PMID- 33804495
OWN - NLM
STAT- MEDLINE
DCOM- 20210506
LR  - 20231111
IS  - 1420-3049 (Electronic)
IS  - 1420-3049 (Linking)
VI  - 26
IP  - 5
DP  - 2021 Mar 1
TI  - Antiproliferative Isoprenoid Derivatives from the Red Sea Alcyonacean Xenia 
      umbellata.
LID - 10.3390/molecules26051311 [doi]
LID - 1311
AB  - From the soft coral Xenia umbellata, seven isoprenoid derivatives were isolated, 
      including a new xenicane diterpene, xeniolide O (5) and a new gorgostane 
      derivative gorgst-3beta,5alpha,6beta,11alpha,20(S)-pentol-3-monoacetate (7), along with three 
      known sesquiterpenes (1-3), a known diterpene (4), and a known steroid (6). The 
      extensive analyses of the NMR, IR, and MS spectral data led to determination of 
      their chemical structures. Compounds 1-7 displayed a cytotoxic effect against 
      breast adenocarcinoma (MCF-7), hepatocellular carcinoma (HepG2), and cervix 
      adenocarcinoma (HeLa), with IC(50) values ranging between 1.5 +/- 0.1-23.2 +/- 1.5; 
      1.8 +/- 0.1-30.6 +/- 1.1 and 0.9 +/- 0.05-12.8 +/- 0.5 mug/mL, respectively. Compound 3 
      showed potent cytotoxic effects against MCF-7, HepG2, and HeLa with IC(50) values 
      = 2.4 +/- 0.20, 3.1 +/- 0.10 and 0.9 +/- 0.05 mug/mL, respectively. Compounds 2, 5, and 
      7 displayed cytotoxic effect against Hela cells with IC(50) values = 12.8 +/- 0.50, 
      6.7 +/- 1.00 and 11.5 +/- 2.20 mug/mL, respectively. Two DNA binding dyes, acridine 
      orange (AO) and ethidium bromide (EtBr) were used for the detection of viable, 
      apoptotic, and necrotic cells. The early apoptotic cell death was observed in all 
      types of treated cells. The late apoptotic cells were highly present in HepG2 
      cells. Compounds 5 and 7 induced a high percentage of necrosis towards HepG2 and 
      HeLa cells. The late apoptosis was recorded as a high rate after treatment with 7 
      on all cancer cells.
FAU - Althagbi, Hanan I
AU  - Althagbi HI
AUID- ORCID: 0000-0003-3351-9688
AD  - Department of Chemistry, Faculty of Science, University of Jeddah, P.O. Box 
      13151, Jeddah 21493, Saudi Arabia.
AD  - Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 
      80203, Jeddah 21589, Saudi Arabia.
FAU - Budiyanto, Fitri
AU  - Budiyanto F
AUID- ORCID: 0000-0003-3967-2122
AD  - Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz 
      University, P.O. Box 80207, Jeddah 21589, Saudi Arabia.
FAU - Abdel-Lateff, Ahmed
AU  - Abdel-Lateff A
AUID- ORCID: 0000-0002-7226-1205
AD  - Department of Natural Products and Alternative Medicine, Faculty of Pharmacy, 
      King Abdulaziz University, P.O. Box 80260, Jeddah 21589, Saudi Arabia.
AD  - Department of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, 
      Egypt.
FAU - Al-Footy, Khalid O
AU  - Al-Footy KO
AD  - Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 
      80203, Jeddah 21589, Saudi Arabia.
FAU - Bawakid, Nahed O
AU  - Bawakid NO
AUID- ORCID: 0000-0002-7294-863X
AD  - Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 
      80203, Jeddah 21589, Saudi Arabia.
FAU - Ghandourah, Mohamed A
AU  - Ghandourah MA
AUID- ORCID: 0000-0002-0247-1338
AD  - Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz 
      University, P.O. Box 80207, Jeddah 21589, Saudi Arabia.
FAU - Alfaifi, Mohammad Y
AU  - Alfaifi MY
AD  - Department of Biology, Faculty of Science, King Khalid University, Abha 9004, 
      Saudi Arabia.
FAU - Elbehairi, Serag Eldin I
AU  - Elbehairi SEI
AUID- ORCID: 0000-0003-4680-3215
AD  - Department of Biology, Faculty of Science, King Khalid University, Abha 9004, 
      Saudi Arabia.
AD  - Cell Culture Laboratory, Egyptian Organization for Biological Products and 
      Vaccines, VACSERA Holding Company, Giza 22311, Egypt.
FAU - Alarif, Walied M
AU  - Alarif WM
AUID- ORCID: 0000-0003-3236-6237
AD  - Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz 
      University, P.O. Box 80207, Jeddah 21589, Saudi Arabia.
LA  - eng
PT  - Journal Article
DEP - 20210301
PL  - Switzerland
TA  - Molecules
JT  - Molecules (Basel, Switzerland)
JID - 100964009
RN  - 0 (Antineoplastic Agents)
RN  - 0 (Terpenes)
SB  - IM
MH  - Animals
MH  - Anthozoa/*chemistry
MH  - Antineoplastic Agents/chemistry/*pharmacology
MH  - Apoptosis
MH  - *Cell Proliferation
MH  - HeLa Cells
MH  - Hep G2 Cells
MH  - Humans
MH  - MCF-7 Cells
MH  - Molecular Structure
MH  - Neoplasms/*drug therapy/pathology
MH  - Terpenes/*chemistry/*pharmacology
PMC - PMC7957567
OTO - NOTNLM
OT  - Alcyonacea
OT  - Red Sea
OT  - Xenia
OT  - apoptosis
OT  - cytotoxicity
OT  - steroids
OT  - terpenes
OT  - xenicane
COIS- The authors declare no conflict of interest.
EDAT- 2021/04/04 06:00
MHDA- 2021/05/07 06:00
PMCR- 2021/03/01
CRDT- 2021/04/03 01:17
PHST- 2021/01/26 00:00 [received]
PHST- 2021/02/23 00:00 [revised]
PHST- 2021/02/24 00:00 [accepted]
PHST- 2021/04/03 01:17 [entrez]
PHST- 2021/04/04 06:00 [pubmed]
PHST- 2021/05/07 06:00 [medline]
PHST- 2021/03/01 00:00 [pmc-release]
AID - molecules26051311 [pii]
AID - molecules-26-01311 [pii]
AID - 10.3390/molecules26051311 [doi]
PST - epublish
SO  - Molecules. 2021 Mar 1;26(5):1311. doi: 10.3390/molecules26051311.