- 2-Methoxycarbonyl-3-prenyl-1,4-naphthoquinone, a Metabolite related to the Biosynthesis of Mollugin and Anthraquinones in Galium mollugo L.
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The structure of 2-methoxycarbonyl-3-prenyl-1,4-naphthoquinone, isolated from Galium mollugo plants, has been elucidated by spectroscopic methods, synthesis, and derivatisation.
- Heide, Lutz,Leistner, Eckhard
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- Mollugin derivatives, optical isomer thereof, or pharmaceutically acceptable salts thereof, and a pharmaceutical composition for preventing or treating inflammatory bowel disease comprising the same as an active ingredient
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The present invention relates to mollugin derivatives, an optical isomer thereof, or pharmaceutically acceptable salts thereof, and a pharmaceutical composition for preventing or treating inflammatory bowel disease comprising the same as an active ingredient. The mollugin derivatives of the present invention become salts easily by introducing an amine group, so that a solubility improvement effect is remarkable compared to existing poorly-soluble substances, and in the case of treatment with the mollugin derivatives, the activity of inhibiting the adhesion of U937 cells, which are monocytic cells, in TNF-andalpha; or IL-6-inducible HT-29 cells was excellent, thereby being useful as pharmaceutical compositions for prevention or treatment of inflammatory bowel disease.(AA) Example 7 (10 andmu;M)(BB) Example 21 (10 andmu;M)COPYRIGHT KIPO 2017
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- New mollugin analogues and their antioxidant and antibacterial activities
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The present invention relates to a new mollugin analogue and medical use thereof and, more specifically to newly synthesized mollugin analogues having both antibacterial and antioxidant activities, which can be effectively used as a medicine for oxidation-related diseases or as an antibacterial agent.
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- Facile synthesis of mollugin by kinetic control and anti-HCV (Hepatitis C Virus) activity of its analogues
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Mollugin has been reported to have various biological activities including antineoplastic, antitumor, antiviral against the hepatitis B virus, anti-aging and antimutagenic activities. An effective and concise synthesis of mollugin in two steps including kinetic control from the cheap starting material 1,4-naphthoquinone has been introduced, and mollugin derivatives thus prepared are screened for their inhibition ability against the hepatitis C virus (HCV) and the dihydrobenzochromene structure might be an additional anti-HCV agent as a new leading compound.
- Choi, Da Hye,Lee, Na Ri,Kim, Cheol Gi,Kim, Jong Woo,Lee, Sang Wook,Jun, Jong-Gab
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p. 3232 - 3238
(2015/04/22)
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- Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities
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Novel and diverse mollugin analogues (1-12) were synthesized using PhB(OH)2/AcOH-mediated electrocyclization reaction as a key step. The newly synthesized compounds were screened for antioxidant and antibacterial activities. Compounds 1, 2, 5, 6, 8, and 10-12 showed high antioxidant activities in DPPH inhibition (IC50 = 0.52-1.11 μM) compared with BHT (IC50 = 9.67 μM). Compounds 3 exhibited potent antibacterial activity against Staphylococcus aureus (KCTC-1916) bacterial strain at 100 μg/mL. Structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR data and high-resolution mass spectrometry.
- Idhayadhulla, Akber,Xia, Likai,Lee, Yong Rok,Kim, Sung Hong,Wee, Young-Jung,Lee, Chong-Soon
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- Synthesis of chromans via [3 + 3] cyclocoupling of phenols with allylic alcohols using a Mo/o-chloranil catalyst system
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(Chemical Equation Presented) The combination of a molybdenum complex (CpMoCl(CO)3 or [CpMo(CO)3]2) and o-chloranil was used as a catalyst in the [3 + 3] cyclocoupling of phenols and allylic alcohols under microwave heating conditions. Substituted chromans were selectively obtained in moderate to good isolated yields.
- Yamamoto, Yoshihiko,Itonaga, Kouhei
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supporting information; experimental part
p. 717 - 720
(2009/08/19)
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- Efficient one-pot trans-dihydroxylation of 2H-pyrans using dimethyldioxirane (DMD): synthesis of trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin natural products
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An efficient one-pot formation of trans-diols on 2H-pyranyl rings was achieved by dimethyldioxirane in wet acetone. This new methodology was applied to the synthesis of natural products containing trans-diol on the pyranyl rings such as trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin.
- Wang, Xue,Lee, Yong Rok
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p. 6275 - 6280
(2008/02/10)
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- Efficient syntheses of mollugin
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Two different strategies are presented to synthesize mollugin, based upon a close investigation of possible natural precursors. The best total synthesis of mollugin, a natural product isolated from rubiaceous herbs, is achieved in an overall yield of 61% starting from 1,4-dihydroxynaphthalene-2-carboxylic acid. The key reaction is the prenylation and spontaneous pyran ring formation. Subsequent oxidation of the intermediate 3,4-dihydromollugin with DDQ afforded mollugin. Georg Thieme Verlag Stuttgart.
- Habonimana, Pascal,Claessens, Sven,De Kimpe, Norbert
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p. 2472 - 2475
(2008/02/11)
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- Synthesis of naturally occurring rubilactone, mollugin, and dihydromollugin of Rubia cordifolia
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Rubilactone (1), dihydromollugin (2), and mollugin (3) are naturally occurring products found in Rubia cordifolia, which is a famous Chinese herb with antitumor, viral inhibition and other activities. Synthetic studies were carried out in these naphthoic acid esters starting from 1,4-dihydroxy-2-naphthoic acid. In this study, we finished the synthesis of rubilactone which has not been reported before and also synthesized dihydromollugin and mollugin with better yields with different approaches compared to those previously reported in the literature.
- Ho, Li-Kang,Yu, Hsi-Jung,Ho, Chen-Ta,Don, Ming-Jaw
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- A novel naphthalene glucoside from Cassia javanica stem bark
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A new glucoside, 3-carbomethoxynaphtho [1,2-b]-3',3'-dimethylpyran-4-O-β-glucopyranoside has been isolated from the stem bark of Cassiajavanica.
- Sanghi,Singh,Singh
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p. 321 - 322
(2007/10/03)
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- BIOSYNTHESIS OF ANTHRAQUINONES AND RELATED COMPOUNDS IN GALIUM MOLLUGO CELL SUSPENSION CULTURES
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From Galium mollugo cell suspension cultures, 1,4-dihydroxy-3-prenyl-2-naphtholic acid methyl ester diglucoside was isolated along with anthraquinones and mollugin.Production of the diglucoside was much increased by administering 2-succinylbenzoate to the cultures.The incorporation of 2-succinylbenzoate into lucidin-3-primeveroside, mollugin and the diglucoside in the mode so far proposed for rubiaceous anthraquinones was verified by administration of 13C-labelled 2-succinylbenzoate to the cell cultures.Key Word Index - Galium mollugo; Rubiaceae; lucidin-3-primeveroside; 1,4-dihydroxy-3-prenyl-2-naphthoic acid methyl ester diglucoside; biosynthesis; cell suspension culture; 13C NMR; mass spectrometry.
- Inoue, Kenichiro,Shiobara, Yoshinori,Nayeshiro, Hidekazu,Inouye, Hiroyuki,Wilson, Graham,Zenk, Meinhart H.
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p. 307 - 312
(2007/10/02)
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- Studies on a Novel Anthraquinone and Its Glycosides isolated from Rubia cordifolia and R. akane
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From Radix Rubiae (dried roots of Rubia cordifolia), mollugin, 1-hydroxy-2-methyl-9,10-anthraquinone, alizarin, 1,3-dihydroxy-2-ethoxymethyl-9,10-anthraquinone, lucidin primeveroside, ruberythric acid and three new anthraquinones, 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone, 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone 3-O-(6'-O-acetyl)-α-rhamnosyl-(1->2)-β-glucoside and 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone 3-O-α-rhamnosyl(1->2)-β-glycoside, were isolated.The new anthraquinone glycosides were also obtained from the roots of R. akane, as the main chemical constituents of anthraquinone glycosides.The structures were established by various chemical and spectroscopic methods.Keywords - Rubia cordifolia; Rubia akane; Rubiaceae; anthraquinone; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone; anthraquinone glycoside; mollugin, 13C-NMR
- Itokawa, Hideji,Mihara, Kazuhiko,Takeya, Koichi
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p. 2353 - 2358
(2007/10/02)
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