Project's information

Project's title Study chemical composition and biological activity of two plant species Nang nang (Callicarpa candicans (Burm f.) Hochr.) and Tu chau la to (Callicarpa macrophylla Vahl) in Vietnam
Project’s code GUST.STS.ĐT2017-HH03
Research hosting institution Institute of Natural Products Chemistry
Project leader’s name Dr. Do Tien Lam
Project duration 01/06/2017 - 30/06/2020
Project’s budget 462 million VND
Classify Excellent
Goal and objectives of the project

- Isolation and structure identification of compounds from different parts of two plant species Nang nang (Callicarpa candicans (Burm f.) Hochr.) and Tu chau la to (Callicarpa macrophylla Vahl) in Vietnam.
- Evaluation of in vitro biological activity (antitumor activity to cancer cells: liver (Hep-G2) and lung (Lu-1)) of pure compounds isolated.

 

Main results

Chemical constituents of the two species:
The thesis studies the chemical constituents of two species of Callicarpa candicans and Callicarpa macrophylla in Vietnam for the first time. As a result, 21 compounds have been isolated, including 2 new compounds, one compound was isolated from nature for the first time.
From n-hexane and ethyl acetate extracts from the leaves of C. macrophylla, up to 10 compounds have been isolated and determined chemical structures, including 7 terpenoid compounds and 3 steroid compounds. In particular, callimacrophylla A (M1) and callimacrophylla B (M8) are new compounds.
3. From the residue of n-hexane and ethyl acetate extracts of the leaves of C. candicans, 11 compounds have been isolated and identified chemical structures, including 4 flavonoid compounds, 5 terpenoid compounds and 2 steroid compounds. In particularly, methyl seco-hinokiol was isolated for the first time from nature.
Essential oil of dried leaves of C. candicans has 39 components, the main component is α-gurjunene (21.97%). Essential oil of fresh leaves of Callicarpa candicans has 47 components, the main component is α-gurjunene (21.31%). Essential oil of fresh leaves of C. macrophylla has 50 components, the main constituent is phytol (11.03%)
Biological activity:
Results of cytotoxic activities test against 3 cancer cell lines: liver (Hep-G2), lung (Lu-1) and breast (MCF-7) of some pure substances isolated revealed the strong activity of the new compound (callimacrophylla A and callimacrophylla B) with most of the rest exhibiting fairly good activity. In particularly, ursolic acid (M6) showed strong cytotoxic activity against liver cancer (Hep-G2), lung cancer (Lu-1) and breast cancer (MCF-7) with IC50 value = 2.5, 0.31 and 0.21 g / mL; compounds ent-1β-acetoxy-7β, 14α-dihydroxy-16-kauren-15-on (M7) and callimacrophylla B (M8) express strong anti-breast cell activity of CF-7 breast with IC50 = 0.23 and 0.21 g / mL, smaller than the IC50 of ellipticine positive control.
Fresh leaves essential oil Callicarpa candicans obtained from microwave-assisted distillation method showed good activity against all 3 cancer cell lines, i.e. liver (Hep-G2), prostate (PC3), lung (A549) with IC50 values of 14,65; 23.87 and 56.21 μg / mL, respectively and exhibited good Fusarium oxysporum inhibition activity with MIC value of 100 μg / mL. The remaining samples: essential oil from dried leaves and fresh flowers of Nang nang or from fresh leaves of the Beauty Berry obtained from conventional steam distillation method did not show activity.
- Applied results:
The research results of the project provide a scientific basis for further research on pharmacological effects on animals and clinical in order to create anti-cancer medicine products, serve and improve the quality of life, raising the use value of Callicarpa medicinal plants, thereby offering solutions to plant, exploit and effectively use these ethnic medicinal plants.
The project helps improve the scientific capacity and project implementation ability of VAST’s scientific staff, and build up co-operation among VAST’s units (VAST: Vietnam Academy of Science and Technology), including the Graduate University of Science and Technology, Institute of Ecology and Biological Resources, and Institute of Natural  Products Chemistry. The project result would help enhance the position of VAST and its units as one of leading scientific research and training organizations in the country and the region. 

Novelty and actuality and scientific meaningfulness of the results

The thesis has studied the chemical constituents of two plants for the first time: C. candicans and C. macrophylla of Callicarpa in Vietnam. 21 isolated compounds were isolated. In particularly, callimacrophylla A and callimacrophylla B are two new compounds and methyl seco-hinokiol compounds first isolated from nature.
The first time the essential oils of two species of Nang nang (C. candicans) and the Beauty Berry (C. macrophylla) have been studied in Vietnam. Particularly Nang nang’s essential oils was investigated for the first time all over the world.
The first time the cytotoxicity of 14 pure compounds isolated from Nang nang and the Beauty Berry leaves was investigated in Vietnam against three cancer cell lines, i.e. liver (Hep-G2), lung (Lu-1) and breast (MCF-7). Specially, 2 new compounds showed strong activity, most of the remaining substances exhibited medium active levels.
Fresh leaves essential oil of Nang nang obtained from the microwave-assisted distillation method showed good activity against all three cancer cell lines: liver (Hep-G2), prostate (PC3), lung (A549) with IC50 values of 14,65; 23.87 and 56.21 μg/mL, respectively and exhibited good Fusarium oxysporum inhibition activity with MIC value of 100 μg/mL. The remaining samples: essential oil from dried leaves and fresh flowers of Nang nang or from fresh leaves of the Beauty Berry obtained from conventional steam distillation method did not show activity.

Products of the project

- Scientific papers in referred journals (list):

  • International Publication ISI/Scopus:

1. Do Tien Lam, Vu Thi Thu Le, Pham Minh Quan, Pham Thi Hong Minh, Bui Huu Tai, and Phan Van Kiem, Two new terpenoids from the leaves of Callicarpa macrophylla, Natural Product Research, 2019, 34, 688 (SCIE).
2. Quoc Toan Tran, Thu Le Vu Thi, Tien Lam Do, Hong Minh Pham Thi,
Bich Hoang Thi, Quang Truyen Chu, Phuong Thao Lai Phuong, Huu Nghi Do,
Hoai Thu Hoang Than, Thu Thuy Ta Thi, Van Huyen Luu, Mai Duong Phuong Thi Thu Huong Phung Thi, Optimization of Microwave-Assisted Extraction Process of Callicarpa candicans (Burm.f.) Hochr Essential Oil and Its Inhibitory Properties against Some Bacteria and Cancer Cell Lines, Processes, 2020, 8(2):173 (SCIE).
    Domestic Publication:
3. Do Tien Lam, Pham Minh Quan, Vu Thi Thu Le, Nguyen Thi Hong Van, Cam Thi Inh, Ta Thi Thu Thuy, Pham Thi Hong Minh, Terpene compounds isolated from Callicarpa macrophylla in Vietnam Journal of Science and Technology, 2018, 56 (4A), 213-220.
4. Vũ Thị Thu Lê, Đỗ Tiến Lâm, Cầm Thị Ính, Phạm Quốc Long, Trần Đăng Thạch, Nguyễn Thị Hồng Vân, Phạm Thị Hồng Minh, Triterpenoid và flavonoid từ dịch chiết etyl axetat của cây Nàng nàng (Callicarpa candicans (Burm. f. Hochr.) ở Việt Nam, Tạp chí Hóa học, 2018, 56(3), 341-345.
- Patents (list):
- Technological products (describe in details: technical characteristics, place):
Scientific and technological products achieved:

  • 01 Sample collecting document
  • 01 report of study results on chemical composition of Nang Nang and Tu Chau la to leaves: 21 pure compounds and the chemical composition of Essential Oil of Nang Nang and Tu Chau la to leaves.
  • 01 report of study results on cytotoxicity activity of total extracts and isolated compounds.

Education/training:

  • 01 PhD training support: PhD. Vu Thi Thu Le, Specialist in Natural Products Chemistry, code: 9.44.01.17. Date of thesis defend round 1: November 9, 2019.
  • 02 students training:

-    Student: Dang Quang Cuong, Hanoi University of Industry. Year of completion: 2018, rank: Excellent.
-    Student: Nguyen Thi Khanh Hoa, Military Technical Academy. Year of completion: 2019, rank: Excellent