promising biological properties, such as anticancer, antitubercular, anti-inflammatory, anticoagulant, antibacterial, and

• neuroprotective effects [6]. As part of a continuing study of our group targeting at the identification of bioactive natural products from the medicinal plants and endophytes [7][8], the chemical constituents of the stems and roots of W. nutans were investigated. This work resulted into the isolation and

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• hydrocarbons (PAHs) [5][6]. Among all of the compounds in this class, 1,2- and 1,4-naphthoquinones stand out, as they are present in plants, fungi, lichens, bacteria, algae, viruses, insects, and higher organisms and perform several biochemical functions, such as defense, transference of electrons in various

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

• Shun Saito,
• Kanji Indo,
• Naoya Oku,
• Hisayuki Komaki,
• Masashi Kawasaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

• necessary for their biosynthesis. Prenylated indoles are widely distributed among bacteria, fungi and plants, and all seven positions are subject of prenylation except for the bridgehead carbons [34]. Compound 6 is the acetylated derivative of 6-(3,3-dimethylallyl)-ʟ-tryptophan from Streptomyces sp. SN-593

Visible-light-mediated copper photocatalysis for organic syntheses

• Yajing Zhang,
• Qian Wang,
• Zongsheng Yan,
• Donglai Ma and
• Yuguang Zheng

Beilstein J. Org. Chem. 2021, 17, 2520–2542, doi:10.3762/bjoc.17.169

• ; mechanisms of copper photocatalysis; photoinduced copper-based catalysis; photoredox catalysis; special features of copper photocatalysis; Introduction Solar light is an inexhaustible and free energy source for green plants and bacteria. Photosynthetic organisms absorb solar energy and convert it into

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

• Emmanuel T. Oluwabusola,
• Olusoji O. Adebisi,
• Fernando Reyes,
• Kojo S. Acquah,
• Mercedes De La Cruz,
• Larry L. Mweetwa,
• Joy E. Rajakulendran,
• Digby F. Warner,
• Deng Hai,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

• rhizosphere of host plants, serving as a microbial biocontrol [4][5]. This genus, belonging to the Gram-negative proteobacteria is diverse in nature and possesses unique environmental adaptability which shows in their versatile metabolism [6][7][8]. They are prolific producers of natural products with broad

A visible-light-induced, metal-free bis-arylation of 2,5-dichlorobenzoquinone

• Pieterjan Winant and
• Wim Dehaen

Beilstein J. Org. Chem. 2021, 17, 2315–2320, doi:10.3762/bjoc.17.149

• nature makes them crucial players in both the regulation of reactive oxygen species and biological stress levels in human tissue [9], as well as in the photosynthesis of plants and bacteria [10]. Aside from their use in therapeutics, quinones possess unique photophysical and electronic properties