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(±)-Gossypol from cotton seeds - 10mM in DMSO, high purity , CAS No.303-45-7

5 Citations COA COA
  • Cas Number:  303-45-7
  • Molecular Weight:  518.55
  • PubChem CID: 3503
In stock
Item Number
G423137
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G423137-1ml
1ml
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$47.90
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Proapoptotic agent; alters cell cycle and apoptosis proteins.

View related series
Compound libraries (12325) Extrinsic Pathway (436) Intrinsic Pathway (690)

Basic Description

Synonyms gossypol | 303-45-7 | 90141-22-3 | (-)-Gossypol | Pogosin | (+)-Gossypol | Tash 1 | (R)-Gossypol | (R)-(-)-Gossypol | No Fertil | AT 101 | (+/-)-Gossypol | 20300-26-9 | 7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnapht
Specifications & Purity Moligand™, 10mM in DMSO
Biochemical and Physiological Mechanisms Gossypol is a male antifertility agent and PAF antagonist/inhibitor. Gossypol is a poisonous pigment found in cottonseed and its name is derived from the botanical name of the cotton plant, Gossypium.. Gossypium is extracted from selected hybrid species b
Storage Temp Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Grade Moligand™
Product Description

Product Description：

Gossypol is a male antifertility agent with antispermatogenic activity and has been shown to contain anitumor, anitviral, and antioxidant properties. Gossypol is a reversible inhibitor of PP2B (protein phosphatase 2B), mitotic kinesin Eg5, and PKC (protein kinase C). Gossypol also potentially inhibits PAF-R, Bcl-2, 5-LO (5-lipoxygenase), 12-LO, and leukotriene-induced guinea pig parenchyma contractions. Gossypol is an inhibitor of Bcl-xl, PKD and p107.
An inhibitor of PKC, Bcl-2, 5-LO, and 12-LO.

Product Application：

Gossypol acts as an inhibitor for several dehydrogenase enzymes. Gossypol has also long been known to possess antimalarial properties. Gossypol provided reliable contraception. gossypol provokes infertility and causes spermatogenesis. Gossypol is used as an active antifertility agent in a variety of male animals, including mice, rats, hamsters, monkeys, rabbits, and bulls.

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
Superclass Lipids and lipid-like molecules
Class Prenol lipids
Subclass Sesquiterpenoids
Intermediate Tree Nodes Not available
Direct Parent Sesquiterpenoids
Alternative Parents Naphthols and derivatives  Aryl-aldehydes  1-hydroxy-4-unsubstituted benzenoids  Vinylogous acids  Polyols  Organic oxides  Hydrocarbon derivatives  
Molecular Framework Aromatic homopolycyclic compounds
Substituents Cadinane sesquiterpenoid - Sesquiterpenoid - 2-naphthol - 1-naphthol - Naphthalene - Aryl-aldehyde - 1-hydroxy-4-unsubstituted benzenoid - Benzenoid - Vinylogous acid - Polyol - Organic oxygen compound - Organooxygen compound - Aldehyde - Hydrocarbon derivative - Organic oxide - Aromatic homopolycyclic compound
Description This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
External Descriptors Cadinane sesquiterpenoids

Associated Targets(Human)

MCL1 Tchem Induced myeloid leukemia cell differentiation protein Mcl-1 (18 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
BAD Tchem Bcl2-associated agonist of cell death (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
BCL2 Tclin Apoptosis regulator Bcl-2 (18 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
BCL2L1 Tchem Bcl-2-like protein 1 (13 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
AKR1B1 Tclin Aldose reductase (1 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
ASPH Tchem Aspartyl/asparaginyl beta-hydroxylase (4 Activities)
Activity Type Activity Value -log(M) Mechanism of Action Activity Reference Publications (PubMed IDs)
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
AR Tclin Androgen Receptor (11781 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
VDR Tclin Vitamin D receptor (26531 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
AKR1B1 Tclin Aldose reductase (1404 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
RXRA Tclin Retinoid X receptor alpha (3637 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
BAD Tchem Bcl2-antagonist of cell death (BAD) (147 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
LDHA Tchem L-lactate dehydrogenase A chain (1573 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
LDHB Tchem L-lactate dehydrogenase B chain (463 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
POLB Tchem DNA polymerase beta (23632 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALB Tchem Serum albumin (2651 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ARSA Tbio Cerebroside-sulfatase (655 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALOX12 Tchem Arachidonate 12-lipoxygenase (3262 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
SLC2A1 Tchem Glucose transporter (14755 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NR1H4 Tclin Bile acid receptor FXR (6228 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MDH1 Tchem Malate dehydrogenase cytoplasmic (119 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HSD17B1 Tchem Estradiol 17-beta-dehydrogenase 1 (2224 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CASP1 Tchem Caspase-1 (6235 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CASP7 Tchem Caspase-7 (3146 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HSD17B2 Tchem Estradiol 17-beta-dehydrogenase 2 (1671 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
YES1 Tclin Tyrosine-protein kinase YES (2781 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
TP53 Tchem Cellular tumor antigen p53 (48468 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MDM2 Tchem p53-binding protein Mdm-2 (4545 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
A498 (42825 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ACHN (49357 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CAKI-1 (44928 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CCRF-CEM (65223 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
COLO 205 (50209 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
DLD-1 (17511 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
DMS-273 (14108 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HL-60 (67320 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
HT-29 (80576 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
K562 (73714 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
ampC Beta-lactamase AmpC (62480 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Cruzipain (33337 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
polC DNA polymerase III (243 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
guaB Inosine-5'-monophosphate dehydrogenase (49 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Ppard Peroxisome proliferator-activated receptor delta (358 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mapk1 MAP kinase ERK2 (650 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Hdac6 Histone deacetylase 6 (222 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MDH2 Malate dehydrogenase mitochondrial (131 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Streptococcus pneumoniae (31063 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Micrococcus luteus (7463 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Staphylococcus epidermidis (22802 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Enterococcus hirae (484 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Bacillus cereus (7522 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Aspergillus fumigatus (16427 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Entamoeba histolytica (2676 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Fusarium oxysporum (3998 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mus musculus (284745 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Human immunodeficiency virus 1 (70413 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Influenza A virus (11224 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
MDCK (10148 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
P388 (20296 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
mdh Malate dehydrogenase (29 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
4T1 (1737 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
B16-F10 (4610 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
lef Anthrax lethal factor (7585 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
CT26 (928 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
H5N1 subtype (135 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
GCN5 Histone acetyltransferase GCN5 (89 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Npsr1 Neuropeptide S receptor (260 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Luciferin 4-monooxygenase (66902 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
pfk 6-phospho-1-fructokinase (7870 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
BCHE Cholinesterase (8742 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Fusarium acuminatum (10 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Fusarium oxysporum f. sp. lycopersici (29 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Rhizoctonia solani (2251 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Trichophyton mentagrophytes (4846 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Eif4e Eukaryotic translation initiation factor 4E (654 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
LDH Lactate dehydrogenase (15 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
TGR Thioredoxin glutathione reductase (28579 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Mapt Microtubule-associated protein tau (6 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
Rorc Nuclear receptor ROR-gamma (89407 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID
fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)
Activity Type Relation Activity value Units Action Type Journal PubMed Id doi Assay Aladdin ID

Mechanisms of Action

Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References

Names and Identifiers

IUPAC Name 7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde
INCHI InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
InChIKey QBKSWRVVCFFDOT-UHFFFAOYSA-N
Smiles CC1=CC2=C(C(=C(C(=C2C(C)C)O)O)C=O)C(=C1C3=C(C4=C(C=C3C)C(=C(C(=C4C=O)O)O)C(C)C)O)O
Isomeric SMILES CC1=CC2=C(C(=C(C(=C2C(C)C)O)O)C=O)C(=C1C3=C(C4=C(C=C3C)C(=C(C(=C4C=O)O)O)C(C)C)O)O
WGK Germany 3
RTECS DU3100000
Molecular Weight 518.55
Reaxy-Rn 1917878
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1917878&ln=

Certificates（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Chemical and Physical Properties

Molecular Weight 518.600 g/mol
XLogP3 6.900
Hydrogen Bond Donor Count 6
Hydrogen Bond Acceptor Count 8
Rotatable Bond Count 5
Exact Mass 518.194 Da
Monoisotopic Mass 518.194 Da
Topological Polar Surface Area 156.000 Ų
Heavy Atom Count 38
Formal Charge 0
Complexity 780.000
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
The total count of all stereochemical bonds 0
Covalently-Bonded Unit Count 1

Citations of This Product

How to Cite Aladdin Scientific Products?
1. Wenqing Li, Jinting Zhu, Xinru Qi, Changyan Sun, Wenjun Li, Zhidong Chang.  (2024)  A novel Zn-MOF fluorescent probe for highly sensitive and rapid detection of gossypol in cottonseed oil and fetal bovine serum.  Food Bioscience,  57  (103569). 
2. Hao Liu, Sijiao Wang, Houyin Shi, Ruirui Zhang, Kunyan Qu, Yue Hu, Xingyu Qu, Chenyun Gan, Jingjing Chen, Xinyu Shi, Mengwu Zhang, Weiling Zeng.  (2021)  Gastric floating tablet improves the bioavailability and reduces the hypokalemia effect of gossypol in vivo.  SAUDI PHARMACEUTICAL JOURNAL,  29  (305). 
3. Qing Yu, Zhiguo Hu, Yanwen Shen, Yihan Jiang, Peichen Pan, Tingjun Hou, Zhen-Qiang Pan, Jing Huang, Yi Sun.  (2020)  Gossypol inhibits cullin neddylation by targeting SAG-CUL5 and RBX1-CUL1 complexes.  NEOPLASIA,  22  (179). 
4. Qing-li Zhu, Rong Shao, Rui Dong, Zhi Yun.  (2014)  An integrated approach for obtaining biodiesel, sterols, gossypol, and raffinose from cottonseed on a biorefinery concept.  ENERGY,  70  (149). 
5. Hongming Liu, Hua Sun, Danyi Lu, Yuchen Zhang, Xingwang Zhang, Zhiguo Ma, Baojian Wu.  (2014)  Identification of glucuronidation and biliary excretion as the main mechanisms for gossypol clearance: in vivo and in vitro evidence.  XENOBIOTICA,  44  (8): (696-707). 

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