Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 35, 2021 - Issue 24
370
Views
9
CrossRef citations to date
0
Altmetric
Research Articles

Calamusins J-K: new anti-angiogenic sesquiterpenes from Sarcophyton glaucum

ORCID Icon, & ORCID Icon
Pages 5720-5731 | Received 28 May 2020, Accepted 12 Sep 2020, Published online: 05 Oct 2020

References

  • Liang CC, Park AY, Guan JL. 2007. In vitro scratch assay: a convenient and inexpensive method for analysis of cell migration in vitro. Nat Protoc. 2(2):329–333.
  • Adair TH, Montani JP. 2010. Angiogenesis.  Morgan & claypool life sciences, Morgan & claypool publishers, San Rafael, California (USA). http://www.ncbi.nlm.nih.gov/books/NBK53238.
  • Aganov V, Antonovskii VL. 1982. 13C NMR spectra of organic peroxides. Russ Chem Bull. 31(2):247–250.
  • Al-Abd AM, Alamoudi AJ, Abdel-Naim AB, Neamatallah TA, Ashour OM. 2017. Anti-angiogenic agents for the treatment of solid tumors: potential pathways, therapy and current strategies - a review. J Adv Res. 8(6):591–605.
  • Bethesda MD. 2007. Biological sciences curriculum study. Understanding Cancer. National Institutes of Health (US). https://www.ncbi.nlm.nih.gov/books/NBK20362.
  • Blunt W, Copp BR, Hu WP, Munro MHG, Northcote PT, Prinsep MR. 2009. Marine Natural Products. Nat Prod Rep. 26(2):170–244.
  • Blunt JW, Copp BR, Keyzers RA, Munro MH, Prinsep MR. 2013. Marine natural products. Nat Prod Rep. 30(2):237–323.
  • Cheng SY, Dai CF, Duh CY. 2007. Sesquiterpenoids and artificial 19-oxygenated steroids from the Formosan Soft Coral Nephthea erecta. J Nat Prod. 70(9):1449–1453.
  • Cheng SY, Huang YC, Wen ZH, Chiou SF, Wang SK, Hsu CH, Dai CF, Duh CY. 2009b. Novel sesquiterpenes and norergosterol from the soft corals Nephthea erecta and Nephthea chabroli. Tetrahedron Lett. 50(7):802–806.
  • Cheng S-Y, Wang S-K, Wen Z-H, Dai C-F, Duh C-Y. 2009a. Three new eudesmanoids from the Formosan Soft Coral Nephthea erecta. J Asian Nat Prod Res. 11(11):967–973.
  • Cheng SY, Wen ZH, Wang SK, Chiang MY, El-Gamal AAH, Dai CF, Duh CY. 2009c. Revision of the absolute configuration at C(23) of lanostanoids and isolation of secondary metabolites from Formosan Soft Coral Nephthea erecta. Chem Biodivers. 6(1):86–95.
  • Dellar JE, Cole MD, Gray AI, Gibbons S, Waterman PG. 1994. Antimicrobial sesquiterpenes from Prostanthera aff. melissifolia and P. rotundifolia. Phytochemistry. 36(4):957–960.
  • El-Gamal AAH, Wang SK, Dai CF, Duh CY. 2004. New nardosinanes and 19-oxygenated ergosterols from the soft coral Nephthea armata collected in Taiwan. J Nat Prod. 67(9):1455–1458.
  • Folkman J. 1971. Tumor angiogenesis: therapeutic implications. N Engl J Med. 285(21):1182–1186.
  • Galal AMF, Soltan MM, Ahmed ER, Hanna AG. 2018. Synthesis and biological evaluation of novel 5-chloro-N-(4-sulfamoylbenzyl) salicylamide derivatives as tubulin polymerization inhibitors. Medchemcomm. 9(9):1511–1528.
  • Hamed A, Issa MY, Ghani MA, Frese M, Neumann B, Stammler HG, Sewald N, Shaaban M. 2019. Crystal structure and configuration revision of 9-hydroxy-7,8-dehydro-sarcotrocheliol and sarcotrocheliol. Nat Prod Res. 33(20):3029–3032.
  • Handayani D, Edrada RA, Proksch P, Wray V, Witte L, van Ofwegen L, Kunzmann A. 1997. New Oxygenated sesquiterpenes from the Indonesian Soft Coral Nephthea chabrolii. J Nat Prod. 60(7):716–718.
  • Hao Z-Y, Liang D, Luo H, Liu Y-F, Ni G, Zhang Q-J, Li L, Si Y-K, Sun H, Chen R-Y, et al. 2012. Bioactive Sesquiterpenoids from the Rhizomes of Acorus calamus. J Nat Prod. 75(6):1083–1089. − 
  • Jonkman JE, Cathcart JA, Xu F, Bartolini ME, Amon JE, Stevens KM, Colarusso P. 2014. An introduction to the wound healing assay using live-cell microscopy. Cell Adhes Migr. 8(5):440–451.
  • Kapojos MM, Mangindaan REP, Nakazawa T, Oda T, Ukai K, Namikoshi M. 2008. Three new nardosinane type sesquiterpenes from an Indonesian soft coral Nephthea sp. Chem Pharm Bull. 56(3):332–334.
  • Kobayashi M, Kanda F, Rao CVL, Kumar SMD, Trimurtulu G, Rao CB. 1990. Marine sterols. XVI. polyhydroxysterols of the soft corals of the Andaman and Nicobar coasts. Isolation of (24S)-24-methylcholest-5-ene-3β,25ξ,26-triol and (24S)-24-methylcholestane-3β,5β,6α,25-tetrol. Chem Pharm Bull. 38(6):1724–1726.
  • Lee KH, Choi SU, Lee KR. 2005. Sesquiterpenes from Syneilesis palmata and their cytotoxicity against human cancer cell lines in vitro. Arch Pharm Res. 28(3):280–284.
  • Liu M, Shao C, Chen M, Qi J, Wang Y, Fang Y, Wang C. 2014. Bioactive 9,11-Secosteroids from Gorgonian Subergorgia suberosa Collected from the South China Sea. Chem Biodivers. 11(7):1109–1120.
  • Liu X, Wu Q-X, Shi Y-P. 2005. Terpenoids from the Flower of Cacalia Tangutica. J Chin Chem Soc. 52(2):369–374.
  • Minh CV, Kiem PV, Nhiem NX, Cuong NX, Thao NP, Nam NH, Anh HLT, Thung DC, Thuy DTT, Kang H-K, et al. 2011. Cytotoxic and antioxidant activities of diterpenes and sterols from the Vietnamese soft coral Lobophytum compactum. Bioorg Med Chem Lett. 21(7):2155–2159.
  • Moon E, Lee YM, Lee O, Lee O-H, Lee M-J, Lee S-K, Chung M-H, Park Y-I, Sung C-K, Choi J-S, et al. 1999. A novel angiogenic factor derived from Aloe vera gel: beta-sitosterol, a plant sterol. Angiogenesis. 3(2):117–123.
  • Raju BL, Subbaraju GV, Reddy MC, Rao DV, Rao CB, Raju VS. 1992. Polyhydroxysterols from the soft coral Sarcophyton subviride of Andaman and Nicobar coasts. J Nat Prod. 55(7):904–911.
  • Rao CB, Satyanarayana C, Rao DS, Srinivasa D, Rao DV, Fahy E, Faulkner DJ. 1993. Metabolites of the soft coral Sinularia ovispiculata from the Indian ocean. J Nat Prod. 56(11):2003–2007.
  • Řezanka T, Dembitsky VM. 2003. Brominated oxylipins and oxylipin glycosides from Red Sea corals. Eur J Org Chem. 2003(2):309–316.
  • Saga Y, Mizukami H, Takei Y, Ozawa K, Suzuki M. 2003. Suppression of cell migration in ovarian cancer cells mediated by PTEN overexpression. Int J Oncol. 23:1109–1113.
  • Shaaban M, El-Hagrassi AM, Abdelghani MA, Osman AF. 2018a. Diverse bioactive compounds from Sarcophtyton glaucom: structure elucidation and cytotoxic activity studies. Z Naturforsch C. 73(9–10):325–334.
  • Shaaban M, El-Metwally MM, Abdel-Razek AA, Laatsch H. 2018b. Terretonin M: a new meroterpenoid from the thermophilic Aspergillus terreus TM8 and revision of the absolute configuration of penisimplicins. Nat Prod Res. 32(20):2437–2446.
  • Shaaban M, Ghani MA, Shaaban KA. 2013b. Zahramycins A-B, two new steroids from the coral Sarcophyton trocheliophorum. Z. Naturforsch. 68(8):939–945.
  • Shaaban M, Ghani MA, Shaaban KA. 2016. Unusual pyranosyl Cembranoid diterpene from Sarcophyton trocheliophorum. Z Naturforsch. 71(12):1211–1217.
  • Shaaban M, Hassan AZ, Soltan MM, Abdelwahab AB. 2018c. Naturally bioactive compounds from Hemimycale aff arabica: antimicrobial, antiglycation, cytotoxicity, and molecular docking studies. Med Chem Res. 27(9):2079–2088.
  • Shaaban M, Issa MY, Ghani MA, Hamed A, Abdelwahab AB. 2019. New pyranosyl cembranoid diterpenes from Sarcophyton trocheliophorum. Nat Prod Res. 33(1):24–33.
  • Shaaban M, Shaaban KA, Abd-Alla HI, Hanna AG, Laatsch H. 2011. Dendrophen, a novel glycyrrhetyl amino acid from Dendronephthya hemprichi. Z. Naturforsch. 66(4):425–432.
  • Shaaban M, Shaaban KA, Ghani MA. 2013a. Hurgadacin: a new steroid from Sinularia polydactyla. Steroids. 78(9):866–873.
  • Sharma K, Suresh PS, Mullangi R, Srinivas NR. 2015. Quantitation of VEGFR2 (vascular endothelial growth factor receptor) inhibitors-review of assay methodologies and perspectives. Biomed Chromatogr. 29(6):803–834.
  • Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR. 1990. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst. 82(13):1107–1112.
  • Su JH, Dai CF, Huang HH, Wu YC, Sung P, Hsu CH, Sheu JH. 2007. Terpenoid-related metabolites from a Formosan Soft Coral Nephthea chabrolii. Chem Pharm Bull. 55(4):594–597.
  • Todaro GJ, Lazar GK, Green HJ. 1965. The initiation of cell division in a contact-inhibited mammalian cell line . J Cell Physiol. 66(3):325–333.
  • Ucuzian AA, Gassman AA, East AT, Greisler HP. 2010. Molecular mediators of angiogenesis. J Burn Care Res. 31(1):158–175.
  • Vichai V, Kirtikara K. 2006. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat Protoc. 1(3):1112–1116.
  • Wang SK, Duh CY. 2007. Nardosinane sesquiterpenoids from the Formosan soft coral Nephthea elongata. Chem Pharm Bull. 55(5):762–765.
  • Wong SL, Chang HS, Wang GJ, Chiang MY, Huang HY, Chen CH, Tsai SC, Lin CH, Chen IS. 2011. Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity. J Nat Prod. 74(12):2489–2496.
  • Wu QX, We QY, Shi YP. 2006. Sesquiterpenes with various carbon skeletons from Ligularia virgaurea spp. oligocephala. Pharmazie. 61(3):241–243.
  • Xie W-D, Niu Y-F, Huang J-J, Row K-H. 2010. Sesquiterpenoids from Senecio argunensis. Helv Chim Acta . 93(12):2448–2453.
  • Xu J, Tan N, Zeng G, Han H, Huang H, Ji C, Zhu M, Zhang Y. 2009. Studies on chemical constituents in fruit of Alpinia oxyphylla. China J Chin Mater Med. 34:990–993.
  • Zhang J, Liu LL, Zhong BL, Liao XJ, Xu SH. 2015. 9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa. Steroids. 98:100–106.
  • Zhang G, Tang X, Cheng C, Gong K, Zhang X, Zhu H, Wu R, Li P, Li G. 2013. Cytotoxic 9,11-secosteroids from the South China Sea gorgonian Subergorgia suberosa . Steroids. 78(9):845–850.
  • Zhang W, Tang H, Wang C, Sun P, Li T, Zhuang C, Li J, Sun Y, Liu D. 2016. Polyhydroxy steroid compounds and purpose thereof. People Republic of China. Patent Information: Aug 2016, 10, CN 105837650A.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.