Santamarine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 461779

CAS#: 4290-13-5

Description: Santamarine is a cytotoxic sesquiterpene lactone.


Chemical Structure

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Santamarine
CAS# 4290-13-5

Theoretical Analysis

MedKoo Cat#: 461779
Name: Santamarine
CAS#: 4290-13-5
Chemical Formula: C15H20O4
Exact Mass: 264.1362
Molecular Weight: 264.32
Elemental Analysis: C, 68.16; H, 7.63; O, 24.21

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Santamarine; Balchanin;

IUPAC/Chemical Name: (5S,6R,6aS,7R,8R)-6,8-dihydroxy-7-methyl-4-methylene-1,4,5,6,6a,7,8,9-octahydro-3H-5,7-ethanobenzo[c]oxocin-3-one

InChi Key: RFPUDMSVTPGQDR-BGPZULBFSA-N

InChi Code: InChI=1S/C15H20O4/c1-8-10-5-6-15(2)11(16)4-3-9(7-19-14(8)18)12(15)13(10)17/h3,10-13,16-17H,1,4-7H2,2H3/t10-,11+,12+,13+,15-/m0/s1

SMILES Code: [H][C@]12C(COC3=O)=CC[C@@H](O)[C@@](C)1CC[C@@H](C3=C)[C@H]2O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 264.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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2: Coronado-Aceves EW, Velázquez C, Robles-Zepeda RE, Jiménez-Estrada M, Hernández-Martínez J, Gálvez-Ruiz JC, Garibay-Escobar A. Reynosin and santamarine: two sesquiterpene lactones from Ambrosia confertiflora with bactericidal activity against clinical strains of Mycobacterium tuberculosis. Pharm Biol. 2016 Nov;54(11):2623-2628. Epub 2016 May 14. PubMed PMID: 27180996.

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4: el-Feraly FS, Chan YM. Isolation and characterization of the sesquiterpene lactones costunolide, parthenolide, costunolide diepoxide, santamarine, and reynosin from Magnolia grandiflora L. J Pharm Sci. 1978 Mar;67(3):347-50. PubMed PMID: 641720.

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9: Duan JA, Hou P, Tang Y, Liu P, Su S, Liu H. A new sesquiterpene and other constituents from Saussurea lappa root. Nat Prod Commun. 2010 Oct;5(10):1531-4. PubMed PMID: 21121241.

10: Mehmood T, Maryam A, Tian X, Khan M, Ma T. Santamarine Inhibits NF-кB and STAT3 Activation and Induces Apoptosis in HepG2 Liver Cancer Cells via Oxidative Stress. J Cancer. 2017 Oct 17;8(18):3707-3717. doi: 10.7150/jca.20239. eCollection 2017. PubMed PMID: 29151958; PubMed Central PMCID: PMC5688924.

11: Li Y, Ni ZY, Zhu MC, Dong M, Wang SM, Shi QW, Zhang ML, Wang YF, Huo CH, Kiyota H, Cong B. Antitumour activities of sesquiterpene lactones from Inula helenium and Inula japonica. Z Naturforsch C. 2012 Jul-Aug;67(7-8):375-80. PubMed PMID: 23016276.

12: Wu X, Zhu H, Yan J, Khan M, Yu X. Santamarine Inhibits NF-κB Activation and Induces Mitochondrial Apoptosis in A549 Lung Adenocarcinoma Cells via Oxidative Stress. Biomed Res Int. 2017;2017:4734127. doi: 10.1155/2017/4734127. Epub 2017 Oct 2. PubMed PMID: 29119107; PubMed Central PMCID: PMC5651150.

13: Matsuda H, Shimoda H, Uemura T, Yoshikawa M. Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying. Bioorg Med Chem Lett. 1999 Sep 20;9(18):2647-52. PubMed PMID: 10509909.

14: Choi HG, Lee DS, Li B, Choi YH, Lee SH, Kim YC. Santamarin, a sesquiterpene lactone isolated from Saussurea lappa, represses LPS-induced inflammatory responses via expression of heme oxygenase-1 in murine macrophage cells. Int Immunopharmacol. 2012 Jul;13(3):271-9. doi: 10.1016/j.intimp.2012.04.016. Epub 2012 May 5. PubMed PMID: 22564506.

15: Navarro JJ, Caballero MC, Morán JR, Medarde M, Grande M, Anaya J. Guaianolides and eudesmanolides from Centaurea ornata. J Nat Prod. 1990 May-Jun;53(3):573-8. PubMed PMID: 2213030.

16: Zhang T, Ma L, Wu F, Chen R. [Chemical constituents from a portion of ethanolicextract of Saussurea lappa roots]. Zhongguo Zhong Yao Za Zhi. 2012 May;37(9):1232-6. Chinese. PubMed PMID: 22803366.

17: Li S, An TY, Li J, Shen Q, Lou FC, Hu LH. PTP1B inhibitors from Saussrurea lappa. J Asian Nat Prod Res. 2006 Apr-May;8(3):281-6. PubMed PMID: 16864436.

18: Matsuda H, Kagerura T, Toguchida I, Ueda H, Morikawa T, Yoshikawa M. Inhibitory effects of sesquiterpenes from bay leaf on nitric oxide production in lipopolysaccharide-activated macrophages: structure requirement and role of heat shock protein induction. Life Sci. 2000 Apr 21;66(22):2151-7. PubMed PMID: 10834299.

19: Yoshikawa M, Shimoda H, Uemura T, Morikawa T, Kawahara Y, Matsuda H. Alcohol absorption inhibitors from bay leaf (Laurus nobilis): structure-requirements of sesquiterpenes for the activity. Bioorg Med Chem. 2000 Aug;8(8):2071-7. PubMed PMID: 11003152.

20: De Marino S, Borbone N, Zollo F, Ianaro A, Di Meglio P, Iorizzi M. New sesquiterpene lactones from Laurus nobilis leaves as inhibitors of nitric oxide production. Planta Med. 2005 Aug;71(8):706-10. PubMed PMID: 16142632.