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Phytoconstituents of Endiandra kingiana; antidiabetic effects and molecular docking studies on alpha-amylase and alpha-glucosidase

Tanazi NNH, Aziz AN, Azmi MN, Abu Bakar MH, Hassim MFN, Wahab NHA, et al.

Nat Prod Res, 2023 Nov 27.
PMID: 38009213 DOI: 10.1080/14786419.2023.2283759

Phytochemical investigation on the bark of E. kingiana plant afforded ten compounds, including six polyketides namely kingianin A 1, kingianin B 2, kingianin E 3, kingianin F 4, kingianin K 5 and kingianin L 6, three endiandric acids; kingianic acid A 7, tsangibeilin B 8 and endiandric acid M 9, and one sesquiterpene; daibuoxide 10. All compounds were separated as racemic mixture by recycling high-performance liquid chromatography (RHPLC), except for daibuoxide. Their structures were elucidated by detailed spectroscopic and comparative literature data analysis. This is the first report on the presence of the sesquiterpene; daibuoxide in Endiandra genus. In vitro enzymatic bio-evaluation of the isolated compounds against α-amylase and α-glucosidase showed that 4 demonstrated the best α-amylase and α-glucosidase inhibitory activity with IC50 values of 181.54 ± 6.27 µg/mL and 237.87 ± 0.07 µg/mL, respectively. In addition, molecular docking analysis confirmed the α-amylase and α-glucosidase inhibitory activities demonstrated by 4.
Fulltext Essential oils of aromatic Egyptian plants repel nymphs of the tick Ixodes ricinus (Acari: Ixodidae)

El-Seedi HR, Azeem M, Khalil NS, Sakr HH, Khalifa SAM, Awang K, et al.

Exp Appl Acarol, 2017 Sep;73(1):139-157.
PMID: 28864886 DOI: 10.1007/s10493-017-0165-3

Due to the role of Ixodes ricinus (L.) (Acari: Ixodidae) in the transmission of many serious pathogens, personal protection against bites of this tick is essential. In the present study the essential oils from 11 aromatic Egyptian plants were isolated and their repellent activity against I. ricinus nymphs was evaluated Three oils (i.e. Conyza dioscoridis L., Artemisia herba-alba Asso and Calendula officinalis L.) elicited high repellent activity in vitro of 94, 84.2 and 82%, respectively. The most active essential oil (C. dioscoridis) was applied in the field at a concentration of 6.5 µg/cm2 and elicited a significant repellent activity against I. ricinus nymphs by 61.1%. The most repellent plants C. dioscoridis, C. officinalis and A. herba-alba yielded essential oils by 0.17, 0.11 and 0.14%, respectively. These oils were further investigated using gas chromatography-mass spectrometry analysis. α-Cadinol (10.7%) and hexadecanoic acid (10.5%) were the major components of C. dioscoridis whereas in C. officinalis, α-cadinol (21.2%) and carvone (18.2%) were major components. Artemisia herba-alba contained piperitone (26.5%), ethyl cinnamate (9.5%), camphor (7.7%) and hexadecanoic acid (6.9%). Essential oils of these three plants have a potential to be used for personal protection against tick bites.
Fulltext The Incidence of Nasopharyngeal Carcinoma in Pahang State of Malaysia from 2012 to 2017

Ahmad A, Yassin WM, Rahman NAA, Leman WI, Rosla L, Paul M, et al.

Malays J Med Sci, 2021 Feb;28(1):66-74.
PMID: 33679222 DOI: 10.21315/mjms2021.28.1.9

Background: Nasopharyngeal carcinoma (NPC) is the fifth most common cancer among Malaysians. While several studies have reported the trend of NPC in other states in Malaysia, no studies have reported the trend of NPC in Pahang state. This study was designed to report the number and distribution of newly diagnosed NPC cases in Pahang.
Methods: NPC cases that were diagnosed between 2012 and 2017 in two referral hospitals in Pahang were traced. The crude incidence rate (CR) and age-standardised rate (ASR) were calculated to investigate the NPC incidence.
Results: There were 143 new cases of NPC reported from the two hospitals. The mean age at diagnosis was 52.0 ± 13.7 years old. The majority of cases involved males (74.1%) with a male to female ratio of 2.9:1. Chinese males were found to have the highest incidence with a mean ASR of 4.7 per 100,000 population. Overall, the mean ASR for Pahang was 2.4 per 100,000 population for males and 0.9 per 100,000 population for females.
Conclusion: The total number of NPC cases reveals an increasing trend from 2012 to 2014 and then a slightly decreasing trend from 2015 to 2017. The incidence of NPC in Pahang was intermediate in males and low in females.
Fulltext Topical Administration Effect of Sargassum duplicatum and Garcinia mangostana Extracts Combination on Open Wound Healing Process in Diabetic Mice

Winarni D, Husna FN, Syadzha MF, Susilo RJK, Hayaza S, Ansori ANM, et al.

Scientifica (Cairo), 2022;2022:9700794.
PMID: 35186344 DOI: 10.1155/2022/9700794

This research aimed to determine the topical administration effect of the combination of Sargassum duplicatum and Garcinia mangostana extracts to ameliorate diabetic open wound healing. The study used 24 adult males of Mus musculus (BALB/c strain, 3-4 months, 30-40 g). They were divided into normal control groups (KN) and diabetic groups. The diabetic group was streptozotocin-induced and divided further into three treatment groups: the diabetic control group (KD), the S. duplicatum treatment group (PA), and the combination of S. duplicatum and G. mangostana treatment group (PAM). The dose of treatment was 50 mg/kg of body weight. Each group was divided into three treatment durations, which were 3 days, 7 days, and 14 days. The wound healing process was determined by wound width, the number of neutrophils, macrophages, fibroblasts, fibrocytes, and collagen density. Histological observation showed that the topical administration of combination extracts increased the re-epithelialization of the wounded area, fibroblasts, fibrocytes, and collagen synthesis. The topical administration of combination extracts also decreased the number of neutrophils and macrophages. This study concluded that the topical administration of the combination of S. duplicatum and G. mangostana extracts improved the open wound healing process in diabetic mice.
Indole alkaloids from Ochreinauclea maingayi (Rubiaceae) as butyrylcholinesterase inhibitors and their paralysis effect in transgenic Caenorhabditis elegans

Osman N, Awang K, Khaw KY, Qi Mak W, Tiamas SG, Maulana S, et al.

Nat Prod Res, 2024 Aug 21.
PMID: 39165195 DOI: 10.1080/14786419.2024.2394096

This study investigated the butyrylcholinesterase (BChE) inhibitory activity of harmane (1), naucledine (2), and dihydrodeglycocadambine (3) isolated from fractions F7 and F9 of Ochreinauclea maingayi. Both fractions demonstrated significant inhibition, exceeding 80%, against BChE at 100 µg/mL. Compound 2, is the most potent inhibitor, exhibiting an IC50 value of 22.08 µM, followed by 1 and 3 (IC50 23.96 and 30.32 µM, respectively). Docking studies revealed that 1 and 2 effectively bind to BChE, with binding energies of -51.24 and -57.17 kcal/mol, respectively. Kinetic analysis of 2 indicated mixed-mode inhibition of BChE, with a Ki of 6.08 μM. In the paralysis assay, 1 showed a weak delay in paralysis and reduced the paralysis ratio from 72.59 ± 4.7% to 60.00 ± 7.0% (12.59% reduction) followed by 2 with 70.00 ± 1.7% (2.59% reduction) compared with negative standard (DMSO 0.1%) on human amyloid β-protein in a transgenic Caenorhabditis elegans (CL4176) model.
Targeted Isolation of Antiviral Labdane Diterpenes from the Bark of Neo-uvaria foetida (Annonaceae) using LC-MS/MS-Based Molecular Networking

Sukumaran SY, Herrscher C, Rasol NE, Othman MA, Liew SY, Ismail NH, et al.

J Nat Prod, 2024 Aug 23;87(8):1941-1951.
PMID: 39028935 DOI: 10.1021/acs.jnatprod.4c00342

In the search of new inhibitors for human coronavirus (HCoV), we screened extracts of endemic Annonaceae plants on an assay using a cellular model of Huh-7 cells infected with the human alphacoronavirus HCoV-229E. The EtOAc bark extract of the rare Southeast Asian plant Neo-uvaria foetida exhibited inhibition of HCoV-229E and SARS-CoV-2 viruses with IC50 values of 3.8 and 7.8 μg/mL, respectively. Using LC-MS/MS and molecular networking analysis guided isolation, we discovered two new labdane-type diterpenoids, 8-epi-acuminolide (1) and foetidalabdane A (4), and three known labdane diterpenoids, acuminolide (2), 17-O-acetylacuminolide (3), and spiroacuminolide (5). A new norlabdane diterpene, 16-foetinorlabdoic acid (6), was also isolated and identified. Excluding compounds 5 and 6, all other metabolites were active against the virus HCoV-229E. Terpenoids 1 and 4 presented antiviral activity against SARS-CoV-2 with IC50 values of 63.3 and 93.5 μM, respectively, indicating lower potency. Additionally, virological assays demonstrated that compounds 1, 2, and 3 exert antiviral effects against Zika virus by specifically interfering with the late stage of its infectious cycle with IC50 values of 76.0, 31.9, and 14.9 μM, respectively.
Chisomicines A-C, limonoids from Chisocheton ceramicus

Najmuldeen IA, Hadi AH, Awang K, Mohamad K, Ketuly KA, Mukhtar MR, et al.

J Nat Prod, 2011 May 27;74(5):1313-7.
PMID: 21428417 DOI: 10.1021/np200013g

Three new limonoids, chisomicines A-C (1-3), have been isolated from the bark of Chisocheton ceramicus. Their structures were determined by 2D NMR, CD spectroscopic methods, and X-ray analysis. Chisomicine A (1) exhibited NO production inhibitory activity in J774.1 cells stimulated by LPS dose-dependently at high cell viability.
Fulltext A Quantum Chemical and Statistical Study of Cytotoxic Activity of Compounds Isolated from Curcuma zedoaria

Hamdi OA, Anouar el H, Shilpi JA, Trabolsy ZB, Zain SB, Zakaria NS, et al.

Int J Mol Sci, 2015 Apr 27;16(5):9450-68.
PMID: 25923077 DOI: 10.3390/ijms16059450

A series of 21 compounds isolated from Curcuma zedoaria was subjected to cytotoxicity test against MCF7; Ca Ski; PC3 and HT-29 cancer cell lines; and a normal HUVEC cell line. To rationalize the structure-activity relationships of the isolated compounds; a set of electronic; steric and hydrophobic descriptors were calculated using density functional theory (DFT) method. Statistical analyses were carried out using simple and multiple linear regressions (SLR; MLR); principal component analysis (PCA); and hierarchical cluster analysis (HCA). SLR analyses showed that the cytotoxicity of the isolated compounds against a given cell line depend on certain descriptors; and the corresponding correlation coefficients (R2) vary from 0%-55%. MLR results revealed that the best models can be achieved with a limited number of specific descriptors applicable for compounds having a similar basic skeleton. Based on PCA; HCA and MLR analyses; active compounds were classified into subgroups; which was in agreement with the cell based cytotoxicity assay.
Fulltext Collected mass spectrometry data on monoterpene indole alkaloids from natural product chemistry research

Fox Ramos AE, Le Pogam P, Fox Alcover C, Otogo N'Nang E, Cauchie G, Hazni H, et al.

Sci Data, 2019 04 03;6(1):15.
PMID: 30944327 DOI: 10.1038/s41597-019-0028-3

This Data Descriptor announces the submission to public repositories of the monoterpene indole alkaloid database (MIADB), a cumulative collection of 172 tandem mass spectrometry (MS/MS) spectra from multiple research projects conducted in eight natural product chemistry laboratories since the 1960s. All data have been annotated and organized to promote reuse by the community. Being a unique collection of these complex natural products, these data can be used to guide the dereplication and targeting of new related monoterpene indole alkaloids within complex mixtures when applying computer-based approaches, such as molecular networking. Each spectrum has its own accession number from CCMSLIB00004679916 to CCMSLIB00004680087 on the GNPS. The MIADB is available for download from MetaboLights under the identifier: MTBLS142 ( https://www.ebi.ac.uk/metabolights/MTBLS142 ).