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Chemical composition and anticholinesterase inhibitory activity of the essential oil of Pseuduvaria macrophylla (Oliv.) Merr. from Malaysia

Salleh WMNHW, Khamis S, Nafiah MA, Abed SA

Nat Prod Res, 2021 Jun;35(11):1887-1892.
PMID: 31293176 DOI: 10.1080/14786419.2019.1639183

This study was designed to examine the chemical composition and anticholinesterase inhibitory activity of the essential oil of Pseuduvaria macrophylla (Oliv.) Merr. (Annonaceae) from Malaysia. The essential oil was obtained by hydrodistillation and fully analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). The analysis led to the identification of thirty-four chemical components that represented 87.7 ± 0.5% of the total oil. The essential oil was found to be rich in germacrene D (21.1 ± 0.4%), bicyclogermacrene (10.5 ± 0.5%), δ-cadinene (5.6 ± 0.2%), α-copaene (5.1 ± 0.3%), and α-cadinol (5.0 ± 0.3%). Anticholinesterase activity was evaluated using Ellman method. The essential oil showed weak inhibitory activity against acetylcholinesterase (I%: 32.5%) and butyrylcholinesterase (I%: 35.4%) assays. Our findings demonstrate that the essential oil could be very useful for the characterization, pharmaceutical and therapeutic applications of the essential oil from Pseuduvaria macrophylla.

Matched MeSH terms: Sesquiterpenes/pharmacology
Vernodalin induces apoptosis through the activation of ROS/JNK pathway in human colon cancer cells

Mohebali N, Pandurangan AK, Mustafa MR, Anandasadagopan SK, Alagumuthu T

J Biochem Mol Toxicol, 2020 Dec;34(12):e22587.
PMID: 32726518 DOI: 10.1002/jbt.22587

Colorectal cancer is one of the most leading death-causing cancers in the world. Vernodalin, a cytotoxic sesquiterpene, has been reported to possess anticancer properties against human breast cancer cells. We aimed to examine the anticancer mechanism of vernodalin on human colon cancer cells. Vernodalin was used on human colon cancer cells, HT-29 and HCT116. The cytotoxicity of vernodalin on human colon cancer cells was determined through in vitro 3-(4,5-dimethylthiazol-2yl)-2,5-diphenyl-tetrazolium bromide assay. Small interfering RNA was used to analyze the cascade activation of mitogen-activated protein kinase (MAPK) pathway, c-Jun N-terminal kinase (JNK) in HT-29, and HCT116 cells against vernodalin treatment. The protein expressions of caspase 3, Bcl-2, and Bax were examined through Western blot analysis. Immunoblot analysis on the JNK, ERK, and p38 MAPK pathways showed increased activation due to vernodalin treatment. It was proven from the JNK and p38 inhibition test that both pathways are significantly activated by vernodalin to induce apoptosis. Our results, collectively, showed the apoptosis-induced anticancer mechanism of vernodalin on human colon cancer cells that was mediated through the activation of JNK pathway and apoptotic regulator proteins. These results suggest that vernodalin could be developed as a potent chemotherapeutic agent for human colorectal cancer treatment.

Matched MeSH terms: Sesquiterpenes/pharmacology
Bioactive chemical constituents from Curcuma caesia Roxb. rhizomes and inhibitory effect of curcuzederone on the migration of triple-negative breast cancer cell line MDA-MB-231

Al-Amin M, Eltayeb NM, Khairuddean M, Salhimi SM

Nat Prod Res, 2021 Sep;35(18):3166-3170.
PMID: 31726856 DOI: 10.1080/14786419.2019.1690489

Rhizomes of Curcuma caesia are traditionally used to treat cancer in India. The aim is to isolate chemical constituents from C. caesia rhizomes through bioassay-guided fractionation. The extract, hexanes and chloroform fractions showed effect on MCF-7 and MDA-MB-231cells in cell viability assay. The chromatographic separation afforded germacrone (1), zerumbone (2), furanodienone (3), curzerenone (4), curcumenol (5), zederone (6), curcumenone (7), dehydrocurdione (8) from hexanes fraction and curcuminol G (9), curcuzederone (10), (1S, 10S), (4S,5S)-germacrone-1 (10), 4-diepoxide (11), wenyujinin B (12), alismoxide (13), aerugidiol (14), zedoarolide B (15), zedoalactone B (16), zedoarondiol (17), isozedoarondiol (18) from chloroform fraction. This is first report of compounds 2, 9-13, 15-18 from C. caesia. The study demonstrated compounds 1-4 and 10 are the bioactive compounds. The effect of curcuzederone (10) on MDA-MB-231 cell migration showed significant inhibition in scratch and Transwell migration assays. The results revealed that curcuzederone could be a promising drug to treat cancer.

Matched MeSH terms: Sesquiterpenes/pharmacology*
The phytochemistry and biological diversity of Ferulago genus (Apiaceae): a systematic review

Salleh WMNHW, Abed SA, Taher M, Kassim H, Tawang A

J Pharm Pharmacol, 2021 Mar 01;73(1):1-21.
PMID: 33791809 DOI: 10.1093/jpp/rgaa034

OBJECTIVES: The genus Ferulago belonging to the family Apiaceae is a flora widely distributed in Central Asia and the Mediterranean and used in folk medicine. It is administered as a sedative, tonic, digestive, aphrodisiac, also as a treatment for intestinal worms and haemorrhoids. Herein, we reported a review on phytochemistry and its biological activities reported from 1990 up to early 2020. All the information and reported studies concerning Ferulago plants were summarized from the library and digital databases (e.g. Scopus, Medline, Scielo, ScienceDirect, SciFinder and Google Scholar).
KEY FINDINGS: The phytochemical investigations of Ferulago species revealed the presence of coumarins as the main bioactive compounds, including daucane derivatives, sesquiterpenes aryl esters, phenol derivatives, flavonoids and essential oils. Moreover, the therapeutic potentials of the pure compounds isolated from the genus Ferulago possess promising properties namely anticholinesterase, antimicrobial, anticoagulant, antileishmanial, antioxidant, antibacterial and antiproliferative.
SUMMARY: Today, significant advances in phytochemical and biological activity studies of different Ferulago species have been revealed. The traditional uses and reported biological results could be correlated via the chemical characterization of these plants. All these data will support the biologists in the elucidation of the biological mechanisms of these plants.

Matched MeSH terms: Sesquiterpenes/pharmacology
Exploring the immunomodulatory and anticancer properties of zerumbone

Haque MA, Jantan I, Arshad L, Bukhari SNA

Food Funct, 2017 Oct 18;8(10):3410-3431.
PMID: 28714500 DOI: 10.1039/c7fo00595d

Plant-derived immunomodulators and anti-cancer agents have attracted a lot of interest from natural product scientists for their efficacy and safety and their significant contribution towards understanding targeted drug action and drug delivery mechanisms. Zerumbone, the main constituent of Zingiber zerumbet rhizomes, has been investigated for its wide-spectrum role in treating multitargeted diseases. The rhizomes have been used as food flavoring agents in various cuisines and in herbal medicine. Many in vivo and in vitro studies have provided evidence of zerumbone as a potent immunomodulator as well as a potential anti-cancer agent. This review is an interesting compilation of all those significant outcomes from investigations carried out to date to explore the immunomodulatory and anticancer properties of zerumbone. The ultimate objective of this comprehensive review is to provide updated information and a critical assessment on zerumbone including its chemistry and immunomodulating and anticancer properties, which may be of paramount importance to provide a new path for ensuing research to discover new agents to treat cancers and immune-related diseases. In addition, updated information on the toxicology of zerumbone has also been summarized to provide its safety profile.

Matched MeSH terms: Sesquiterpenes/pharmacology*
Fulltext Standardized ethanol extract, essential oil and zerumbone of Zingiber zerumbet rhizome suppress phagocytic activity of human neutrophils

Akhtar NMY, Jantan I, Arshad L, Haque MA

BMC Complement Altern Med, 2019 Nov 21;19(1):331.
PMID: 31752812 DOI: 10.1186/s12906-019-2748-5

BACKGROUND: Zingiber zerumbet rhizome and its bioactive metabolites have previously been reported to exhibit innumerable pharmacological properties particularly anti-inflammatory activities. In the present study, the 80% ethanol extract, essential oil and zerumbone of Z. zerumbet rhizomes were explored for their in vitro immunosuppressive properties on chemotaxis, CD11b/CD18 expression, phagocytosis and chemiluminescence of isolated human polymorphonuclear neutrophils (PMNs).
METHODS: The extract was analyzed quantitatively by performing a validated reversed phase high performance liquid chromatography (RP-HPLC). Zerumbone was isolated by chromatographic technique while the essential oil was acquired through hydro-distillation of the rhizomes and further analyzed by gas chromatography (GC) and GC-MS. Chemotaxis assay was assessed by using a 24-well cell migration assay kit, while CD18 integrin expression and phagocytic engulfment were measured using flow cytometry. The reactive oxygen species (ROS) production was evaluated by applying lucigenin- and luminol-enhanced chemiluminescence assays.
RESULTS: Zerumbone was found to be the most abundant compound in the extract (242.73 mg/g) and the oil (58.44%). Among the samples tested, the oil revealed the highest inhibition on cell migration with an IC50 value of 3.24 μg/mL. The extract, oil and zerumbone showed moderate inhibition of CD18 integrin expression in a dose-dependent trend. Z. zerumbet extract showed the highest inhibitory effect on phagocytic engulfment with percentage of phagocytizing cells of 55.43% for PMN. Zerumbone exhibited strong inhibitory activity on oxidative burst of zymosan- and PMA-stimulated neutrophils. Zerumbone remarkably inhibited extracellular ROS production in PMNs with an IC50 value of 17.36 μM which was comparable to that of aspirin.
CONCLUSION: The strong inhibition on the phagocytosis of neutrophils by Z. zerumbet extract and its essential oil might be due the presence of its chemical components particularly zerumbone which was capable of impeding phagocytosis at different stages.

Matched MeSH terms: Sesquiterpenes/pharmacology*
Bioactive sesquiterpenes from Curcuma ochrorhiza and Curcuma heyneana

Aspollah Sukari M, Wah TS, Saad SM, Rashid NY, Rahmani M, Lajis NH, et al.

Nat Prod Res, 2010 May;24(9):838-45.
PMID: 20461629 DOI: 10.1080/14786410903052951

Curcuma ochrorhiza ('temu putih') and C. heyneana ('temu giring') are two Zingiberaceous species which are commonly used in traditional medicine in Malaysia and Indonesia. Phytochemical investigations on these Curcuma species have resulted in the isolation of six sesquiterpenes, namely zerumbone (1), furanodienone (2), zederone (3), oxycurcumenol epoxide (4), curcumenol (5) and isocurcumenol (6), along with phytosterols stigmasterol and alpha-sitosterol. Compounds 1 and 2 were obtained for the first time for C. ochrorhiza while 4 was new to C. heyneana. The hexane extract of C. ochrorhiza and sesquiterpenes 1 and 3 showed very strong cytotoxicity activity against T-acute lymphoblastic leukaemia cells (CEM-SS), with IC(50) values of 6.0, 0.6 and 1.6 microg mL(-1), respectively. Meanwhile, constituents from C. heyneana (4-6) demonstrated moderate inhibition against CEM-SS in cytotoxic assay, with IC(50) values of 11.9, 12.6 and 13.3 microg mL(-1), respectively. The crude extracts and sesquiterpenes isolated were moderately active against certain bacteria tested in antimicrobial screening.

Matched MeSH terms: Sesquiterpenes/pharmacology*