Records of Natural Products

Articles In Press

Original Article

1) Diterpenoids from the Seeds of Euphorbia Lathyris and their Cytotoxic Acitivity

Rec. Nat. Prod. (2022) in press ; 1 - 9
by Na Liu , Yajie Sun , Yulin Sun , Yilin Sun , Tingting Luo , Fengying Yang , Peng Wang and Di Ge

 A new lathyrane-type diterpenoid, named euphorbia factor L35 (1), along with twenty-two known analogues (2-23) were isolated from the seeds of Euphorbia lathyris. Their structures were elucidated by using 1D- and 2D-NMR spectra and HRESIMS analysis. The cytotoxic effects of the isolated compounds against BT-549 and MDA-MB-231 cancer cells lines were evaluated by the SRB assay. Compounds 3, 10, 14, and 22 were found to exhibit considerable cytotoxic activities against BT-549 cells, with IC50 values ranging from 4.7 to 10.1 μM. Compounds 1, 2, 14 and 22 were able to inhibit the MDA-MB-231 cells growth with IC50 values of 5.7 to 21.3 μM, while other compounds showed no obvious inhibitory effects.

DOI
http://doi.org/10.25135/rnp.365.2205.2459
Keywords
Euphorbia lathyris; lathyrane-type diterpenes; cytotoxic activity.
Available online: November 26, 2022
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Original Article

2) Essential Oil Compositions and Antimicrobial Activity of the Leaves of Alphonsea monogyma Merr. & Chun and Goniothalamus banii B. H. Quang, R. K. Choudhary & V.T. Chinh from Vietnam

Rec. Nat. Prod. (2022) in press ; 1 - 6
by Le Thi Huong , Le Duc Giang , Do Ngoc Dai and Isiaka Ajani Ogunwande

Essential oils from the leaves of Alphonsea monogyma Merr. & Chun and Goniothalamus banii B. H. Quang, R. K. Choudhary & V.T. Chinh from Vietnam were obtained by hydrodisitllation and the chemical components determined by gas chromatography (GC) and gas chromatography coupled with mass spectrometry (GC/MS). Also the microdilution broth assay was used to test the antimicrobial activity of the essential oils. The respective yields of the essential oils were 0.18% (v/w) and 0.355% (v/w), respectively. The major components of A. monogyma were (E)-caryophyllene (13.8%), d-cadinene (12.5%), bicyclogermacrene (12.4%), cis-β-elemene (12.1%), and germacrene D (11.4%). However, myrcene (47.1%), α-pinene (9.7%) and (E)-caryophyllene (9.1%) were the dominant constituents of the essential oil of G. banii. The leaf essential oil of A. monogyma displayed potent antimicrobial activity towards the Gram-positive microorganisms of Enterococcus faecalis ATCC299212, Staphylococcus aureus ATCC25923 and Bacillus cereus ATCC14579 with minimum inhibitory concentration (MIC) values of 2.23 µg/mL, 10.45 µg/mL and 10.33 µg/mL, respectively. On the other hand, essential oil from G. banii exhibited the most effective antibacterial against Gram-negative Pseudomonas aeruginosa ATCC27853 (MIC 5.67 µg/mL), and anti-candidal action towards Candida albicans ATCC10231 (MIC 32.67 µg/mL). The chemical constituents and antimicrobial activity of the essential oils of A. monogyma and G. banii were being reported for the first time.

DOI
http://doi.org/10.25135/rnp.367.2208.2547
Keywords
Alphonsea monogyma essential oil composition terpenes antimicrobial activity anti-candidal activity
Available online: November 26, 2022
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Original Article

3) Comparative Analyses on Chemical Constituents and Biological Activities of Laserpitium siler L. from Serbia

Rec. Nat. Prod. (2022) in press ; 1 - 23
by Ksenija S. Mileski , Ana D. Ćirić , Uroš M. Gašić , Lazar D. Žarković , Zoran Đ. Krivošej and Ana M. Džamić

The traditional European medicinal plant Laserpitium siler L. was studied for the first time for the chemical composition and in vitro biological potential of extracts from fruits and aerial parts. Eight extracts were subjected to spectrophotometric detection and LC-MS quantification of phenolics. The bioactivity assessment comprised antioxidant, antimicrobial, anti-denaturation, acetylcholinesterase, tyrosinase, α-amylase, and α-glucosidase inhibition assays. The spectrophotometric analyses showed that the alcoholic extracts contained the most phenolic acids and coumarins. Among the twenty quantified compounds in the methanolic extracts, chlorogenic acid (29.098 mg/kg in the fruits; 47.438 mg/kg in the aerial parts) and p-coumaric acid (7.468 mg/kg in the fruits; 9.482 mg/kg in the aerial parts) were the most abundant. The DPPH/ABTS/BBT tests showed the strongest antioxidant effect of the methanolic extract of the aerial parts. The results of the microdilution assay referred to stronger antibacterial than antifungal activity, with the essential oil being as effective as the antibiotics used. The extracts expressed promising activity against P. aeruginosa PAO1 biofilm formation and pyocyanin synthesis. The prevention of BSA denaturation by the ethanolic extracts was comparable to diclofenac (91.08%-fruits, 95.08%-aerial parts, and 95.60%-diclofenac). IC50 values showed greater enzyme inhibitory potential of aerial parts and the highest reduction of α-glucosidase activity.

DOI
http://doi.org/10.25135/rnp.364.2207.2528
Keywords
Laserpitium siler phenolics LC-MS antioxidant antimicrobial enzyme inhibitory activity
Available online: November 25, 2022
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Original Article

4) Anti-inflammatory Continents from the Heartwood of Dalbergia melanoxylon

Rec. Nat. Prod. (2022) in press ; 1 - 7
by Qing Zhu , Can Yue Ouyang , Yang Liu , Zhangjun Xu , Ying Zhang , Ronghua Liu and Lanying Chen

A new chalcone compound, methyl 5-cinnamoyl-2-hydroxy-4-methoxybenzoate (1), and a new cinnamylphenol compound, methyl 3-cinnamyl-5-hydroxy-4-methoxybenzoate (2) together with four known compounds (3-6) were obtained from the CH2Cl2 soluble fraction of Dalbergia melanoxylon. Their structures were elucidated by comprehensive spectral measurements, single crystal X-ray diffraction and literature data. According to the determination results of compound 1 and 2 on RAW 264.7 cell viability, the IC50 values of compounds 1-2 were 4.11 and 113.99 μg/mL, respectively. Compared with LPS model group, compound 1 and 2 could significantly reduce the release of NO in the concentration rages of 0.375~3.0 μg/mL and 10 μg/mL (P<0.01), and significantly inhibit the secretion of LDH with 1.5~3 μg/mL and 5~10 μg/mL.

DOI
http://doi.org/10.25135/rnp.366.2208.2560
Keywords
Dalbergia melanoxylon chalcone cinnamylphenol anti-inflammatory activity
Available online: November 08, 2022
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Original Article

5) Essential Oil of Satureja montana L. from Herzegovina: Assessment of Composition, Antispasmodic, and Antidiarrheal Effects

Rec. Nat. Prod. (2022) in press ; 1 - 13
by Milan Kulić , Dragana Drakul , Dragana Sokolović , Jelena Kordić-Bojinović , Slobodan Milovanović and Duško Blagojević

Satureja montana L. (SM) has a long traditional use as a spice and a medicine for various gastrointestinal disorders, including painful spasms and diarrhea. Contrary to conventional drugs, administration of SM and its extracts are considered safe. Previous studies have shown that the essential oils (EOs) of SM from different areas are rich in monoterpenes, sesquiterpenes, diterpens, and phenolic compounds, including flavonoids, tannins, and acids with great composition variability. Determination of composition of EO from Herzegovinian SM done by gas chromatography-flame ionization detection and gas chromatography mass spectrometry (GC-FID and GC/MS, respectively) revealed carvacrol as a primary substance followed by γ-terpinene, p-cymene, and β-caryophyllene. Ex vivo spasmolitic activity caused  by EO was evident in different types of isolated rat ileum function with the most potent effect on spontaneous activity followed by electrical field stimulation and KCl- and CaCl2-induced activity. SMEO produced in vivo antidiarreal activity on castor oil-induced diarrhea in young rats and showed the potential to cause a decrese water content in the feces of adult Wistar rats.This study indicates that effects of SM on the intestinum could be mediated through combination of Kv channel activation and Ca channel blockade, but additional mechanisms might be involved. The results of this study corroborate the traditional use of SM as antispasmodic, antidiarrheal, and antisecretory agents.

DOI
http://doi.org/10.25135/rnp.358.2207.2522
Keywords
Satureja montana antispasmodic antidiarrheal
Available online: October 31, 2022
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Original Article

6) Secondary Metabolites from Marine-Derived Fungus Aspergillus carneus GXIMD00519

Rec. Nat. Prod. (2022) in press ; 1 - 9
by Chun-Ju Lu , Zhen-Zhou Tang , Zhi-Wei Su , Hai-Yan Li , Geng-Si Zhang , Cheng-Hai Gao , Yong-Hong Liu and Xinya Xu

Two new compounds, carneusins A-B (1-2), as well as fifteen known compounds (3-17), were isolated from the marine-derived fungus Aspergillus carneus GXIMD00519. Their structures were elucidated by the analysis of detailed spectroscopic data and quantum chemistry calculations. All the compounds were evaluated for their antibacterial, antibiofilm and cytotoxic effects. Compound 1 showed a moderate inhibitory effect against MRSA with the MIC value of 32 µg/mL. Compound 2 exhibited an anti-microfouling effect against biofouling bacterial Vibrio rotiferianus and Alteromonas macleodii with MIC value of 64 µg/mL. Compound 5 displayed antibiofilm activity against A. macleodii with the EC50 value of 10.42 ± 0.58 µg/mL. Compounds 1, 3, 4, 8 and 15 showed cytotoxicity against human pancreatic cancer cell lines SW1990, colorectal adenocarcinoma cell line DLD1, human pancreatic cancer cell line PANC1, and human hepatocellular carcinoma cell line Bel7402 with IC50 values ranging of 2.75-17.77 µM.

DOI
http://doi.org/10.25135/rnp.355.2207.2518
Keywords
Aspergillus carneus GXIMD00519 antibacterial antibiofilm cytotoxicity
Available online: October 29, 2022
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Short Report

7) Polyketides and Alkaloids from the Fungus Penicillium sp.

Rec. Nat. Prod. (2022) in press ; 1 - 5
by Qian Chen , Yifang Chen , Ying Lu and Jianyong Zhao

The marine-derived fungus SCZ-1 was cultured on a rice solid medium. The fermented materials was extracted using ethyl acetate to afford an extract, which was separated by repeated column chromatography to afford three polyketides and five alkaloids, including 2 new polyketides (1 and 2). The known compounds were identified to be penipyrol A (3), cyclopenin (4), cyclopenol (5), terretrione D (6), viridicatol (7), and viridicatin (8). The structures of 1 and 2 were determined by extensive analyses of spectroscopic data (1D and 2D NMR, and HRESIMS). The absolute configuration of 2 was assigned by comparing the experimental and calculated ECD spectra. Compound 1, bearing a two-carbon side chain at C-2, is seldom found among isocoumarins. The metabolites were screened for their inhibitions toward a-glucosidase, only compound 8 showed weak inhibitory effect with an IC50 value of 548 mM.

DOI
http://doi.org/10.25135/rnp.363.2210.2593
Keywords
Marine fungus Penicillium sp. new polyketides
Available online: October 29, 2022
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Original Article

8) A New Monoterpene Rhamnoside from Cercis glabra Legumes

Rec. Nat. Prod. (2022) in press ; 1 - 8
by Ting Xu , Yueyue Lou , Yabing Ge , Xiaoqing Lu , Pengpai Zhang and Penghua Shu

A new monoterpene rhamnoside, (+)-(R)-α-terpineol α-L-rhamnoside (1), along with ten known compounds (211) were obtained after purification of the ethanol extract of Cercis glabra legumes. Their structures were elucidated by spectroscopic evidence including NMR, optical rotatory dispersion (ORD), HR-ESI-MS and chemical hydrolysis. In the acetylcholinesterase inhibitory assay, compounds 3 and 8 showed high percentages of inhibition which were comparable to the activity of donepezil (a commercial drug, the positive control), and exhibited IC50 values of 0.488, 0.391 mg/mL. These bioactive components could be promising acetylcholinesterase inhibitors.

DOI
http://doi.org/10.25135/rnp.362.2209.2593
Keywords
Cercis glabra monoterpene acetylcholinesterase acid hydrolysis
Available online: October 27, 2022
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Original Article

9) Two New Spirostanol Glycosides from the Roots and Rhizomes of Helleborus thibetanus Franch.

Rec. Nat. Prod. (2022) in press ; 1 - 9
by Yuze Li , Zilong Zhang , Wenli Huang , Huawei Zhang , Yi Jiang , Jianli Liu , Xiaomei Song and Dongdong Zhang

 Two new spirostanol glycosides, thibetanosides J and K (1 and 2), along with three known ones (3-5) were isolated from the roots and rhizomes of Helleborus thibetanus. Their structures were elucidated by extensive use of spectroscopic techniques and chemical evidence. In this study, compounds 1-5 were evaluated for their cytotoxic activity against HCT116, A549 and HepG2 tumor cell lines. Among them, compound 1 exhibited moderate cytotoxicity against A549 cells (IC50 7.69 ± 1.13 μM) and HepG 2 cells (IC50 8.32 ± 2.63 μM). Compound 2 exhibited moderate cytotoxicity against HCT116 cells (IC50 20.67 ± 1.06 μM).

DOI
http://doi.org/10.25135/rnp.361.2207.2520
Keywords
Helleborus thibetanus spirostanol glycosides cytotoxic activity
Available online: October 25, 2022
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Short Report

10) (8S, 9R)-Dihydroisoflavipucine, a New Isoflavipucine Derivative from the Endophytic Fungi Botryosphaeria dothidea

Rec. Nat. Prod. (2022) in press ; 1 - 5
by Hui Chen , Wendan Li , Lian Xue , Xiuji Liu , Yiqing Zhou and Zhangshuang Deng

A new isoflavipucine derivative, (8S, 9R)-dihydroisoflavipucine (1), is isolated from an ethyl acetate extract of endophytic fungi Botryosphaeria dothidea (D4-2) derived from Taxus mairei. The structure of 1 is elucidated based on nuclear magnetic resonance, circular dichroism, and mass spectrometry. The antiproliferative activity of the isolates against breast cancer cells MDA-MB-231, MCF7 and 4T1 are evaluated.

DOI
http://doi.org/10.25135/rnp.360.2206.2500
Keywords
Dihydroisoflavipucine isoflavipucine Taxus mairei endophytic fungi Botryosphaeria dothidea antiproliferative activity
Available online: October 25, 2022
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Original Article

11) Clinopodium nepeta (L.) Kuntze from Bosnia and Herzegovina: Chemical Characterisation of Headspace and Essential Oil of Fresh and Dried Samples

Rec. Nat. Prod. (2022) in press ; 1 - 12
by Emina Boškailo , Hurija Džudžević-Čančar , Alema Dedić , Zvonimir Marijanović , Amra Alispahić , Ismet Fatih Čančar , Danijela Vidic and Igor Jerković

The samples of Clinopodium nepeta (L.) Kuntze (Lamiacae) aerial parts were collected from four different localities in sub-Mediterranean area of Bosnia and Herzegovina and subjected to phytochemical profiling. Shade-dried and fresh samples were used to determine their headspace volatile organic composition by solid-phase microextraction on two differently coated fibers. Corresponding essential oils were obtained by hydrodistillation. Both headspace and essential oil were analysed by gas chromatography-mass spectrometry Among detected compounds, trans-piperitenone oxide and pulegone were dominant in the headspace of shade-dried and fresh C. nepeta samples. The essential oils contained 42 compounds including pulegone (44.8%), piperitenone (48.8%) and trans-piperitenone oxide (60.2%) as the major compounds, followed by limonene, cis-piperitone oxide, p-menthone and dihydrocarvyl acetate. In this work, a wide range of volatile compounds present in C. nepeta samples from Bosnia and Herzegovina was determined. The obtained data provides detail phytochemical analysis of the volatiles of C. nepeta and therefore completes earlier researches of this plant from the other geographical areas. 

Keywords: Clinopodium nepeta (L.) Kuntze; Lamiaceae; headspace solid-phase microextraction; hydrodistillation; essential oil. 

DOI
http://doi.org/10.25135/rnp.357.2207.2504
Keywords
Clinopodium nepeta (L.) Kuntze Lamiaceae headspace solid-phase microextraction hydrodistillation essential oil
Available online: October 11, 2022
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Original Article

12) A New Lignan from the Herbaceous stems of Ephedra intermedia Schrenket C. A. Meyer.

Rec. Nat. Prod. (2022) in press ; 1 - 7
by Xiling Fan , Yangang Cao , Mengnan Zeng , Ru Wang , Yanling Liu , Chen Xu , Xinyi Ma , Yingjie Ren , Chen He , Xiangda Li , Xiaoke Zheng and Weisheng Feng

A new lignan eplignan A (1), along with six konwn lignans (27) was isolated from the herbaceous stems of Ephedra intermedia Schrenket C. A. Meyer. Their structures were elucidated based on the spectroscopic evidence, mainly including NMR and HRESIMS data. The absolute configuration of 1 was determined by comparing calculated and experimental electronic circular dichroic (ECD) spectra. Moreover, all compounds (17) were evaluated for their protective effects against the BEAS-2B cells injury induced by TGF-β1 in vitro, and the results showed that compounds 12, 4, and 6 exhibited significantly protective activities at the concentration of 10 μM.

DOI
http://doi.org/10.25135/rnp.359.2207.2519
Keywords
Ephedra Ephedrae intermedia lignans lung protective activity
Available online: October 09, 2022
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Short Report

13) Todasinoid A, a New Eremophilane-type Sesquiterpene from the Plant Toddalia asiatica

Rec. Nat. Prod. (2022) in press ; 1 - 6
by Lijing Cai , Mengying Zhang , Jie He and Tingting Lin

A new sesquiterpene, named todasinoid A (1), together with eight known compounds (2-9) were isolated from the roots of Toddalia asiatica. The gross structure of todasinoid A were established by analyses of the NMR and HRESIMS data. A comparison of the experimental ECD spectrum of 1 with the calculated ECD spectra for a model compound (1a) resolved the absolute configuration of 1. The known compounds were identified to be bullatantriol (2), aculeatin (3), 6-(3-ethoxy-2-hydroxy-3-methylbutyl)-5,7-dimethoxy-2H-1-benzopyran-2-one (4), trans-N-p-coumaroyltyramine (5), feruloyltyramine (6), b-sitosterol (7), sitosterol D-glucoside(8), 7α-hydroxysitosterol (9) by comparing the NMR data and specific rotations with reported data in literature. Compound 1 is an eremophilane-type sesquiterpenoid containing a mercaptolactate side-chain that is rarely found in nature. Compounds 2, 5, and 9 were isolated from this plant for the first time. Bioassay study revealed that compound 5 exhibited inhibitory effects against a-glucosidase with an IC50 of 320 mM, being more active than the positive control acarbose.

DOI
http://doi.org/10.25135/rnp.356.2206.2486
Keywords
Toddalia asiatica Todasinoid A sesquiterpenoid ECD calculation
Available online: September 22, 2022
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Short Report

14) Plagranline A, a Novel β-carboline and the First Alkaloid Isolated from Platycodon grandiflorus

Rec. Nat. Prod. (2022) in press ; 1 - 5
by Ju-Tao Wang , Lan Ding , Ren-nai Yang , Liang-ping Zha , Yang Yu and Shuang-ying Gui

 A novel β-carboline, namely Plagranline A (1), and a known alkaloid (2) were isolated from the roots of Platycodon grandiflorus. Their structure was elucidated using a combination of spectroscopic analyses and computational chemistry, including electronic circular dichroism (ECD) and optical rotatory dispersion (ORD). Alkaloids 1 and 2 exhibited moderate inhibitory effects against NO production. Interestingly, 1 and 2 are the first alkaloid constituents reported from the plant P. grandifloras.

DOI
http://doi.org/10.25135/rnp.354.2207.2510
Keywords
Platycodon grandiflorus β-carboline computational chemistry alkaloid anti-inflammatory activity
Available online: August 26, 2022
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Original Article

15) A New Monoterpene Alkaloid From the Stems of Rauvolfia vomitoria

Rec. Nat. Prod. (2022) in press ; 1 - 9
by Kailing Yang , Tao Yang , Xiaolei Li , Ruixi Zhou , Rongkun Miao , Yuyan Guan , Yang Teng , Guanqun Zhan and Zengjun Guo

One new monoterpene alkaloid (1) and eight known compounds (29), belonging to two monoterpene alkaloids (12), one pyridine alkaloid (3), four phenylpropanoid derivatives (47), and two matrine-type alkaloids (89), were isolated from Rauvolfia vomitoria Afzel. The structure of new compound 1 was determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculation. Notably, this is the first reported monoterpene alkaloids from R. vomitoria. Besides, compounds 3, 5, and 79 were first discovered in the Apocynaceae family and compounds 4 and 6 were first reported in the Rauvolfia genus. This is also the first example of matrine-type alkaloids reported in the Apocynaceae family, indicating that matrine-type alkaloids are not unique to the Leguminosae/Fabaceae family. All isolated compounds were evaluated for their anti-acetylcholinesterase, anti-α-glucosidase, and antioxidant activities. Compound 6 showed significant α-glucosidase inhibitory activity and remarkable DPPH radical scavenging capacity, both of which are superior to the positive controls. Molecular docking of compound 6 with α-glucosidase was further performed, suggesting that compound 6 could form hydrogen bonds with residues ALA-292, ASN-259, and ARG-263.

DOI
http://doi.org/10.25135/rnp.353.2204.2432
Keywords
Rauvolfia vomitoria AChE DPPH α-glucosidase monoterpene alkaloids molecular docking
Available online: August 26, 2022
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Review Article

16) Genus Lactuca (Asteraceae): A Comprehensive Review

Rec. Nat. Prod. (2022) in press ; 1 - 32
by Fatma M. Abdel Bar , Nouran H. Abdel Fatah , Yhiya Amen , Ahmed F. Halim and Hassan-Elrady A. Saad

Genus Lactuca L. belongs to one of the major families of flowering plants, Asteraceae. It includes about 150 species, distributed in warm and temperate areas, commonly in the Northern Hemisphere. Since ancient times, numerous Lactuca L. species have been cultivated for their economic and medicinal significance. Cultivated lettuce (Lactuca sativa), a representative member of the genus, is the most important leafy salad vegetable. The current review aims to provide comprehensive information on the taxonomy, phytochemistry, traditional uses, and biological activities of plants of the genus Lactuca.

DOI
http://doi.org/10.25135/rnp.350.2205-2474
Keywords
Lactuca Asteraceae Lettuce Phytochemistry Sesquiterpene lactones Biological activities
Available online: August 21, 2022
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Short Report

17) Cytotoxic Constituents from the Rhizomes of Monstera deliciosa

Rec. Nat. Prod. (2022) in press ; 1 - 5
by Marwa Elsbaey , Kadria F. Ahmad , Fathy Behery , Mohamed Amer and Mohamed Farid Lahloub

A phytochemical study of the rhizomes of Monstera deliciosa has led to isolation of fourteen compounds (1-14) for the first time from the plant species. The structure elucidation was carried out using 1D and 2D NMR data. The cytotoxic activities of the compounds against the liver (HepG-2), larynx (Hep-2), colon (HCT-116), and breast (MCF-7) cancer cell lines were evaluated using MTT assays. Syringaresinol (6) showed remarkable IC50 values against the four tested cell lines. In addition, 9, 12, 13-trihydroxy-10-octadecenoic acid (14) was highly cytotoxic against Hep-2 and HCT-116 cell lines.

DOI
http://doi.org/10.25135/rnp.352.2203.2390
Keywords
Monstera Araceae cytotoxic lignan
Available online: August 20, 2022
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Short Report

18) TTrichocarotin N: a New Carotane Sesquiterpene from the Marine-Derived Fungus Trichoderma virens QD-11

Rec. Nat. Prod. (2022) in press ; 1 - 4
by Wen-Ting Yang , Wei Gao , Jin-An Liu , Xiao-Xiao Liu and Lin-chuan Jia

A new carotane sesquiterpene, trichocarotin N (1), was isolated from the culture of marine-derived fungus Trichoderma virens QD-11. Its structure was established by detailed analysis of 1D/2D NMR and HRESIMS data. Trichocarotin N (1) exhibited moderate cytotoxicity against HeLa and MCF-7 cancer cell lines, with IC50 values of 32.4 and 41.6 μM, respectively.

DOI
http://doi.org/10.25135/rnp.349.2206.2492
Keywords
richoderma virens carotane sesquiterpeneT secondary metabolites cytotoxic activity
Available online: August 14, 2022
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Original Article

19) Chemical Constituents of Tectus maximus Koch, 1844

Rec. Nat. Prod. (2022) in press ; 1 - 7
by Nguyen Trong Dan , Le Thi Giang , Nguyen Dinh Cu , Truong Ba Hai , Nguyen Dang Hoi , Vu Thi Loan , Dan Thi Thuy Hang , Nguyen Xuan Nhiem , Tai Bui Huu and Kiem Van Phan

Two previously unreported compounds (1 and 2) together with eight known compounds (3-10) were isolated from the methanol extract of sea snail Tectus maximus Koch, 1844. Their chemical structures were determined to be 6-acetoxy-deoxyinosine (1), 6-acetoxy-inosine (2), deoxyinosine (3), inosine (4), adenosine (5), deoxyadenosine (6), deoxyuridine (7), thymidine (8), glycerol arachidonate (9), and arachidonic  acid (10) on the basis of HR-ESI-MS and NMR spectroscopic analyses. This is the first report of those compounds from the genus Tectus

DOI
http://doi.org/10.25135/rnp.351.2205.2462
Keywords
Tegulidae Tectus maximus 6-acetoxy-deoxyinosine 6-acetoxy-inosine
Available online: August 14, 2022
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Original Article

20) Antidepressant-Like Effect of Aromatherapy with Magnolia sieboldii Essential Oils on Depression Mice

Rec. Nat. Prod. (2022) in press ; 1 - 15
by Yan Ai , Lin Geng , Xian Xu , Xiaolu Chen , Baoshan Rong , Zhiting Zhang , Lu Ren , Ni Song , Minghui Tang , Lanyue Zhang , Yong Ai and Tinggang He

 Globally, depression is the fourth most common disorder. It is difficult to treat and prone to recurrent episodes. To elucidate the antidepressant effect and mechanism of action of Magnolia sieboldii aromatherapy, the main components of M. sieboldii essential oils were analyzed using GC-MS. A mouse model of depression, established by repeated intraperitoneal injection of reserpine, was used to probe antidepressant efficacy. Behavioral tests were used to evaluate depressive behavior in mice. In in vivo animal studies, changes in the number of measured neurons were detected using Nissl staining, and GR protein expression was examined using immunohistochemistry. The relative expression levels of 5-hydroxytryptamine (5-HT1A) and brain-derived neurotrophic factor (BDNF) were detected using western blot (WB). The results showed that the essential oils of M. sieboldii are mainly composed of β-elemene (22.11%), trans-β-ocimene (14.87%), germacrene D (7.27%), and nerolidol (4.51%). The expression of GR protein was substantially upregulated in the tissues of mice treated with the essential oils of M. sieboldii. WB showed that the components of M. sieboldii essential oils modulated the expression of BDNF and 5-HT in serum, which remarkably attenuated depressive behavior in mice. In addition, a medium concentration of M. sieboldii substantially ameliorated depressive-like behavior in mice and increased the serum levels of 5-HT1A and BDNF. This study suggests that a medium concentration of M. sieboldii has a prominent antidepressant effect.

DOI
http://doi.org/10.25135/rnp.341.2204.2434
Keywords
Magnolia sieboldii essential oils depression BDNF 5-HT
Available online: August 14, 2022
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Short Report

21) Polyketides and Alkaloids from the Deep-Sea-Derived Fungus Aspergillus fumigatus CBC18132

Rec. Nat. Prod. (2022) in press ; 1 - 6
by Yu Liu , Fan Yang , Xiaoqian Zhang , Ying Qiao , Wei Xu , Qin Li and Zhongbin Cheng

Abstract: The fungal strain Aspergillus fumigatus CBC18132, isolated from deep-sea sediment, was investigated for secondary metabolites. Fermentation on rice medium followed by chromatographic separation led to the isolation of three polyketides (13) and nine alkaloids (413). The structures were determined by analyses of spectroscopic data (1H and 13C NMR, and MS data). The absolute configuration of the anthraquinone-derivative trypacidin was resolved for the first time by a combination of ECD and specific rotation calculation. All isolated compounds were inactive toward the -glucosidase at the initial concentration of 2 mM.

DOI
http://doi.org/10.25135/rnp.348.2204.2447
Keywords
Aspergillus fumigatus trypacidin absolute configuration
Available online: August 06, 2022
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Original Article

22) Tigliane-Type Diterpenoids from the Seeds of Croton tiglium

Rec. Nat. Prod. (2022) in press ; 1 - 6
by Lijuan Zhang , Fei Li , Jianyong Zhu and Qian Niu

A new tigliane-type diterpenoid (1) and three known analogues (2-4) were isolated from the seeds of Croton tiglium. Extensive spectroscopic analyses, especially the 2D NMR experiments were used to determine their structures. The absolute configuration of 1 was defined by single-crystal X-ray diffraction data. The cytotoxicity 1-4 was evaluated against melanoma cell line A375, and the results showed that compounds 1, 3, and 4 exhibited certain cytotoxicities.

DOI
http://doi.org/10.25135/rnp.344.2205.2455
Keywords
Croton tiglium tigliane-type diterpenoid cytotoxicity
Available online: July 29, 2022
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Original Article

23) The First Example of Di--Methane Rearrangement in Nature: Cephalotanols A and B, Two Novel Rearranged Norlignan Glycosides from Cephalotaxus fortunei Hook

Rec. Nat. Prod. (2022) in press ; 1 - 9
by Xiaoyan Xie , Qingqing Zhou , Yanting Zhou and Jinbiao Xu

A pair of unique diastereoisomers of norlignan glycosides named cephalotanols A (1) and B (2), together with two known compounds, have been isolated from the twigs and leaves of Cephalotaxus fortunei Hook. Their structures were elucidated by using a combination of spectroscopic techniques and comparison of experimental and calculated electronic circular dichroism (ECD) data. To our knowledge, cephalotanols A and B represent the first rearranged norlignan glycosides with diphenylvinylcyclopropane core found in natural sources, of which biosynthetic pathways originating from co-occurring precursors 3S-4'-O-β-D-glucopyranosylhinokiresinol (3) and 3S-4''-O-β-D-glucopyranosylhinokiresinol (4) via di-π-methane rearrangement is proposed.

DOI
http://doi.org/10.25135/rnp.345.2205.2461
Keywords
Cephalotaxus fortune norlignan diphenylvinylcyclopropane structural elucidation di-π-methane rearrangement
Available online: July 28, 2022
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Original Article

24) Sesquiterpenes from theLeaves of Dalbergia odorifera

Rec. Nat. Prod. (2022) in press ; 1 - 10
by Chenxiao Shen , Can Yue Ouyang , Ying Zhang , Qing Zhu , Ronghua Liu and Lanying Chen

Two new sesquiterpenes (1R,5R,6R)-11-hydroxyl-drocostuslactone (1) and (1R,10S)- gibberodione A (2) were acquired from the leaves of Dalbergia odorifera. The structures of two new sesquiterpenes were revealed by broad NMR exploration, and X-ray crystallography analyses. In addition, the bioactivity assay showed that two compounds had potential anti-inflammatory activity with less toxicity (their IC50 values were 107.2 ± 4.02 and 54.64 ± 1.89 μg/mL), could significantly decrease the production of NO (P<0.01) with 8~16 and 1~2 μg/mL and inhibited LDH (P<0.01) with 1~16 and 1~2 μg/mL in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages, respectively.

 

DOI
http://doi.org/10.25135/rnp.347.2205.2466
Keywords
Dalbergia odorifera sesquiterpenoids anti-inflammatory activity
Available online: July 28, 2022
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Short Report

25) Myrrhalindenane C, a New Eudesmane Sesquiterpenoid From Lindera Myrrha Roots

Rec. Nat. Prod. (2022) in press ; 1 - 6
by Hoang-Dung Nguyen , Huy Truong Nguyen , Thi-Hoai-Thu Nguyen , Jirapast Sichaem , Huu-Hung Nguyen , Ngoc-Hong Nguyen and Thuc-Huy Duong

Phytochemical investigation of Lindera myrrha roots growing in Vietnam afforded a new eudesmane sesquiterpenoid, myrrhalindenane C (1), along with seven known compounds, rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo[3,2,1]-oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (2), 1-O-(4-hydroxy-2,6-dimethoxyphenoxy)-6-O-[rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo[3,2,1]-oct-8-yl)-3-methyl-2Z,4E-pentadienoyl]-β-D-glucopyranose (3), curcumin (4), demethoxycurcumin (5), bisdemethoxycurcumin (6), (1E,6E)-1,7-bis(4-methoxyphenyl)-1,6-heptadiene-3,5-dione (7), and 2',4',4,2''-tetrahydroxy-3'-[3''-methylbut-3''-enyl]chalcone (8). The structure was determined by analysis of their MS and NMR data as well as by comparison with literature values. All compounds were evaluated for antimicrobial activity against antibiotic-resistant, pathogenic bacteria Enterococcus faecium, Staphylococcus aureus, and Acinetobacter baumannii.

DOI
http://doi.org/10.25135/rnp.343.2203.2396
Keywords
Lauraceae Lindera myrrha myrrhalindenane C eudesmane antimicrobial activity
Available online: July 25, 2022
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Original Article

26) The Effect of Cynara cornigera L. in HepG2 Hepatocellular Carcinoma Cells

Rec. Nat. Prod. (2022) in press ; 1 - 13
by Erdal Sanlidag , Eda Becer , İhsan Çalış , Kemal H. C. Baser , Azmi Hanoğlu , Fatih Göger and H. Seda Vatansever

Amongst all cancer types, liver cancer is the fourth leading cause of cancer mortality. It is frequently stated as hepatocellular carcinoma (HCC) and occurs in hepatocytes. Genetic alterations of hepatocytes such as Wnt/β-catenin and JAK / STAT signaling pathways play a key role for the development of the HCC. Currently, there are a few available treatments for HCC; such treatments include transplantation, surgical resections and anticancer drugs. Most of the anti-cancer drugs target the signaling pathways for achieving an effective treatment. However, these treatments have some undesirable side effects. Thus, there is a need for discovering alternative anti-cancer agents with no or lesser side effects. Plant constituents are promising anti-cancer agents. Cynara cornigera L. contains plenty of phenolic compounds including quercetin, apigenin, etc. This study aimed to analyze the anti-cancer property of the fractionated methanol extract of the flowers of C. cornigera. All the fractions obtained were analyzed to determine the cytotoxic activity on HepG2 cells. Two of the fractions containing polyphenolic compounds had a significant cytotoxic activity related to non-canonical Wnt11 signaling pathways on HepG2 cells.

DOI
http://doi.org/10.25135/rnp.335.2106.2092
Keywords
Cynara cornigera phenolic compounds HepG2 HepG2 Wnt11 liver cancer
Available online: July 04, 2022
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