Highly oxygenated caryophyllene-type and drimane-type sesquiterpenes from Pestalotiopsis adusta, an endophytic fungus of Sinopodophyllum hexandrum

Lin, Ligen; Hu, Jia-Yao; Jiao, Fu-Rong; Duan, Dongzhu; Zhang, Qiang; Tang, Huibin; Gao, Jin‐Ming; Wang, Le; Wang, Xiaoling

doi:10.1039/c7ra04267a

Cited by 26 publications

(18 citation statements)

References 37 publications

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“…Moreover, three methyl signals with a singlet ( δ H 1.07 s, 1.07 s, and 0.93 s; 32.1 CH 3 , 24.3 CH 3 , and 18.3 CH 3 ) were also observed in the 1 H and 13 C NMR spectra of 1 . The above characteristic NMR data revealed that 1 should be a drimane-type sesquiterpene with a lactone ring [17,18,19]. Comparison of the NMR data of 1 with those of strobilactone B from the marine-derived fungus Aspergillus ustus [20] suggested that 1 shares a similar nucleus structure with the known compound strobilactone B.…”

Section: Resultsmentioning

confidence: 99%

Asperienes A–D, Bioactive Sesquiterpenes from the Marine-Derived Fungus Aspergillus flavus

et al. 2019

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Marine-derived fungi of the genera Aspergillus could produce novel compounds with significant bioactivities. Among these fungi, the strain Aspergillus flavus is notorious for its mutagenic mycotoxins production. However, some minor components with certain toxicities from A. flavus have not been specifically surveyed and might have potent biological activities. Our investigation of the marine-derived fungus Aspergillus flavus CF13-11 cultured in solid medium led to the isolation of four C-6′/C-7′ epimeric drimane sesquiterpene esters, asperienes A–D (1–4). Their absolute configurations were assigned by electronic circular dichroism (ECD) and Snatzke’s methods. This is the first time that two pairs of C-6′/C-7′ epimeric drimane sesquiterpene esters have successfully been separated. Aperienes A–D (1–4) displayed potent bioactivities towards four cell lines with the IC50 values ranging from 1.4 to 8.3 μM. Interestingly, compounds 1 and 4 exhibited lower toxicities than 2 and 3 toward normal GES-1 cells, indicating more potential for development as an antitumor agent in the future.

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Section: Resultsmentioning

confidence: 99%

Asperienes A–D, Bioactive Sesquiterpenes from the Marine-Derived Fungus Aspergillus flavus

et al. 2019

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“…Including a trans -endocyclic (4–5) double bond in the nine-membered ring of caryophyllane system leads to the generation of the caryophyllene skeleton [ 115 ]. This structure is susceptible to rearrangements and cyclization reactions, thus allowing the formation of various polycyclic derivatives, such as pestaloporins, highly oxygenated caryophyllene-type sesquiterpenes, bicyclohumulenone, and bicyclohumuladiol [ 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 ].…”

Section: Caryophyllane Sesquiterpenesmentioning

confidence: 99%

“…Although several novel caryophyllane-type molecules (e.g., rumphellatins, cytosporinols, suberosols, kobusone, isokobusone, rumphellolides, nanonorcaryophyllenes, pestalotiopsins, pestaloporonins, punctatins, and punctaporins) have been identified in different natural kingdoms [ 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 ], because of the limited characterization of their pharmacological properties, the present overview is focused on the most representative compounds isolated from plants, i.e., β-caryophyllene, β-caryophyllene oxide, α-humulene, and isocaryophyllene.…”

Section: Introductionmentioning

confidence: 99%

Chemopreventive Potential of Caryophyllane Sesquiterpenes: An Overview of Preliminary Evidence

Sotto

Mancinelli

Gullì

et al. 2020

Cancers

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Chemoprevention is referred to as a strategy to inhibit, suppress, or reverse tumor development and progression in healthy people along with high-risk subjects and oncologic patients through using pharmacological or natural substances. Numerous phytochemicals have been widely described in the literature to possess chemopreventive properties, although their clinical usefulness remains to be defined. Among them, caryophyllane sesquiterpenes are natural compounds widely occurring in nature kingdoms, especially in plants, fungi, and marine environments. Several structures, characterized by a common caryophyllane skeleton with further rearrangements, have been identified, but those isolated from plant essential oils, including β-caryophyllene, β-caryophyllene oxide, α-humulene, and isocaryophyllene, have attracted the greatest pharmacological attention. Emerging evidence has outlined a complex polypharmacological profile of caryophyllane sesquiterpenes characterized by blocking, suppressing, chemosensitizing, and cytoprotective properties, which suggests a possible usefulness of these natural substances in cancer chemoprevention for both preventive and adjuvant purposes. In the present review, the scientific knowledge about the chemopreventive properties of caryophyllane sesquiterpenes and the mechanisms involved have been collected and discussed; moreover, possible structure–activity relationships have been highlighted. Although further high-quality studies are required, the promising preclinical findings and the safe pharmacological profile encourage further studies to define a clinical usefulness of caryophyllane sesquiterpenes in primary, secondary, or tertiary chemoprevention.

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“…Chemical studies of the resulting crude extracts had afforded two cytotoxic spiroketals and their putative biosynthetic precursors ( Liu et al, 2016a ), nine cytotoxic and antioxidant polyketides ( Guo et al, 2020a ), and five cytotoxic caryophyllene-derived sesquiterpenoids with 4/6/5 ring system ( Guo et al, 2020b ). Further chemical investigations of these fractions led to the isolation of two new humulane-derived sesquiterpeniods, pestalothenins A ( 1 ) and B ( 2 ), one new caryophyllene-derived sesquiterpeniod pestalothenin C ( 3 ), together with five known compounds, 14-acetylhumulane ( 4 ) ( Liu et al, 2016b ), 9,15-Dihydroxy-2,6-humuladiene-5,10-dione ( 5 ) ( Pulici et al, 1996a ), punctaporonin H ( 6 ) ( Wu et al, 2014 ), pestalotiopsin E ( 7 ) ( Xiao et al, 2017 ), and pestalotiopsin C ( 8 ) ( Pulici et al, 1997 ; Figure 1 ). Here we report the isolation, structure elucidation and biological activities of these compounds.…”

Section: Introductionmentioning

confidence: 99%

New Bioactive Sesquiterpeniods From the Plant Endophytic Fungus Pestalotiopsis theae

et al. 2021

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Three new secondary metabolites pestalothenins A–C (1–3), including two new humulane-derived sesquiterpeniods (1 and 2) and one new caryophyllene-derived sesquiterpeniod (3), together with five known compounds (4–8) were isolated from the crude extract of the plant endophytic fungus Pestalotiopsis theae (N635). Their structures were elucidated by the extensive analyses of HRESIMS and NMR spectroscopic data. The absolute configurations of 1–3 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. The cytotoxic effects of these compounds were evaluated in vitro. Compound 6 showed moderate cytotoxicity against T24 and MCF7 cell lines. In addition, compounds 1–8 were also evaluated for antibacterial activity.

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Highly oxygenated caryophyllene-type and drimane-type sesquiterpenes from Pestalotiopsis adusta, an endophytic fungus of Sinopodophyllum hexandrum

Abstract: Four new highly oxidized caryophyllene-type sesquiterpenes (1–4), and two new drimane-type sesquiterpenes (6, 7), along with nine known compounds have been isolated from an endophytic fungus Pestalotiopsis adusta.

Cited by 26 publications

References 37 publications

Asperienes A–D, Bioactive Sesquiterpenes from the Marine-Derived Fungus Aspergillus flavus

Asperienes A–D, Bioactive Sesquiterpenes from the Marine-Derived Fungus Aspergillus flavus

Chemopreventive Potential of Caryophyllane Sesquiterpenes: An Overview of Preliminary Evidence

New Bioactive Sesquiterpeniods From the Plant Endophytic Fungus Pestalotiopsis theae

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