Identification and quantification of cannabinol as a biomarker for local hemp retting in an ancient sedimentary record by HPTLC-ESI-MS

Cannabis products have been used in various fields of everyday life for many centuries, and applications in folk medicine and textile production have been well-known for many centuries. For traditional textile production, hemp fibers were extracted from the stems by water retting in stagnant or slow-moving waters. During this procedure, parts of the plant material‚ among them phytocannabinoids‚ are released into the water. Cannabinol (CBN) is an important degradation product of the predominant phytocannabinoids found in Cannabis species. Thus, it is an excellent indicator for present as well as ancient hemp water retting. In this study, we developed and validated a simple and fast method for the determination of CBN in sediment samples using high-performance thin-layer chromatography (HPTLC) combined with electrospray ionization mass spectrometry (ESI-MS), thereby testing different extraction and cleanup procedures‚ as well as various sorbents and solvents for planar chromatography. This method shows a satisfactory overall analytical performance with an average recovery rate of 73%. Our protocol enabled qualitative and quantitative analyses of CBN in samples of a bottom sediment core‚ having been obtained from a small lake in Northern India, where intense local retting of hemp was suggested in the past. The analyses showed a maximum CBN content in pollen zone 4 covering a depth range of 262–209 cm, dating from approximately 480 BCE to 1050 CE. These findings correlate with existing records of Cannabis-type pollen. Thus, the method we propose is a helpful tool to track ancient hemp retting activities

5-epi-Incensole: synthesis, X-ray crystal structure and absolute configuration by means of ECD and VCD studies in solution and solid state

Incensole 1 and its acetate 2, found in incense, demonstrate interesting biological activities. Incensole acetate 2 was prepared on a large scale by employing the Paul and Jauch protocol from the crude extracts of Boswellia papyrifera Hochst. 5-epi-Incensole 3, obtained as colorless crystals, was prepared from incensole acetate via three steps; deacetylation, oxidation and reduction. The structure of 5-epi-incensole 3 was elucidated by means of spectroscopic data analysis, and the absolute configuration was established by single crystal X-ray analysis in combination with electronic and vibrational circular dichroism. In particular, the applicability of the solid-state ECD/TDDFT protocol to a compound with only two non-conjugated alkene chromophores was verified

The ancient CYP716 family is a major contributor to the diversification of eudicot triterpenoid biosynthesis

Triterpenoids are widespread bioactive plant defence compounds with potential use as pharmaceuticals, pesticides and other high-value products. Enzymes belonging to the cytochrome P450 family have an essential role in creating the immense structural diversity of triterpenoids across the plant kingdom. However, for many triterpenoid oxidation reactions, the corresponding enzyme remains unknown. Here we characterize CYP716 enzymes from different medicinal plant species by heterologous expression in engineered yeasts and report ten hitherto unreported triterpenoid oxidation activities, including a cyclization reaction, leading to a triterpenoid lactone. Kingdom-wide phylogenetic analysis of over 400 CYP716s from over 200 plant species reveals details of their evolution and suggests that in eudicots the CYP716s evolved specifically towards triterpenoid biosynthesis. Our findings underscore the great potential of CYP716s as a source for generating triterpenoid structural diversity and expand the toolbox available for synthetic biology programmes for sustainable production of bioactive plant triterpenoids

An Improved Scalable Synthesis of α- and β-Amyrin

The synthesis of α- and β-amyrin was accomplished starting from easily accessible starting materials, oleanolic, and ursolic acid. The procedures allow the preparation of β-amyrin in an exceptionally short scalable manner via selective iodation and reduction. For α-amyrin, a different synthetic approach had to be chosen providing access to α-amyrin in medium-to-large scale

Ester and amide derivatives of rhodamine B exert cytotoxic effects on different human tumor cell lines

<jats:title>Abstract</jats:title><jats:p>Three esters of rhodamine B (<jats:bold>1</jats:bold>–<jats:bold>3</jats:bold>) differing in their alkyl chain lengths as well as several rhodamine B amides (<jats:bold>4</jats:bold>–<jats:bold>9</jats:bold>) were synthesized in good yields and tested for their cytotoxicity in SRB assays employing several human tumor cell lines. The rhodamine B esters were unselective but showed cytotoxicity of as low as EC<jats:sub>50</jats:sub> = 0.15 ± 0.02 µM. The rhodamine B amides were slightly less cytotoxic but showed good selectivity against MCF-7 and A2780 tumor cell lines. Especially a morpholinyl derivative <jats:bold>4</jats:bold> was ~20 time more cytotoxic for MCF-7 than for nonmalignant NIH 3T3 cells.</jats:p&gt

Fig. 4 in Cembranoids from Boswellia species

Fig. 4. Structure of boscartin-A (30).Published as part of Al-Harrasi, Ahmed, Avula, Satya Kumar, Csuk, René & Das, Biswanath, 2021, Cembranoids from Boswellia species, pp. 1-17 in Phytochemistry (112897) 191 on page 9, DOI: 10.1016/j.phytochem.2021.112897, http://zenodo.org/record/838074

Fig. 1 in Cembranoids from Boswellia species

Fig. 1. Structure of cembrene (1).Published as part of Al-Harrasi, Ahmed, Avula, Satya Kumar, Csuk, René & Das, Biswanath, 2021, Cembranoids from Boswellia species, pp. 1-17 in Phytochemistry (112897) 191 on page 2, DOI: 10.1016/j.phytochem.2021.112897, http://zenodo.org/record/838074

Fig. 6 in Cembranoids from Boswellia species

Fig. 6. Structural relationship between incensole (wrong structure) and boscartin M (42).Published as part of Al-Harrasi, Ahmed, Avula, Satya Kumar, Csuk, René & Das, Biswanath, 2021, Cembranoids from Boswellia species, pp. 1-17 in Phytochemistry (112897) 191 on page 10, DOI: 10.1016/j.phytochem.2021.112897, http://zenodo.org/record/838074

Fig. 5 in Cembranoids from Boswellia species

Fig. 5. Structural relationship between cembrenol and incensole.Published as part of Al-Harrasi, Ahmed, Avula, Satya Kumar, Csuk, René & Das, Biswanath, 2021, Cembranoids from Boswellia species, pp. 1-17 in Phytochemistry (112897) 191 on page 10, DOI: 10.1016/j.phytochem.2021.112897, http://zenodo.org/record/838074

Fig. 2 in Cembranoids from Boswellia species

Fig. 2. Structures of cembranoids of Boswellia species.Published as part of Al-Harrasi, Ahmed, Avula, Satya Kumar, Csuk, René & Das, Biswanath, 2021, Cembranoids from Boswellia species, pp. 1-17 in Phytochemistry (112897) 191 on page 5, DOI: 10.1016/j.phytochem.2021.112897, http://zenodo.org/record/838074