• Journal of Microbiology and Biotechnology
• /
• 제34권8호
• /
• pp.1563-1579
• /
• 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.

• 한국자원식물학회지
• /
• 제4권2호
• /
• pp.35-38
• /
• 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.

• 한국응용약물학회:학술대회논문집
• /
• 한국응용약물학회 1998년도 Proceedings of UNESCO-internetwork Cooperative Regional Seminar and Workshop on Bioassay Guided Isolation of Bioactive Substances from Natural Products and Microbial Products
• /
• pp.159-160
• /
• 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
• /
• 한국약용작물학회 2008년도 춘계학술발표회
• /
• pp.266-266
• /
• 2008

• 한국작물학회지
• /
• 제41권6호
• /
• pp.692-697
• /
• 1996

담배의 생육단계 및 환경조건에 따른 duva-trlenediols와 cis-abienol의 함량을 조사하였던 바 얻어진 결과는 다음과 같다. 1. 담배생육 단계별 duvatrlenediols와 cis-abienol의 함량은 이식묘일 때 매우 낮았고 이식후 40일 후부터 많은 양이 생성되었다. 2. 담배생육 환경조건에 따른 duvatrienediols와 cis-abienol의 함량은 3$0^{\circ}C$ 인공광실이 가장 높았고 그 다음은 $25^{\circ}C$ 인공광실과 자연광실 그리고 18$^{\circ}C$ 인공광실은 매우 낮았다. 3. 자연광실에 재배된 연초는 도장에서 담배된 담배보다 duvatrienediols와 cis-abienol의 함량 이 높았다. 4. 개화기 때 엽위별 duvatrienediols와 cis-abienot의 함량은 하위엽이 가장 낮았고 중위엽과 상위엽은 비슷하였다. 5. 강우 전에 채취한 시료는 강우 후 즉시 채취한 시료 보다 duvatrienediols와 cis-abienol의 함양이 현저히 높았다.

• 대한약학회:학술대회논문집
• /
• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
• /
• pp.374.2-374.2
• /
• 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)

• 생약학회지
• /
• 제43권4호
• /
• pp.286-290
• /
• 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
• /
• 제23권4호
• /
• pp.265-269
• /
• 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
• /
• 제27권1호
• /
• pp.36-44
• /
• 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.

• 헤리티지:역사와 과학
• /
• 제54권4호
• /
• pp.78-89
• /
• 2021

유기잔존물 분석(organic residues analysis)은 동식물의 종에 따라 물질을 구성하고 있는 주요 성분이 다르다는 특성을 이용하여 유기물 시료의 종류를 밝혀내는 분석 방법이다. 본 연구에서는 의정부 신곡동 유적에서 출토된 조선시대 회묘 내 목관 부착 유기잔존물과 현대 재료에 대한 과학적 분석을 적용하여 유기잔존물의 주성분을 확인하고 유기물의 용도를 추정하여 과거 생활 모습을 밝힐 수 있는 자료를 확보하고자 하였다. 목관 부착 유기물과 현대 재료는 적외선 분광 분석(FT-IR)과 기체 크로마토그래피-질량 분석(GC-MS)을 수행하였다. 목관 내부에 부착된 유기물의 FT-IR 분석 결과 식물성 천연 수지 물질로 확인되었다. 또한 천연 수지의 특성 인자를 확인하기 위해 GC-MS 분석 결과 디하이드로아비트산(dehydroabietic acid), 피마릭산(pimaric acid) 등 아비탄(abietane)과 피마란(pimarane)의 디터페노이드(diterpenoid) 화합물과 포화·불포화지방산 성분이 함께 검출되었다. 디터페노이드 화합물은 주로 소나무과 수지에서 나타나는 성분이다. 소나무과 수지에서 기인하는 송진은 문헌에 접착제 재료로 사용된 기록이 있으며, 유기물 시료가 목관 이음새 부분에 잔존하고 있었던 점을 고려한다면 목관에 부착되어 있던 유기물은 소나무과 수지로 만들어진 접착 물질로 추정된다. 또한 디터페노이드 화합물과 함께 검출된 지방산은 식물성 기름에서 유래된 성분으로, 문헌의 기록처럼 송진과 기름을 혼합하여 만든 것으로 추정할 수 있다. 본 연구를 통해 고고자료에 남아 있는 유기물이 매장 환경에서도 그 특성이 남아 있는 것을 확인할 수 있었고, 당시 사용되었던 천연 수지의 종류와 용도를 밝힘으로써 과거 생활 모습 복원에 중요한 정보를 확보하였다는 점에서 큰 의미가 있다고 본다.