Naphtho[1,2-b]furan-2(3H)-one,3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-,(3aS,5aR,6R,9aS,9bS)- - CAS 4290-13-5
Catalog number: 4290-13-5
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C15H20O3
Molecular Weight:
248.3
COA:
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Chemical Family:
Sesquiterpenoids
Description:
Santamarine, which is found in the root of Dolomiaea souliei (Franch.) Shih, induced apoptosis of L1210 cells via activation of caspase 3. It also exhibits significant anticancer activity in vitro. The inhibitory effects of Santamarine on L1210 cells is cytotoxic rather than just cytostatic.
Purity:
>98%
Appearance:
Powder
Synonyms:
SANTAMARIN; (3aS)-2,3,3aβ,4,5,5a,6,7,9aβ,9bα-Decahydro-6α-hydroxy-5aα,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one; Balchanin; (3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g]benzofuran-2-one; (3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
MSDS:
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Application:
Anticancer
Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
1.Alcohol absorption inhibitors from bay leaf (Laurus nobilis): structure-requirements of sesquiterpenes for the activity.
Yoshikawa M;Shimoda H;Uemura T;Morikawa T;Kawahara Y;Matsuda H Bioorg Med Chem. 2000 Aug;8(8):2071-7.
Through a bioassay-guided separation using inhibitory activity on blood ethanol elevation in oral ethanol-loaded rat, various sesquiterpenes having an alpha-methylene-gamma-butyrolactone moiety, costunolide (1), dehydrocostus lactone (2), zaluzanin D (3), reynosin (4), santamarine (5), 3alpha-acetoxyeudesma-1,4(15),11(13)-trien-12,6alpha-+ ++olide (6) and 3-oxoeudesma-1,4,11(13)-trien-12,6alpha-olide (7), were isolated as the active principle from the leaves of Laurus nobilis (bay leaf, laurel). In order to characterize the structure requirement for the activity, several reduction products (2a-2d) and amino acid adducts (2e, 2f) of the alpha-methylene-gamma-butyrolactone moiety were synthesized from 2 and the inhibitory activities of these sesquiterpenes, together with alpha-methylene-gamma-butyrolactone (12) and its related compounds (13-16), were examined. These results indicated that the gamma-butyrolactone or gamma-butyrolactol moiety having alpha-methylene or alpha-methyl group was essential for the inhibitory activity on ethanol absorption.
2.Cytotoxic and antibacterial activities of sesquiterpene lactones isolated from Tanacetum praeteritum subsp. praeteritum.
Gören N;Woerdenbag HJ;Bozok-Johansson C Planta Med. 1996 Oct;62(5):419-22.
Ten sesquiterpene lactones and one sesquiterpene isolated from Tanacetum praeteritum subsp. praeteritum: 1 alpha, 6 alpha -dihydroxyisocostic acid methyl ester (2), 1 alpha-hydroxy-1-deoxoarglanine (3), douglanin (5), santamarin (6), reynosin (7), 1-epitatridin B (8), ludovicin A (10), armexin (12), armefolin (13), armexifolin (14), and 3 alpha-hydroxyreynosin (15) were tested against the human lung carcinoma cell line GLC4 and the colorectal cancer cell line COLO 320 as well as against the bacteria Bacillus subtilis, Staphylococcus aureus, Proteus mirabilis, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Enterococcus, beta-hemolytic Streptococcus, and the yeast Candida albicans. In addition, two germacranolides tatridin A (16) and tamirin (17) were included in the study. All compounds showed cytotoxic activity (IC50 = 124 microM) but most of them were not effective in the antimicrobial tests.
3.Seasonal Variability of the Biochemical Composition and Antioxidant Properties of
Paiva L;Lima E;Neto AI;Baptista J Mar Drugs. 2018 Jul 26;16(8). pii: E248. doi: 10.3390/md16080248.
This study evaluates, for the first time, the seasonal (winter and summer) and geographical (São Miguel⁻SMG and Santa Maria⁻SMA Islands) variability of ;Fucus spiralis; (Fs) biochemical composition (dry weight basis) and antioxidant properties. Protein and carbohydrates presented higher values in Fs-SMG;winter;, lipids, total dietary fiber, and energy value in Fs-SMA;summer;, and ash and soluble dietary fiber/insoluble dietary fiber ratio in Fs-SMA;winter;. The fatty acid (FA) profiles showed a lower SFA in Fs-SMG;summer;, whereas MUFA and PUFA presented higher values in Fs-SMG;summer; and Fs-SMG;winter;, respectively. Excellent dietary ratios of ;n;6/;n;3 PUFA and hypocholesterolemic/hypercholesterolemic FA were found, with lower values in Fs-SMA;winter; and higher in Fs-SMG;summer;, respectively. The highest total phenolics was found in Fs-SMA;summer; acetone:water extract and total flavonoids showed the higher value in Fs-SMG;winter; methanol extract.
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Chemical Structure

CAS 4290-13-5 Naphtho[1,2-b]furan-2(3H)-one,3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-,(3aS,5aR,6R,9aS,9bS)-

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