• Journal of Microbiology and Biotechnology
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• v.34 no.8
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• pp.1563-1579
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• 2024

More and more diterpenoids have attracted extensive attention due to the diverse chemical structures and excellent biological activities, and have been developed into clinical drugs or consumer products. The vast majority of diterpenoids are derived from plants. With the long-term development of plant medicinal materials, the natural resources of many plant diterpenoids are decreasing, and the biosynthetic mechanism of key active components has increasingly become a research hotspot. Using synthetic biology to engineer microorganisms into "cell factories" to produce the desired compounds is an essential means to solve these problems. In this review, we depict the plant-derived diterpenoids from chemical structure, biological activities, and biosynthetic pathways. We use representative plant diterpenes as examples to expound the research progress on their biosynthesis, and summarize the heterologous production of plant diterpenoids in microorganisms in recent years, hoping to lay the foundation for the development and application of plant diterpenoids in the future.

• Korean Journal of Plant Resources
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• v.4 no.2
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• pp.35-38
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• 1991

Two new diterpene compounds have been isolate from the roots of Eragrostis ferruginea (Thunb.) Beauv. and their structures were elucidated as isopimara-9(11), 15-0ien-l9-ol-3-one and cassa-13(14), 15-diene-3, 12-dione by various spectroscopic me-thods. We have also isolated a known diterpene diol isopimara-9(11). 15-diene-3$\beta$, 19-dio1.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1998.11a
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• pp.159-160
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• 1998

Results of chemistry and biological activity of many years indicate that plants belonging to the Isodon genus are rich in ent-kaurane diterpenoids, which have been revealed to possess biological activities such as antitumor, antibacterial and antiinflammatory effects. In continuation of our research on diterpenoids in medicinal plants of this genus, the acetone extract from the leaves of I. xerophilus, which is a plant native to Yunnan province of China, showed potent antitumor activity against K562. After partition, the most active EtOAc part was studied. Four new diterpenoids named xerophilusin A(l), B(2), C(3), D(4), and eight known compounds including macrocalin B(5) and rabdorosthomin A(6) were isolated, whose structures were elucidated through a series of one- and two-dimensional NMR techniques(DEPT, COSY, HMQC, HMBC and ROESY experiments). Among them, compound 1, 2 and 5 had two unique epoxy units formed by two ether bridges from C-20 to C-7, C-14. Up to now, there are four compounds having such an peculiar structure besides these three compounds. Compound 3 and 4 were two of the few examples possessing $1{\beta}$ substitutes. All the diterpenoid compounds were subjected to the antitumor screening. It is interesting that only xerophilusin A(l), B(2) and macrocalin(5) exhibited significant antitumor activity against K562 by the method of MTT($IC_{50}$ were listed in Table 1.). The results inspired us to infer that the unique ether bridges from C-20 to C-7, C-14 possibly played an important role in the antitumor activity.

• 한국약용작물학회:학술대회논문집
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• 2008.05a
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• pp.266-266
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• 2008

• KOREAN JOURNAL OF CROP SCIENCE
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• v.41 no.6
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• pp.692-697
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• 1996

This experiment was conducted to determine the influences of growth stage, stalk position and growth environment on duvatrienediols(DVT-diols) and cis-abienol production in Nicotiana tabacum L. The leaves of plants at transplanting stage contained very small amount of duvatrienediols and cis-abienol. Comparing leaves on different stalk position at flowering stage, upper and middle leaves contained more DVT-diols and cis-abienol than lower leaves. Plants grown under controlled environmental room at 3$0^{\circ}C$ contained more DVT-diols and cis-abienols than room at 18$^{\circ}C$, $25^{\circ}C$ and glass room. Tobacco plant grown under field condition produced lower levels of duvatrienediols and cis-abienol contents than glass room-grown plants. The amounts of duvatrienediols and cis-abienol of tobacco leaves significantly decreased after rain under field conditions.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.374.2-374.2
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• 2002

Siegesbeckia pubesence (Cempesitae). a perenial herb, is widely distributed in our country and has been used for rheumaic arthritis, hypertension, malaria. neurasthnia and snake-bite in traditional Chinese medicine. On reviewing the literatures of this plant. diterpenoids and alkaloids were isolated and some pharmacological activities were investigated. As part of our systematic study fer Korean Compositae plants, we have investigated Siegesbeckia pubesence (7kg), cellected from Mt. Odae on Aug. 2001. (omitted)

• Korean Journal of Pharmacognosy
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• v.43 no.4
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• pp.286-290
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• 2012

Many diterpenoids from Siegesbeckia species (Compositae) and their anti-inflammatory actions have been examined. In this research, high-performance liquid chromatography-ultraviolet spectrophotometer (HPLC-UV) method was used to compare the quantitative level of kirenol (ent-pimarane-type diterpenoid) in the aerial parts of Korean S. glabrescens and S. pubescens and the Chinese Siegesbeckiae Herba. Fingerprints of the two HPLC chromatograms of Korean S. glabrescens and S. pubescens were similar, but considerably different from Chinese Siegesbeckiae Herba. The content of kirenol in S. pubescens ($16.51{\pm}0.10$ mg/ml dry weight as mean${\pm}$RSD) was higher than S. glabrescens ($13.48{\pm}0.12$ mg/g dry weight). These values were considerably higher than the Chinese Siegesbeckiae Herba ($1.55{\pm}0.74$ mg/g dry weight). Thin layer chromatography (TLC) analysis demonstrated the containing of kirenol in the three plant materials, but the presence of siegeskaurolic acid (entkaurane-type diterpenoid) only in the Chinese Siegesbeckiae Herba.

• Natural Product Sciences
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• v.23 no.4
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• pp.265-269
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• 2017

Pseudolaric acids of Pseudolarix kaempferi (Pinaceae) have been known as diterpenoids with potent anti-fungal-, anti-microbial, and cytotoxic activities. In the present study, the five MeOH extracts were prepared from the five plant part (root bark, stem bark, leaf, the inner part of root, and cone) to find the relation between the concentration of pseudolaric acids and cytotoxicity. Pseudolaric acids B and C were isolated from the root bark of P. kaempferi to use them as standard compounds. The five extracts were tested on cytotoxicity against six cancer cell lines, A549 (lung), HCT116 (colon), MDA-MB-231 (breast), SNU638 (stomach), and SK-hep-1 (liver) by SRB assay, but against K562 (leukemia) by SRB- or MTT assay. HPLC quantification were performed on a Shisheido Capcell PAK C18 column ($5{\mu}m$, $4.6mm{\times}250mm$) using 254 nm wavelength. The cytotoxicity ($IC_{50}$, $0.36{\mu}g/ml$ on K562 cell lines) of the root bark extract was potent and the content (101.1 mg/g extract) of pseudolaric acid B was very high in the root bark. These results suggest that the MeOH extract obtained from the root bark could be developed as the anti-cancer agent with a high quantity of pseudolaric acid B.

• Natural Product Sciences
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• v.27 no.1
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• pp.36-44
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• 2021

The essential oils from the aerial parts (leaves and flowers) of Spiraea hypericifolia L. (Rosaceae), collected in Northern Kazakhstan, were obtained by distillation in two dispersion media (distilled water and 15% NaCl solution). The chemical composition of the essential oils was evaluated by GC-MS for the first time. The yield of the essential oil was 0.04% (in fresh growth conditions) and 0.02% (in dry growth conditions) respectively regardless of which dispersion media (H2O or 15% NaCl solution) was used at the isolation of essential oil. The main compounds were aliphatic hydrocarbons (alkanes) (40.6-53.2%), aldehydes (8.4-17.4%), diterpenoids (9.1-16.7%) and ketones (6.2-8.7%). Content of monoterpenoids was depended on dispersion media (2.2-3.6% where H2O was dispersion media and 8.4-8.5% where 15% NaCl solution was dispersion media). n-Heneicosane (17.4-34.1%) and n-tricosane (14.3-19.5%) were the main constituents of the essential oil of S. hypericifolia. There were many insects from different classes in S. hypericifolia at flowering. Important components such as α-methylene-γ-butyrolactone (0.8-2.8%), benzyl cyanide (0.7-1.1%), β-damascenone (1.2-2.9%), (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene (1.8-2.7%), β-ionone (0.5-1.8%) and others were detected in small amounts.

• Korean Journal of Heritage: History & Science
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• v.54 no.4
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• pp.78-89
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• 2021

Organic residues analysis is an analysis method that reveals the types of organic material samples by using the characteristic that main components constituting substances are different depending on the species of animals and plants. In this study, scientific analysis of the organic residues attached to wood coffins in the Joseon Dynasty Hoemyo excavated from the site of Singok-dong, Uijeongbu was used to identify the types of remnants and to use them as information to restore the uses of organic materials and the way they lived in the past. As a result of FT-IR analysis of the residue attached to the inside of the wood, it was estimated to be a natural plant resin material. In addition, as a result of analysis by GC-MS to confirm the characteristic factors of natural resins, diterpenoids (abietane) and pimaran (pimarane), such as dehydroabietic acid and pimaric acid (diterpenoid) compounds, and saturated and unsaturated fatty acid components were detected together. Diterpenoid compounds are components mainly found in Pinaceae resins. It is confirmed in the literature that rosin, a representative material of Pinaceae resin, was used as an adhesive material. Considering the situation where an organic material remained at the joint of the wood, the organic material attached to the wood is judged to be an adhesive material made of Pinaceae resin. In addition, the fatty acid component detected together is a component derived from plant oil, and it is presumed to be made by mixing rosin and oil as recorded in previous studies. This study confirms that organic residues remain in the burial environment without losing their characteristics. It is expected that scientific analysis of organic residues will be conducted in the future to accumulate information necessary for the interpretation of past living culture.