Project's information

Project's title Study on chemical constituents and bioactivity of Syzygium myrsinifolium, Syzygium attopeuense, Syzygium antisepticum
Project’s code THTEXS.04/23-25
Research hosting institution Institute of Chemistry
Project leader’s name Dr. Do Thi Trang
Project duration 01/01/2023 - 31/12/2025
Project’s budget 1,000 million VND
Classify Grade B
Goal and objectives of the project

 - Study of chemical composition of Syzygium myrsinifolium, Syzygium attopeuense, Syzygium antisepticum
 - Evaluation of Anti-inflammatory, α-Glucosidase, and α-Amylase Inhibitory activities

Novelty and actuality and scientific meaningfulness of the results

- Fourteen compounds (SM1-SM14) were isolated and their structures elucidated from the leaves of S. myrsinifolium. Among them were two new compounds, syzyfolium A (SM1) and syzyfolium B (SM2), along with twelve known compounds, including terminolic acid (SM3), actinidic acid (SM4), piscidinol A (SM5), threo-dihydroxydehydrodiconiferyl alcohol (SM6), lariciresinol-4-O-β-D-glucoside (SM7), icariol A2 (SM8), 14β,15β-dihydroxyklaineanone (SM9), garcimangosone D (SM10), (+)-catechin (SM11), myricetin-3-O-α-L-rhamnopyranoside (SM12), quercitrin (SM13), and 3, 4, 5-trimethoxyphenyl-(6ʹ-O-galloyl)-O-β-D-glucopyranoside (SM14).
- Ten compounds (SA1-SA10) were isolated and their structures elucidated from the fruits of S. attopeuense. These isolates comprised three new compounds: 2α,3β,6β-trihydroxy-24-nor-urs-4(23),12,20(30)-trien-28-oic acid 28-O-β-D-glucopyranoside (SA1), 3β,6β,23-trihydroxyurs-12-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (SA2), và (2R,3R)-5,7,3ʹ,4ʹ-tetrahydroxyflavanone 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (SA3). The remaining seven compounds were identified as centelloside C (SA4), syzygiumursanolide C (SA5), chebuloside II (SA6), quadranoside IV (SA7), epifriedelanol (SA8), friedelin (SA9), lupenyl acetate (SA10).
- Ten compounds (SAA1-SAA10) were isolated and characterized from the leaves of S. antisepticum. Among the isolated compounds were 3 new compounds: 2α,3β,20α,23-tetrahydroxy-nor-30-urs-12-en-28-oic acid 28-O-β-D-glucopyranoside (SAA1), 2α,3β,6β,23-tetrahydroxyoleana-11,13(18)-dien-28-oic acid (SAA2), and 4,6-dihydroxy-3-methyl-2-O-β-D-glucopyranosylbenzophenone (SAA3), and 7 known compounds: centelloside C (SAA4), syzygiumursanolide C (SAA5), chebuloside II (SAA6), quadranoside IV (SAA7), epifriedelanol (SAA8), friedelin (SAA9), lupenyl acetate (SAA10).
- All compounds isolated from S. myrsinifolium, S. attopeuense, and S. antisepticum were evaluated for anti-inflammatory activity by inhibiting NO production. The results indicated that the isolates from S. antisepticum exhibited moderate NO production inhibitory activity (IC50 ranging from 16.3 to 74.6μM), whereas those from S. myrsinifolium and S. attopeuense displayed weaker activity."
- All isolated compounds from S. myrsinifolium, S. attopeuense, and S. antisepticum were evaluated for their inhibitory activities against α-glucosidase and α-amylase. Compounds SM1 and SM2 exhibited potent α-amylase inhibitory activity with IC50 values of 35.48 and 43.60 μM, respectively, which were stronger than the positive control (IC50 = 144.54 μM). In addition, compounds SM3 and SAA9 displayed strong α-glucosidase inhibitory activity with IC50 values of 23.99 and 23.60 μM, respectively, both of which were more active than the positive control (IC50 = 46.80 μM).
Novelty and actuality and scientific meaningfulness of the results:
- Undescribed triterpenes syzyfolium A (SM1) and syzyfolium B (SM2) were isolated and their structures were determined from the leaves of S. myrsinifolium
- Three new compounds 2α,3β,6β-trihydroxy-24-nor-urs-4(23),12,20(30)-trien-28-oic acid 28-O-β-D-glucopyranoside (SA1), 3β,6β,23-trihydroxyurs-12-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (SA2), và (2R,3R)-5,7,3ʹ,4ʹ-tetrahydroxyflavanone 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (SA3) were isolated and structurally characterized from the fruits of S. attopeuense.
- Three previously unreported compounds, namely 2α,3β,20α,23-tetrahydroxy-nor-30-urs-12-en-28-oic acid 28-O-β-D-glucopyranoside (SAA1), 2α,3β,6β,23-tetrahydroxyoleana-11,13(18)-dien-28-oic acid (SAA2), and 4,6-dihydroxy-3-methyl-2-O-β-D-glucopyranosylbenzophenone (SAA3), were isolated from the leaves of S. attopeuense. Their chemical structures were elucidated by IR, HR-ESI-MS, 1D and 2D NMR spectra.

Products of the project
- Scientific papers in referred journals (list):
[1] Do Thi Trang, Bui Huu Tai, Nguyen Huy Hoang, Nguyen Thi Cuc, Ngo Anh Bang, Duong Thi Dung, Duong Thi Hai Yen, Phan Thi Thanh Huong, Nguyen Viet Dung, Dan Thi Thuy Hang, Pham Hai Yen, and Phan Van Kiem; Undescribed triterpenes from the leaves of Syzygium myrsinifolium with their α-glucosidase and α-Amylase inhibition activity. Chemistry & Biodiversity, doi.org/10.1002/cbdv.202400124.
[2] Do Thi Trang, Nguyen Huy Hoang, Ngo Anh Bang, Pham Hai Yen, Duong Thi Dung, Le Thi Huyen, Phan Thi Thanh Huong, Duong Thi Hai Yen, Bui Huu Tai,Phan Van Kiem; Discovery of undescribed triterpenoids and flavonoid from the fruits of Syzygium attopeuense with their α-Glucosidase and α-Amylase inhibitory activity. Chemistry & Biodiversity, doi: 10.1002/cbdv.202403233.
 [3] Do Thi Trang, Nguyen Viet Dung, Ngo Anh Bang, Vu Kim Thu, Le Thi Thuy Hang, Pham Hai Yen, Bui Huu Tai, and Phan Van Kiem. Three previously undescribed compounds isolated from the leaves of Syzygium antisepticum with their α-glucosidase and nitric oxide inhibitory activity, Chemistry & Biodiversity, accepted for puplication, pending online release.
10. Technological products (deposited in the Institute of Chemistry):
+ Report on isolation and structure elucidation of compounds from Syzygium myrsinifolium (02 reports)..
+ Report on isolation and structure elucidation of compounds from Syzygium attopeuense (02 reports).
+ Report on isolation and structure elucidation of compounds from Syzygium antisepticum (02 reports).
+ Report on the results of anti-inflammatory and α-glucosidase and α-amylase inhibitory activity of compounds isolated from Syzygium myrsinifolium, Syzygium attopeuense và Syzygium antisepticum (03 reports)..

 

Recommendations

Excellent α-amylase inhibitory efficacy was noted for SM1 and SM2, while SM3 and SAA9 showed strong α-glucosidase inhibitory activity. This suggests that these compounds could play a significant role in the treatment of diabetes mellitus, which is consistent with previous reports on the uses of the folk medicinal plant. Therefore, these compounds should be studied further in vivo and included as potential drug leads for the supportive treatment of diabetes.             

Images of project
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