• Title/Summary/Keyword: natural lactone

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Structure Activity Relationships of PAF Receptor Binding Antagonists from Natural Products

  • B.H. Han;H.O. Yang;Kim, Y.C.;Y.H. Kang;H.J. Go;D.Y. Suh
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1995.04a
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    • pp.60-60
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    • 1995
  • 새로운 혈소판 활성화인자 (PAF) 수용체 결합 저해활성 유효성분인 pinusolide ($IC_{50}$/=2.5$\times$$10^{-7}$M)와 arctigenin($IC_{50}$/=5.2$\times$$10^{-6}$M)을 측백엽(Biota orientalis)과 우방자(Arctium lappa)로부터 분리하여 이미 보고한 바 있다. PAF 수용체에 대한 구조활성 상관관계를 규명하고자 또한 용해도가 우수한 강력한 PAF 길항제를 개발하고자 이 길항제들의 유도체들을 다양한 유기화학반응을 이용하여 합성하였고 in vitro PAF receptor binding assay로 그 활성의 강도를 비교 검토하였다. 그 결과, lactone ring 부분은 unsaturated lactone이 saturated lactone보다 활성이 강하였고 ring이 개열되면 활성이 현저히 감소하였다. pinusolide 경우 exocylclic double bond 부분은 sp$^2$구조의 hydrophobic한 유도체가 활성이 강하였으며, methyl ester 부분은 hydrophobic한 유도체가 활성이 강하였다. Arctigenin의 경우 aromatic unit가 hydrophobic할수록 활성이 강하였다.

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Sapogenins from albizzia julibrissin

  • Kang, Sam-Sik;Woo, Won-Sick
    • Archives of Pharmacal Research
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    • v.6 no.1
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    • pp.25-28
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    • 1983
  • From the stem bark of Albizzia julibrissin (Leguminosae) two known sapogenins, acacigenin B, and machaerinic acid lactone, were isolated and identified by chemical and spectral data. It is the second time that the former was isolate dform the plant sources.

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Isolation of a new sapogenin from alibizzia julibrissin

  • You, Yong-Hyo;Woo, Won-Sick;Park, Jae-Sue;Kang, Sam-Sik
    • Archives of Pharmacal Research
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    • v.5 no.2
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    • pp.33-38
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    • 1982
  • From the hydrosate of the strong uterotonic active saponin of Albizzia julibrissin a new sapogenin, mechaerinic acid mmethylester together with acacic acid lactone was isolated and characterized.

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Two-Stage Microbial Biotransformation for the Production of 6-Dodecen-4-olide (Butter Lactone) from Plant Oils Containing Unsaturated Fatty Acids (불포화 지방산 함유 식물유를 이용한 천연 6-Dodecen-4-oilde (Butter Lactone) 생산을 위한 2-Stage Microbial Biotransformation)

  • Kwon, Soon-Hyang;Kim, Kyoung-Ju;Kim, Yang-Hwi Augustine
    • Korean Journal of Microbiology
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    • v.43 no.2
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    • pp.130-136
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    • 2007
  • Natural 6-dodecen-4-olide (Butte lactone) was produced from plant oils containing high unsaturated fatty acids via two-stage microbial hiotransformation. After unsaturated fatty acids were liberated from plant oil by microbial lipase, these were converted to optically active hydroxyl fatty acid (HFA) by hydroxylation reaction of Pseudomonas sp. NRRLB-2994. When safflower oil containing >75% unsaturated fatty acid, linoleoic acid wasused, Pseudomonas sp. produced 8g/L of 10-hydroxy-12(z)-octadecanoicacid with average of 39.2% bioconversion efficiency during 48 hr biotransformation period. The recovered 10-hydroxy-12-octadecanoic acid was further bioconverted to 4-hydroxy-6-dodecenoic acid via partial ${\beta}-oxidation$ by Yarriowia lipolytica ATCC34088. 4-hydroxy-6-dodecenoic acid in culture was lactonized by lowering pH to 4.0 using $4N\;H_{2}SO_{4}$ and heating for 5 min to 6-dodecen-4-olide (Butter lactone). Natural 6-dodecen-4-olide had characteristic aroma properties when compared to 6-dodecan-4-oilde (dodecalactone) and 4-decen-4-olide (decalactone).

Microbial Metabolism of Yangonin, a Styryl Lactone from Piper methysticum (Kava)

  • Kim, Ji-Hye;Kim, Hyun-Jung;Lee, Ik-Soo
    • Natural Product Sciences
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    • v.16 no.3
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    • pp.148-152
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    • 2010
  • Microbial metabolism studies of yangonin (1), a major styryl lactone from Piper methysticum, have resulted in the production of three hydroxylated metabolites (2-4). The chemical structures of these compounds were elucidated to be 4-methoxy-6-(12-hydroxystyryl)-2-pyrone (2),4-methoxy-6-(11,12-dihydroxystyryl)-2-pyrone (3),and 4,12-dimethoxy-6-(7,8-dihydroxy-7,8-dihydrostyryl)-2-pyrone (4) on the basis of the chemical and spectroscopic analyses. The compounds 3 and 4 are reported herein as microbial metabolites of yangonin for the first time.

Cytotoxic Terpenes and Lignans from the Roots of Ainsliaea acerifolia

  • Choi Sang-Zin;Yang Min-Cheol;Choi Sang-Un;Lee Kang-Ro
    • Archives of Pharmacal Research
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    • v.29 no.3
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    • pp.203-208
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    • 2006
  • The chromatographic separation of the MeOH extract of the roots of Ainsliaea acerifolia (Compositae) led to the isolation of six known terpenes and two known lignans. Their structures were identified by spectroscopic methods as mokko lactone (1), betulonic acid (2), betulinic acid (3), zaluzanin C (4), $1{\beta}-hydroperoxygermacra-4(15)$, 5, 10(14)-triene (5), pluviatilol (6), (+)-syringaresinol (7), and glucozaluzanin C (8). Compounds $1{\sim}4$ and 8 showed non-specific significant cytotoxicity against five human tumor cell lines with $ED_{50}$ values ranging from $0.36{\sim}5.54{\mu}g/mL$.

Isolation and Biological Activity of Sesquiterpene Lactone

  • Kim Myung-Ju;Oh Hyun-Ju;Baek Seung-Hwa
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.19 no.5
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    • pp.1375-1378
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    • 2005
  • Sequiterpene lactone (1) has determined by spectroscopic analysis. This compound (1) inhibited the growth of the dermatophytic fungus Trichophyton mentagrophytes (ATCC 28185, 2 mm zone at $15{\mu}g/disk$), cytotoxic to murine leukaemia cell lines ATCC CCL 46 P388Dl, ($IC_{50}$ 1,125 ng/mL at $7.5{\mu}g/disk$) and BSC monkey kidney cell lines (100% of well at $15{\mu}g/disk$).

Dehydrocostus Lactone Suppresses the Expression of iNOS Induced by TLR Agonists

  • Kim, Su Yeon;Heo, Sunghye;Kim, Seung Han;Kwon, Minji;Park, Sin-Aye;Youn, Hyung-Sun
    • Biomedical Science Letters
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    • v.25 no.3
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    • pp.267-274
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    • 2019
  • Toll-like receptors (TLRs) are one of the families of pattern recognition receptors (PRR) to recognize pathogen-associated molecular patterns (PAMPs). PAMPs stimulate TLRs to initiate specific immunoactivity. The activation of TLRs signaling leads to the expression of pro-inflammatory gene products such as cytokines and inducible nitric oxide synthase (iNOS). To evaluate the therapeutic potential of dehydrocostus lactone (DHL), which is a natural sesquiterpene lactone derived from various medicinal plants, iNOS expression induced by LPS (TLR4 agonist), MALP-2 (TLR2 and TLR6 agonist), or Poly[I:C] (TLR3 agonist) were examined. DHL suppressed the iNOS expression induced by LPS, MALP-2, or Poly[I:C]. DHL also inhibited nitrite production induced by LPS, MALP-2, or Poly[I:C]. These results suggest that DHL can modulate TLRs signaling pathways resulting in anti-inflammatory effect.