Records of Natural Products

Articles In Press

Review Article

1) Phytochemistry and Pharmacology of Genus Cercis: A Review

Rec. Nat. Prod. (2024) in press ; 1 - 13
by Yu Meng , Shuo Zang , Xin Wang , Huiying Wang , Jiahui Deng , Mengjiao Wu , Tingting Guo , Wenhao Zou , Fugang Xiao , Lin Zhang , Penghua Shu and Pengpai Zhang

The genus Cercis, belonging to the Fabaceae family, is widely distributed in China and traditionally employed in Chinese medicine to treat various disorders, like irregular menstruation, pain, cough and carbuncle swelling. Despite the availability of numerous scientific studies on this genus, reviews that comprehensively cover its phytochemistry and pharmacology remain limited. This review aims to systematically consolidate the scientific literature on the phytochemistry and pharmacology of eight Cercis species, retrieved from databases like PubMed, Web of Science, SciFinder, Google Scholar, and the China National Knowledge Infrastructure platform. Based on a thorough analysis of the literature, more than 100 compounds have been identified from Cercis species, including flavonoids, phenols, terpenoids, lignins, dibenz[b,f]oxepins and others. Extracts and chemical constituents derived from Cercis species exhibite significant antioxidant, analgesic, anti-inflammatory, antitumor, antibacterial activities. These findings contribute to a deeper understanding of the medicinal potential of Cercis species and their potential applications in healthcare.

DOI
http://doi.org/10.25135/rnp.458.2404.3190
Keywords
Cercis phytochemistry pharmacology bioactivity flavonoid
Available online: May 20, 2024
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Short Report

2) In vitro α-Glucosidase inhibitors of Polyscias serrata Roots in a Parallel Study of Network Pharmacology

Rec. Nat. Prod. (2024) in press ; 1 - 6
by Le Thi Tu Anh , Hoang Thai Dang , Nguyen Thi Thu Ha , Nguyen Thanh Tra , Nguyen Thi Thuy Linh , Ba Thi Cham , Bui Thi Thuy Luyen , Hoang Huy Do and Tiep Khac Nguyen

Nine known compounds were isolated from the P. serrata roots and showed promising inhibitory activity against α-glucosidase. The molecular docking study of them was exhibited the 4-hydroxyl group in the aromatic ring of benzoic acid derivatives improves the bioactivity. Network pharmacology was performed to investigate the molecular mechanisms of isolated compounds and suggested that the insulin resistance pathway would be a primary mechanism of action. This is the first time the α-glucosidase inhibitors of P. serrata roots were reported.

DOI
http://doi.org/10.25135/rnp.457.2401.3038
Keywords
Polyscias serrata α-glucosidase inhibitor molecular docking network pharmacology
Available online: April 30, 2024
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Short Report

3) A New Sterol-Related Metabolite from the Soft Coral Capnella imbricata

Rec. Nat. Prod. (2024) in press ; 1 - 6
by Zheng-Zhe Tsai , Chih-Kai Hsu , Po-Jen Chen , Yu-Li Chen , Su-Ying Chien , Zhi-Hong Wen , Ping-Jyun Sung , Kuei-Hung Lai and Hsu-Ming Chung

Exploratory research was carried out on the ethyl acetate extract derived from the soft coral Capnella imbricata, sourced from the southeastern waters of Taiwan. This investigation yielded the isolation of three sterol-related compounds (13). Among these compounds, one previously unidentified metabolite, designated as 4β-hydroxy-24-methylene-5-cholesten-7-one (1), was discovered, along with two known metabolites, namely, 3β-hydroxy-24-methylene-5-cholesten-7-one (2) and gorgostan-5,25-dien-3β-ol (3). The structures of these isolated metabolites were determined through comprehensive spectroscopic analyses. Furthermore, the relative stereochemistry of metabolite 3 was established for the first time in this study using single-crystal X-ray diffraction analysis. The potential anti-inflammatory properties of metabolites 13 were evaluated by investigating their ability to suppress the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins in lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells.

DOI
http://doi.org/10.25135/rnp.455.2402.3141
Keywords
Capnella imbricata Sterol X-ray iNOS COX-2
Available online: April 30, 2024
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Original Article

4) Structure Characterization and Anti-tumor Activity of Polysaccharides from Rohdea chinensis

Rec. Nat. Prod. (2024) in press ; 1 - 8
by Shihao Zhang , Minghua Ma , Sicheng Liu , Guoce Jin , Wencong Li , Yu Zhao , Yanyu Li , Xueyan Li , Zixuan Zhu , Chengxiong Liu , Zhaoxia Liu , Xiaocong Li and Kun Zou

Three crude polysaccharides of RCP-A, B, and C were derived from the rhizome of Rohdea chinensis by means of hot water extraction, gradient ethanol precipitation and dialysis. Three different polysaccharides of RCP-C1-1, RCP-C1-2, and RCP-C1-3 were isolated using cellulose DEAE-52 and Sephadex G-200 chromatography from RCP-C. The average molecular weights of RCP-C1-1, RCP-C1-2, and RCP-C1-3 were measured as 1.51×104, 1.06×104, and 4.86×103 by means of MALDI-TOF MS and UHPGC, respectively. All three polysaccharides were found to consist of D-fructose and D-glucose following hydrolysis and comparison with literature data. Based on FT-IR and NMR analysis, the polysaccharides were identified as inulin-type fructans, with their backbone composed of α-D-glucopyranosyl-(1→2)-(β-D-fructofuranosyl)n-(1→2)-β-D-fructofuranoside (nRCP-C1-1=79, nRCP-C1-2=58, nRCP-C1-3=27). The anti-tumor activity of the polysaccharides (RCP-A, B, and C) was evaluated in H22 tumor-bearing mice. The results suggested that the polysaccharides (RCP-A, RCP-B, and RCP-C) inhibited the growth of H22 hepatocellular. Further, the treated groups of RCP-A, RCP-B, and RCP-C exhibited improvements in body weight as well as spleen/thymus indexes in H22 tumor-bearing mice.

DOI
http://doi.org/10.25135/rnp.454.2403.3165
Keywords
Rohdea chinensis polysaccharides anti-tumor activity inulin-type fructans
Available online: April 30, 2024
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Short Report

5) 9,11-Cycloneren-3,7-diol: a New Cyclonerane Sesquiterpene from the Marine-Sediment-Derived Fungus Trichoderma harzianum WH-22

Rec. Nat. Prod. (2024) in press ; 1 - 5
by Xin Dong , Lin-Chuan Jia , Hai-Quan Chai , Xiao-Xiao Liu and Lei Yang

One new cyclonerane sesquiterpene, 9,11-cycloneren-3,7-diol (1), along with four known ones, 11-cycloneren-3,7,10-triol (2), 9-cycloneren-3,7,11-triol (3), 11-methoxy-9-cycloneren-3,7-diol (4), and cyclonerodiol (5), were obtained from the extract of marine-derived fungus Trichoderma harzianum WH-22. The structure of 9,11-cycloneren-3,7-diol (1) was elucidated by comprehensive spectroscopic analysis, including 1D/2D NMR and HRESIMS data. 9,11-Cycloneren-3,7-diol (1) exhibited weak cytotoxicity against HeLa and HepG2 cancer cell lines with IC50 values of 68.2 and 59.7 μM, respectively.

DOI
http://doi.org/10.25135/rnp.456.2403.3175
Keywords
Cyclonerane sesquiterpene Trichoderma harzianum structure elucidation cytotoxic activity
Available online: April 30, 2024
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Original Article

6) A New Sesquiterpene from the Fungus Penicillium sp. LPFH-hzw-zw1

Rec. Nat. Prod. (2024) in press ; 1 - 7
by Wei Zhang and Qi Wang
An investigation into the secondary metabolites of the sea sediment-derived Penicillium sp. LPFH-ZW-1 led to the isolation of a new compound, named penicipeneacid (1), along with seven known compounds. The structures of these compounds were identified through extensive analysis of the 1D and 2D NMR data, combined with HRESIMS data. The absolute configuration of 1 was determined by comparing the experimental and predicted ECD spectra. The bicyclo[4.1.0]heptane nucleus in compounds 1 and 2 was rarely found in nature. The known compounds were identified to be sesquicaranoic acid B (2), 9-cycloneren-3,7,11-triol (3), fumiquinazoline J (4), versiquinazoline H (5), penipurdin A (6), questinol (7), 2-hydroxy-4-ethoxybenzoic acid (8). Compounds 4 and 7 exhibited moderate cytotoxicity against MCF-7 and K562 tumor cell lines, with IC50 values ranging from 12.6 to 37.1 M.
DOI
http://doi.org/10.25135/rnp.453.2402.3149
Keywords
marine fungus Penicillium sesquiterpene penicipeneacid
Available online: April 08, 2024
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Original Article

7) Antimicrobial and α-Glucosidase Inhibitory Compounds from the Branches of Uvaria siamensis

Rec. Nat. Prod. (2024) in press ; 1 - 8
by Ngoc-Hong Nguyen , Boi-Phong Vuong , Chuong Hoang Nguyen , A Dong Huynh , Dinh-Manh Nguyen , Thuc-Huy Duong , Hoang-Thanh Kpa , Thi-Kim-Dung Le , Thi-Ngoc-Duyen Nguyen , Huy Truong Nguyen and Jirapast Sichaem

A new γ-butenoid, (Z)-6-acetylsphaerodol (2), along with seven known compounds, (4E)-7-benzoyloxy-6-hydroxy-2,4-heptadien-4-olide (1), (6S)-melodorinol (3), (6S)-acetylmelodorinol (4), (Z)-sphaerodiol (5), (Z)-7-acetylsphaerodol (6), dichamanetin (7), and pinocembrin (8), were isolated and structurally elucidated from Uvaria siamensis growing in Thailand. Their chemical structures were assigned by extensive spectroscopy (NMR and HRESIMS), as well as comparisons with the previous literature. Compounds 1-8 were evaluated for the antimicrobial activity against two multidrug-resistant Staphylococcus aureus strains, 23Sa1 and SA-ATCC. Compounds 4 and 6 displayed moderate activity with inhibitory zones of 13 and 12 mm against 23Sa1 and SA-ATCC strains, respectively. Compounds 3 and 7 exhibited significant efficacy, displaying IC50 values of 157.7 and 94.2 µM, respectively, against α-glucosidase. According to the docking data, compounds 3 and 7 have a greater influence on binding contacts with the α-glucosidase active pocket, thereby affecting the inhibitory activity of the enzyme.

DOI
http://doi.org/10.25135/rnp.452.2402.3145
Keywords
Annonaceae Uvaria siamensis (Z)-6-acetylsphaerodol γ-butenoid antibacterial activity α-glucosidase inhibition
Available online: April 08, 2024
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Short Report

8) A Novel Limonoid from the Seeds of Chisocheton macrophyllus

Rec. Nat. Prod. (2024) in press ; 1 - 6
by Nurlelasari , Muhammad Huda , Wahyu Safriansyah , Unang Supratman , Yudha Budiman , Desi Harneti P. Huspa , Rani Maharani , Tri Mayanti , Kindi Farabi and Sofa Fajriah

This study aimed to isolate a novel limonoid compound, (6R,7S, 8R, 9R, 10R, 11R, 13S, 17R)-17-(furan-3-yl) -4, 4, 8, 10, 13-pentamethyl-3-oxo-4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 16, 17-dodecahydro-3H-cyclopenta[a]phenanthrene-6,7,11-triyltriacetate (11α-acetoxydysobinin) (1), and 3 pre-existing limonoids, namely dysobinin (2), dysobinol (3), and 7-deacetylepoxyazadiradione (4) from the seeds of Chisocheton macrophyllus (Meliaceae). In addition, the structure of the isolated compounds was determined using various spectroscopic techniques, including UV, IR, HRTOFMS, 1D, and 2D NMR. The cytotoxic effects of each compound were then evaluated against breast cancer cells of the Michigan Cancer Foundation-7 (MCF-7), but no significant activity was observed.

DOI
http://doi.org/10.25135/rnp.451.2311.2960
Keywords
Chisocheton macrophyllus Meliaceae limonoid cytotoxic activity MCF-7
Available online: March 17, 2024
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Review Article

9) Chemical Constituents and Pharmacological Activities of the Genus Nageia

Rec. Nat. Prod. (2024) in press ; 1 - 22
by Lijun Zou , Xiao Chen , Jialin Zhang , Qi Sun , Shuoshuo Fu , Sha Yang , Huiyou Xu , Jian Zhou and Lin Ni

There are seven species in the genus Nageia, a member of the Podocarpaceae family; five are found in China. They are primarily found in eastern and southern Asia, close to the equator at the 30th parallel north and south, and in coastal mountainous areas and islands in the western Pacific. These herbs are extremely valuable for medicinal purposes. The three species of Nageia that are the subject of most current research on their chemical composition and pharmacological properties are N. nagi, N. fleuryi, and N. wallichiana. There are currently 232 known chemical components, which include steroids, flavonoids, sesquiterpenoids, and diterpenoids. Of these, 86 diterpenoid dilactones comprise most of the chemical components, and only plants of the Nageia genus contain C-ring decarbonized diterpenoid dilactones. These plants exhibit promising pharmacological activities such as anti-tumor, antioxidant, antibacterial, and anti-inflammatory properties. For the first time, an in-depth and systematic evaluation of the chemical constituents and pharmacological properties of plants in the Nageia genus is presented in the this article. This theoretical framework will help in the future investigation and development of medicinal resources and active ingredients within the genus.

DOI
http://doi.org/10.25135/rnp.435.2311.2979
Keywords
Nageia diterpenoids nagilactones antitumor antioxidants bacteriostatic
Available online: February 21, 2024
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