1.Endophytic Fungi Inhabiting Medicinal Plants and Their Bioactive Secondary Metabolites
Natural Product Sciences 2020;26(1):10-27
Endophytes are defined as microorganisms that spend part of lifetime interior of plant tissues without causing negative effects. They have been used for agricultural purpose, biofuel production, bioremediation, medication, etc. In particular, endophytes have been emerged as a good source for bioactive secondary metabolites. A large number of secondary metabolites are currently being reported. In this report, we focus on the secondary metabolites that were originated from endophytic fungi inhabiting medicinal plants. They were classified into several groups such as nitrogenous compounds, steroids, sulfide-containing metabolites, terpenoids, polyketides, and miscellaneous for discussion of chemical structures and biological activities.
2.1,3,5-Tricaffeoylquinic Acid from Ipomoea batatas Vines Induced Ovarian Cancer Cell Apoptosis and Inhibited Endothelial Tube Formation
Dahae LEE ; Jaekyoung KIM ; Soyoon BAEK ; Jin Woo LEE ; Changyeol LEE ; Ki Sung KANG ; Sang Hee SHIM
Biomolecules & Therapeutics 2025;33(3):483-493
Ovarian cancer usually metastasizes from the ovary to adjacent organs through direct invasion with blood vessels formed by endothelial cells. Targeting apoptosis of ovarian cancer and angiogenesis is promising for anticancer therapy. Leaves of Ipomoea sp. have reportedly shown promise in treating ovarian cancer. Here, we investigated the apoptosis-inducing and anti-angiogenic effects of compounds isolated from Ipomoea batatas vines (IBV). Phytochemical examination of IBV led to the isolation and verification of eight compounds (1-8): chlorogenic acid (1), 3,4-dicaffeoylquinic acid (2), 3,5-dicaffeoylquinic acid (3), 4,5-dicaffeoylquinic acid (4), 1,3,5-tricaffeoylquinic acid (5), N-trans-feruloyltyramine (6), scopoletin (7), and esculetin (8). Of these, 1,3,5-tricaffeoylquinic acid (5) showed the highest cytotoxicity in A2780 human ovarian cancer cells, inducing apoptotic death in more than 37% cells and decreasing viability to less than 25% at 100 μM. Compound 5 increased the levels of cleaved caspase-8, Bax, cleaved PARP, and caspase-3/9, and decreased the levels of cleaved Bcl-2. Further, 5 inhibited tubule formation in HUVECs.VEGFR2, ERK, PI3K, Akt, and mTOR protein expression was also suppressed by 5. Then, a simple, rapid, and reliable LC-MS/ MS method was developed to determine the contents of the isolated compounds from IBV. Overall, 5 has potential for treating ovarian cancer as it induces apoptosis in ovarian cancer cells and inhibits tube formation.
3.1,3,5-Tricaffeoylquinic Acid from Ipomoea batatas Vines Induced Ovarian Cancer Cell Apoptosis and Inhibited Endothelial Tube Formation
Dahae LEE ; Jaekyoung KIM ; Soyoon BAEK ; Jin Woo LEE ; Changyeol LEE ; Ki Sung KANG ; Sang Hee SHIM
Biomolecules & Therapeutics 2025;33(3):483-493
Ovarian cancer usually metastasizes from the ovary to adjacent organs through direct invasion with blood vessels formed by endothelial cells. Targeting apoptosis of ovarian cancer and angiogenesis is promising for anticancer therapy. Leaves of Ipomoea sp. have reportedly shown promise in treating ovarian cancer. Here, we investigated the apoptosis-inducing and anti-angiogenic effects of compounds isolated from Ipomoea batatas vines (IBV). Phytochemical examination of IBV led to the isolation and verification of eight compounds (1-8): chlorogenic acid (1), 3,4-dicaffeoylquinic acid (2), 3,5-dicaffeoylquinic acid (3), 4,5-dicaffeoylquinic acid (4), 1,3,5-tricaffeoylquinic acid (5), N-trans-feruloyltyramine (6), scopoletin (7), and esculetin (8). Of these, 1,3,5-tricaffeoylquinic acid (5) showed the highest cytotoxicity in A2780 human ovarian cancer cells, inducing apoptotic death in more than 37% cells and decreasing viability to less than 25% at 100 μM. Compound 5 increased the levels of cleaved caspase-8, Bax, cleaved PARP, and caspase-3/9, and decreased the levels of cleaved Bcl-2. Further, 5 inhibited tubule formation in HUVECs.VEGFR2, ERK, PI3K, Akt, and mTOR protein expression was also suppressed by 5. Then, a simple, rapid, and reliable LC-MS/ MS method was developed to determine the contents of the isolated compounds from IBV. Overall, 5 has potential for treating ovarian cancer as it induces apoptosis in ovarian cancer cells and inhibits tube formation.
4.1,3,5-Tricaffeoylquinic Acid from Ipomoea batatas Vines Induced Ovarian Cancer Cell Apoptosis and Inhibited Endothelial Tube Formation
Dahae LEE ; Jaekyoung KIM ; Soyoon BAEK ; Jin Woo LEE ; Changyeol LEE ; Ki Sung KANG ; Sang Hee SHIM
Biomolecules & Therapeutics 2025;33(3):483-493
Ovarian cancer usually metastasizes from the ovary to adjacent organs through direct invasion with blood vessels formed by endothelial cells. Targeting apoptosis of ovarian cancer and angiogenesis is promising for anticancer therapy. Leaves of Ipomoea sp. have reportedly shown promise in treating ovarian cancer. Here, we investigated the apoptosis-inducing and anti-angiogenic effects of compounds isolated from Ipomoea batatas vines (IBV). Phytochemical examination of IBV led to the isolation and verification of eight compounds (1-8): chlorogenic acid (1), 3,4-dicaffeoylquinic acid (2), 3,5-dicaffeoylquinic acid (3), 4,5-dicaffeoylquinic acid (4), 1,3,5-tricaffeoylquinic acid (5), N-trans-feruloyltyramine (6), scopoletin (7), and esculetin (8). Of these, 1,3,5-tricaffeoylquinic acid (5) showed the highest cytotoxicity in A2780 human ovarian cancer cells, inducing apoptotic death in more than 37% cells and decreasing viability to less than 25% at 100 μM. Compound 5 increased the levels of cleaved caspase-8, Bax, cleaved PARP, and caspase-3/9, and decreased the levels of cleaved Bcl-2. Further, 5 inhibited tubule formation in HUVECs.VEGFR2, ERK, PI3K, Akt, and mTOR protein expression was also suppressed by 5. Then, a simple, rapid, and reliable LC-MS/ MS method was developed to determine the contents of the isolated compounds from IBV. Overall, 5 has potential for treating ovarian cancer as it induces apoptosis in ovarian cancer cells and inhibits tube formation.
5.A New Ring-opened Azaphilone from a Fungus Talaromyces sp. FB15
Tae Yeon KIM ; Changyeol LEE ; Jin Woo LEE ; Sang Hee SHIM
Natural Product Sciences 2024;30(1):59-63
Eleven compounds (1–11), including a new azaphilone derivative (1), were isolated from cultures of Talaromyces sp. FB15, a marine fungus collected in the Beaufort Sea in northern Alaska. The structures of the isolated compounds were established by analysis of 1D and 2D NMR data, and they all were turned out to be polyketides such as azaphilone, anthraquinone, and anthrones. Interestingly, the structure of the new metabolite (1) was determined to have an azaphilone scaffold with the pyran ring opened, and to our knowledge, this is the second report on the isolation of this type of azaphilones.